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Tuscany Wine & Walking Tour

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  • Location: Italy
  • Duration: 6 days/5 nights
  • Departing from: Florence, 9:30 a.m. on Sunday, Day 1
  • Tour finishes: Chiusi train station 10:00 a.m. on Saturday Day 8
  • Departures 2021: Private departures only, contact us for details.
  • Price 2021: Final price depends on hotels, number of people, and any other special events that you request.
  • Departures 2022: Private departures only, contact us for details.
  • Price 2022: Final price depends on hotels, number of people, and any other special events that you request.

Wine and walking do mix!
Customwalks founder Brett Naisby has been living in the Chianti region of Tuscany since 1994, where he has been expanding his knowledge of the wines of Montalcino, Chianti, and Bolgheri, but also getting to know the owners and wine-makers from many of the region’s top producers, big and small. This makes all the difference when it comes to gaining access to special wineries, special wines, and the people behind them. Join us as we spend a week walking from winery to winery, through Tuscany’s sublime wine country learning from local wine makers, agronomists, chefs and sommeliers about the area’s wine, cuisine, and culinary culture. This tour offers up the perfect combination of natural beauty, exercise, and learning along with just the right amount of hedonistic wine and food consumption!

Tuscany Wine & Walking Tour Includes

  • Accommodation: 5 nights accommodation (3 nights Gaiole in Chianti or Radda in Chianti, 2 nights Montalcino)
  • Meals: 5 breakfasts, 5 lunches, and 5 dinners
  • Luggage: Bags are transferred starting with pick-up from Florence and ending with the final transfer to Chiusi train station
  • Special events: Guided visits of the Castello di Brolio & Castello di Meleto, numerous winery visits and tastings, guided visit of Siena
  • Transport: Private van transfers as indicated in the itinerary
  • Active days: 5 days of guided hiking
  • Guides: At least 1 bilingual Customwalks guide accompanies departures of 2 - 8 people; 2 guides accompany departures of 9 or more
  • Max group size: Tours are capped at 14 people

 

Booking: Please e-mail us at info@customwalks.com to receive a booking contract or simply click on the BOOK NOW button or the 'Contact Us' tab. Thanks!

Tuscany Wine & Walking Tour itinerary Request full itinerary

Day 1 – Sunday

We pick you up from Florence at 9:30 a.m. for a private transfer to the Castello di Brolio. Our morning walk takes us under the massive walls of the castle, through their vineyards and olive groves to the castle itself, whose gray stone walls have stood for 900 years. Visit the park and gardens of the castle and the Ricasoli family private museum, then begin a short walk to a very special lunch with our friend Massimiliano Biagi. “Massi” is the manager at the famous Barone Ricasoli vineyards and is responsible for the 2,500-acre estate of the Castello di Brolio. Five hundred of those acres regularly produce wines of exceptional quality, scoring consistently above 90 points in Wine Spectator magazine. Massi’s other passion is cooking, and we're lucky to be invited into his home for a fabulous home-cooked lunch.  Afterwards, visit the cellars and enjoy a tasting with Massi as your guide. A short van transfer then takes you to your hotel in Gaiole in Chianti, the four-star Castello di Spaltenna. (or similar). Keen walkers can do a late afternoon walk up to the medieval hamlet of Vertine, otherwise just relax until we meet at 7 p.m. for aperitivo, the Italian version of cocktail hour. Dinner tonight is in the village square.

The Walk:  1 hour in the morning, relatively flat but sometimes rolling. Optional afternoon walk: 6 km (4 mi) loop over rolling, hilly terrain. Overnight Gaiole in Chianti or Radda in Chianti. 

Hotel, breakfast, lunch and dinner included.

Day 2 – Monday

Our morning walk starts directly from the hotel and leads up into the Chianti hills to the tiny hamlet of Bricciano, where we will meet Rory O’Kelly for a visit of his cantina. Yesterday we visited one of the largest producers in Chianti, today we visit one of the smallest! Rory’s South African father established this small boutique winery in the 1990s and Rory is continuing his father’s passion for the winery. He is intent on making world-class wine and the result is very persuasive. After the visit, we have a short walk to a private home where we have lunch. The afternoon walk takes us to the Castello di Meleto, a 13th century fortress that evolved over time into a Baroque summer residence. From here you have a short van transfer back to Gaiole. Dinner tonight is al fresco at Ristorante Le Contrade.

The Walk:  1.5 hrs in the morning, 2.5 hrs in the afternoon through rolling terrainOvernight in Gaiole in Chianti or Radda in Chianti. 

Hotel, breakfast, lunch and dinner included.

