Tuscany Walks

The Tuscan countryside is a region rich in history, culture, cuisine, and natural beauty. You will walk over rolling hills, through vast vineyards, and along paths trodden for thousands of years. You will experience cities that have birthed some of the world’s greatest masterminds and artists, ancient towns seemingly untouched by the modern world, and delightful traditional cuisine.

At the end of each night, you will be greeted by kind hosts at your comfortable accommodations, enjoy delicious cuisine made from recipes passed down through generations, and have the opportunity to taste exquisite wines from one of the most famous producers in the world. It doesn’t matter which path you take in this region, you will always find something extraordinary.

Each city, vineyard, tiny town, and walking path is steeped in tradition, history, and friendliness.


Hilltop Towns of Tuscany – 6 Days


Explore the Tuscan hill towns of Volterra, San Gimignano and Monteriggioni, following Etruscan trails and ancient pilgrim routes to Siena.

img Self-guided img 6 Days img From $ 905 img Moderate What's Included

Hilltop Towns of Tuscany – 6 Days

What's Included
  • 5 nights ensuite room accommodation in Guesthouses & 3* Hotels
  • All luggage transfers
  • All taxi transfers as described in the itinerary
  • Flexibility to add or remove days
  • 5 breakfasts
  • Maps, daily walk notes and information pack
  • 24/7 telephone support
  • Enjoy worry-free navigation with your comprehensive maps, walk notes and guidebook

Florence to Siena: Through the Chianti Winelands – 7 Days


Journey from the Renaissance city of Florence to the rolling hills of Tuscany’s Chianti wine region, ending at the grandeur of Siena’s Piazza del Campo.

img Self-guided img 7 Days img From $ 1075 img Moderate What's Included

Florence to Siena: Through the Chianti Winelands – 7 Days

What's Included
  • 7 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 6 breakfasts
  • Maps, daily walk notes and information pack
  • Flexible itinerary to suit your walking needs
  • Enjoy worry-free navigation with your comprehensive maps, route notes and guidebook

Classic Trails of Tuscany: Siena to Montepulciano – 8 Days


Walk through southern Tuscany from Siena to Montepulciano. Explore hilltop towns, dine on rustic  dishes and sample Brunello wines from the UNESCO protected Val d’Orcia region.

img Self-guided img 8 Days img From $ 1190 img Moderate What's Included

Classic Trails of Tuscany: Siena to Montepulciano – 8 Days

What's Included
  • 7 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers and all taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 7 breakfasts and 1 dinner
  • Flexible itinerary to suit your walking needs
  • Enjoy worry-free navigation with your comprehensive maps, route notes and guidebook

Tuscany Explorer: Florence to Montepulciano – 10 Days


South of Florence, walk across the rolling vineyards of Chianti. Visit the medieval city of Siena and hike through the Val d’Orcia, to the hilltop town of Montepulciano.

img Self-guided img 10 Days img From $ 1470 img Moderate What's Included

Tuscany Explorer: Florence to Montepulciano – 10 Days

What's Included
  • 9 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers
  • All taxi transfers as described in the itinerary
  • Flexibility to add or include days
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 9 breakfasts
  • Maps, daily walk notes and information pack


  • Visit Florence, Siena and walk through splendour of Tuscany
  • Explore the UNESCO city of Florence, birthplace of the Renaissance
  • Stay in the Chianti wine towns of Radda and Gaiole in Chianti
  • Walk through lyrical landscapes of golden wheat fields, vineyards, chestnut and olive groves
  • Marvel at the grandeur of Piazza del Campo in Siena
  • Follow ancient pilgrim trails deep into southern Tuscany
  • Soak in the hot springs of Bagno Vignoni
  • Spend each night in historic family run hotels
  • Stroll through the cobbled streets and piazza’s of Montepulciano
  • Picnic on local Pecorino cheese, cured meats and crusty bread
  • Enjoy fresh bowls of pasta paired with local wine
  • Visit medieval abbeys, hilltop towers and Romanesque churches
  • Sample the award-winning Brunello wines of Montalcino
  • Sample the world class Chianti wines of Volpaia and Brunello


The region of Tuscany has a rich and complex history. Originally, Tuscany was home to the wine-loving Etruscans but was annexed by Rome in 351 BC. After the fall of the Roman empire, the area was ruled by ever-changing powers until individual Tuscan cities began gaining their independence during the 12th century. While there were many wars between these city-states, they all accrued extraordinary wealth from trade, banking, agriculture, textile manufacturing, and, of course, wine.

Florence rose above the rest and introduced the world to the Renaissance by way of its flourishing artistic community. This incredible city was home to famous individuals like Michelangelo, Dante, Machiavelli, Leonardo Da Vinci, and more. While Florence declined in power after the Medici family died out, it still remained a central hub for the area. After Tuscany voted in favour of annexation to Italy, Florence became the capital of Italy from 1865 to 1871.

Today, Tuscany is still considered one of the significant cultural centres of the world. The museums, churches, and galleries, with their exquisite architecture and exhibits, garner millions of tourists each year who want to experience the height of Tuscany’s magnificent culture. The small towns receive almost as much interest with their ancient buildings, traditional foods, and kind townspeople.

Additionally, wine connoisseurs come to this region from around the world to learn about the origins of one of the world’s most excellent wine manufacturers. Tuscan vineyards, with traditions thousands of years in the making, produce some of the highest quality wines on the market. There are tastings around every corner, and tourists love the opportunity to sample such exquisite wines.


