Night 1-2
See Tripadvisor ReviewsHotel La Cisterna in San Gimignano
This hotel overlooks the ancient Piazza della Cisterna, and offers fancy decoration, free Wi-Fi, air conditioning, and a good breakfast.
Tuscany 5-day Cycling Tour
Prices
Highlights
This self-guided tour explores the beautiful landscape of Tuscany by bicycle
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 Itinerary
Day 1 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.
- Overnight Location
- Hotel in San Gimignano
- Distance
- None
- Meals
- Dinner
Day 2 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.
- 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
Day 3 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.
- Overnight Location
- Hotel in Volterra
- Distance
- 4 hours, 36 km, 922m elevation gain
- Meals
- Breakfast
Day 4 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.
- 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
Day 5 Farewell, Volterra!
A final breakfast caps off your adventure. Rest your legs on the way home and come back soon!
- Overnight Location
- None
- Distance
- None
- Meals
- Breakfast
Tuscany 5-day Cycling Tour Price and Dates
This self-guided cycling tour of Tuscany’s San Gimignano and Volterra region is always run as a custom tour for your group only, therefore the prices depend on your traveling dates and whether you are staying in a single, double or a triple room.
The departure is available on any day of the week. Prices below are per person:
Departure on April 1st – June 18th:
- Price per solo traveller: $925USD
- Price per person staying in single room (min 2 travelers): $750USD
- Price per person sharing a double/twin room: $575USD
- Price per person sharing a triple room: $475USD
Departure on June 19th – July 18th:
- Price per solo traveller: $895USD
- Price per person staying in single room (min 2 travelers): $725USD
- Price per person sharing a double/twin room: $575USD
- Price per person sharing a triple room: $450USD
Departure on July 19nd – October 14th:
- Price per solo traveller: $925USD
- Price per person staying in single room (min 2 travelers): $750USD
- Price per person sharing a double/twin room: $575USD
- Price per person sharing a triple room: $475USD
Departure on October 15th – 14th:
- Price per solo traveller: $895USD
- Price per person staying in single room (min 2 travelers): $725USD
- Price per person sharing a double/twin room: $575USD
- Price per person sharing a triple room: $450USD
Accommodation on the 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).
Night 3-4
See Tripadvisor ReviewsAlbergo Etruria in Volterra
This small hotel, located in the very center of Volterra, is a great option to enjoy the city.
Hotels on Standard Tour
What’s included in the 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
Frequenty Asked Questions about 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.
Reviews
All tours on 10Adventures are operated by highly vetted local tour operators and guides.
Having local tour operators and guides means you get a more authentic experience, and your booking creates jobs in the local communities you visit.
Details of the local tour operator will be listed on your booking invoice. If you have questions about the local operator prior to booking, please click the “Ask a Question” button below.
4.9
27 ratings
Written Reviews
There are no written reviews yet.
27 total ratings, 0 with reviewsPrices
What travellers say
Stephen L.
I’ve been using 10Adventures route guides for a while, but had never booked a tour. My wife and I booked a self-guided hike in Greece and were so impressed with how we were able navigate the route without a guide with the detailed and easy to follow itinerary. We enjoy travelling independently, and 10Adventures made that happen.
Melinda S.
I was going through a tough time and really needed a getaway so I decided to book a tour through 10Adventures. My trip to Peru changed my life in so many positive and eye-opening ways. I am so thankful for the kind, empathetic team at 10Adventures.
Lina K.
I’ve adventured around a lot of Canada and the US, but I’ve always wanted to explore other parts of the world. I felt a bit scared before booking my trip to Israel, but my conversations with the team at 10Adventures helped ease any worry. I can’t wait to explore more of the world!
Gabriela H.
Travel companies have had to go through a lot during the pandemic but 10Adventures were super flexible and accommodating nonetheless. I had to cancel my tour in France due to the pandemic. 10Adventures was great and let me reschedule for a later date!
Mikael V.
My wife Sarah and I had a great experience booking our 7-day cycling trip through Portugal via 10Adventures. The communication between us and Nadine leading up the trip was top-notch!
Alexandra D.
Communicating with 10Adventures feels like talking with a family-run business. I love to explore and travel, and exploring with the comfort of knowing I can talk to the team at 10Adventures with almost immediate feedback helps to ease any stress that comes with adventuring!
Eric S.
Whenever I’m looking for my next adventure 10Adventures never fails. Their routes all over England are my main go to for exploring and I have only had great experiences booking both guided and self-guided trips in Europe and South America with them. I am looking into Africa next.
Valeria R.
I tend to have a lot of questions before travelling and was so happy to find that the team at 10Adventures responded to every single one of my inquiries in a timely fashion. I was never left waiting and waiting for a response. This was much appreciated!
Isabella N.
I have horrible dietary issues making it super hard to book a pre-planned trip sometimes, but the communication through 10Adventures helped me navigate this situation! I am so grateful for all of their help. I cant wait to book with them again!
Erika S.
I just got back from backpacking in the Sierra Nevada, and WOW. What an unreal journey! The alpine meadows, waterfalls, and the lakeside camping spot were memorable highlights! I wonder what other tours 10Adventures has to offer. That one went so well that I am now convinced I need to book another!
Robert D.
I'm not a big fan of traveling because of my fear of flying, but my girlfriend convinced me to go on the Aurora Borealis Tour in the Yukon. I will never forget the mesmerizing northern lights. Such a romantic (and cold) getaway. I would highly recommend it.
Monica L.
Wow! I am so happy with the experience I had with booking through 10Adventures for my tour in Italy! I worked with Nadine and she was super easy-going and helpful when it came to tweaking the itinerary provided on the website. 10/10 would book through 10Adventures again.
When can I do this tour?
J
F
M
A
M
J
J
A
S
O
N
D
Why 10Adventures?
Rated 4.9 on Google Reviews
Tour Difficulty
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.
Read about our scale for Tour Difficulty Ratings.
Get in touch
Book your next Adventure on 10Adventures
Hassle-free Adventure Travel
Sit back, relax, and enjoy! Let us take care of all the travel planning details, so you don’t have to.
Don't Just Take A Trip, Take YOUR Trip
Let us help you get exactly what YOU want with a customizable adventure tour centred around your active interests and passions.
No Hidden Fees
We don’t believe in hidden fees like credit card fees, booking fees or more. Even better, most people can pay in their local currency!
Happiness Guarantee
We want your journey to meet your expectations, and we will work with you to solve any issues you’ve encountered.
Personal Adventure Travel Concierge
Our dedicated adventure travel concierge will curate the perfect itinerary to make your travel dreams a reality.
Vetted Local Guides
Book with confidence, knowing that our team has carefully hand-picked each tour operator and they use local, experienced guides.