Day 3 – Tuesday

Today we have a scenic 40-minute van transfer to Siena, one of Italy’s most beautiful and historic cities. We have a guided visit with Rita, our favorite city guide. Only a native of this Gothic city can explain the furor and passion that surround the famous bareback Palio horserace, which is run around the city’s 12th century Piazza del Campo twice a year. You will have free time to explore the exquisite historic center and admire its Gothic architecture. Of course, you might get side-tracked by the shops and cafés along the Banchi di Sopra, Siena’s main pedestrian shopping street. Enjoy lunch in Siena and then meet up again for a transfer to Castellina in Chianti, where we will stop at what we consider to be the best gelateria in Tuscany. We then carry on to the workshop and showroom of Rampini ceramics, arguably the finest producer of hand-painted ceramics in Italy. Our friend Pino will explain how traditional majolica ceramics are made, and of course the showroom will be open should you want to pick up a few pieces to take home. If you've got energy to burn, return to your hotel on foot (1.5 hours), otherwise return by van. Dinner tonight under a canopy of sycamore trees at Osteria Il Ponte. Overnight Gaiole in Chianti or Radda in Chianti. 
The Walk:  Urban walking in Siena. Overnight in Gaiole in Chianti or Radda in Chianti. 

Hotel, breakfast and dinner included.

Day 4 - Wednesday

Today we transfer from the Chianti region southwards to the hilltop town of Montepulciano and the region known as the Val d’Orcia (Valley of the Orcia River). It’s a beautiful drive, and we stop on the way for a pretty morning walk through the estate of the historic Villa Arceno to the charming village of San Gusmé, where we can enjoy a mid-morning cappuccino.  A short drive takes us into the stark and gorgeous clay hills of the Crete Senesi, where we will stop for lunch in the walled village of Asciano. After lunch, we have a beautiful walk to the village of Petroio, where we visit a producer of terra-cotta. This is quite different from the ceramics that we saw yesterday since here they produce the huge planters and olive oil urns that have been used for centuries by the great “fattoria” and villas of Tuscany. We arrive in Montalcino in late afternoon so you will have time to explore this beautiful hilltop town, renowned for its Brunello wine. Our hotel for the next two nights is centrally located at the entrance to the medieval walls of the town.  It has a charming, old-world feel, being a renovated and re-purposed 18th century olive press. Risrorante Boccon di Vino welcomes us for dinner tonight. Besides its fantastic cuisine, the view from the terrace over the expanse of the valley below is breathtakingly beautiful.
The Walk:  1.5 hrs in the morning, 1 hour in the afternoon through rolling terrainOvernight Montalcino. 

Breakfast, lunch, dinner and hotel included.

Day 5 – Thursday

After breakfast we leave Montalcino on foot for our walk to the 13th century Abbey of Sant’Antimo. The walk takes us through Brunello vineyards, verdant woods, and rustic farming villages before we arrive at the abbey. Sant’Antimo is one of the most important and famous examples of Romanesque architecture in Italy. After lunch at the trattoria in Castelnuovo dell’Abate we have a short drive to “Uccelliera,” one of Brunello’s premier small wineries, for a truly unique and insightful tasting in their cantina. We start in the cellar and taste directly from the barrels the still unblended San Giovese wines from two different vineyards. Here we taste the difference that terroir makes to a wine, and also age and even the type of oak barrel that is used. We then move to the tasting room to taste a flight of their Brunellos. Return to Montalcino for free time to relax by the pool and take in the sweeping views of the countryside or explore the town’s shops, cafés, and wine bars. Tonight’s dinner is at our favourite trattoria in Montalcino, which also happens to have a superb wine list with many old vintages cellared to perfection.
The Walk:  2.5 hrs in the morning, through rolling terrain, mostly downhillOvernight Montalcino.

Breakfast, lunch, and hotel included.

Day 6 – Friday

The trip ends with one van transfer to the Chiusi train station after breakfast. We arrive around 10:00 a.m. to make connections to Florence. There are later trains for Rome or other destinations.

Activity rating2 = Easy to Moderate

In general: This is an easy to moderate tour for fit hikers, and will be do-able with some effort by less fit hikers.
 

Terrain: Flat to gently rolling terrain with some rocky areas. Perhaps some short, relatively steep climbs and descents, but nothing longer than 20 minutes.
 

Actual walking time: Between 2 - 4 hours per day, mostly in the morning but sometimes also in the afternoon
 

Distances: Usually 7 - 10 km (4.5 - 6 mi). Max distance is 12 km (7 mi).
 

