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Tours/Europe/Italy/Tuscany

Tuscany 5-day Cycling Tour

This self-guided tour explores the beautiful landscape of Tuscany by bicycle

4.7 (54 ratings)

Italy, Europe

Happiness Promise

As Seen In

From $475USDBook Now

Lifetime Deposit - Lifetime deposit means if you need to cancel your booking you’ll get a credit for your full deposit to use on your next booking.

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About this tour:

5 days

Apr-Oct

Standard Biking

Self-guided, Private

Hotels

Easy (2/5)

What travellers are saying about 10Adventures

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Why travellers choose this tour

At 10Adventures, we take care of the details so that our guests can focus on making memories. Enjoy these key features on this tour.

We're Canadian

Book with a Canadian company whose mission is to help you travel the world.

Meals

Don't worry about meals. 4 breakfasts and one dinner are included.

Transfers

Check out the 'What's Included' tab for more info on personal transfers during your tour.

Local Support

Travel stress-free knowing in-country local support is available by regular phone or WhatsApp to support you during your tour.

Payments Made Easy

Enjoy the flexibility and ease of staggered payments in your own currency using your choice of credit card.

Route Resources

Route notes, maps, and/or a trail app make navigation on this tour a breeze.

Park Entrance Fees

Included where possible! Check the 'What's Included' tab for more info on park entrance fees during your tour.

Luggage transfers

Take a load off, with optional or included luggage transfers. Check inclusions for further details.

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).

Hotels on Standard Tour

Night 1-2

See Tripadvisor Reviews

Hotel La Cisterna in San Gimignano

The hotel is both overlooking the ancient Piazza della Cisterna used to welcome pilgrims from all over the world and charming hills of San Gimignano.

Night 3-4

See Tripadvisor Reviews

Albergo Etruria in Volterra

This small hotel, located in the very center of Volterra, is a great option to enjoy the city.

Planning a group trip?

Learn how we help group of friends, outdoor clubs and families get the tour they’ve been dreaming about.

Tuscany 5-day Cycling Tour Details

Overview

Itinerary

Tuscany 5-day Cycling Tour Itinerary

Day 1

Day 1: Arrival in San Gimignano

Overnight Location - Hotel in San Gimignano | Distance - None | Meals - Dinner

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.

Day 2

Day 2: Ulignano, Certaldo Alto, and Barberino

Overnight Location - Hotel in San Gimignano | Distance - 4 hours, 35 km, 736m elevation gain, optional extension 1 hour, 25 km, 702m elevation gain | Meals - Breakfast

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.

Day 3

Day 3: Cycle to Volterra

Overnight Location - Hotel in Volterra | Distance - 4 hours, 36 km, 922m elevation gain | Meals - Breakfast

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.

Day 4

Day 4: Montecatini Val di Cecina or Ulignado loop

Overnight Location - Hotel in Volterra | Distance - 3 hours, 38.3 km, 805m elevation gain or 3.5 hours, 37 km, 924m elevation gain | Meals - Breakfast

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.

Day 5

Day 5: Farewell, Volterra!

Overnight Location - None | Distance - None | Meals - Breakfast

A final breakfast caps off your adventure. Rest your legs on the way home and come back soon!

Tour Highlights

What's Included

Dates & Prices

Solo Traveller

Single Room (2+)

Double/Twin Room

Triple Room

Dates	Solo Traveller	Single Room (2+)	Double/Twin Room	Triple Room
Apr 1, 2025 to Apr 15, 2025	$950USD	$795USD	$595USD	$495USD
Apr 16, 2025 to Jun 21, 2025	$975USD	$825USD	$625USD	$495USD
Jun 22, 2025 to Jul 13, 2025	$950USD	$795USD	$595USD	$495USD
Jul 14, 2025 to Jul 23, 2025	$975USD	$825USD	$625USD	$495USD
Jul 24, 2025 to Aug 31, 2025	$950USD	$795USD	$595USD	$495USD
Sep 1, 2025 to Oct 18, 2025	$975USD	$825USD	$625USD	$495USD
Oct 19, 2025 to Oct 31, 2025	$950USD	$795USD	$595USD	$495USD

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):$175USD
Helmet rental:$25USD
Printed trip documents:$50USD

Accommodation

Map

Reviews (54)

Tour Booking Process

FAQ

FAQ 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.

Tour Difficulty

From $475USD

This tour was made for you!

Start filling out your booking details. Once you submit your request, we'll review availability for this tour and contact you within 24 hours to further customize your perfect adventure.

Start Your Booking

Planning a group trip?

Learn how we help group of friends, outdoor clubs and families get the tour they’ve been dreaming about.

Why book with 10 Adventures?

Your trip. Your way.

Make lifelong memories with the people you care about most. We specialize in custom & private active travel experiences.

Travel made easy.

Spend your time making memories, not planning them. Enjoy a stress-free vacation and leave the trip logistics to us.

You matter to us.

No bots here. A real human is always a click or a call away to ensure you get the adventure of your dreams.

Travel authentically.

Immerse yourself in the destination with highly-vetted, local tour operators who love to showcase where they live.

As Seen On

We make it easy for travellers to book private travel experiences, so they can make memories exploring the world with the people that matter most.

— Richard Campbell, CEO

Tuscany 5-day Cycling Tour

What travellers are saying about 10Adventures

Why travellers choose this tour

We're Canadian

Meals

Transfers

Local Support

Payments Made Easy

Route Resources

Park Entrance Fees

Luggage transfers

Accommodation for Tuscany 5-day Cycling Tour

Hotels on Standard Tour

Night 1-2

Hotel La Cisterna in San Gimignano

Night 3-4

Albergo Etruria in Volterra

Tuscany 5-day Cycling Tour Details

Tuscany 5-day Cycling Tour Overview

Tuscany 5-day Cycling Tour Itinerary

Day 1: Arrival in San Gimignano

Day 2: Ulignano, Certaldo Alto, and Barberino

Day 3: Cycle to Volterra

Day 4: Montecatini Val di Cecina or Ulignado loop

Day 5: Farewell, Volterra!

Highlights for Tuscany 5-day Cycling Tour

What’s included in the Tuscany 5-day Cycling Tour?

Meals

Accommodations

Transportation during the Tour

Also Included

Not included

Optional Extras

Solo Traveller

Single Room (2+)

Double/Twin Room

Triple Room

Accommodation for Tuscany 5-day Cycling Tour

Hotels on Standard Tour

Night 1-2

Hotel La Cisterna in San Gimignano

Night 3-4

Albergo Etruria in Volterra

Map of Tuscany 5-day Cycling Tour

Reviews for Tuscany 5-day Cycling Tour

Tour Booking Process

FAQ for Tuscany 5-day Cycling Tour

Tour Difficulty

Why book with 10 Adventures?

Your trip. Your way.

Travel made easy.

You matter to us.

Travel authentically.

As Seen On

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