Italy has a long-standing civilisation that has dramatically changed the natural landscape over the past few thousand years. Much of the original flora and fauna have been wiped out over time. When one thinks of Italy nowadays, they dream of the rolling pastures, abundant crops, and extensive vineyards that make up the landscape.

The flora of the Italy of today has been primarily established by humankind. The landscape is dotted with olive groves, pines, and cypresses. Vineyards and crop fields take up the majority of free space, so there are very few sections of untouched nature left. Yet, nature always finds a way to make itself known even if it is only the tiniest of flowers.

Come springtime, the grassy fields and rolling pastures will be adorned with stunning bursts of colour. Bright red poppies and white Marguerite daisies bring smiles to many. Wild roses and yellow gorse can be seen along the road as well as many types of orchids. Bee orchids, Orchiaceras bergonii orchids, and Pyramidal orchids are easy to spot if you know what to look for.

Initially, the Italian peninsula was home to species like ibexes, chamois, wolves, bears, marmots, and eagles. Now, it is rare that you will see one of these creatures wandering free in the wild. However, a few can still be found in isolated natural parks.

Today, you will still find smaller species out in the wild. One beautiful creature that can be found is the butterfly. Tuscany is located on the butterfly migration path from Africa to Northern Europe. Sixty species can be found making their way north at the beginning of Spring, including the very well-known Painted Lady. Other insects can be found among the grassy areas such as ascalaphids, dragonflies, and even hornets.

Italy is also home to 19 species of snake, and you may see one or two along your walking holiday. While most are harmless and unaggressive, it is best to stay out of their way. Frogs are also common to see when nearby water, and you will likely witness a lizard or two basking in the sun as you travel along the paths.

You may expect to see birds on the trail, but you likely won’t. Birds are not all that common in Italy given to the lack of resources available to them. However, you may be able to spot raptors, hoopoe, or owls in the evening.

Tuscan cuisine boasts some of the best flavours in all of Italy. Freshly grown tomatoes, creamy mozzarella, potent basil, homemade loaves of bread, and world-famous wine are just the beginning of what Tuscany has to offer. Each breakfast, lunch, and dinner is an experience of its own. Here are a few of our favourites along the way that would be well worth your while.

Trattoria Sabatino

There is nothing better than traditional cooking, just like grandma used to make. Trattoria Sabatino is a family-run, blue-collar restaurant that prides itself on having delicious food at a reasonable price. You can enjoy reasonably priced pasta dishes. Simple, yet timeless, is the perfect description for this beloved restaurant.

Ristorante II Guscio

Let the wine flow at Ristorante II Guscio where classy Tuscan cuisine meets gourmet flair. Let your taste buds go wild with roast suckling pig, baked cod heart, and yellow pumpkin risotto. Pair these spectacular dishes with locally made wine for the ideal combination of flavours. The portions are large, so it may be wise to share with a friend so that you have plenty of room for some of their delectable desserts.

S. Forno

It is impossible to visit Florence without gorging on a least one sweet treat. S. Forno is a bakery unlike any other. Locally grown grains and ingredients are the basis for everything from their sweet cakes to their traditional loaves of bread. Enjoy a toasty panini with freshly churned butter or a savoury coffee when in need of a pick-me-up.

Gelaterie La Carraia

When one visits Italy, it is a must to eat their weight in gelato. There is no better place to do that than Gelaterie La Carraia. Located close to the Ponte Vecchio, you can delight in their incredibly soft and creamy gelato. Let the flavours of dark chocolate, pistachio, coconut, mango, melon, and more wash over your taste buds.

Torre a Cona

Just outside of Florence is the Torre a Cona vineyard. This wine resort sits in an idyllic location among the foothills where visitors can experience a fabulous wine tasting in their old but remodelled barn. The tastings are by appointment, but you can alternatively make a reservation at their restaurant to savour their traditional Tuscan dishes and try a glass or two of wine.

The Casa del Chianti Classico

This unique house of wine opened in 2014 within a former Convent of Santa Maria al Prato in the charming town of Radda. You can taste and take home wines from the most extensive collection of Chianti Classico labels in the world. Sip on a delectable wine paired with a locally-sourced product like cheese or meat, all while enjoying the glorious view of the vineyard.

Osteria Volpaia

Located in the heart of the Volpaia Estate is the Osteria Volpaia. This tavern takes organic herbs and vegetables from the estate’s garden and uses them to create a modern twist on traditional Tuscan cuisine. Bursting with flavours from around the world and featuring lots of locally produced wine, this is a lovely spot to stop for a meal.

Bar Ucci

Owned by a woman who was born and raised in this tiny town, Paola Barucci, Bar Ucci is a classy yet homely bar that will give you a true taste of the region. Paola has an extensive background working with wine and will easily be able to find the perfect drink for you.

Ristorante Le Contrade

Surrounded by the Chianti hills, Ristorante Le Contrade considers each dish to be a work of art. Enjoy their beef tenderloin, crispy lasagna, duck breast and more before ending the meal with a sweet dessert. This charming restaurant proudly accommodates vegetarian, vegan, and celiac diets so everyone can enjoy the taste of Italy.

