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Tuscany Retreat

13th - 18th May 2018

The perfect blend of riding and relaxation, in the most elegant Italian surroundings.

Since ancient times Tuscany has been a centre of art and culture, and, of course, fine food and wine. It is also one of the most beautiful places in the world to ride a bike. Our exclusive accommodation is a converted 8th century Etruscan village owned by winemakers, nestled in the hills of the Gallo Nero region of Chianti. There, you can relax on the terraces or by the pool and you will be wined and dined in style with local and homegrown produce. The Tuscan roads, meanwhile, will test your legs as you explore the rolling hills and gravel tracks made famous by the Giro d’Italia and Strade Bianche races.

Single occupancy — $5,000 per person
Double occupancy — $4,150 per person

Request a call back

Please only pay the balance when prompted.

Who is it for?

Rapha Travel pioneered the idea of the cycling Retreat, a luxurious break where the emphasis is as much on unwinding and enjoying stunning surroundings as it is on challenging yourself on the bike. With exclusive accommodation in which to stretch out, and the best regional specialities, local wines and culture, the Retreats set a standard that other trip providers cannot match. Rapha Retreats are always based in one stunning location, for the ultimate in stress relief, and you can tailor-make the riding itinerary to suit you. Choose 150km over the high mountains, or a gentle coffee spin before an afternoon of relaxation; guided or solo, it’s up to you. Non-riding partners are welcomed along to share the experience with you.

How Hard is it?

Retreats suit all types of riders, except for those who want packed days and relentless riding. Although you will have the chance to do big days in the saddle and test yourself on amazing roads, your time can be as demanding or as gentle as you like: wine tastings, market trips, swimming and massages are examples of indulgences that are positively encouraged. You’ll return home fitter and happier, and recharged in mind and body.

*Please note that all routes are subject to change depending on local conditions.

All Retreats include

  • Airport transfers
  • All meals including alcohol
  • On-road food
  • Daily massage
  • Laundry

Double occupancy as standard

All trips include

  • Expert planning and guide support from guides and vehicles
  • Pre-trip discounts on Rapha apparel
  • High guide-to-client ratios
  • Unique routes
  • Top-level mechanics

Flights, bike hire* and travel insurance are not included
*Bike hire only available for EU trips

Day Distance Climbing
Arrival Day Gaiole Loop 32 KM 734 M
Day 1 Panzano Panorama 82 KM 1841 M
Day 2 Dudda Loop 54 KM 1307 M
Day 3 Siena for dinner 44 KM 633 M
Day 4 Monteluco and Strade Bianche 84 KM 1782 M
Day 5, Departure Day Departure

See full itinerary

Arrival Day

Gaiole Loop

Arrive into Florence airport or central train station, to be greeted by the Rapha Travel team. We’ll transfer together to the hotel ahead of an afternoon spin to Gaiole in Chianti, the home of the world famous and original Eroica (hero) cycling event, which now attracts nine thousand riders every October.


32 KM


734 M

Day 1

Panzano Panorama

Explore and enjoy the unique landscape as your Rapha Travel guides navigate you to the quieter roads of the Chianti Classico region. We’ll enjoy the vistas from Panzano before heading to lunch at a small family run local restaurant, where a big welcome is guaranteed.


82 KM


1841 M

Day 2

Dudda Loop

Dudda is the name and coffee destination for today’s ride. The route climbs past the area’s famous vineyards and down past rows of the Tuscan Cypress trees. Post-ride we will enjoy a private wine tasting experience, at a historic crypt where monks once discovered that the location was the perfect temperature to age and store wine.


54 KM


1307 M

Day 3

Siena for dinner

Today we’ll ride through the valley to Siena, with a short climb to reach the town itself. Arrival drinks and showers will be followed by a private walking tour to discover the Unesco World Heritage Center and the infamous Palio horse race. The evening is then spent dining within Siena’s city walls.


44 KM


633 M

Day 4

Monteluco and Strade Bianche

Monteluco is one of the highest points in the area providing fabulous views of the region which has remained untouched for generations. The Strade Bianche is a network of gravelled routes linking the villages together and offer an exciting opportunity to enjoy road cycling from another perspective. This will be a particularly memorable day on the bike.


84 KM


1782 M

Day 5, Departure Day


Breakfast at your leisure before transfers back to Florence Airport or train station for your onwards travel, full of the best Tuscan food, wine and memories to savour.

Request a call back

Please only pay the balance when prompted.

Customer Testimonials

Loved the venue, the team, the food, the rides, the whole experience was hard to fault.

— Retreat Provence, 2015

Absolutely brilliant trip. Entire team looking after us were fabulous and made everything run extremely smoothly. Can't wait till my next trip with Rapha!

— Rider - Retreat Tuscany, 2015


Can I bring a non-riding companion?

We welcome non-riding partners on our Retreats, but not on other trips.

Am I strong enough for the trip?

All our trips are physically demanding, but some are harder than others. Retreats are among the most relaxing. Our guides, soigneurs and mechanics will support every rider to go beyond their usual level of riding. Each individual trip is rated for difficulty.

See all FAQ

Contact Us



Telephone: +44 (0) 207 482 9175

Hours: 9.30am-6.00pm (BST)



Telephone: 877.907.2742

Hours: 8.30am-5.30pm (PDT)

Asia Pacific


Telephone: +44 (0) 207 482 9175

Hours: 9.30am-6.00pm (BST)