- Experience classic Tuscany on foot: rolling vineyards, Renaissance cities and medieval villages
- Sip chianti and other local wines on three separate tasting experiences
- See Siena through the eyes of local on a history and culture tour with a local guide
- Discover magnificent Florence on a walking tour with a local guide
- Feel like one of the family with a stay in the Tuscan hills at Hotel Le Renaie
Tuscany Walks & Chianti Wines
8 Days
Excluding Flights From
8 Days
from
Walking & Trekking
Activity Level
Easy & Moderate
See our Activity Level Guidelines to check if this holiday is right for you.
Comfort Level
Classic
Share the beauty of Tuscany with new-found friends on vineyard walks and expertly led wine tastings
The intoxicating beauty of Tuscany is there for all to see. But that’s just the start on this gentle small-group hiking adventure. Guided by an expert tour leader, we experience the Garden of Italy through the eyes of a local, staying in the small village of Pancole, where we’re treated to classic Italian hospitality by the Sabatini family. Our walks take us through beautiful vineyards and we explore the Renaissance cities of Siena and Florence with expert local guides. Of course, we also sample several varieties of the local chianti together, forging friendships that could last a lifetime.
Highlights
Key Information
- Accommodation: 7 Classic nights (Hotel Le Renaie)
- Five days of walking and sightseeing
- Group normally 4 to 16, plus leader. Minimum age: 18
- Countries visited: Italy
What's Included
- All breakfasts, five dinners, three wine tastings
- All accommodation
- All transport and listed activities
- Tour leader throughout
- Group arrival and departure transfers available
What's Not Included
- Travel insurance
- Single accommodation (available on request)
- Visas or vaccinations
- Local taxes (approx. €10)
5 Days of Walking & Trekking
Pace:
Leisurely/Moderate
Terrain:
Paved tracks, forest trails and gravel
Day 2
9 km / 5.6 miles
Day 3
8 km / 5 miles
Day 4
8 km / 5 miles
Day 6
4 km / 2.5 miles
Day 7
10 km / 6.2 miles
Start
Finish
Availability
Land Only Trip Price
Optional Single Supplement
Saturday Saturday
11 Apr 2026 11 Apr 2026
Saturday Saturday
18 Apr 2026 18 Apr 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 1999 Book with £ 499 deposit Book with £ 499 deposit
Optional Single Supplement +£ 475
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
18 Apr 2026 18 Apr 2026
Saturday Saturday
25 Apr 2026 25 Apr 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 2229 Book with £ 499 deposit Book with £ 557 deposit
Optional Single Supplement +£ 475
Guaranteed flights from London available for this departure
Guaranteed flights from London available for this departure
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
02 May 2026 02 May 2026
Saturday Saturday
09 May 2026 09 May 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 2079 £ 2379 Book with £ 519 deposit Book with £ 594 deposit
Optional Single Supplement +£ 475
Guaranteed flights from London available for this departure
Guaranteed flights from London available for this departure
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
09 May 2026 09 May 2026
Saturday Saturday
16 May 2026 16 May 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 2249 Book with £ 499 deposit Book with £ 562 deposit
Optional Single Supplement +£ 475
Guaranteed flights from London available for this departure
Guaranteed flights from London available for this departure
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
23 May 2026 23 May 2026
Saturday Saturday
30 May 2026 30 May 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 1999 Book with £ 499 deposit Book with £ 499 deposit
Optional Single Supplement +£ 475
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
30 May 2026 30 May 2026
Saturday Saturday
06 Jun 2026 06 Jun 2026
Availability Available
Land Only Trip Price £ 1999 £ 2249 Book with £ 499 deposit Book with £ 562 deposit
Optional Single Supplement +£ 475
Guaranteed flights from London available for this departure
Guaranteed flights from London available for this departure
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
13 Jun 2026 13 Jun 2026
Saturday Saturday
20 Jun 2026 20 Jun 2026
Availability Available
Land Only Trip Price £ 1999 £ 1999 Book with £ 499 deposit Book with £ 499 deposit
Optional Single Supplement +£ 475
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
29 Aug 2026 29 Aug 2026
Saturday Saturday
05 Sep 2026 05 Sep 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 1999 Book with £ 499 deposit Book with £ 499 deposit