La Taverna di San Giuseppe

La Taverna di San Giuseppe focuses on tradition and creativity in order to create a menu that delights the senses and allows patrons to embrace genuine Italian cuisine. Six hundred labels of wine are waiting in the cellar to provide you with the ideal pairing for your delicious meal. Located just 300 metres from the Piazza del Campo in Siena, this restaurant is definitely worth a visit.

Tre Cristi

Nestled inside a 15th century building is the Mediterranean restaurant Tre Cristi. Named after its painting of Christ on the wall, this restaurant captivates its patrons with a refined atmosphere and exquisite food. Fish dishes are the specialty of this classy restaurant and it features a carefully crafted selection of wines.

Il Re di Macchia

Il Re di Macchia, the King of Macchia, is a quiet restaurant with excellent food. Taste the spectacular meat sauce of the Maremma tortello or the perfectly cooked grilled beef. The head chef and his wife run Il Re Di Macchia with a passion that shows their love of cooking and their love of the Chianti region.

La Taverna del Panfilo

Enjoy traditional Tuscan dishes or new creations by the owner and chef, Miss Cinzia. Her Mediterranean dishes are crafted with high-quality ingredients to delight your senses. Try her gnocchi with mussels, baked cod in a pistachio crust, and other delicious dishes. Make sure to save room for her tiramisu with custard or tartlet with a chocolate heart to end the evening on a sweet note.


In the quaint town of Pienza you will find Canape. It is “neither a restaurant, nor a bar, nor a bistro.” It is a place to get a quick bite to eat that will fill your stomach and warm your heart. Take a moment to relax and enjoy a cup of soup with freshly baked bread; it is just what you need to recharge.

La Grotta

La Grotta is run by a brother-sister duo that create modern dishes with their own unique flair, utilising traditional Tuscan ingredients; combine this with one of their local wines and you will have yourself a rejuvenating meal. This cozy restaurant prides itself on quality service and a relaxed atmosphere. On sunny days, you can even enjoy your meal out in the garden.

Trattoria di Cagnano

Trattoria di Cagnano produces everything possible in-house, from fresh pasta to bread to jam to liqueurs, they really do it all. The open kitchen and wood-burning stove make for a comforting atmosphere that will put you at ease while you enjoy your meal. Order one of their gnocchi with walnut dishes or the Maremma with radicchio and pecorino cheese. If you prefer to keep it simple, you can have one of their tasty pizzas.

The Macchiaioli Winery

Are you craving a mid-afternoon snack? Visit the Macchiaioli Winery to get a sample board of cold cuts and cheeses along with your first glass of wine for the evening. Courteous and hospitable staff are more than happy to help choose the best selection of wines for you.

Le Vecchie Mura

Appreciate typical Tuscan cuisine in San Gimignano with the home-cooking style of Le Vecchie Mura. Start off with a selection of cheese, honey, and jams by ordering the Varieta’ di Pecorino. Next, warm your belly with the hearty Ribollita Toscana soup before having their famous rabbit dish cooked with local wine (Coniglio alla Vernaccia) which has been a town favourite for over 20 years! Finish your meal off with one of their cakes of the day!


Hotel David

The award-winning hotel, Hotel David, was an 1800s villa that was transformed into a popular hotel in the 1950s. This classy hotel still holds the period furniture from the original dwelling, giving the hotel a homey and loving atmosphere. Comfortable rooms come with a free buffet breakfast, happy hour, minibar, and Sky TV. Hotel David prides itself on providing quality service while making each guest feel welcomed and at home.

Hotel Palazzo San Niccolo

Located in the heart of the historic centre of Radda is the beautiful Hotel Palazzo San Niccolo. It has been recently renovated to provide the best possible experience for its patrons. Enjoy dinner at the Caffe San Niccolo and wander through their private gardens after exploring the village. A pleasant night’s sleep awaits you in their comfortable rooms, ensuring that you are rejuvenated and ready to continue your journey the following day.

Cavarchino B&B

Nestled among the splendid vineyards and winding roads of the Chianti region is the Cavarchino B&B. This ancient farmhouse offers its guests old-world style combined with modern comforts. Magnificent views can be seen from every window and while swimming in the infinity pool. If that wasn’t enough, you can lounge in their personal gardens, read a book in their relaxation area, or just breathe in the fresh country air.

Hotel Chiuserlli

Built in 1870, this neoclassical villa is located in the heart of Siena. In 2013, the hotel was renovated to combine its old-world charm with modern amenities. Quaint rooms are perfect for singles, couples, and families to relax in. Sip a glass of wine on the terrace, explore the gorgeous city of Siena, or get pampered at their partnered spa, Antica Querciolaia, at a discounted rate.

Hotel dei Capitani

Located in the 18th century Catasto Leopoldino, in the historic centre of Montalcino, is the gorgeous Hotel dei Capitani. It is believed this building was used in the Middle Ages as a shelter for the Sienese people when they were fleeing from the Florentine Army. No signs of war remain today except for the swimming pool which is designed to look like a medieval fountain. Take advantage of the large, splendid rooms (some with two stories) that are waiting for you. Take a dip in the enchanting pool and ask the kind hotel employees about the best wines in the area. They will be more than happy to tell you all about them.

La Locanda Loggiato

La Locanda Loggiato dates all the way back to the 13th century. Fast forward to modern day and it’s the perfect blend of charm, simplicity, and romance. Owned by two amazing women, this accommodation will provide you excellent service with a smile. Enjoy bathing in the thermal pools, relaxing to the sweet sounds of nature, and getting special rates at the famous Bagno Vignoni Spa where you can be pampered to your heart’s content. Charming rooms await you here, promising an evening of peaceful rest before resuming your walking holiday the next morning.