Surfaces: Trails consist mainly of compact earth and/or gravel and sometimes gravel roads
 

Footing: Easy/good. Proper hiking shoes with thick soles and good treads are required. Sport sandals, running shoes and tennis shoes are not adequate.
 

Specifics: There are a couple of short, steep climbs but they're not long, and you can take your time.
 

Hiking Poles: Not required, but if you habitually use hiking poles then you will find them helpful
 

Compared to the Cinque Terre: This tour is significantly easier than the hikes in the Cinque Terre
 

Other: This tour is appropriate for fit, first-time “hikers” who enjoy walking
 

Easy to Moderate Tours: Puglia & Basilicata, Piedmont Walk. All of our boat–based tours in Turkey, Croatia, and Greece Dodecanese Islands would be “easy to moderate” IF you decide to skip the one or two of the more challenging hikes. Your guides of course can advise you of the difficulty level and the terrain and footing of each walk. 

Getting There: the trip starts in Florence on Sunday morning at 9:30 a.m. Florence is well connected by road, rail and air with the rest of Italy and Europe.

Air: Florence airport receives both domestic and international flights through European hubs such as London, Paris, Frankfurt, Amsterdam, Munich and Brussels. You can also fly into Pisa (about an hour away by train) on many low-cost airlines. For a complete list of Italian airports and a selection of low-cost airlines, see our "Transport Info" page.

Rail: The Eurostar and new Italo high-speed trains connect Florence with Milan (travel time about 2.5 hours), Bologna (travel time 35 mins) and Rome (travel time 1.5 hrs). See the Trenitalia website (in English) at this link. For alternative high-speed rail travel, see the Italo website. For complete information on using the Italian train system, see our blog post.

Road: The A1 Autostrada connects Florence with the rest of Italy. Travel time from Milan is about 5 hours, from Bologna 1.5 hours, and from Rome about 3 hours.

Getting Away at the End of the Trip: The trip ends with a van transfer to the Chiusi train station after breakfast on Saturday. We arrive around 10:00 a.m. to make connections to Florence, Rome, or other destinations.

If you book a trip with us you will receive detailed information about how to get to and from the trip, and of course you can e-mail us with any questions.

5/5
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5 out of 5
Ratings based on 2 Verified Reviews



Average ratings
5.0
Guides
5.0
Quality of itinerary
5.0
Food quality & variety
4.5
Value for money
5.0
Right amount of activity
5.0
Overall satisfaction

Reviews
5
by N. Fisher
Posted Oct 05, 2015

Four of my friends and I decided to take this tour back in March. We worked with Brett, the owner, to set up a private tour...We are sooooo happy we did that. The experience was truly a unique and special one! This was a fantastic trip! Spending time with great friends, eating delicious food, drinking some fantastic wine and seeing a beautiful part of Italy! What more could one ask for!! One thing that made this trip so unique and wonderful was our guide, Marco. His love for his country and culture was palpable and it wonderfully oozed into every part of our trip and made it a one of a kind experience. Brett and his Custom Walks Team (Marco and Manu) are fantastic and we felt they truly \customized\ the tour just for us. Thank you for a wonderful vacation!!!

4.8
by MSL
Posted Jan 31, 2015

We did this walk in 2007. It was our first walk with CW staff. It and Puglia were the easiest walking trips we have done. We particularly liked the food on this tour, probably our favorite, but all have been very good.



If you have any questions or specific requests about any of our tours, we’re here to help. You can fill in the form below, send us an email, or call us and we’ll get back to you as soon as possible.

Contact us
info@customwalks.com
Contact us by email

1-877-315-9053
Toll free Canada & USA 

(+64) 021 0711972
New Zealand

(+39) 0577 749198
Italian operations office

Four of my friends and I decided to take this tour back in March. We worked with Brett, the owner, to set up a private tour...We are sooooo happy we did that. The experience was truly a unique and special one! This was a fantastic trip! Spending time with great friends, eating delicious food, drinking some fantastic wine and seeing a beautiful part of Italy! What more could one ask for!! One thing that made this trip so unique and wonderful was our guide, Marco. His love for his country and culture was palpable and it wonderfully oozed into every part of our trip and made it a one of a kind experience. Brett and his Custom Walks Team (Marco and Manu) are fantastic and we felt they truly \customized\ the tour just for us. Thank you for a wonderful vacation!!!
by N. Fisher


We did this walk in 2007. It was our first walk with CW staff. It and Puglia were the easiest walking trips we have done. We particularly liked the food on this tour, probably our favorite, but all have been very good.
by MSL


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info@customwalks.com
Contact us by email

1-877-315-9053
Toll free Canada & USA 

(+64) 021 0711972
New Zealand

(+39) 0577 749198
Italian operations office

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