Essential Tuscany
Beyond Siena & Florence
The Journey
Discover what locals love in the heart of Tuscany on this immersive cycling journey through medieval villages, rolling vineyards, and the region's most celebrated landscapes. From the iconic towers of San Gimignano to the intimate wine cellars of Chianti, every pedal stroke reveals the authentic soul of Italy.
What to Expect
Why This Journey
We created this cycling adventure to showcase the very best of Tuscany, combining world-class cycling with authentic Italian experiences, exceptional cuisine, and carefully selected accommodations.
Day-by-Day Itinerary
A detailed look at what each day of your adventure holds
Welcome to Tuscany! Meet your Domestique guides in Florence and transfer to our first accommodation in the heart of Chianti. After settling in, enjoy a welcome aperitivo overlooking the vineyards followed by an authentic Tuscan dinner featuring local specialties.
Today's Highlights
- Cycle through the UNESCO-listed Val d'Orcia, with its iconic cypress-lined roads and golden wheat fields
- Visit world-renowned Chianti wineries for private tastings of Sangiovese and Super Tuscans
- Stay in carefully selected boutique agriturismos and historic villas
Begin your cycling adventure through the rolling hills of Chianti Classico. Wind through vineyards and olive groves on quiet back roads, stopping at a historic cantina for a private wine tasting. Lunch is a leisurely affair at a family-run trattoria, before continuing to the medieval village of Radda in Chianti.
Today's Highlights
- Cycle through the UNESCO-listed Val d'Orcia, with its iconic cypress-lined roads and golden wheat fields
- Visit world-renowned Chianti wineries for private tastings of Sangiovese and Super Tuscans
- Stay in carefully selected boutique agriturismos and historic villas
Today's ride takes us to the iconic towers of San Gimignano, a UNESCO World Heritage site. Cycle through a patchwork of vineyards and forests, arriving in time to explore the medieval streets and enjoy a gelato made with local Vernaccia wine. This afternoon, visit an artisan saffron producer.
Today's Highlights
- Cycle through the UNESCO-listed Val d'Orcia, with its iconic cypress-lined roads and golden wheat fields
- Visit world-renowned Chianti wineries for private tastings of Sangiovese and Super Tuscans
- Stay in carefully selected boutique agriturismos and historic villas
Transfer to the Val d'Orcia for the most scenic cycling of the trip. Pedal through the postcard-perfect landscapes that have inspired Renaissance painters for centuries. Visit Pienza, the 'ideal Renaissance city,' and sample its famous pecorino cheese. End the day in enchanting Montepulciano.
Today's Highlights
- Cycle through the UNESCO-listed Val d'Orcia, with its iconic cypress-lined roads and golden wheat fields
- Visit world-renowned Chianti wineries for private tastings of Sangiovese and Super Tuscans
- Stay in carefully selected boutique agriturismos and historic villas
Cycle to Montalcino, home of the legendary Brunello wine. Visit a prestigious estate for a cellar tour and vertical tasting of different vintages. The afternoon ride winds through the Orcia Valley before returning to our hotel for a farewell dinner celebrating the best of Tuscany.
Today's Highlights
- Cycle through the UNESCO-listed Val d'Orcia, with its iconic cypress-lined roads and golden wheat fields
- Visit world-renowned Chianti wineries for private tastings of Sangiovese and Super Tuscans
- Stay in carefully selected boutique agriturismos and historic villas
After a leisurely breakfast, bid farewell to the Tuscan countryside. We'll transfer you to Florence or the nearest train station, with memories of incredible cycling, wines, and cuisine to last a lifetime.
Today's Highlights
- Cycle through the UNESCO-listed Val d'Orcia, with its iconic cypress-lined roads and golden wheat fields
- Visit world-renowned Chianti wineries for private tastings of Sangiovese and Super Tuscans
- Stay in carefully selected boutique agriturismos and historic villas
What's Included
Included
- 5 nights at hand-picked boutique hotels and agriturismos
- All gratuities for hotel staff and porters
- Daily luggage transfers between accommodations
- Daily breakfasts featuring local products
- 5 gourmet lunches at our favorite local restaurants
- 5 cyclist-friendly dinners with wine pairings
- Daily energy snacks and hydration during rides
- Premium carbon road bike or e-bike
- Domestique Tours cycling jersey and cap
- GPS device with pre-loaded routes
- Helmet, water bottles, and saddlebag
- Expert bilingual guides with extensive local knowledge
- Support vehicle following the route with spare gear
- Daily bike maintenance and cleaning
- Private wine tastings and culinary experiences
- All entrance fees and activities as listed
Not Included
- Airfare
- Travel insurance
- Gratuities for Domestique guides
- Personal expenses
Where You'll Stay
Castello di Fonterutoli
Tuscany
A stunning 15th-century estate in the heart of Chianti, offering elegant rooms with vineyard views and a renowned restaurant.
Relais La Cappuccina
Tuscany
A beautifully restored farmhouse near San Gimignano with panoramic views, pool, and exceptional Tuscan hospitality.
Il Borghetto
Tuscany
A charming boutique hotel in Montepulciano with stunning Val d'Orcia views and authentic Renaissance character.
Tour Gallery
Details
Upcoming Journeys
Each departure brings together a small group. If the dates work, we'd enjoy having you with us.
Private Journeys
Prefer your own group? We can arrange this experience on dates that work for you.
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