Piccolo Hotel La Valle

Piccolo Hotel La Valle is made in the traditional style of stone and brick to give visitors a glimpse of simplistic beauty. The staff are kind and attentive, the rooms are made for relaxation, and the views are beyond gorgeous. The hotel boasts a sweeping panoramic view of the Val d’Orica; take it all in from the balconied rooms or while sipping a coffee on the expertly-manicured lawn. Before heading out on the next leg of your walking holiday, be sure to enjoy the goodies at the buffet breakfast included with your stay.

Hotel II Rondo

The Hotel II Rondo prides itself on maintaining a warm, old-world charm that leaves guests in a familiar atmosphere. Each bedroom is decorated with pastels, antique furniture, and handmade embroidered linen curtains. It will feel as though you are stepping back in time but with the enjoyment of modern amenities. One of the most spectacular parts of this stay is the buffet breakfast where everything is grown or made within 15km. Delight in seasonal fruits, local cheeses, sweet pancakes, and freshly made pastries in the elegant breakfast room or out in their gorgeous garden.

Albergo del Chianti

Albergo del Chianti is a perfect place for relaxing. Designed with peacefulness in mind, their rooms are structured to guarantee quietness and to suit all types of visitors. Take a dip in the shimmering blue pool or dine in their coastal-themed restaurant. If you are lucky, you may pass through this beautiful hotel during the time that the festivals are going on. Albergo del Chianti is perfectly positioned in the main square where art exhibitions, weekly markets, and colourful festivals are held. Right outside your door could be an authentic taste of Italian culture.

Pieve a Salti

Located among the green rolling hills of Siena is the gorgeous Pieve a Salti. The Prandi family have spent the past 30 years creating a paradise on their 700 hectares of farmland. Here you can eat organically grown food in the restaurant, relax in the spa, take a horseback riding adventure, swim in the outdoor or indoor pools, play tennis, go biking, or even hunt for mushrooms. Once the day is over, relax in one of their traditionally-styled Tuscan rooms that are both comfortable and charming.

Hotel la Cisterna

Take a step back in time to an age of simplicity at the Hotel la Cisterna. San Gimignano is steeped in age-old world culture, with travellers coming back again and again to experience its ageless traditions. The goal of Hotel La Cisterna is to provide the elegant warmth of hospitality. They pride themselves on having classically furnished rooms and excellent service. Dine in Tuscan style and taste secret recipes passed down from generation to generation, all while enjoying cascading views of the countryside.


As a part of your walking holiday with us, we will transfer your main luggage between accommodations. Therefore, you will only have to carry a light daypack as you traverse the Tuscan landscape. However, it is your responsibility to manage how you will arrive at the first city and how you will depart from the final destination. We have listed some suggestions below.

If you have any questions, please feel free to get in contact with your service representative; after doing so, we will happily guide you through your best options.

If you are arriving from a town or city near Florence, you will likely be able to catch a train or bus to the city’s two main railway stations. Firenze Santa Maria Novella (Firenze SMN) is located close to the city’s major tourist attractions. The second railway station is Firenze Campo di Marte, which is used by national and international train stations.

Arrive at: Florence

Florence has a small airport. The larger airports of Pisa and Rome generally offer a more comprehensive range of routes across Europe and beyond.

From Florence Airport:
You can travel by either bus or tram from Florence airport to Florence centre. The direct tram services terminate next to the Florence mainline station, whereas the bus service terminates in central Florence. Both journeys are no longer than 20 minutes.

From Pisa Airport:
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station and change to a direct service to Florence. Journey time is approximately 1 hour to 1 hour and 30 minutes.

From Rome Airport:
Rome has two airports: Fiumicino and Ciampino. Fiumicino airport connects through to Florence central station in around 2 hours and 30 minutes (with a change of trains in Rome central station). If you’re arriving into Rome Ciampino airport, you will need to take the airport bus to Ciampino station and change at Rome central station for services to Florence. Journey time from Ciampino to Florence is around 2 hours and 30mins (depending on times and services).

If you are arriving from a town or city near Florence, you will likely be able to catch a train or bus to the city’s two main railway stations. Firenze Santa Maria Novella (Firenze SMN) is located close to the city’s major tourist attractions. The second railway station is Firenze Campo di Marte, which is used by national and international train stations.

Arrive at: Sienna

From Pisa:
You can take a unique “people mover” from the airport to the Pisa Centrale Train Station and then board a train to Siena. The trains leave every 30 minutes and the full journey takes approximately 1 hour and 45 minutes, with one transfer.

From Rome:
Take a Leonardo Express Train into Rome centre and then board a train to Siena (however, you have to go to Florence, then change). The trains leave approximately every hour, and the journey will take around 3 hours and 30 minutes.

You can also take the Flix Bus from the Rome Tiburtina Bus Station for a direct trip to Siena that will take less than 3 hours.

From Florence:
From Florence, you can take the train or the bus to Siena. The journey time by train is about 1 hour and 30 minutes. Some trains and buses are direct whereas on others you will have to transfer in Empoli. By taking the regional bus, you will be provided with a shorter trip that drops you off within the city walls.

