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Expresso Tuscany: Florence to Siena for Avid Riders

Admire the Ponte Vecchio in Florence 5
Cycle along the Florence Canal Sunset on the Florence Canal Admire the Ponte Vecchio in Florence Take the time to admire the Duomo di Firenze in Florence This cycling tour takes you through Tuscan countryside
Admire the Ponte Vecchio in Florence

Expresso Tuscany: Florence to Siena for Avid Riders

  • Level
  • PriceFrom 630 euros
  • DAY4 nights / 5 days

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

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When you want to soak in the birthplace of the Italian Renaissance but are short on time, it’s time to go …expresso.

Our 4-night/5-day Expresso Tuscany tour takes you on challenging rides through medieval Italian villages and the world-famous Tuscan wine region. Ride past mountain ranges and fertile plains as you pedal from town to town; from the artistically inspired city of Florence to the lesser-known but equally spectacular Siena.

Along the way, enjoy a glass of the local Chianti or Brunello di Montalcino—just enough to fill your legs with more energy for the rides to come! Sup on traditional Tuscan fare, visit a castle or two and admire the sun-kissed landscape as you tackle its hills. It really is a ride for the senses!

If you have more time to spare, try our 6-night/7-day Giro of Tuscany from Florence to Pisa.


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


D1Saturday: Arrival in Florence


Find yourself under the Tuscan sun in the region’s capital—Florence. This is the city that inspired the genius of Da Vinci and Michelangelo, Dante and Petrarch…explore its cobblestone streets and maybe you’ll be inspired to write a sonnet about your love of cycling! 

The Duomo (Florence’s domed cathedral) and the Ponte Vecchio (Vecchio Bridge) are not to be missed. You won’t start riding until tomorrow, so take some time to admire the art, culture, and delicacies that Florence has to offer.

D2Sunday: Florence — Radda-in-Chianti 69 km/43 miles, 1,537 meters/5,043 ft of climbing


After meeting with our local representative and being outfitted with your bikes, pedal off towards Impruneta, a city known for its terracotta art, quaint villas, and a famous basilica called the Sanctuary of Santa Maria.

From here, just ten kilometers (6 miles) of cycling will take you to Mercatele, a little town surrounded by the hills of Chianti, and—you guessed it—famous for its wineries! As you follow the Tuscan wine road, indulge in the local reds and take a well-deserved break at the unique triangular public square at Greve.

Tonight, you will nestle in the hills at Radda in Chianti, with its medieval Pretorio Palace. Rest up in your hotel, and get ready for more exciting rides.

D3Monday: Radda-in-Chianti — Siena 43 km/27 miles, 753 meters/2,470 ft of climbing


As you cycle down from the hills of the Chianti towards Siena, keep an eye out for Meleto's Castle, an ancient fort that is now a Tuscan countryside villa! Proceed through Castagnolli and take a break at the Castle of Brolio for a quick Ricasoli wine tasting. With good pacing, you'll soon reach the city of Siena, whose historic centre is a UNESCO World Heritage Site.

Don't miss the Piazza del Campo where the Palio, Siena's famous horse race is still held bi-annually (a very different kind of riding!) Among your must-sees: the Siena Cathedral, with its strong Gothic-inspired architecture and Palazzo Pubblico, which houses Siena's city hall.

D4Tuesday: Siena — Montalcino — Siena Short option: 70 km/44 miles; Long option: 116 km/72 miles, 1,869 meters/6,132 ft of climbing


We know one day isn’t enough to fully appreciate the warded city of Siena, so we’ve included two! Today’s ride is a loop taking you through lush, green hills towards the renowned Brunello vineyards and, inevitably, a wine-tasting session at Montalcino.

After a glass or two, start cycling your way to the walled city of Asciano and the nearby Monte Oliveto Abbey, the perfect place for a quiet break. You are in the heart of the “Crete Senesi” territory, home to all Tuscan things: rolling hills spanned by fields, olive groves, and vineyards, dotted with cypress trees and tiny villages that seem to disappear into the hillsides.
From here, you can explore more of the land's secrets by cycling the long option (116 km) or cut it short by taking a train from Montalcino to Siena.

D5Wednesday: Departure


On the last day of your tour, you can wander around the city after breakfast.
Visit a few of Siena’s many museums, and don’t forget to pick up a few souvenirs (for those who weren’t lucky enough to cycle with you through Tuscany).

Booking & Pricing

  • Option A
  • 4 nights in 3-star properties

  • 630 euros per person in April and October. Single supplement is 155 euros
  • 650 euros per person in May, June and September. Single supplement is 160 euros
  • 670 euros per person in July and August. Single supplement is 165 euros
  • Option A+
  • 4 nights in 4-star properties

  • 850 euros per person in April and October. Single supplement is 315 euros
  • 870 euros per person in May, June and September. Single supplement is 320 euros
  • 890 euros per person in July and August. Single supplement is 325 euros

These prices include:

  • 4 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)
  • Service charges and most taxes

These prices do not include:

  • Nominal city taxes, to be paid in cash directly at each hotel (total of approx. 12-13 euros).
  • Expenses of a personal nature
  • Travel insurance
  • Bicycle rentals. Full-carbon bikes are available at the rate of 170 euros per bike (this price includes the drop-off fee for the bike's return to Florence.

Suggested Cycling Trips