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Tuscany Wine & Walk

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Tuscany Wine & Walk

  • Location: Italy
  • Duration: 7 days/6 nights
  • Departing from: Florence, 9:30 a.m. on Sunday, Day 2
  • Tour finishes: Chiusi train station 10:00 a.m. on Saturday Day 8
  • Departures 2018: Private departures only, contact us for details.
  • Price 2018: For private departures, final price depends on hotels, number of people, and any other special events that you request.

Wine and walking do mix!
Nearly all of our tours find us hiking and biking through Europe’s most famous vineyards. Brett, the founder of Customwalks has been living in the Chianti region of Tuscany for 18 years and been leading tours through the heart of the Cotes du Rhone,for over 20 years. Take advantage of our knowledge and passion for great food and wine and let us develop an itinerary for you. We know many small wineries, whose excellent wines are unknown outside of Europe; as well as having contacts with more famous producers, like Château Beaucastel in Châteauneuf du Pape or Castello di Brolio in Tuscany.

Our “Wine and Walking” trip to Tuscany focuses on the wines and producers of Chianti Classico, Vino Nobile di Montepulciano, Brunello di Montalcino, and the emerging coastal areas of Tuscany. We have also done wine-oriented trips in France, including Bordeaux-Médoc, Burgundy, Cahors, Alsace, the Loire Valley, and Provence.

Our forte is in Tuscany and Provence. We have we been sampling the wines of our home regions and become friends with wine makers, big and small. This makes all the difference when it comes to gaining access to special wineries, and special wines!

Traveling by foot is the best way to discover Europe’s beautiful wine country. Not only will you see first-hand the different types of vines and the pruning and trellising techniques, but the fresh air and exercise will help you better enjoy the great food and wine on offer.  We also know the best local trattorias as well as the fine dining establishments where you can combine wonderful wines with excellent food.

We would be happy to organize a private departure for you and your friends, and tailor it to suit your interests and needs (for example, we can add a cooking course or upgrade the accommodations, etc.).  Below is a sample itinerary, and we have many other ideas and possibilities for you to discover!

Tuscany Wine & Walk itinerary

Day 1 – Sunday

We pick you up from Florence at 09:30 a.m. for a private transfer to Castello di Brolio and the start of our our morning walk. Our walk takes us under the massive walls of Brolio castle, through their vineyards and olive groves to the castel itself whose gray stone  walls have stood for 900 years. After visiting the park and gardens of the castle and the Ricasoli family private museum we have a short walk to a very special lunch with our friend Massimiliano Biagi. “Massi” is the manager at the famous Barone Ricasoli vineyards. He is responsible for the 2,500-acre estate of the Castello di Brolio, 500 acres of which are vineyards which regularly produce wines of exceptional quality, scoring consistent 90 plus points from the Wine Spectator. Massi’s other passion is cooking.

Massi invites to his house for lunch, and what a lunch!  Afterwards we visit the cellars and enjoy a tasting with Massi. A short van transfer to Gaiole in Chianti and our hotel, the four star Castello di Spaltenna. Keen walkers can do a late afternoon walk up to the medieval hamlet of Vertine, otherwise relax until we meet at 7 p.m. for an aperitivo in the piazza. Dinner tonight is in the village square at Trattoria Sfizio. Here the Bianchi family makes simple but tasty Tuscan dishes including excellent truffle ravioli or tagliatelle with porcini mushrooms. The walk:  1 hour in the morning, relatively flat, but rolling. Optional afternoon walk 6 km loop, up and down.  Overnight in Gaiole in Chianti. Hotel, breakfast and dinner included.

Day 2 – Monday

Our morning starts directly from the hotel and leads us up into the Chianti hills to the tiny hamlet of Bricciano where we will meet Peter O’Kelly for a visit of his cantina. Yesterday we visited one of the largest producers in Chianti, today we visit with one of the smallest! Peter, originally from South Africa, has been living in Chianti for twenty years and his hobby and passion is his wine. 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 it is 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 hours in the afternoon through rolling terrain. Overnight in Gaiole in Chianti. Hotel, breakfast and dinner included.