Arrive at: Volterra

From Pisa:
From Pisa, you can take the train service provided by Trenitalia from the Pisa Central Station. It will take approximately 1 hour and 30 minutes to arrive at the Saline Ex Coop Station. Here you will transfer to the bus to Volterra. It will take about 30 minutes to reach Volterra.

From Florence:
Take the train from the Firenze SMN Station to the Pontedera – Casciana T. Station. It is approximately a 45-minute ride. Upon arrival, transfer to the Volterra bus line. It will take about 1 hour and 30 minutes to arrive in Volterra.

From Rome:
To reach Volterra from Rome, you must first travel to Florence. You can take the Venezia S. Lucia line from Roma Termini into Firenze SMN Railway Station. From here, follow the same directions given above for traveling from Florence.

Depart from: Montepulciano

If departing from Montepulciano, there are a variety of buses that you can take from the Montepulciano Autostazione that will connect you to nearby train stations. Depending on where you wish to travel to, there are regular connections through to Florence, Pisa, and Siena.

Depart from: Sienna

If departing from Siena, you will need to take a train since the city does not have an airport. There are excellent train connections to Florence (direct service, 1hr 30mins), Pisa (change at Empoli, 1hr 45mins) and Rome (via Chiusi Chianciano Terme, 4hrs).

More Options:

For all train travel in Italy prices, timetables and ticket reservations can be made through The Trainline or Tren Italia. Another useful generic planning tool for travel is Rome2Rio should you be travelling from, or to, other destinations.


The region of Tuscany boasts an average of 2300 hours of sunshine per year with hardly any rainfall to break it up. In spring, the temperature starts to warm but the rainy season sets in. Luckily, the rain mostly dissipates by April and ushers in warm weather and average temperatures of 8°C – 19°C. In the summer months, the weather is sunny and can reach 40° C; at night, the weather rarely drops below 30° C.

Come September, the high temperatures begin to dissipate and temperatures range from 15°C – 27°C. Many tourists flock to Tuscany during this time as the sunny weather remains, but it’s no longer scorching hot. As winter approaches, the temperatures continue to cool and rain becomes more frequent.


You will be walking an average of 10km-19km per day with up to 500m of ascent and descent. You will be traversing a variety of landscapes including forest trails, gravel tracks, rolling farmlands, and vineyards, as well as within the towns and villages. It is common in Italy for there to be no separate footpaths, so you will often be walking along the edge of the road while in town; please be mindful of all road users when doing so.

For each of the walks, you will be provided with daily notes, a map, and the GPX tracks if you require them for use on your own device.


Our walking holiday runs from late April to the end of June and from mid-August through October, with departures available daily. To best enjoy the warm, bright days that this region has to offer, we avoid the rainy months of early spring and winter as well as the scorching heat of mid-summer.

During this time although there is generally very little rainfall, Tuscany does have some spectacular thunderstorms which usually occur in the late afternoon or evening. However, generally, the paths will be dry, and the spectacular scenery will be easily visible under the bright, clear skies. Plus, the grape harvest season begins from mid-August to September and with it comes lively local festivals that you may have the opportunity to enjoy. For more information on Tuscany’s seasonal weather, please see our climate/weather section.


The trails you will be walking through Tuscany are rated as moderate. The majority of these trails are well-defined, although some of the tracks may have short, steep hill sections or rough surfaces. You will be passing through a diverse set of landscapes, but none are considered particularly challenging in nature.

It is recommended that you have a moderately active lifestyle if you want to participate in this walk. You should maintain an exercise regime of 2 to 3 times a week and be able to walk 10km-19km per day. If you are unsure of your level of fitness, consult with your doctor.


Your main piece of luggage will be transported for you each day as you walk, so when you arrive at your accommodation, it will be there waiting for you. You will only have to carry a light day pack with your essentials.

As with any journey, it is essential to be prepared for your self-guided walking holiday. While we will be transporting your luggage from accommodation to accommodation, you will still be carrying a lightweight day pack with you. Here is what we suggest that you take with you each day:

  • Walking notes, map and a map case
  • Picnic lunch packed in an insulated container (when supplied)
  • Waterproof jacket with a hood
  • Quick drying fleece or jumper
  • Sun protection (hat, sunglasses & cream, at least 15SPF+)
  • Comfortable walking shoes or boots
  • 2 to 3 litres of water
  • First aid kit (including personal medication & insect repellent)
  • Toilet paper
  • Local currency and credit cards
  • Mobile phone (please note that reception is not available in all walk areas)
  • Small container of salt mixed with rice grains
  • Any other personal effects
  • And don’t forget to waterproof your bag!

Now that we have the essentials packed, it is time to think of any additional items that may be worth taking along with you. These items may include but are not limited to:

  • Waterproof over-trousers
  • Warm hat & gloves (if travelling early or late in the season
  • Extra socks
  • Camera (with an extra battery or SIM cards)
  • Battery pack and charging cable for phone
  • Binoculars
  • Notebook and pen
  • Matches
  • Small torch
  • Walking stick / walking poles
  • Additional snacks

If you have any questions, please feel free to contact our office and have a chat with our friendly team. We will happily advise you on what types of clothing, backpacks, boots, and other materials you may need for your walking holiday.



Florence is considered one of the great cultural and historical centres of Italy and the world as a whole. Great artists were inspired by this magnificent city’s rich history and incredible architecture. A birthplace of art, science, and incredible food, Florence is one city where you could spend a lifetime and never experience everything.

