Question 1

What happens if I don’t want to walk one of the days?

Accepted Answer

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.

Question 2

Where would you suggest adding an extra night?

Accepted Answer

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).

Question 3

Can you extend our stay in Montepulciano?

Accepted Answer

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.

Question 4

Can my children walk with me?

Accepted Answer

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

Question 5

We’re travelling as friends, can we get a triple room?

Accepted Answer

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.

Question 6

Can we reduce the days walked?

Accepted Answer

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.

Question 7

Can we extend the days walked?

Accepted Answer

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.

Question 8

Can you extend our stay in Siena?

Accepted Answer

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.

Question 9

How does luggage transfer work?

Accepted Answer

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.

Question 10

Are there any important cultural dress codes?

Accepted Answer

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.

Question 11

What should I carry each day?

Accepted Answer

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.

Question 12

What currency do I need, and can I use cards?

Accepted Answer

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.

Question 13

Is tipping expected?

Accepted Answer

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.

Question 14

Is travel insurance compulsory?

Accepted Answer

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.

Question 15

Can my dietary requirements be accommodated?

Accepted Answer

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).

Question 16

Will there be grocery stores along the way?

Accepted Answer

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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Hilltop Towns of Tuscany - 6 Days

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April 2026

May 2026

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