Day 3 – Tuesday

Today we visit Siena, one of Italy’s most beautiful and historic cities. A scenic 40-minute van ride takes us there. We have a guided visit with Rita, a native of Siena and 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 Siena’s 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. Lunch in Siena and then rendezvous in the Piazza del Campo for our return ride to Castellina in Chianti, where we will stop at what we consider to be the best gelateria in Tuscany. We then carry on the workshop and showroom of Rampini ceramics, arguably the finest producer of hand painted ceramics in Italy. The head designer will take time to explain to you how traditional majolica ceramics are made. For those who are interested there is also the showroom to explore! For those who want some walking, we can leave Rampini’s on foot (1.5 hours) while others can return to the hotel by van. Overnight Gaiole in Chianti.  Dinner tonight under a canopy of sycamore trees at Osteria Il Ponte.  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 at Rampini’s, 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 will arrive in Montepulciano in late afternoon so you will have time to explore this beautiful hilltop town, renowned for its Vino Nobile wine. Our hotel for the next three nights is centrally located within the medieval walls of the town.  It has a charming, old world feel. Tonight’s dinner is at the best restaurant in Montepulciano – which also happens to have a superb wine list and a selection of amazingly good grappa!  Overnight Montepulciano. Breakfast, dinner and hotel included.

Day 5 – Thursday

A 25-minute van transfer brings us to Montalcino, a small village famous for its powerful “Brunello di Montalcino” wine. We stop in the village for a coffee break and purchase our picnic lunch before we begin our walk to the 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. Then take a late afternoon walk to the small town of Castelnuovo dell’Abate where we will have the chance to visit the cellars of a local winery and taste a variety of aged Brunello wines. Or if you prefer, we can arrange a visit and tasting at Casanova di Neri, whose wines have won perfect 100 scores from the Wine Spectator as well as “Wine of the year.” You decide! We then transfer by van back to Montepulciano.  Dinner tonight is at the Café Poliziano, the second-best restaurant in Montepulciano! Overnight Montepulciano. Breakfast, dinner and hotel included.

Day 6 – Friday

A pleasant morning walk takes us past the imposing villa and fortress of Massaini. Then we continue to Castelmuzio for lunch followed by a visit of a very small olive oil producer who has won the top prizes at both Italian and international olive oil fairs and competitions. Here you will be schooled in the art of distinguishing characteristics of different kinds of olive oils.  After your education (and indoctrination!) about the merits of Tuscany’s olive oil, we can enjoy a short walk from the village of Castelmuzio to the monastery of Sant’Anna where “The English Patient” was filmed, or you can choose to return to Montepulciano. One last delicious meal awaits us at one of our favorit e restaurants, the “Osteria Acquacheta.” Overnight Montepulciano.  Breakfast, dinner and hotel included.

Day 7 - Saturday

The trip ends with a van transfer to the Chiusi train station after breakfast on Saturday. We arrive around 09:00 a.m. to make connections to Florence. There are later trains for Rome, or other destinations.

The walks in Tusany

The walks in Tuscany cover a variety of terrain, from trail to dirt road, with many rolling hills to climb or descend. We have designed the trip so that there is always some free time in the late afternoon so you can relax, read, or enjoy the towns where we stay. Breakfast is included every day, and dinners reflect the excellent traditional food of the region. Daily distance between 8 and 14 kms.

Activity rating: 2 out of 5 = Easy to Moderate: rolling terrain. Daily activity usually between two to two and a half hours in the morning and two to two and a half hours in the afternoon. Max distance  16 kms. 

Trip Cost Includes: 6 nights accommodations (3 nights Gaiole in Chianti, 3 nights Montepulciano); 6 breakfasts and 6 dinners; bilingual Customwalks guide(s) to accompany the tour and lead you on the walks; all van and luggage transfers starting with pick up from Florence and ending with the final transfer to Chiusi train station.

Booking: e-mail us at info@customwalks.com to receive a booking contract (or use the 'Contact Us' link at the top of this page), or click on the 'Book Now' button to the right.

Insurance: We highly recommend the purchase of Trip Insurance. We recommend “Travel Guard” to our North American clients, just click on the logo below. Australian, New Zealander, and British travelers, please consult your insurance brokers.

travel Guard insurance

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.

4.92/5
RatingRatingRatingRatingRating  
4.92 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 from USA, Atlanta, GA
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 from Reston, VA, USA
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.



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 from USA, Atlanta, GA

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