Ponte Vecchio Bridge

The Ponte Vecchio, or Old Bridge, has stood the test of time and is one of Florence’s famous landmarks. The Ponte Vecchio was the only bridge across the Arno River into Florence until 1218. Even though it was soon destroyed by a flood, it was subsequently rebuilt in 1345; it miraculously survived World War II and another flood. Today you can walk across the bridge at any time and during business hours gorgeous shops line its sides. These shops have been here for hundreds of years and sell some of the most beautiful jewellery in all of Italy.

Uffizi Art Gallery

The Uffizi Art Gallery was not intended to become a famous museum where 10,000 tourists pass through each day. It originally served as a grandiose building for hosting magistrates when the Medici family was in power; “Uffizi” actually means “offices” in Italian. The Medici’s were avid art collectors, and eventually their collection was open to the public for everyone to enjoy. By visiting the Uffizi Art Gallery, you will be able to view some incredible art and take a veritable walk through history.

Galleria dell’ Accademia

It is here that you will have the opportunity to view Michelangelo’s David, a world-famous marble sculpture. David is featured in the centre of the hall, drawing countless visitors each year. However, he is not all there is to offer. Explore the rest of the museum to learn about botany, music, and art. If you can’t get enough of Michelangelo’s work, you can visit his Hall of Prisoners to see all the pieces that he didn’t finish.

Piazza del Duomo

In the heart of Florence, you can experience the magnificent architecture within the Piazza del Duomo. In this square, standing tall as one of Florence’s most famous landmarks, is the Cathedral of Santa Maria del Fiore (also known as the Duomo). This enormous Gothic structure was built on the ruins of a 7th century church, which can still be seen in the crypt. It took over 200 years to be deemed finished, and once you enter, you will understand why. The cathedral has a corresponding Bell Tower (which you can climb up) and a baptistery. It is simply not enough to see these structures from the outside, you must take the time to explore the inside as well!

Chianti Winelands

The Chianti Winelands is a region where the high-quality “Chianti Classico” wines are produced. It covers a range of towns, but only those within this region can put the famous black rooster symbol on their wine. Looking over the region is like admiring a painting. Green squares of vineyards, cypress-lined roads, and wildflowers add bright splashes of colours to the landscape. It is hard to believe that this area was once a constant battlefield, but out of war came beauty.


This tiny, fortified village is known to Italians as a “Castello.” It takes less than an hour to explore, but you will be amazed by the original Tuscan architecture that this town prides itself on restoring to its original grandeur. You can pop into one of the three restaurants for a snack or just take a moment to rest in the shade.

Santa Maria Novella Church

The Santa Maria Novella is considered one of the most important Gothic churches in all of Tuscany. Fra Jacopo Talenti and Leon Battista Alberti were the masterminds behind the exterior of this church. Inside, you can examine the spectacular works of Masaccio, Ghirlandaio, and Giotto. Another reason why this church is so famous is that it features the oldest façade in all of Florence. Moreover, it is the only church with its original façade still intact today!


This medieval town has been inhabited since the 9th century and was once the capital of Chianti. Located on an ideal hilltop location between the Arbia and Pesa valleys, this small town still has an ancient vibe to it. Massive defensive walls span the perimeter, narrow streets twine through the city, and towering buildings make you feel as though a knight will ride past at any moment.

San Giusto

This tiny hamlet in Salcio overlooks the Chianti vineyards and woodlands. Consisting of just a couple small stone houses and an ancient church that dates back farther than 1018, it is a joy to stop here and ponder what life must have been like centuries ago.


Gaiole is another important city to the historical and cultural creation of the Chianti Region. This city boasts exquisite castles and churches, a beautiful byproduct of the long-lasting power struggles between Gaiole and its surrounding Tuscan cities hundreds of years ago. Now, Gaiole is no longer focused on power but rather on wine. It is home to the largest winery in the Chianti Classico region where the Chianti formula was created in 1872. You will find no better location to hop from wine tasting to wine tasting than here.

Badia a Coltibuono

This hamlet used to be a monastery. It was founded in 1051 and was ruled by the Vallombrosan order of Benedictine monks for almost 800 years. This monastery held numerous manuscripts that have now been moved to the archives in Florence. After the monastery closed, it was transformed into a farm-house villa boasting an enclosed garden, medicinal plants, and natural decorations that will please any nature lover.

Badia a Passignano Abbey

This abbey was founded in 1049 in response to the Vallombrosan monastic reforms. It is perched on an isolated site that makes for a beautiful hike looking over the green landscape of the Chianti region. Within the abbey, you can see an ancient courtyard, the Church of Saint Michael Archangel, and the bell tower.

Siena City

You may know Siena from the famous James bond movie Quantum of Solace, where you can see the city and the Palio featured. However, Siena is much more than just a quick stop in a movie. After being transferred to Siena, you will have the opportunity to explore this gorgeous city. It is said that Siena was founded by one of the legendary founders of Rome, depicted by the famous she-wolf statues all over the city. We suggest staying an extra day so that you can truly experience all that Siena has to offer.

Piazza del Campo

Formerly the meeting point of 3 primary routes in and out of Siena, the piazza was developed as a neutral meeting ground where political holidays and festivals could be staged. Featuring a unique design said to be in the shape of Virgin Mary’s cloak, the piazza attracts many tourists and twice a year hosts the colourful Palio horse event. Nearby the plaza, you can visit the Palazzo Pubblico, the Torre del Mangia, the Capella di Piazza, and the beautiful fountain known as Fonte Gaia.


