Tuscany 5-day Cycling Tour
Overview
This Tuscan bike tour is the perfect way to experience the rich sights, sounds, and tastes of Tuscany in an efficient bicycle trip.
Your Tuscan cycling tour will take you to some of the region’s most remote, culturally significant villages and allow you to immerse yourself in the renowned landscape along the way.
This cycling tour of Tuscany begins in San Gimignano, a UNESCO World Heritage Site. The town is fascinating, with ancient architecture still intact.
You’ll spend the next day riding through prestigious vineyards up to Ulignano and the lovely hilltop village of Certalo. The ceramic-clad central square is a perfect place to relax a moment and soak up the atmosphere.
Next, your cycling tour of Tuscany takes you to the ancient Etruscan village of Volterra. Here, the surrounding patchwork of fields creates a beautiful setting for this gated ancient town.
Then, your bike will take you through a valley and through the beautiful Val d’Era, where you’ll cruise down typical white Tuscan roads. The day is filled with inspiring views at each kilometre, and it’s sure to be a highlight of your time cycling through this wonderful portion of Italy.
The Tuscany 5-day Cycling Tour is the perfect way to pack plenty of Tuscan charm into a quick trip, so book soon!
Tuscany 5-day Cycling Tour Overview
This Tuscan bike tour is the perfect way to experience the rich sights, sounds, and tastes of Tuscany in an efficient bicycle trip.
Your Tuscan cycling tour will take you to some of the region’s most remote, culturally significant villages and allow you to immerse yourself in the renowned landscape along the way.
This cycling tour of Tuscany begins in San Gimignano, a UNESCO World Heritage Site. The town is fascinating, with ancient architecture still intact.
You’ll spend the next day riding through prestigious vineyards up to Ulignano and the lovely hilltop village of Certalo. The ceramic-clad central square is a perfect place to relax a moment and soak up the atmosphere.
Next, your cycling tour of Tuscany takes you to the ancient Etruscan village of Volterra. Here, the surrounding patchwork of fields creates a beautiful setting for this gated ancient town.
Then, your bike will take you through a valley and through the beautiful Val d’Era, where you’ll cruise down typical white Tuscan roads. The day is filled with inspiring views at each kilometre, and it’s sure to be a highlight of your time cycling through this wonderful portion of Italy.
The Tuscany 5-day Cycling Tour is the perfect way to pack plenty of Tuscan charm into a quick trip, so book soon!
Cycle between remote villages rich with cultural and historical significance, like Volterra and San Gimignano.
Ride through the best of Tuscan landscape, including vineyards, olive groves, and rolling green hills.
Dine on authentic Tuscan cuisine and sample regionally produced wine.
Stay in luxurious accommodations that capture the essence of Tuscany.
Trip map for Tuscany 5-day Cycling Tour
Barbara C.
Amalfi Coast Bicycle Tour
We went through 10Adventures not familiar with them at all, and it was the best decision we ever made!
Allyson K.
Everest Base Camp
Just an amazing experience. Absolutely lifechanging!
Amy D.
XC Skiing in the Dolomites
It was a fantastic trip and Nadine was extremely responsive to all of our questions.
Itinerary for Tuscany 5-day Cycling Tour
Arrival in San Gimignano
Your cycling adventure in Tuscany begins with arrival at the beautiful hotel you’ll call home for the duration of the trip. Unwind a moment, or take a walk through the medieval town of San Donato. The rolling green countryside is always visible, and the tranquility is sublime.
Ulignano, Certaldo Alto, and Barberino
Start your Tuscan cycling adventure by riding through the classy vineyards that lead to Ulignano. Resist the urge to stop for a glass just yet, because the lovely hilltop village of Certaldo awaits. Literature fans will appreciate that this was the hometown of renowned Italian writer Boccaccio. Let your legs relax after the steep climb by spending some time in the central square, which is ceramic decorated and features several stunning churches. Then, an optional extension takes you to the Chianti Classico region, where you can appreciate expansive views from Barberino and Tavernelle.
Cycle to Volterra
Leaving San Gimignano behind, today’s trip will take you to the ancient Etruscan village of Volterra. The road there is dotted with patchwork fields, olive groves, and lovely Tuscan villas. The last push up the hill to Volterra is well worth it when you arrive at your incredible new hotel, which is nestled inside the gates of a former convent.
Montecatini Val di Cecina or Ulignado loop
Today you can choose between two rides. The first option is a trip from Volterra to Montecatini Val di Cecina, which begins with a speedy downhill cruise into the Val d’Era, where you’ll fly across traditional “strade bianche” or white Tuscan roads. As you cycle further through the rolling hills and past villas and farms, you’ll be wishing today’s beautiful ride will never end.
The second option is a loop ride through Ulignano. It’s an easy trip with very rewarding scenery, starting with a ride into the eroded gullies that surround Volterra. This unique landscape then gives way to unpaved trails that pass Strada del Cornocchio, which is undoubtedly scenic.
Farewell, Volterra!
A final breakfast caps off your adventure. Rest your legs on the way home and come back soon!
