Tour Description

Under the Tuscan Sun Lifestyle Cycling Tour

please inquire about other tour dates, as we're flexible and happy to offer different dates for your group 

If you've ever dreamed of Italy, there's no better way to experience it than by bike. But if you had to choose one Italian region to visit, Tuscany would always come on top of the list. If you don’t know why already, let us show you. 
Tuscany has a lot to offer the cyclist. The rolling hills of its countryside provide plenty of opportunities for challenging climbs and exhilarating descents that will leave you feeling like you've earned your bruschetta. This tour is more than just an afternoon’s ride, as we will take famous bike routes such as one of many Strada del Vino (the Wine Road), Via Francigena (St. Francis’ Way), or Strade Bianche (White Roads). These full-day rides follow scenic routes through vineyards, olive groves, and fields of sunflowers, past medieval castles, and Renaissance villas—and they're all equally beautiful without being overwhelming.


Italy's food and wine are better when you're part of the landscape. When you travel to Tuscany, you will experience local wine, cheese, and olive oil every day. But have you ever thought about how to taste them? It is more than just a matter of taste: during this tour, you will learn to pair your Tuscan wines with pecorino cheeses and virgin olive oils in order to enhance the flavors of both products.

When you get to the end of your Tuscan cycling vacation, you'll be filled with a deep sense of satisfaction and wonder. You'll have left the stresses of everyday life behind and found a new way to appreciate nature's beauty. And you will have experienced Italy's food and wine in ways that are different from any other time spent in this incredible country.

All these reasons are why this might be the year you should pack your bags and hit the road on two wheels.

Our base will be a classical upscale Tuscany villa with a swimming pool. Forget about packing and unpacking every day, relax and indulge in the comfort of your home away from home. If you decide to have a relaxing day and skip cycling, feel free to kick your feet up, jump into the pool and sip on your cocktail. 

*while booking, please let us know your bike size preference (subject to availability)

**if your arrival/departure airport is different from what is specified in the tour description, we will be happy to arrange your shuttle transfer (surcharge to be applied)

8 days / 6 cycling days
Route length
275 km / 170 mi
Group size
min. 4 participants / max. 7 participants
4 950 €
Activity level
7 / 10
Average mileage
45 km / 28 mi
Average riding time
5 h
Tour Map

Tour Characteristics

Tour Overview

Activity level:
Avg. riding time:
Avg. mileage:
  • iconic rolling hills with vineyards and olive orchards,
  • medieval towns of Siena, San Gimignano, Volterra, Montepulciano, Cortona and others,
  • local specialty food tastings,
  • Strade Bianche (White Roads),
  • Elba Island,
  • Renaissance capital Florence
Tour starts / ends
Florence Airport (FLR)
Dates in 2025

approximately 80% paved and 20% of good gravel (white) roads

Tour transport
Electric motor assisted bicycle
upscale Tuscany villa with a private swimming pool

Tour Overview

Day By Day

Day 1
Day 2
Day 3
Day 4
Day 5
Day 6
Day 7
Day 8

Florence Airport - San Gimignano, Tuscany


Welcome to Tuscany’s capital – city of Florence. After arrival at Florence Airport, the Adventure Roads team will transfer you to our dinner and briefing venue in the heart of Tuscany. After welcome drinks, a tour overview and briefing are in order, where our intrepid tour leaders will fill you in with all the details. The abundant welcome dinner will get your taste buds on high alert for the following week. 

We strongly suggest early arrival to Florence. As a European Renaissance capital and a wealthy city, it's filled with wonders, from ancient and medieval architecture, museums, and fine dining worth exploring at least for a few days.

San Gimignano - Siena (return by shuttle)

distance 40 km (30 mi) / ascent 600 m (2000 ft)

The biggest small city of Tuscany and a synonym for Tuscan architecture is today’s destination, the graceful Siena. Siena was one of the most important cities in medieval Europe and its historic center is a UNESCO World Heritage Site. It is also famous for its cuisine, art, museum, medieval cityscape, and the Palio, a horse race held twice a year in Piazza del Campo square. The route will take us over typical Tuscan rolling hills countryside, dotted with green vineyards and with views of colorful medieval towns like Monteriggioni.

San Gimignano - Volterra (round trip)

distance 65 km (40 mi) / ascent 1600 m (5200 ft)

After getting accustomed to your bikes the day before, we have a long but marvelous riding day ahead of us. Riding the Strade Bianche (white gravel roads) we will be a part of the picture postcard scenery, riding between the vineyards and olive orchards. Don’t let the many hills ahead of us give you a fright, since e-bikes can make them flat or challenging, depending on your assistance setting.