You will have the opportunity to take the train to Buonconvento. This small village has a vibrant historical centre; there’s a church, the town hall, some museums, and a variety of restaurants and cafes on Via Soccini. This fortified city was once a place of trade and commercial activities, which is how it got its name; Buonconvento means “happy place.” Now it is a quiet little city that enjoys inviting in tourists to learn about its rich history.


Montalcino is considered “the birthplace of Tuscany’s fullest, richest wine: the long-aging Brunello di Montalcino.” Visiting this town is like stepping into a fairytale. Little has changed here since the 16th century, and it remains nestled within the Val d’Orica Natural Park. Fortified walls surround the town, leading up to a castle that towers high into the sky. While you are here, you must sample the famous red Brunello wine.

Castelnuovo dell’ Abate

This small medieval village is closer to a hamlet than anything else. It lies within the borders of Montalcino and was once a fortress of the Abbey of Sant’Antimo. Here you can visit the Romanesque parish church of Saints Philip and James which has preserved some of its 16th century frescos, as well as the Palazzo Bellanti.

Abbey of Sant’ Antimo

This 12th century abbey was built in a Romanesque style and has stood the test of time. It is said that Charles the Great founded the abbey in 781 after his soldiers were afflicted with some kind of unknown illness. Legend has it that an angel appeared before them, offering guidance on a cure. In gratitude to this kind angel, the king decided to build the church to demonstrate his appreciation. Surrounding the grounds are beautiful views of vineyards, olive groves, rolling hills, and wheat fields, making it a perfect location to stop and rest.

Bagno Vignoni

A private transfer will take you into the Roman spa town of Bagno Vignoni. Instead of a traditional town square, Bagno Vignoni sports a pool in the centre of its village where hot water bubbles up from a natural spring. Although you can’t take a dip in the main square pool, there is a spring that you can enter for free at the Parco dei Mulini. Relax as the therapeutic waters work their magic.

Vignoni Alto

Just uphill from Bagno Vignoni is the tiny village of Vignoni Alto. Entering this village is like stepping back in time into a medieval village. A gorgeous chapel, flower-filled gardens, and an 11th century castle are all waiting for you here. Appreciate the old-world beauty as you wander through the village. Make sure to think about what life would have been like when this village was bustling with activity.

San Quirico d’Orcia

Located at a central position between Pienza, Montalcino, and Montepulciano, San Quirico d’Orcia is an ideal destination to use as a home base while exploring the Chianti region; it was also a vital stop along ancient pilgrimage routes on the Via Francigena. Enjoy the lovely churches, visit the gorgeous plaza, wander through the Horti Leonini gardens, and taste the delicious food that Tuscany has to offer.


Known as the “ideal city of the Renaissance,” this city was formed by Enea Silvio Piccolomini who later became Pope Pius II. Built quickly, this city was designed to be elegant and harmonious. Here you can find the Cattedrale dell’Assunta which holds work from many famous painters, the bell tower that commands attention, and a beautiful hanging garden just off the central plaza. There are endless architectural wonders to explore and many charming shops just waiting for you to discover them.


You may recognise this town from the Twilight movie sequel New Moon, but this charming place is much more than just the setting for a vampire movie. This medieval hilltop town is filled with Renaissance palaces, features an inspiring tower, and (most importantly) is home to the internationally known Vino Nobile, one of the top Tuscan wines. Walking through town is the best way to visit every hidden nook and cranny that you might find interesting.

Piazza Grande

The Piazza Grande is the heart of Montepulciano and is one of the few flat areas in this slope-filled city. In this ancient square, you will find the beautiful town hall with its striking tower, bearing a close resemblance to the Palazzo Vecchio in Florence. At the top of the tower, you can experience panoramic views of the Tuscan countryside. In the plaza, you will also find the rough façade of the Duomo and the fancy Il Pozzo dei Grifi e dei Leoni fountain. The contrasting styles and levels of elegance give the plaza an odd but exciting appearance. In the evening, it’s worth strolling out to the edge of the old town to see the sunset over the Val d’Orcia.


After a private transfer, you will have the ability to explore the busy little town of Greve. This town was once caught between the duelling city-states of Florence and Siena, but now it is the epitome of peaceful small-town life. Wine is for sale around every corner and there are many boutique shops to peruse. The strangely shaped town square is where all the action happens, with plenty of churches and museums to explore nearby; one in particular that you must see is the Wine Museum.


Just above the small town of Greve is the village of Montefioralle. Montefioralle is one of the oldest and most stunning villages in the Chianti Region. During the Middle Ages, Montefioralle was once one of the greatest military centres of the area. Even to this day, it’s still surrounded by defensive walls. With stone houses, old-style streets, and ancient towers, it’s no surprise that this charming little town dates all the way back to 1085. At the top of the village is the church of Saint Stefano, which is well worth the climb to see.

Via Francigena

Long ago, pilgrims would make their way south to pray at the tomb of St. Peter and Paul in Rome. Unfortunately for them, they didn’t have Google Maps to guide them on how to get there. Despite this, many followed the same road: Via Francigena. This road starts in Canterbury, England and ends in St Peter’s Square in Rome. Via Francigena passes through the Chianti region, so you will have the opportunity to walk along this path taken by pilgrims for centuries.