Reviews
These reviews reflect all trips offered by this local tour partner on 10Adventures, not just the tour you’re viewing.
Dates and prices for Tuscany 5-day Cycling Tour
Solo Traveller
Single Room (2+)
Double/Twin Room
Triple Room
| Solo Traveller | Single Room (2+) | Double/Twin Room | Triple Room | |
|---|---|---|---|---|
| Apr 1, 2025 to Apr 15, 2025 | $1,075USD | $875USD | $675USD | $550USD |
| Apr 16, 2025 to Jun 21, 2025 | $1,095USD | $895USD | $695USD | $575USD |
| Jun 22, 2025 to Jul 13, 2025 | $1,075USD | $875USD | $675USD | $550USD |
| Jul 14, 2025 to Jul 23, 2025 | $1,095USD | $895USD | $695USD | $575USD |
| Jul 24, 2025 to Aug 31, 2025 | $1,075USD | $875USD | $675USD | $550USD |
| Sep 1, 2025 to Oct 18, 2025 | $1,095USD | $895USD | $695USD | $575USD |
| Oct 19, 2025 to Oct 31, 2025 | $1,075USD | $875USD | $675USD | $550USD |
| Optional Extras | ||||
| Hybrid bike rental (incl. rear bag, odometer, repair kit, phone holder):$125USD | ||||
| E-bike rental (incl. rear bag, odometer, repair kit, phone holder):$195USD | ||||
| Helmet rental:$25USD | ||||
| Printed trip documents:$50USD | ||||
What’s included for Tuscany 5-day Cycling Tour
Meals
4 breakfasts and one dinner are included.
Accommodations
Accommodation for 4 nights is included.
Transportation during the Tour
This tour includes rental bike delivery and pick up, as well as one luggage transfer (day 3).
Also Included
- Route guides and notes
- Maps and detailed information packs
- 24/7 telephone guidance and support
- Bike theft insurance
Not Included
- Bike rental
- Travel insurance
- Any transfers not mentioned as ‘included’
- Lunches and dinners or drinks and snacks not previously mentioned
- Tourist taxes
- Personal equipment
Optional Extras
- Bike rental
- Any additional nights before or after tour
- Airport transfers
Accommodation for Tuscany 5-day Cycling Tour
This tour is based in 3-star hotels.
The hotels offer luxurious rooms with gorgeous decoration and great proximity to village centers.
In some cases, accommodation listed below may need to be substituted for other, comparable accommodations.
Single Rooms and Solo Travelers
Solo travellers must pay a supplement that varies based on the season and the size of the group (please check Dates and Prices for more info).
Frequently asked questions for Tuscany 5-day Cycling Tour
How hard is the Tuscany 5-day Cycling Tour?
We rate this tour as a 2 / 5. You will cycle longer distances through varied terrain. Most roads are well-maintained and not highly trafficked, but you should expect up to 1,000 m of elevation gain daily and 1/3 of the tour is on dirt roads.
Do I need a Visa to travel to Italy?
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
I’ve never been on a self-guided trip! How does it work?
Self-guided travelling is not difficult! For many, it is a preferred type of travel as you are in charge of your own time and pace. You are provided all the information on which direction you need to go daily. You don’t need to carry lots of things with you and can only carry your daypack, as your luggage will be picked up from your hotel daily in the morning and delivered to your destination hotel.
Are meals included on the Tuscany 5-day Cycling Tour?
4 breakfasts and 1 dinner are included.
Do I need insurance?
Yes. You will need to acquire travel insurance that covers hiking/walking. Get your Travel Insurance.
How do I get to San Gimignano to start this tour?
The best airports to arrive at are Florence (FLR), Pisa, (PSA), and Bologna (BLQ). From any airport, take the bus to Santa Maria Novella train station and then transfer to a train for Poggibonsi, and then a direct bus to San Gimignano. Check train schedules here.
Is the Tuscany 5-day Cycling Tour guided?
No, you will be provided with maps, route guides, notes, and 24/7 telephone support to complete your self-guided tour.
Where does the Tuscany 5-day Cycling Tour end?
The tour ends in Volterra, where you can take the bus and train to the airport.
Can I rent a bike?
Yes, you can rent an electric or hybrid bike. Your rental includes lights, bags, odometer, padlock, repair kit, and water bottle. Helmets are available for a small fee. Rental bikes available for this tour are:
- Specialized Sirrus Elite Carbon Disc
- Specialized Crossover
- Wilier Triestina GTR
- Winora Y420.X Yamaha (e-bike)
Do I need special vaccines to travel to Italy?
Check with your family doctor.
Are there any travel restrictions for Italy?
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.
Why book with 10 Adventures?
Self-guided Specialists
Combine the freedom of travelling on your own with the confidence that all of the logistics are taken care of.
Packed with Inclusions
Accommodations, luggage transfers, gear rentals, and more - all taken care of so you can focus on making memories.
World Class Support
Have peace of mind for when travel plans change with our hassle-free booking process and unbeatable support.
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