Today’s highlight is the small town of Volterra, one of the most popular and visited medieval towns of Tuscany. A place of long history, since its being continuously inhabited for almost 3000 years.

San Gimignano - Radda in Chianti (return by shuttle)

distance 40 km (25 mi) / ascent 900 m (3000 ft)

Tuscany is more than just medieval history and dazzling countryside. For some, its main allure is its cuisine, and more importantly wine. The wine center of Tuscany is situated in the hilly region of Chianti which is the home of the red wine of the same name. Our visit to the Chianti region won’t be complete without tasting its exquisite top-quality wine

Today’s route winds between numerous vineyards and wine-tasting rooms, where we’ll try to whisk and sip a few authentic wines and other delicacies.


Montepulciano - Cortona (there and back by shuttle)

distance 60 km (37 mi) / ascent 700 m (2300 ft)

To reach the southern part of Tuscany, we’ll employ our shuttle and get straight to the point. Less visited, but still authentic and tranquil villages of Montepulciano and Cortona will delight you with their charm. Montepulciano, the route start, is a Renaissance hilltop town, the center of the wine-producing region of the wine of the same name. The route will also take us along the shores of largest lake in Tuscany and the fourth largest in Italy, Lake Trasimeno.

Elba Island (there and back by shuttle and ferry)

distance 40 km (25 mi) - ascent 1100 m (3600 ft)

Experience Elba Island on two wheels. The island of Elba is the largest in the Tuscan Archipelago and a popular holiday destination for cyclists. It was a famous banquet place for Napoleon Bonaparte and it's also home to one of the UNESCO World Heritage Sites, Portoferraio Fortress.

The shuttle will bring us to the port in Piombino, where we will embark on an hour-long ferry crossing. What awaits us on Elba is the spectacularly charismatic Portoferraio town, views of turquoise Mediterranean beaches, and a relaxing route over the ridge of the island with 360 degrees stunning views.

Greve in Chianti - Florence

distance 30 km (19 mi) / ascent 500 m (1600 ft)

A seemingly easy day will be full of cultural delights, photo stops, and fine architecture as we’re heading to the Renaissance world capital, Florence. To give you a head start, the shuttle will take us to the Chianti region from where we’ll descend slowly to the city of Florence and cross probably the most famous bridge in Italy, Ponte Vecchio (The Old Bridge).

Florence was the center of medieval European trade and finance and one of the wealthiest cities of that era, putting Florence in a position of enormous influence in Italy, Europe, and beyond. Florence City Centre is a UNESCO World Heritage Site full of spectacular basilicas, churches, monuments, and art galleries, such as the iconic basilica of Santa Maria Novella, Uffizi and Accademia museums, and the peculiar Fontana del Porcellino.

Our final group dinner will take place in the crown jewel of the Tuscan towns, our neighboring town of San Gimignano, a town of medieval towers, authentic ambiance, finger-licking meats, and artisanal gelato.

San Gimignano - Florence Airport


Departure day to Florence airport with complimentary shuttle. We recommend an extended visit to Italy and the glorious surrounding area, like Florence, Bologna, Rome or Naples, and the Amalfi Coast, where you can expand and reaffirm your memories of Italy and have a different style of your vacation.

Tour Notes

Important Notes

Included in the price:

  • Airport transfers upon your arrival and departure (only on official arrival / departure dates)  
  • Experienced English and local language speaking Tour Leader on a bicycle and in the luggage/support van
  • Premium full suspension bicycle with electric motor assistance
  • Bike luggage; enough for small daily necessities (snacks, windbreaker, personal items, etc.)
  • Support vehicle for your luggage and support necessities, it can accommodate seven (7) passengers - for at least 7 people, otherwise with an additional charge
  • Hand-selected accommodation for the tour
  • Breakfasts during the tour  
  • Lunches during the tour except on free/rest days; water and soft drinks included     
  • Dinners except on free/rest days; always aimed to be in authentic local restaurants; water and soft drinks included  
  • Refreshment water and snacks during the entire course of the tour (tap water is perfectly drinkable and of high quality)
  • Entrance fees to National and Nature Parks   
  • Transfers between planned rides and ferries   
  • Tour description booklet with maps and highlighted routes
  • 24/7 support from your Tour Leader and Tour Director
  • Small group guarantee
  • Premium Welcome package

Not included in the price:

  • cycling gear (if needed, please let us know in advance)
  • airline tickets
  • additional alcoholic drinks
  • personal spending
  • traffic violation penalty tickets
  • Tour Leader gratuities are welcome
  • anything else not listed under "Included in the price".

Tour Cancellation Insurance: more information HERE.

*if you're using your own clip-on pedals, we'll be happy to install them on your bike 

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