Optional Single Supplement +£ 475
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
12 Sep 2026 12 Sep 2026
Saturday Saturday
19 Sep 2026 19 Sep 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 2359 Book with £ 499 deposit Book with £ 589 deposit
Optional Single Supplement +£ 475
Guaranteed flights from London available for this departure
Guaranteed flights from London available for this departure
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
19 Sep 2026 19 Sep 2026
Saturday Saturday
26 Sep 2026 26 Sep 2026
Availability Available
Land Only Trip Price £ 1999 £ 2309 Book with £ 499 deposit Book with £ 577 deposit
Optional Single Supplement +£ 475
Guaranteed flights from London available for this departure
Guaranteed flights from London available for this departure
Availability
This departure is available for new bookings, and will be guaranteed to go ahead once it reaches minimum numbers. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
26 Sep 2026 26 Sep 2026
Saturday Saturday
03 Oct 2026 03 Oct 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 2239 Book with £ 499 deposit Book with £ 559 deposit
Optional Single Supplement +£ 475
Guaranteed flights from London available for this departure
Guaranteed flights from London available for this departure
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
10 Oct 2026 10 Oct 2026
Saturday Saturday
17 Oct 2026 17 Oct 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 1999 Book with £ 499 deposit Book with £ 499 deposit
Optional Single Supplement +£ 475
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip NotesSaturday Saturday
17 Oct 2026 17 Oct 2026
Saturday Saturday
24 Oct 2026 24 Oct 2026
Availability Guaranteed (Available)
Land Only Trip Price £ 1999 £ 1999 Book with £ 499 deposit Book with £ 499 deposit
Optional Single Supplement +£ 475
Availability
This departure is available for new bookings and has reached the minimum number of passengers required to go ahead. Please click Continue to proceed with booking or contact our Sales team for assistance.
View Trip Notes
Itinerary
Pancole Pancole
Adventure starts in Pancole
Start at Hotel Le Renaie, our welcoming family-run hotel 4mi (6.5km) from San Gimignano. In the evening, our tour leader holds a welcome meeting to discuss the week ahead, give advice on the local area and answer any questions.
If you have extra days at hand and wish to extend your adventure, consider booking additional nights in Pisa or Florence. Speak to your sales representative for more information.
Walk a section of the Via Francigena • Afternoon local wine tasting
Get ready for a day full of history and nature as we explore one of the most popular sections of the Via Francigena, which links the villages of Gambassi Terme to San Gimignano. The Via Francigena is an ancient pilgrimage route that links Canterbury in the UK to Rome; the full trip takes well over 90 days, but our section is far gentler, cutting through olive groves and vineyards.
Later in the afternoon, we head to Azienda Agricola Pietralta, a picturesque farmhouse in the heart of the countryside, where we enjoy three glasses of wine, a trio of cheeses and a tour around the farm.
Dinner this evening is back at the hotel, where we have time to relax, perhaps with a game of billiards or another glass of local wine on the garden-view terrace.
Walk in Radda in Chianti
This morning, we enjoy local history in the heart of the Chianti area, covering a scenic circular route. We cut through woodlands, where we can admire the emerald vineyard valleys. In the afternoon, you have some free time to wander around and maybe join an optional tasting of the much-acclaimed chianti classico at one of the many local wineries.
Explore Siena • Learn about Tuscan and Italian wines at a wine school
After breakfast, we head to Certaldo station and catch a train to Siena (approximately 45 minutes). This medieval city is dominated by impressive gothic monuments and is divided into 17 contrade (districts), each of which goes head-to-head in the twice-annual Palio, a thunderous horse race around the central square for which the whole city turns out.
We join a local guide on a tailor-made tour of the city, stopping at the landmarks, plus captivating sites most tourists normally pass by. Our tour includes a visit to a contrada museum, which is typically closed to the public, and dips into botteghe (small, traditional shops) to sample traditional local sweets.
You may also opt to visit the medieval Siena Cathedral.