Monteroni d’Arbia

Sitting along the Via Francigena is the beautiful mountain village of Monteroni d’Arbia. Surrounded by olive groves and fields of sunflowers, this little village feels like something out of a movie. Unlike the surrounding cities, which are known for their culture and art, Monteroni d’Arbia’s historical significance was primarily agricultural. It was home to many farming families and remnants of their old practices are still visible today.


This tiny hamlet’s foundation dates all the way back to the year 1000, but newly discovered artefacts suggest that there were settlements here much earlier. For years, this tiny town was known for “follatura” (the working and dyeing of wool) and its peaceful serenity. While the wool working is less apparent now, this location is still known for its relaxed vibe. You can visit the Church of San Leonardo, the Church of San Bartolomeo, and the Palazzo della Giustizia while passing through.


Volterra was one of the twelve main towns of the Etruscan confederation at the end of the 4th century. Even though Volterra fell under Roman control, its peculiar city layout still holds true to the original Etruscan style. You can see it for yourself at the remaining sections of the protective walls, the two gates that allow passage into the city, and the Acropolis. What makes Volterra famous worldwide is its hand-made alabaster objects, which are perfect for souvenirs or gifts.

Castelvecchio Nature Reserve

Just outside of San Gimignano is the Castelvecchio Nature Reserve. Chalky hills, dense shrubland, and rocky walls provide a great environment for a rich diversity of flora and fauna. Peregrine falcons love to spend their winters among those rocky walls. On the far end of the reserve are the ruins of the medieval fortress of Castelvecchio.

San Gimignano

San Gimignano became a UNESCO World Heritage Site in 1990 and is known for its spectacular medieval architecture. The original families built approximately 72 tower-houses to display their extreme power and wealth. Only 14 of these structures remain today. Walk among the ancient streets, visit shops in one of the plazas, traverse through a museum, or even read a book in their public library. There is much to see and do in this precious city, but you must try their saffron and signature white wine, the Vernaccia di San Gimignano.

Colle Di Val d’Elsa

Known for its crystal glass production, Colle Di Val d’Elsa is a fascinating location for visitors from around the world. Colle di Val d’Elsa produces 95% of Italy’s crystal glass, which accounts for 14% of production worldwide. Each month they host a market and glass making show that draws in countless tourists. After the festivities, there is still so much to see. Be sure to check out the local church, the museums, and the sweeping views of the Tuscan countryside.


Monteriggioni is considered one of the most incredible walled castles in the Chianti region due to its ageless elegance. It is hard to believe that this beautifully preserved structure was originally built in 1219. The perfect circular perimeter was not an intentional design choice, it actually followed the lay of the land. The village hasn’t changed very much in the past few centuries, undergoing only a couple modifications. Upon entering the main square, you will see the stunning Church of Santa Maria Assunta and thus begin your exploration of this charming village.


Florence Leather Market

Located a little outside the centre of Florence is the famous Florence Leather Market. The streets are filled to the brim with vendors selling their wares. Practically anything you could want to be made out of genuine Italian leather can be found in this market. They also sell colourful scarves, unique trinkets, and souvenirs that are perfect for friends back home. We suggest looking through the entire market before buying anything because there will be duplicates. It’s important to note that the more affordable prices will be on the edge of the market; be wary of knock-offs or poor craftsmanship that sometimes comes with a “great deal.”

Castello di Brolio

Perched on top of a hill just outside of Gaiole is the Castello di Brolio. This incredible castle has been a part of the Ricasoli family since 1141 and was used as a strategic outpost by Florence for centuries. After visiting the gardens and the small museum, you can enjoy a spectacular wine tasting within the castle walls. You will have a great experience learning about this castle’s fascinating journey through history.

Vitaleta Chapel

Take the time to visit one of the most photographed churches in all of Tuscany. This charming little church is perched outside of the village of Vitaleta in the middle of a hill. While the true origins of this tiny church remain a mystery, it was restored by architect Giuseppe Partini in 1184 and is now considered a World Heritage Site by UNESCO. This quaint church is a photographers dream; it is surrounded by a magnificent landscape that makes it effortless to capture its beauty, regardless of the weather or season.

Brunello Museum

The Museum of the Community of Montalcino and Brunello was created to remember the rich history and triumphs of the people who call this region home. Everything from the history of their skills to how they dressed to the simple objects that made up their lives are featured here. These things are on display in order to offer perspective into a time long since past.

Museo del Vino

The Chianti region is world-famous for its exquisite wines, but how much do you really know about the winemaking process? The Wine Museum in Greve demonstrates all of the loving work that goes into creating that delightful bottle of wine you adore each night. At the end of the tour, you will have the opportunity to taste the 200 wines in the museum. Now that’s a tour!

Crystal Museum

Colle Val d’Elsa is the primary producer of crystal glass in Italy and one of the leading producers in the world. This town knows a thing or two about glass, and they share it all with anyone who visits the Crystal Museum. Learn the history of glassmaking along with the details that make it so challenging to master. In the end, you will get to witness the crystal forest and experience all of the emotions that it evokes.

Vineyards and Wineries

The Chianti region is known as one of the best wine producers in the world, and it is here that you must take advantage of the vineyards, wineries, and their tastings. Each location offers a unique experience with incredible wine and service. Some of our favourite spots include Viticcio, the Enoteca del Barone Ricasoli, the Casa del Chianti Classico, and Torre a Cona, just to name a few.





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