Stroll
Florence to Siena: Through the Chianti Winelands - 7 Days
ItalyTuscany

Florence to Siena: Through the Chianti Winelands - 7 Days

7 Days
Moderate

Overview

Discover the fine wines and rustic dishes of Tuscany's Chianti region as you explore the trails and medieval walled towns between Florence and Siena. Starting out at Europe's most celebrated city of art, Florence, stroll across the Ponte Vecchio bridge and visit the Uffizi gallery where the Renaissance masterpieces of Carravagio, Botticelli and Da Vinci hang.

Journey south into a perfectly formed landscape of rolling hills, cloaked in olive groves and neatly terraced vineyards. Follow forested trails and farmers tracks into a succession of historic hilltop towns. Meander through the piazza in Radda in Chianti and the idyllic setting of Gaiole in Chianti. The finale of this tour takes you into the majesty of Siena's Piazza del Campo, the perfect opportunity to round off the walk with a local Chianti.

Highlights

  • Journey from Florence to Siena and discover Tuscany's Chianti winelands
  • Explore the UNESCO city of Florence, the birthplace of the Renaissance
  • Walk through classic Tuscan landscapes of rolling hills, vineyards and olive groves
  • Option to sample the world-class Chianti wines of Volpaia, and Brunello
  • Explore the wine towns of Greve, Radda, Gaiole, and Lecchi in Chianti
  • Option to visit the Uffizi Gallery in Florence
  • Marvel at the grandeur of Piazza del Campo in Siena

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What's Included

Accommodation

Hotel (5 nights), 3-star Hotel (1 night)

Transfers

  • Private Vehicle Transfers
  • Luggage Transfers

Meals

6 breakfasts, 0 lunches, and 0 dinners

Guidance & Support

  • Itinerary & Walk Notes
  • Walking App for Navigation
  • 24/7 on-trip support

How We Rate This Walk

3

Stroll Walking Grade

Moderate

Rated by our team — we walk every route before we recommend it.

Expect some hills and longer walking days. A reasonable level of fitness will help you enjoy the experience.

View Fitness Guide

5

Days on the trail

9-19 km

Average per walking day

332-685 m

Gain per day

6/10

Trail difficulty

Where You'll Stay

Nights are spent in small family-run boutique guesthouses and three and four-star hotels, each chosen for their character, location and connection to the Chianti region. Your hosts are genuinely knowledgeable about the local history, food and wine and are always happy to share recommendations. Occasional substitutions of equivalent quality may be made depending on availability — these will always be discussed during the booking process.

What You'll Eat

Six breakfasts are included throughout the walk. Lunch and dinner are yours to explore independently each day, with cafes, food stores and excellent restaurants available in the villages and towns along the route. Your hosts will happily provide a list of local dining recommendations each evening. Please advise us of any food allergies or intolerances at the time of booking — if you have severe allergies, bringing some of your own snacks is recommended.

More About This Trip

The walk starts in Florence and finishes in Siena. Florence has its own small airport, with tram and bus services connecting to the city centre in around 20 minutes. For a wider range of international routes, Pisa and Rome airports are excellent options. From Pisa Airport, take the Pisa Mover shuttle to Pisa Centrale and connect to Florence by direct train in around one to one and a half hours. From Rome's Fiumicino Airport, trains connect to Florence in around two and a half hours with one change in Rome. From Ciampino Airport, take the airport bus to Ciampino station and connect via Rome to Florence, also around two and a half hours.

At the end of the walk, Siena has good train connections back to all three airports for onward travel.

This walk is available from late April to the end of June and from mid-August through to October. Spring is a wonderful time to walk, with warm sunny days, flowering vineyards and sunflowers coming into bloom through June. Mid-August into September marks the beginning of the grape harvest, bringing a festive energy to the villages and the chance of stumbling across a local harvest celebration. October offers warm days with cooler evenings and a quieter, more contemplative atmosphere. Tuscany can experience afternoon thunderstorms during the warmer months, so packing layers and a waterproof jacket is always wise, regardless of the season.

This walk is graded moderate, with daily distances ranging from 10 to 19km and up to 500m of ascent and descent. The trails are well-defined and varied, covering forest tracks, gravel paths, rolling farmland and vineyards, with short steep sections and some rough surfaces along the way. As is common in Italy, separate footpaths are not always available, so some walking on roads is inevitable — please be mindful of other road users at all times. A training regime of two to three times per week is recommended. Daily walk notes, maps and GPX tracks are provided for each day.

Travel insurance is required for all Stroll walking holidays, covering cancellation costs, loss of luggage and injury. For international trips, your policy must also include medical evacuation coverage. A cancellation fee applies if you cancel after your holiday has been confirmed. See the FAQ section for full details.

A detailed information pack and itinerary will be sent to you around six weeks before departure, covering everything you need to know for a seamless experience. In the meantime, our team is always on hand to answer any questions.

Dates & Pricing

Choose Your Start Date

Pick any available date — this is your trip, your schedule

August 2026

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Prices shown are per person, twin/double share basis.