In the afternoon, learn about Tuscan wines during a one-hour lecture at the Tuscan Wine School. Unlike traditional wine tastings, this expert-led experience is more educational, offering in-depth insights into Tuscany’s most important wines.
Free day to visit other Chianti villages or relax by the pool
Today is free to rest by the poolside. Alternatively, your tour leader can advise on local chianti wine-tasting tours, cooking classes, e-bike and vespa hire or offer assistance for unguided walks or daytrips.
Discover the magnificent city of Florence
Our destination today is Florence, the birthplace of the Italian Renaissance. We reach Florence from Certaldo by train, approximately a one-hour journey. Most of the greats from the movement lived or passed through here: Leonardo da Vinci, Michelangelo, Sandro Botticelli and more. Learn all about it by joining one of the free local tours, which typically take in the highlights.
Join one of the morning tours and you’ll have time to visit the Uffizi, an art gallery housing works by Renaissance masters, including The Birth of Venus by Botticelli and the gruesome Medusa by Caravaggio. If you do wish to visit, we recommend prebooking your ticket online to avoid lengthy queues. An ideal time is around 2pm if you’re joining the morning walking tour. Tickets can be purchased at www.uffizi.it/en/tickets.
Explore San Gimignano • Afternoon wine-tasting
Take a short transfer to the medieval town of San Gimignano, where we can visit the Palazzo Comunale, a 13th-century stone palace that’s home to the Pinacoteca (Art Gallery) and 177ft (54m) tall medieval Torre Grossa (you can purchase the €15 entrance ticket locally). There’s free time to wander and soak up the atmosphere. Before your farewell dinner, we visit the family-run Cesani estate, which produces some of the finest wines in the region. Here we enjoy an expertly led tasting, sampling three glasses accompanied by bruschetta, extra-virgin olive oil and a selection of Tuscan cheeses and charcuterie.
Adventure ends in Pancole
You’ve walked some of the most scenic trails in Tuscany and explored the local wine scene, but now it’s time to bid Hotel Le Renaie a fond farewell and begin your return journey home.
Alternatively, speak to your sales representative to extend your adventure and spend more time exploring the Renaissance flair of Florence.
Extend Your Trip
Florence City Break Extension
Extend your adventure and discover Florence, the birthplace of the Italian Renaissance.
Extend your love affair with Italy by crossing the Ponte Vecchio. Marvel at Michelangelo’s David, and climb the Duomo for sweeping views. With every cobbled corner tempting you to linger, and pit stops for carpaccio, ribollita or creamy gelato all but essential, it’s time to lean in and live your best dolce vita.
Stay for as many nights as you wish in a choice of hotels, including a boutique property within walking distance of major attractions or a luxury hotel with a rooftop terrace. Let us know your preferences and we’ll take care of all the details, including transfers.
Essential Info
Joining Instructions
Key information
Start hotel: Hotel Le Renaie, Località Pancole, 53037 San Gimignano (SI)
Phone: +39 0577 1607452
Recommended arrival time: You can arrive at any time today. There will be a welcome briefing in the evening, but if you miss it the leader will update you separately
Airport: Pisa (PSA)
Getting to the start hotel
The start hotel is approximately 1hr 20min drive from the airport. We provide one group arrival transfer from the airport, which is timed to coincide with the arrival of a chosen flight from London, UK. You may join this transfer at no extra cost, provided you can be at the airport before the transfer leaves. Speak to your sales representative for the group arrival transfer times or to arrange a private transfer.
The usual meeting point for the group transfer is Pisa Airport, where the guide will be waiting for you. Occasionally, unpredictable parking restrictions at the airport mean the group transfer includes a five-minute journey on the Pisamover from the airport to the railway station. In this case, the guide will still meet you at the airport on arrival and accompany you on the Pisamover.
Make your own way
It’s possible to reach the start hotel by public transport, but the journey is complicated. We therefore recommend joining the group transfer where possible. If not, you can pre-order a taxi through Exodus. This will take you from Pisa Airport directly to Hotel Le Renaie. It will take approximately 1hr 20min to reach the accommodation and costs approximately €200, paid locally.
