We are excited to be collaborating with La Dolce Vigna on this once in a lifetime wine + bike tour through Tuscany! Ride the ancient roads at your own pace, enjoying stunning panoramas of hillsides dotted with cypresses, castles and vineyards at every turn.  The appetite we work up will be appeased by culinary wonders from the region: Think al fresco lunches under the Tuscan sun, picnics in secluded groves, and dinners in winery cellars. And, of course, we can’t forget about the wine! Lucky for us, we’ll be in the homeland of Chianti Classico, Brunello, as well as some lesser-known but incredibly good Tuscan wines.  When not biking, eating or drinking, explore beautiful Tuscan towns, dip into the restorative thermal waters of Bagno Vigoni, or take the time to write a few postcards back home, gushing about what an amazing time you are having!  Your entourage for the week will be two local bike guides and an accompanying sommelier, who are not only super knowledgeable and there to make your trip run smoothly, but are all-round good company. You’ll be in good hands, allowing you to concentrate on more important things like living la dolce vita!


  • Biking throughout the voluptuous countryside of Chianti and Val d’Orcia, a UNESCO heritage site, with knowledgeable and local bike guides
  • Visits to some of the most treasured wineries in all of Tuscany, hand-selected for you by your accompanying sommelier guide
  • Activities including soaking in thermal springs, learning how to cook traditional Tuscan recipes, and city visits to Siena, Pienza, and Montalcino

Getaway Adventures + La Dolce Vigna = ITALY ON A BIKE

Here is what sets us apart

  • Small Groups | Our tours are always limited to a maximum of 10 people to assure you an intimate experience.
  • Family-Run and Historic Wineries | Our tours are centered around small, eco-conscious, family-run wineries that make truly outstanding wine, and packed with cultural insights.
  • Foodie Central | Be prepared to eat. Alot. We’ve picked out amazing spots for you, from the small, beloved by locals osteria to the Michelin-starred restaurant
  • Bike + Sommelier Guides | This is the only bike tour in Tuscany that has an accompanying sommelier guide to answer all of your wine-related questions on the road.
  • No Cookie Cutter Tours |  Depending on the season and local events, we will custom organize the best and most insider experience for each group.
  • All-Inclusive | Rest assured that your tour price includes all meals (except for one lunch), activities, hotels, transportation from the moment we meet till when we part.
  • Down Time | For those of you who have been on other group tours, you know what we’re talking about. Part of living la dolce vigna is taking the time to truly savor your experiences and surroundings. We’ve built in time for you to do just that at your own pace and on your own terms.
  • Helping others |  Besides helping local, artisanal economies through visiting small wine and food producers, eating at traditional trattorie and staying at charming agriturismi, a donation on behalf of each individual that takes one of our tours will be made to 10,000 Gardens in Africa, a Slow Food initiative aimed at cultivating sustainable and healthy communities throughout Africa.

7 days and 6 nights. Private on Demand tours only

$3850 pp doc. 4 or more $4650 per person double occupancy

  For more information and to book — 800-499-2453



We invite you to an intimate dinner and wine tasting with our friends and owners of a small winery in Fiesole, the lovely hill town just 15 minutes drive from Florence. Spend the evening getting to know your fellow Tuscan travelers, while eating a delicious homemade meal and drinking exceptional organic wines.


We meet at a historic villa in Fiesole. While sipping on a cappuccino and enjoying the breathtaking views of Florence below, your bags will be loaded into our comfortable shuttle bus. From there, we head straight to Panzano in the Chianti Classico region of Tuscany and our home for the next three nights. We will have our bike fitting and meet our local bike guides. A lovely 15km ride passing vineyards and cypress lined roads will bring us to the charming hamlet of Volpaia where we will have an al fresco lunch. We’ll then hop on our bikes again and take off for Radda-in-Chianti, where we will have a wine tasting at a special Chianti Classico winery. Our shuttle will take us back to our Tuscan farmhouse for a sumptuous dinner paired with the estate’s line of incredible wines.

Total Miles: 15 | Elevation: 1000 feet


After a leisurely breakfast, we’ll shuttle over to Gaiole and bike from there to Brolio Castle—the birthplace of Chianti wine. We’ll take a private tour of the stunning estate, concluding with a wine tasting, then bike to an idyllic spot for a picnic lunch. After having our fill of food and photographic moments, we’ll get back our bikes to Castelnuovo to explore another stunning Tuscan castle. Our bus will bring us back to our farmhouse for a little needed R&R. Dinner tonight will be down the road at a famous butcher’s restaurant. Prepare yourselves!

Total Miles: 20 Miles | Elevation: 530 feet


Today, we’ll take off directly from Panzano, biking up and down the rolling hills toward Monte San Micheli. After taking in the panorma of panoramas, we’ll descend down toward Lamole, passing vineyards and oak forests until we reach our traditional trattoria for lunch. Those who want to continue biking will be taken on a nice long ride back to Panzano. Otherwise, our bus will bring us back to the farmhouse where we can relax and then get our hands dirty with a cooking lesson from a local culinary star. Dinner will be the pasta of our labor.

Total Miles: 20 | Elevation: 1120 feet


Today is all about taking it easy. Mid-morning, our bus will pick us up and bring us to the medieval city of Siena. We’ll have a private city tour, touching upon several important historic buildings as well as their fountain system, which was incredibly advanced for the time. Your local guides will provide you with suggestions for lunch and shopping on your own. In the afternoon, we’ll depart for our next home base: a charming , boutique hotel in the idyllic hamlet of Bagno Vignoni (Population 50!). You will have time to take a dip in the thermal springs before a delicious dinner in town.


Today we get to stretch out across the vast Valley of Orcia, a UNESCO World Cultural Landscape and the setting for various bucolic scenes from the film The Gladiator. Our loop will take us to lunch in Pienza, created in the 15th Century as an ideal expression of Renaissance urbanism, then back to Bagno Vignoni. Enjoy the thermal springs or explore the various walking paths that lead from the city. Dinner will be at another one of the town’s fantastic osterie.

Total Miles: 18 miles | Elevation: 510 feet


This morning, we’ll ride to Sant’Antimo, a stunning monastery dating back to the early 12th Century. We’ll have some time to explore the interior and environs and then bike over to a winery with a special relationship to cyclists (you’ll see why!). Afterward, we’ll bike over to a small, family-run winery that makes incredible wines, including Brunello, one of Italy’s most important red wines. We’ll shuttle back to our boutique hotel to rest and change. Our last supper will be at a gourmet restaurant in Montalcino, where we will toast our wonderful week together!

Total Miles: 24 miles | Elevation: 530 feet


Sleep in, take a final dip in the thermal baths, write postcards over the delectable breakfast spread, or stroll around the town this leisurely morning. Our bus will pick us up at noon to bring us back to Florence., dropping us off at the Santa Maria Novella Train Station.

Looking for the same luxury experience stateside? Check out our week-long, Wine Country tour Sonoma on a Bike!