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Frequently Asked Questions

As some of the walks on this itinerary are loop walks you can relax in the grounds of your accommodation (some of which have a pool) or explore the local town and its wineries. On the days where you will be walking to the next town, it might be possible to travel with the taxi service which transports your luggage. You can also use the local bus service between towns. Your accommodation hosts will have up to date information and advice should you wish to travel to the next destination by local transport. There is always plenty of information about options for the day in your daily walk notes and as always, you can call us at the office for help during your walk should you need any assistance.

SIENA - An incredibly well-preserved city with the show stopping Piazza del Campo at the heart of Sienese life. It is also possible to take a short bus journey to the hilltop towers of San Gimignano (an hour journey, or private transfers can be quoted and arranged).

Of course, please let us know at the time of booking if you would like to extend your time in Montepulciano. There is so much to see, we’d suggest at least 1 extra night.

We don't allow under 16's to do this walk. No discounts can be offered for children who do book.

Triple rooms can be difficult to book. Many accommodations don’t always offer them but we can offer a twin/double together with a single room.

You can start this tour by taking the train on day 1 direct from Siena to Buonconvento or Montalcino. This would reduce the trip to 7 or 6 days. Alternatively, we can discuss booking an additional taxi transfer for you to omit any 1 of the walks.

Of course, you may want to start by looking at our Tuscan Explorer which is 10 days and 9 nights, starting in Florence and ending in southern wine town of Montepulciano.

Of course, please let us know at the time of booking if you would like to extend your time in Siena. There is so much to see, we’d suggest at least 1 extra night.

Your main luggage is transported between accommodations each day while you walk, so you only carry a daypack on the trail. One bag per person, no more than 20kg. Don't tie bags together or attach loose items like shoes or umbrellas — these will be removed and not transferred. Leave your clearly labelled bag at reception for collection each morning.

When visiting churches, cathedrals, and religious sites, modesty is expected. Covered shoulders and knees are the standard. Comfortable, smart-casual clothing is appropriate for evenings at restaurants. Some accommodations are in fine historic buildings where a slightly smarter outfit for dinner is a nice touch, though nothing formal is required.

A 20–30 litre daypack with a waterproof cover and liner. Key items include a quality waterproof jacket, warm layer, lightweight walking trousers, sturdy boots (not trainers), wide-brimmed sun hat, sunscreen (SPF 15+ minimum), sunglasses, at least 2–3 litres of water, food and snacks for the day, a personal first aid kit, your passport, cash in Euros, and your walk notes and maps. Gaiters are worth considering — they help keep grass seeds and debris out of your boots on the country tracks. Walking poles are optional but useful on steeper descents, particularly in the Chianti hills.

Italy uses the Euro (€). Cards are accepted almost everywhere, but carry cash too — many smaller villages have no ATMs, and you'll want Euros for local cafés, food shops, and tourist taxes. Stock up in larger towns when you can. Keep a note of the tourist tax requirement — this is paid directly to the accommodation on checkout and is typically not included in your package price.

Tipping is not mandatory in Italy, but rounding up the bill or leaving a few Euros at a restaurant is a perfectly normal and appreciated gesture for good service. There's no set expectation — tip at your own discretion.

Yes. Travel insurance is mandatory and must cover walking activities, trip cancellation, loss of luggage, and helicopter rescue. Emergency helicopter evacuation in Italy is a chargeable service — without adequate cover, the costs can be very high.

Flag any allergies or dietary needs at the time of booking and reconfirm with your host on arrival at each property. Tuscan cuisine is ingredient-driven and beautiful, but it can be harder to accommodate complex requirements in smaller rural accommodations. Be specific when you book — there can be confusion around what "vegetarian" means in this context (some places consider fish or white meat acceptable). If you have severe allergies, bring supplementary snacks as backup. A useful phrase: "Sono allergico a..." followed by "noccioline / latticini / glutine" (nuts / dairy / gluten).

Yes. Most towns along the route have cafés, alimentari (food shops), bakeries, and in larger centres like Montalcino and San Gimignano, CO-OP supermarkets. Note that CO-OPs are typically closed on Sundays — plan your lunch supplies accordingly if you're walking on a Sunday. Your daily walk notes include recommendations for where to eat and stock up along the way.

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The Tuscany Experience

Wonder
Stroll from Etruscan Volterra to Montepulciano through UNESCO-protected Val d’Orcia region
Walking with genuine historical weight beneath your boots. Step into San Gimignano’s UNESCO-listed centre beneath its medieval tower skyline
Explore Siena’s glorious Piazza del Campo and Monteriggioni’s ancient ramparts
Wellness
Tuscany invented slow travel before anyone thought to name it. Slow Down. Breathe in. This is Tuscany at its most honest.
The therapeutic power of this landscape is not dramatic or demanding, it works quietly, through the eyes and the nose and the slow accumulation of beautiful moments
Walk through the World's most painted landscape. Moderate walks along strade bianche, vineyards and gently rolling Siena landscapes
Nature
Follow cypress-lined white roads through Brunello vineyards and chestnut groves.
Picnic beneath olive trees near Poggio Alloro and Poggio Casaglia & enjoy the sunset over the Val d’Orcia from Montepulciano’s hilltop edge.
Recharge in family-run boutique B&Bs, classic townhouses and rural hotels. Soak in Bagno Vignoni’s thermal baths.

From

£1,430/person