If you would like further information on joining this trip, please speak to your sales representative.
Catching your return flight
There’s a group departure transfer to the airport for customers who Exodus booked onto a chosen flight to London, UK. Please speak to your sales representative if you wish to join. If the group departure transfer does not suit your flight time, speak to your sales representative to arrange an alternative transfer.
Note on the group flights
The inbound flight can sometimes be late in the evening, especially during summer. In this instance, you will have additional time to spend in Pisa. The tour leader will take care of all arrangements in terms of transport from/to the airport and the city centre and luggage storage. It may also happen that, for logistical reasons, we must be at the airport earlier than normally scheduled on return. This will mean a longer waiting time before checking in.
Full joining instructions including local emergency numbers will be sent to you as part of our Final Joining Instructions. If you do not receive these at least a week before departure, or require them earlier please contact our office or your travel agent.
Location start: Pancole
Location end: Pancole
Passport
Remember to check the expiration date of your passport if travelling internationally. Many countries require your passport to be valid for at least six months after the date of your scheduled return.
Hotel Le Renaie, a family-run albergo in Pancole
Surrounded by Tuscan hills, Le Renaie occupies a privileged spot in the little village of Pancole, just 4mi (6.5km) from San Gimignano. Here, the Sabatini family has created an intimate, friendly retreat with 25 air-conditioned rooms and plenty of places to mingle.
Under the Italian summer sun, the swimming pool area (which has a separate hot tub) is the perfect place to cool down; alternatively, find a shady spot in the flower-filled gardens to sit, chat or read a book. Come evening, gather in the bar-restaurant for delicious Tuscan cuisine and a glass or two of local wine. It’s a popular stop for Pancole residents, so you know it’s good. There are also games tables to keep the entertainment going or you can take your drinks onto the bar terrace for views over the garden, which is filled with hydrangeas and citrus plants.
Amenities
- Swimming pool (usually open May to mid-October)
- Restaurant serving traditional Tuscan meals
- Bar/cafeteria for light snacks and lunches (open every day)
- Games tables
Worth knowing
- Upgrade to a room with a balcony (facing the pool or garden) – speak to your sales representative for more details
- Our hotel is in a quiet area with just a couple of wineries and agriturismos nearby. If you did want to explore, San Gimignano is a short taxi ride away
- Pool opening dates are subject to local weather conditions and pool maintenance requirements; cooler months may not be suitable for swimming
Trip Experts
Liz Proctor
Expert Leader: Italy
Reviews
Add your own reviewBeautiful Tuscan countryside, good wine, delicious food, and history
I thoroughly enjoyed this trip. It was a great blend of walking through the beautiful Tuscan countryside, tasting organic wines, sampling delicious local foods, and getting a bit of Renaissance and medieval history with visits to Sienna, Florence, and San Girmignano.
Most Inspirational Moment
Witnessing the passion of the younger generation who have chosen to continue the legacy of small family run wine and olive farms. This is very heartening in an over commercialized world.
Thoughts on Group Leader
I can’t say enough about Roberta. She has a wonderful, positive energy and sincere passion for the area. She is extremely caring and has a natural ability to make everyone feel included without it feeling forced at all.
Advice for Potential Travellers
Bring your appetite,
Tuscany Walks & Chianti Wines
A wonderful trip with a great group leader who went above and beyond to make sure we were all comfortable and well taken care of.
Most Inspirational Moment
Not really one moment for me. I loved the walks in beautiful Tuscany. The suppers we had together were really nice.
Thoughts on Group Leader
Jordan was amazing. He really went above and beyond to make sure we all had an amazing trip, which we did.
Advice for Potential Travellers
The number of kilometres each day was not a lot, but be ready to do up and down of hills - Tuscany is a beautiful mountainous region.
It's Not Just About the Wine
The whole week was fantastic! The walks were beautiful, the group was lovely and gelled well, the wine and food were delicious, the hotel staff was gracious and accommodating, and Jordan (our guide) made the whole experience work!
