Tuscany Wine & Walk Write a review
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 has been leading tours through the heart of the Côtes du Rhône 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
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. 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 Wine Spectator magazine. Massi’s other passion is cooking, and we're lucky enough to be invited into his home for lunch, and what a lunch! Afterwards we visit the cellars and enjoy a tasting with Massi. A short van transfer then takes you to your hotel in Gaiole in Chianti, 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. 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 over rolling, hilly terrain. Overnight in Gaiole in Chianti. Hotel, breakfast and dinner included.
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 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 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 hours in the afternoon through rolling terrain. Overnight in Gaiole in Chianti. Hotel, breakfast and dinner included.
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 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 how traditional majolica ceramics are made. For those who are interested there is also the showroom to explore! If you've got energy to burn, return to your hotel on foot (1.5 hours), otherwise return by van. Overnight Gaiole in Chianti. Dinner tonight under a canopy of sycamore trees at Osteria Il Ponte. Hotel, breakfast and dinner included.
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.
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 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.
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 favorite restaurants, the “Osteria Acquacheta.” Overnight Montepulciano. Breakfast, dinner and hotel included.
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. There are later trains for Rome, or other destinations.
Activity Level 2 = Easy to Moderate:
In general: This is an Easy to Moderate tour for fit hikers, and with some effort do-able for not-so-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 of sustained climbing or descents.
Actual walking time: Between 2-4 hours per day, mostly in the morning but sometimes also in the afternoon.
Distances: Usually between 7 and 10 kms/4.5 and 6 miles. Max distance is 12 kms/7 miles.
Surfaces: Trails consisting of mostly compact earth, gravelly earth, and sometimes dirt-gravel roads.
Footing: Easy/good. Proper hiking shoes with thick soles with 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. Note: on our boat-based tours we usually do a walk in the morning, return to the boat for a swim and then lunch, then cruise, and then occasionally drop off for late afternoon hike. Your guides of course can advise you of the difficulty level and the terrain and footing of each walk.
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 firstname.lastname@example.org 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.
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.
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!!!
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