Classic Tuscany Bike Tour
Essential Italy: What Locals Love Beyond Siena and Florence
Itinerary
Print Itinerary- Day 1
La Dolce Vita
Meet your guides at the Chiusi train station for a transfer to the tiny village of Montefollonico. Here, an authentic Tuscan welcome awaits with lunch on the scenic terrace of a centuries-old olive mill. After, get fitted on your bike and set off on a ride through the classic Tuscan countryside—you’ll feel as though you’ve traveled back to the 13th century pedaling on the cobbled streets of tiny Petroio and greeting locals as they tend their olive groves. Choose your own adventure with longer or shorter ride options that lead to our boutique hotel in the heart of Pienza, tucked in amongst the town’s Renaissance architecture. This evening, watch the sun set over the Tuscan hills as we dine al fresco on the terrace of a local organic farm.
Meals: Lunch / Dinner
Destinations: Pienza, Petroio
Accomplished: 19 miles / 29 km, elevation gain: 1,919 feet / 585 meters
Shorter Option: 14 miles / 22 km, elevation gain: 1,332 feet / 406 meters
Accommodations: La Bandita Townhouse - Day 2
Montalcino: Castles, Brunello, and Home-Cooking
Set off riding through the Val d’Orcia, an area so beautiful that UNESCO designated it a World Heritage Site—you may also recognize it from the movie Gladiator’s famous wheat field scene. Climb up to the craggy medieval fortress of Castiglione for a coffee stop (a key component of Italian cycling culture), then enjoy an endless downhill through the olive groves. The final push brings us to our favorite Brunello winery, where the reward for our efforts is a gorgeous tasting lunch. Spend the afternoon relaxing by the pool or getting pampered at the spa of our five-star castle hotel. This evening we’ll head into Montalcino for a cooking class and dinner in the 15th-century home of our friend Lina.
Meals: Breakfast / Lunch / Dinner
Destinations: Montichiello, Castiglione d’Orcia, Montalcino
Accomplished: 24 miles / 39 km, elevation gain: 2,247 feet / 685 meters
Longer Option: 38 miles / 62 km, elevation gain: 3,487 feet / 1,063 meters
Accommodations: Castello di Velona - Day 3
Hilltown Loop
Today’s loop ride begins with a climb to Montalcino, followed by a downhill section through vineyards into the Asso Valley (home to some of Italy’s finest truffles). Pedal along the valley floor, then follow a scenic ridgeline to our friend Paolo’s olive mill for lunch cooked by his mother and a tasting of organic olive oil. After lunch, revel in majestic views towards the dormant volcano of Monte Amiata as we pedal to medieval San Quirico. From here, complete the full loop ride or opt for a quick shuttle back to the hotel. This evening, treat yourself to some rest and relaxation at the hotel before another satisfying dinner.
Meals: Breakfast / Lunch / Dinner
Destinations: Montalcino, San Giovanni d’Asso, Castelmuzio, San Quirico
Accomplished: 33 miles / 53 km, elevation gain: 2,893 feet / 882 meters
Longer Option: 50 miles / 81 km, elevation gain: 4,497 feet / 1,371 meters
Accommodations: Castello di Velona - Day 4
Across the Crete Senesi: Monks and Masterpieces
Say goodbye to the Castello di Velona as we ride through the mystical morning light that bathes the Romanesque Abbey of Sant’Antimo. Pedal across the Brunello region before we stop to visit the Renaissance frescoes at the Abbey of Monte Oliveto. Crossing into Chianti Classico country, the views turn positively panoramic, and we’ll pedal through the wide-open landscapes of the Crete Senesi to a well-earned lunch at a family-run winery. Tonight, spend the evening in Siena as you wish: dine on your own, explore the medieval city, or have dinner right at our hotel.
