San Gimignano Volterra short
Tuscany 5-day Cycling Tour

Tuscany 5-day Cycling Tour

5 days

Tuscan countryside views around San Gimignano seen on self guided biking tourSan Guisto in Volterra visited by biking tour in TuscanyVineyards of San Gimignano Tuscany ItalyVolterra in Tuscany visited on self guided biking tour in San Gimignano and VolterraLooking at San Gimignano from afar biking tour in ItalyVisiting San Gimignano is one of the highlights of the self guided biking tour in TuscanyCypres trees near San Gimignano Tuscany Italy

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!

Highlights of the Tuscany 5-day Cycling Tour

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.

Prices

From $425USD
5 days
Difficulty
Self-Guided
Hotels
  • No Booking or Credit Card Fees
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San Gimignano Volterra short

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

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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 – 11th:

  • Price per person staying in single room (min 1 traveler): $875 USD
  • Price per person staying in single room (min 2 travelers): $725 USD
  • Price per person staying in double room (min 2 travelers): $525 USD
  • Price per person staying in triple room (min 3 travelers): $425 USD

Departure on April 12th – May 1st:

  • Price per person staying in single room (min 1 traveler): $925 USD
  • Price per person staying in single room (min 2 travelers): $750 USD
  • Price per person staying in double room (min 2 travelers): $575 USD
  • Price per person staying in triple room (min 3 travelers): $475 USD

Departure on May 2nd – 23rd:

  • Price per person staying in single room (min 1 traveler): $895 USD
  • Price per person staying in single room (min 2 travelers): $725 USD
  • Price per person staying in double room (min 2 travelers): $550 USD
  • Price per person staying in triple room (min 3 travelers): $450 USD

Departure on May 24th - June 19th:

  • Price per person staying in single room (min 1 traveler): $925 USD
  • Price per person staying in single room (min 2 travelers): $750 USD
  • Price per person staying in double room (min 2 travelers): $575 USD
  • Price per person staying in triple room (min 3 travelers): $475 USD

Departure on June 20th – July 18th:

  • Price per person staying in single room (min 1 traveler): $895 USD
  • Price per person staying in single room (min 2 travelers): $725 USD
  • Price per person staying in double room (min 2 travelers): $550 USD
  • Price per person staying in triple room (min 3 travelers): $450 USD

Departure on July 19nd – August 16th:

  • Price per person staying in single room (min 1 traveler): $925 USD
  • Price per person staying in single room (min 2 travelers): $750 USD
  • Price per person staying in double room (min 2 travelers): $575 USD
  • Price per person staying in triple room (min 3 travelers): $475 USD

Departure on August 17th – August 31st:

  • Price per person staying in single room (min 1 traveler): $895 USD
  • Price per person staying in single room (min 2 travelers): $725 USD
  • Price per person staying in double room (min 2 travelers): $550 USD
  • Price per person staying in triple room (min 3 travelers): $450 USD

Departure on September 1st – October 15th:

  • Price per person staying in single room (min 1 traveler): $925 USD
  • Price per person staying in single room (min 2 travelers): $750 USD
  • Price per person staying in double room (min 2 travelers): $575 USD
  • Price per person staying in triple room (min 3 travelers): $475 USD

Departure on October 16th – 31st:

  • Price per person staying in single room (min 1 traveler): $895 USD
  • Price per person staying in single room (min 2 travelers): $725 USD
  • Price per person staying in double room (min 2 travelers): $550 USD
  • Price per person staying in triple room (min 3 travelers): $450 USD
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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).

Hotels on Standard Tour

Hotel 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.

Albergo Etruria in Volterra ★★★

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

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 (3 days):
    • E-bike (incl. 1 bag and odometer) - $175 USD
    • Hybrid bike (incl. 1 bag and odometer) - $95 USD
    • Helmet rental - $25 USD
  • Any additional nights before or after tour
  • Airport transfers

Frequently Asked Questions about Tuscany 5-day Cycling Tour

S-Cape Travel is a boutique tour operator focused on sharing the best walking, cycling, cultural and food & wine tours in Europe. Book one of their self-guided tours to live La Dolce Vita for a week or two, as you walk or cycle around Europe, enjoying incredible views and amazing food and wine.

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Tuscany 5-day Cycling Tour Map

Click map for a larger version

Is this tour for me?

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.

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