Tuscany San Gimignano and Chianti Cycling Tour

Italy
E-Bike
Self-Guided
San Gimignano Chianti Short

Tuscany San Gimignano and Chianti Cycling Tour

Prices

From $525USD

Difficulty

Self-guided

Hotels

Active Travel is what we do

10Adventures knows Active and Adventure Travel because everything we do is focused on Active and Adventure Travel. We understand the needs of travellers and partner with excellent local guides who specialize in active, experiential and adventure travel.

Real humans are always a click or call away

Your time is important, and you shouldn't have to deal with automated bots or a confusing phone system. At 10Adventures you are assigned an Adventure Concierge, who is a real person who has one job: to support you during the planning & booking of your trip.

Customize or go private and get the perfect trip for you

Taking a holiday can be the most fun you have all year. At 10Adventures we believe that you should have the ability to personalize the trip, to get it just the way you want. Sometimes that's joining a group, but more often it's going private with your loved ones, and getting the dates and itinerary that's just right for you.

Rated 4.9 on Google Reviews
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Highlights

Explore the beautiful landscape of Tuscany by bicycle

Cycle through some of Tuscany’s most appreciated countryside, including vineyards and olive groves.

Explore San Gimignano, a UNESCO World Heritage town full of medieval history.

Dine on authentic Tuscan cuisine and sample regionally-produced wine.

Cycle to visit charming country towns like Siena, Certaldo, and Volterra.

The Tuscany San Gimignano and Chianti Cycling Tour is an ideal way to experience the magic of the Tuscan countryside via bicycle in an efficient trip. You’ll cycle between charming villages, through stellar landscapes, and enjoy Tuscan wine and food at each stop.

This cycling tour of Tuscany begins in San Gimignano, a UNESCO World Heritage Site. This fascinating medieval town will be your home base for the duration of your stay, so you’ll have plenty of time to explore the village and appreciate the tranquil setting.

On the first full day of your Tuscan cycling tour, choose between two rides: the first covers the rolling hills of the Val d’Elsa, where you’ll cycle through woods and vineyards to the spellbinding views of Castellina in Chianti. The second ends instead at Lilliano, an equally gorgeous destination. Tough choice!

The next ride on your Tuscan cycling adventure starts in prestigious vineyards and continues uphill to the village of Certaldo. It’s a workout, but the ceramic-adorned main square and incredible churches are worth the trip.

The last full day of the Tuscany San Gimignano and Chianti cycling tour begins with a transfer to the fascinating ancient Etruscan city of Volterra. Peruse the unique shops and theatres before a smooth ride back down to San Gimignano.

Book now, the San Gimignano and Chianti Cycling Tour is waiting!

Tuscany San Gimignano and Chianti Cycling Tour Itinerary

Day 1 Arrival in San Gimignano

Your cycling adventure in Tuscany begins with arrival at the expansive farmhouse inn 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 Colle Val d’Elsa and Monteriggioni

Start your Tuscan cycling adventure with a morning transfer to Colle Val d’Elsa, an area surrounded by classic Tuscan hills and woods. The carefully preserved hamlet of Monteriggioni is the perfect break before an uphill ride to Lilliano. Here, views across the countryside are sublime and definitely worth the effort! If you’d prefer an extra challenge, an optional extension of your ride will take you to Castellina in Chianti, a commune with extraordinary views over neighbouring villages.

Overnight Location
Hotel in San Gimignano
Distance
3 hours, 40 km, 226m elevation gain, optional extension 2 hours, 12 km
Meals
Breakfast

Day 3 Ulignano and Certaldo Alto

Today’s adventure starts with a ride through the prestigious vineyards that lead the way to Ulignano and the hilltop Certaldo Alto. Literature buffs will be excited to know that this was the hometown of famous Italian writer Boccaccio. Make sure you take some time to stroll through the ceramic-adorned main square, snap a photo of the impressive churches, and stretch your legs. After this, you can choose to take an optional extension to Tavernelle and Barberino in the Chianti Classico area, which is an area with simply wonderful views.

Overnight Location
Hotel in San Gimignano
Distance
4.5 hours, 47.3 km, 1070m elevation gain, optional extension 1 hour, 19 km
Meals
Breakfast

Day 4 Volterra to San Gimignano

Start your morning with a transfer to the magical ancient Etruscan town of Volterra. Here, alabaster artisan shops offer souvenirs, sky-high palaces beckon to be explored, and authentic Roman theatres wait for their photo op. After exploring, it’s all downhill back to San Gimignano! Enjoy the patchwork fields and villages whizzing by on the way home.

Overnight Location
Hotel in San Gimignano
Distance
3.5 hours, 43.5 km, 882m elevation gain
Meals
Breakfast

Day 5 Farewell, San Gimignano!

A final breakfast caps off your Tuscan adventure. Rest your legs on the way home and enjoy safe travels.

