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Tuscany’s Jewels and Treasures

This cycling tour start from Florence 5
This cycling tour start from Florence Admire the tilted tower of Pisa Cycle the vineyards of the Tuscan countryside The itinerary takes you pass cozy countryside villages Cycle to some of Tuscany's historical monuments
This cycling tour start from Florence

Tuscany’s Jewels and Treasures

  • Level
  • PriceFrom 795 euros
  • DAY7 nights / 8 days

More info: Receive detailed hotel list, bike specs, and route description

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For leisurely riders, Jewels and Treasures is perhaps the best way to enjoy Tuscany in an independent cycling tour. You will travel on a variety of routes, experiencing all the wonders Tuscany has to offer; from fine panoramas to culture and of course, their delicious cuisine! This unique route involves a jumpstart in Florence, a passing through Siena, a trailing by the road of wines and the finish line: the spectacle of the Leaning Tower of Pisa. In between the paths, you will enter bustling, medieval cities, preserved Tuscan towns and rich hillsides filled with wineries. This 8-day adventure is perfect for small groups and individuals looking for pleasurable, less rigorous paths within Tuscany's borders.

For a more challenging route, we recommend our 6-night/7-day Giro of Tuscanywhich also starts from Florence and ends in Pisa.


For travel and cycling tips to Tuscany, visit our "travel and cycling tips" section.


D1Saturday: Arrival in Florence


Land in the historic city of Florence, Tuscany's capital known for its wealth in culture, architecture and art. This bustling metropolis is considered the birthplace of the Renaissance and upon your arrival, you can immediately see hints of artisan decor embellished upon buildings and plazas.

You will be spending the night here, so you may want to visit its prominent sites, such as Santa Maria del Fiore, Giotto's Campanile, Piazza della Signora and the shops at Ponte Vecchio.

D2Sunday: Florence – Greve in Chianti 44 km/27 miles, 800 meters/2,625 ft of climbing


It's time to start your journey! After ensuring that your biking essentials are all in place, take a stroll around Florence and then trot off to Impruneta, a neighboring district filled with terracotta art. Here, you'll discover Gothic-inspired buildings and the town's gem, the Sanctuary of Santa Maria. After ten kilometers, you'll reach a small town by the hills called Mercatale, where you will be given wine-tasting opportunities from its local wine cellars.

Wander around Palagio castle and then head onward to your hotel either in Greve (Option A) or in the Greve countryside (Option A+).

D3Monday: Greve – Radda in Chianti 31 km/19 miles, 792 meters/2,598 ft of climbing


Today you will discover Tuscany’s “road of wines”! Pedal off from the Greve public square where the famous Chianti Classico Wine Festival is held every year in September. As you go on, you'll get a glimpse of the Montefiorallevillage, a medieval town, and Panzano, a lush green district with a countryside charm. Radda in Chianti is up next; this classic Chianti village is nestled inside the verdant hill regions and cradles remnants of the Etruscan age.
From here, you can view the Pretorio Palace, discover wine tours and enjoy a leisurely stay at a nearby hotel.

D4Tuesday: Radda in Chianti - Siena 41 km/25 miles, 756 meters/2,480 ft of climbing


After a restful night in the pastoral hills of Chianti, you will now move on to your next destination: Siena. First stop is Meleto's Castle, its stern-looking architecture tucked in the elevated, tree-covered lands. At Castagnolli, you will view yet another fortress, the Castle of Brolio, home to the Ricasoli family and also, a well-managed wine cellar. A sip of the local wine will fire up your senses, inspiring you as you go along your route. Siena is just ahead; easily distinguish it by old brick buildings and the crown of Torre del Mangia.
Slow down and enjoy the views, as you spend the night here.

D5Wednesday: Siena – Colle Val d’Elsa 27 km/17 miles, 298 meters/978 ft of climbing


By taking the olden paths of Francigena, you'll be welcomed by the views of Mount Maggio and the castle of Monteriggioni, Dante's subject in his famous literary pieces. Abbadia a Isola is your next stop, famous for its nostalgic architecture.

Proceed to Colle Val d'Elsa, Italy's Bohemia, an industrial village known for its artisan glassware. Walk around the workshops and indulge in the local cuisine.

D6Thursday: Colle Val d’Elsa - Volterra 46 km/29 miles, 1,083 meters/3,553 ft of climbing


Launch today's tour with a stride to San Gimignano-—a hilltop village offering medieval landscapes. This UNESCO-awarded walled village is known for its many towers. Follow the Francigena Way and arrive at Volterra, a Tuscan industrial city famous for its alabaster works. The rather imposing setting offers a legitimate, medieval air, but don't be intimidated by its large walls and architecture. Immerse yourself in the backdrop and enjoy its local sights, such as the Roman Theater and the Museo Etrusco Guarnacci.
Admire the sunset as you lodge in your hotel, and enjoy the rest of the hours according to your liking.

D7Friday: Volterra - Pontedera + Train to Pisa 54 km/34 miles, 294 meters/965 ft of climbing


On the last leg of your independent cycling tour, you'll be departing from Volterra to reach the famous city of Pisa. Your ride will take you through olive groves and vineyards, perfect for an immersion with nature. After a two hour ride, you'll arrive at Calcinaia, a quiet municipality by the banks of Arno River. Pontedera is just a few kilometers away. This rather modernized district is home to the wine company Castellani, and a sweets factory called Amedei.

You may take a break from pedaling; here, you'll have a train transfer to Pisa, where you'll be spending your night.

D8Saturday: Departure


On the last day of your tour, you can wander around the city after breakfast.
Make sure you drop by Pisa's most famous highlights, such as the Leaning Tower, the Piazza del Miracoli, and Regatta of St. Ranieri—famous for its boat race. Dive into the city's wealth of art and gastronomy before you leave.

Booking & Pricing

  • Option A
  • 1 night in a 4-star hotel and 6 nights in 3-star hotels

  • 795 euros per person in April and October. Single supplement is 265 euros
  • 820 euros per person in May, June and September. Single supplement is 270 euros
  • 835 euros per person in July and August. Single supplement is 280 euros
  • Option A+
  • 1 night in a restored medieval castle and 6 nights in 4-star hotels

  • 1,105 euros per person in April and October. Single supplement is 565 euros
  • 1,130 euros per person in May, June and September. Single supplement is 570 euros
  • 1,150 euros per person in July and August. Single supplement is 575 euros

These prices include:

  • 7 nights’ accommodation (as described above)
  • Daily breakfast
  • Meeting with our local representative
  • Luggage transfers
  • Marked maps and/or cue sheets and route notes
  • Smartphone app. (Android or iPhone) with downloadable directions/roadbook (no data necessary) - A cell phone holder is provided
  • Tourist information
  • Assistance if necessary (you will be provided with our local rep’s mobile number)
  • All tax and service charges

These prices do not include:

  • Nominal city taxes, to be paid in cash directly at each hotel (total of approx. 15-18 euros).
  • Train from Pontedera to Pisa on Day 7
  • Expenses of a personal nature
  • Travel insurance
  • Bicycle rentals. Hybrid bikes are available at the rate of 115 euros per bike. E-bikes are available at the rate of 245 euros per bike. These prices include the drop-off fee for the bike’s return to Florence.

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