Most Inspirational Moment
Sitting around during down times or at meal times hearing other people's stories. It was great getting to know the other travelers, laughing and sharing experiences.
Thoughts on Group Leader
Jordan was brilliant! He set the tone for the whole week, making it fun and safe. He provided great routes to walk, all sorts of fascinating knowledge, and kept an eye out for the needs of each individual. His passion was evident in his respect and care for the group and the locals.
Advice for Potential Travellers
Be willing to be open and engage with the other travelers. It makes a huge difference in the whole experience, even if you are doing this solo.
A fabulous week in Tuscany
The week was full of many different experiences. Despite a smaller group than usual, the walking was excellent, even though it was very hot. The wine-tastings were very different, and all informative, some with some nice nibbles included. The hotel is lovely with an excellent (ask for a room with a view) with a swimming pool and home made pizzas to die for. City-wise, we visited St Gimignano, Siena (brilliant guided tour included) and Florence. Our guide, Jordan, did a great job keeping us under control.
Most Inspirational Moment
Meeting El Magnifico in his bakery in Siena
Thoughts on Group Leader
Brilliant
Advice for Potential Travellers
Make sure you get a room with a view Take lots of water on the walks!
Tuscany Kevin
An excellent tour with sensible walks, great food and marvellous sightseeing.
Most Inspirational Moment
Revisiting Siena
Thoughts on Group Leader
Outstanding
Advice for Potential Travellers
Enjoy!
A wonderful trip from beginning to end!
I had a brilliant experience walking and wine tasting in Tuscany, led by our fantastic guide, Jordan. This trip has a good balance of picturesque walks, wine tasting and city days and offers a great introduction to one of Italy’s most beautiful and historic regions. Our itinerary ran seamlessly and there was never a moment where I felt it was too full-on, as we were given plenty of free time between activities. I would do this trip again in a heartbeat!
Most Inspirational Moment
Visiting Florence - a city steeped in history and culture!
Thoughts on Group Leader
Fantastic - Jordan went above and beyond to ensure we enjoyed our holiday.
Advice for Potential Travellers
Plan ahead for the free day. There are activities you can book through the hotel but availability can be limited.
Tuscany Walks & Chianti Wines is set in a beautiful rural location.
A very relaxed but full itinerary walking holiday. Challenging walks at times with lots to do but well balanced with down time to enjoy the surroundings and wine.
Most Inspirational Moment
It's hard to pick one moment as the scenery is beautiful. We were inspired by the views every day, the countryside, the villages, Siena and Florence. Not to mention the local wines!
Thoughts on Group Leader
Liz was amazing, it was all about the groups needs and keeping us safe, doing her utmost to ensure we had the best possible experiences. Liz's knowledge of the region was impeccable. Liz was friendly and a great part of the group.
Advice for Potential Travellers
The hotel is quite rural, be prepared for the lack of a convenient shop!
Excellent and interesting trip
A good all round trip with a good balance between low key leisurely walking, wine tasting and exploring old medieval towns and cities.
Most Inspirational Moment
Local walk followed by lovely local wine tasting
Thoughts on Group Leader
Excellent. Friendly , professional, knowledgeable and a very good driver.
Advice for Potential Travellers
No
Great trip
Lovely wine and hill walking with excellent town/city tours. All very well organised.
Most Inspirational Moment
Lovely Florence.
Thoughts on Group Leader
Superb. Such a lovely person and so helpful.
Advice for Potential Travellers
Good walking shoes/boots are essential and poles are useful.
Super relaxing walking and wine in Chianti with brilliant tour leader
Brilliant tour leader, lovely group of travellers, excellent hotel, and varied mix of activities.
Most Inspirational Moment
Relaxed dining with a lovely group of fellow travellers.
Thoughts on Group Leader
Roseanna was fantastic. She had a great personality and made sure everyone in the group feel relaxed. Nothing was too much trouble. She deserves 'Guide of the year' trophy if you award one.
Advice for Potential Travellers
Make sure you get Roseanna as your guide. I believe she will be running this trip next year and I might well book it again.
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Tuscany Walks & Chianti Wines
8 Days
Excluding Flights From
8 Days
from