Overnight Location
None
Distance
None
Meals
Breakfast

Tuscany San Gimignano and Chianti Cycling Tour Price and Dates

This self-guided cycling tour of Tuscany’s San Gimignano and Chianti region is always run as a custom tour for your group only, therefore the price depends 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 March 1st – April 12th:

  • Price per person staying in single room (min 1 traveler): €995EUR
  • Price per person staying in single room (min 2 travelers): €795EUR
  • Price per person staying in double room (min 2 travelers): €625EUR
  • Price per person staying in triple room (min 3 travelers): €475EUR

Departure on April 13th – 18th:

  • Price per person staying in single room (min 1 traveler): €1,050EUR
  • Price per person staying in single room (min 2 travelers): €850EUR
  • Price per person staying in double room (min 2 travelers): €650EUR
  • Price per person staying in triple room (min 3 travelers): €495EUR

Departure on April 19th – 27th:

  • Price per person staying in single room (min 1 traveler): €995EUR
  • Price per person staying in single room (min 2 travelers): €795EUR
  • Price per person staying in double room (min 2 travelers): €625EUR
  • Price per person staying in triple room (min 3 travelers): €475EUR

Departure on April 28th – September 30th:

  • Price per person staying in single room (min 1 traveler): €1,050EUR
  • Price per person staying in single room (min 2 travelers): €850EUR
  • Price per person staying in double room (min 2 travelers): €650EUR
  • Price per person staying in triple room (min 3 travelers): €495EUR

Departure on October 1st – November 30th:

  • Price per person staying in single room (min 1 traveler): €995EUR
  • Price per person staying in single room (min 2 travelers): €795EUR
  • Price per person staying in double room (min 2 travelers): €625EUR
  • Price per person staying in triple room (min 3 travelers): €475EUR
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Accommodation on the Tuscany San Gimignano and Chianti Cycling Tour

This tour is based in a 3-star farmhouse bed and breakfast. The hotel offers country-style rooms with an excellent proximity to San Gimignano centre. 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). However, it’s definitely possible to match single travellers up.

Fattoria San Donato in San Gimignano

This charming country house, also serving as a vinery, is a stunning gem in San Gimignano region.

Hotels on Standard Tour

What’s included in the Tuscany San Gimignano and Chianti Cycling Tour?

Meals

4 breakfasts and one dinner on day 1 are included.

Accommodations

Accommodation for 4 nights is included.

Transportation during the Tour

This tour includes the rental bike delivery and pick-up and two transfers (return transfer on day 2 and one-way transfer on day 4). Airport transfers, as well as getting to and from San Gimignano are not included.

Also Included

  • Route guides and notes
  • Maps and detailed information packs
  • 24/7 telephone guidance and support
  • Bike theft insurance

Not included

  • Travel insurance
  • Lunches and dinners or drinks and snacks not previously mentioned
  • Tourist taxes
  • Personal equipment

Optional Extras

  • Bike and biking equipment rental (for 3 days):
    • E-bike (including 1 bag and odometer): €150EUR
    • Hybrid bike (including 1 bag and odometer): €95EUR
    • Helmet: €25EUR
  • Any additional nights before or after tour
  • Airport transfers

Frequenty Asked Questions about Tuscany San Gimignano and Chianti Cycling Tour

How hard is the Tuscany San Gimignano and Chianti Cycling Tour?

We rate this tour as a 4 / 5. You will cycle longer distances through varied terrain. Most roads are well-maintained and not highly trafficked, but you should expect up to 1,070 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.

Are meals included on the Tuscany San Gimignano and Chianti Cycling Tour?

4 breakfasts and 1 dinner are included.

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.

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 airport to arrive at is Florence (FLR). From FLR, 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 San Gimignano and Chianti 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 San Gimignano and Chianti Cycling Tour end?

The tour ends in San Gimignano, 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 a helmet, bags, odometer, padlock, repair kit, and water bottle.

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.

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Learn More

Prices

From $525USD

Difficulty

Self-guided

Hotels

Active Travel is what we do

10Adventures knows Active and Adventure Travel because everything we do is focused on Active and Adventure Travel. We understand the needs of travellers and partner with excellent local guides who specialize in active, experiential and adventure travel.

Real humans are always a click or call away

Your time is important, and you shouldn't have to deal with automated bots or a confusing phone system. At 10Adventures you are assigned an Adventure Concierge, who is a real person who has one job: to support you during the planning & booking of your trip.

Customize or go private and get the perfect trip for you

Taking a holiday can be the most fun you have all year. At 10Adventures we believe that you should have the ability to personalize the trip, to get it just the way you want. Sometimes that's joining a group, but more often it's going private with your loved ones, and getting the dates and itinerary that's just right for you.

Rated 4.9 on Google Reviews
Start Your Booking

What travellers say

When can I do this tour?

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Tour Difficulty

We rate this tour as a 4 / 5. You will cycle longer distances through varied terrain. Most roads are well-maintained and not highly trafficked, but you should expect up to 1,070 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

+1 (587) 327-9828

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