Chianti to the Coast



Chianti to the Coast

Surrender to the magic of Tuscany as you cycle along quiet roads bordered by rolling hills, lush with vineyards and olive groves…

Surrender to the magic of Tuscany as you cycle along quiet roads that meander through rolling hills, lush ancient vineyards and shady olive groves. Stay in the heart of Chianti, reknowned for its rich wines - the perfect accompaniment to the delicious cuisine. Explore the medieval hilltop village of Radda; discover the breathtaking beauty of Siena, Italy; and marvel at the landscape of the Crete Senesi on your journey to the coast. Blessed with charming locals, the warm Tuscan sun and the deep blue Mediterranean this alluring region is sure to capture your heart.…

2014 Dates

Sep /
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Group Discounts [?]

Rider Type [?]



Hotel Style [?]



Start | End

Florence, Italy | Grosseto, Italy


6 days | 5 nights

Beyond Biking

Historical Site Visit, Cultural Tour, Wine Tasting, Beach, Shopping

DAYs 1 & 2


Stay at Palazzo Leopoldo

Cycle through the rolling hills of the Chianti countryside | Discover exclusive Chiantis during a private wine tasting | Stay in Radda, the charming capital of the ancient League of Chianti



Stay at Borgo Pretale

Discover Italy's best preserved medieval city - Siena - with a private walking tour | Challenge yourself on rides to hilltop towns

DAYs 4 - 6

Massa Marittima

Stay at La Cianella

Enjoy the small winding roads to the Tuscan coast and alongside the Mediterranean | Explore the wildly beautiful Maremma, home to Etruscan ruins and sparkling beaches.

Add On

Rome or Florence Package

Two Nights Accommodation

Explore the city of Rome or Florence and let Trek Travel take care of the details. Purchase one of our exciting 3 day, 2 night add on package to enjoy before or after your trip.


Dates & Pricing


7th / 6 days / 5 nights
$3299 / Person, $700 / Single OCC.
14th / 6 days / 5 nights
$3299 / Person, $700 / Single OCC.
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Palazzo Leopoldo hotel on our Chianti bike tour

Palazzo Leopoldo

Radda in Chianti, Italy

Dating back to the 13th century and set in the historical center of Radda in Chianti, Trip Advisor award winner, Palazzo Leopoldo is an elegant villa with its own wine shop and spa. The hotel’s design melds ancient architectural details and contemporary comforts for an unparallelled stay. Enjoy the views of the surrounding Chianti hills from their specacular terrace with a glass of Prosecco in hand.
Villa Sabolini

Villa Sabolini

Siena, Italy

Nestled in the tranquil forests of central Tuscany, this historic home has been lovingly restored and converted into a beautiful hotel. Soak in the history of this ancient place that provides ancharming blend of ancient and modern Tuscany.
La Cianella on our Chianti bike tour

La Cianella

Massa Maritima, Italy

La Cianella takes its name from the 19th century fountain located on the grounds, "Fontana delle Cianelle." Surrounded by olive trees, La Cianella is set high on a hill with fantastic views of surrounding valleys. Intimate and inviting, the 19th century main structure now houses 12 charming, comfortable rooms. The outdoor swimming pool and tennis courts each offer scenic views of the surrounding countryside.

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General FAQs

Didn't find what you were looking for? Check out our General FAQs section. You will find answers to all the most common questions that don't necessarily pertain to a specific trip.

Our Guides

Besides our many options in travel styles, dates, prices and destinations, we also accommodate your vacation style each day of your trip. You decide how to spend your time whether it is with the group or exploring on your own, riding a little, a lot, or not at all.

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the full-carbon, ultra smooth Trek Domane 5.9, to the comfortable Trek 7.6 FX Hybrid–both included in the trip cost, to our numerous upgrade options, you deserve the best ride on your vacation.

Your Day. You decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.