Meals: Breakfast / Lunch
Destinations: Buonconvento, Monte Oliveto, Asciano, Siena
Accomplished: 29 miles / 46 km, elevation gain: 2,083 feet / 635 meters
Longer Option: 48 miles / 77 km, elevation gain: 3,972 feet / 1,211 meters
Accommodations: Borgo San Felice or Le Fontanelle - Day 5
Chianti Classico: The Tuscan Heartland
Olive and cypress trees surround us as we ride deep into the hills of Chianti. We’ll see plenty of fortified hamlets and castles—relics of Florence and Siena’s 300-year struggle for regional dominance and ownership over the birthplace of Chianti Classico wines found in ancient cellars around the area. Pedal past countless estates as we weave our way through forests and vineyards, completing our loop for lunch back at the hotel. Enjoy a relaxed afternoon at the pool or spa before regrouping for a final dinner with our friend Serena featuring top wines and generous Tuscan hospitality.
Meals: Breakfast / Lunch / Dinner
Destinations: Castelnuovo, Brolio, Castagnoli
Accomplished: 31 miles / 50 km, elevation gain: 2,673 feet / 815 meters
Longer Option: 40 miles / 64 km, elevation gain: 3,575 feet / 1,090 meters
Accommodations: Borgo San Felice or Le Fontanelle - Day 6
Ride to Florence
On our last day, choose between a late morning at the hotel or ride all the way across Chianti for a triumphant finish in Florence’s Piazzale Michelangelo. Whether you rode here or took a transfer, we say our goodbyes with the stunning Florentine skyline as our backdrop as guides see you off to your next adventure.
Meals: Breakfast
Destinations: Panzano, Greve, Florence
Optional Ride: 32 miles / 52 km, elevation gain: 2,470 feet / 753 meters
Longer Option: 43 miles / 69 km, elevation gain: 3,477 feet / 1,060 meters
DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.
Arrival Details
Airport City: Rome or Florence, Italy Pick-Up Location: Chiusi Train Station Pick-Up Time: 11:00 am
Departure Details
Airport City: Rome or Florence, Italy Drop-Off Location: Florence Piazzale Michelangelo Drop-Off Time: 1:30 pm
Arrival and departure details for 2025 tours may be subject to change.
Dates + Availability
Confirm the hotels on your desired date by speaking with a Travel Specialist.
Single Supplement From: $1,900- DatesPriceSpecial Events
- Apr 20 – 25$6,295
- May 4 – 9$6,295
- May 11 – 16$6,295
- May 18 – 23$6,295
- May 25 – 30$6,295
- Jun 8 – 13$6,295
- Jun 15 – 20$6,295
- Jun 29 – Jul 4$6,295
- Jul 6 – 11$6,295
- Jul 20 – 25$6,295
- Aug 3 – 8$6,295
- Aug 17 – 22$6,295
- Aug 31 – Sep 5$6,295
- Sep 7 – 12$6,295
- Sep 14 – 19$6,295
- Sep 21 – 26$6,295
- Sep 28 – Oct 3$6,295
- Oct 12 – 17$6,295
To reserve call +1 888 396 5383
- Oct 19 – 24$6,295
To reserve call +1 888 396 5383
Inclusions + Details
Accommodations
- Thoughtfully selected accommodations that reveal the true character of the region
- Luggage transfers
Meals
- Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
- 4 gourmet dinners at our favorite local restaurants and renowned culinary establishments
- Carefully selected local wine, beer, or spirits with every meal
Activities
- Wine tastings and activities as outlined in the tour itinerary
- Entrance fees to historic sites, museums, parks, and all other exclusive events
- Gratuities for baggage, porters, and hotel service
Gear
- Top-of-the-line bicycle selection
- Bike helmet
- Complimentary DuVine gear including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
- GPS in most destinations
Support
- Expert bilingual guides with extensive local knowledge
- Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
- Pick-up and drop-off before and after your tour from predetermined meeting points
- Daily bike maintenance to ensure optimal performance