Tour Highlights
- Ride surrounded by olive groves, cypress trees, sunflower fields, and bucolic cow pastures
- Meet the locals as we learn to cook a Tuscan lunch with our friend Barbara and her mother at their beautiful farmhouse
- Taste exquisite vintages during a private wine-paired lunch at our favorite local winery
- Pedal along the shores of Lake Trasimeno in the silent stillness of the Val di Chiana
Eat
Hand-rolled pici pasta, pecorino cheese, olio nuovo (fresh-pressed olive oil), truffles, fava beans, artichokes, chestnuts, porcini mushrooms, Chianina beef, and cinghiale (wild boar)
Drink
World-famous wines made from native Sangiovese grapes including Brunello, Chianti Classico, and Vino Nobile; international blends known as Super Tuscans; Syrah from Cortona’s distinctive appellation; and—in classic Italian fashion—espresso and cappuccino
Itinerary
Print Itinerary- Day 1
Welcome to Tuscany
Meet your guides at the Chiusi train station for a transfer to the medieval village of Montefollonico where the adventure begins. We’ll toast our arrival with a light lunch at our favorite local restaurant. After a bike fitting and safety review, we’ll set off on our first ride through the Tuscan countryside past cows, sheep, olive groves, and vineyards. Stop to admire the stunning architecture of the Temple of San Biagio in Montepulciano, then cruise through the Vino Nobile vineyards to our boutique winery hotel. We’ll celebrate tonight with a dinner featuring homemade pastas, fresh seasonal vegetables, and, of course, a selection of local wines.
Meals: Lunch / Dinner
Destinations: Montefollonico, Montepulciano
Accomplished: 17 miles / 28 km, elevation gain: 935 feet / 285 meters
Longer Option: 27 miles / 44 km, elevation gain: 1,551 feet / 473 meters
Accommodations: Villa Svetoni or La Bandita Townhouse - Day 2
Cooking and Cortona
Cycling from our hotel, we’ll make our way across the Val di Chiana, home of Tuscany’s famed white Chianina cows. Cypress trees, sunflowers, apple orchards, and wheat fields line our route as we pedal deep into the countryside. Learn how to make fresh pasta during a stop for lunch at our friend Barbara’s local farmhouse; our meal will feature fresh, seasonal ingredients straight from the farmhouse’s very own garden. We’ll leave feeling part of the family. Opt to ride or transfer to our next luxurious villa hotel. This evening we’ll head into Cortona, an ancient hill town with Etruscan walls and a medieval core. Wander the streets, take in the gorgeous views of the valley below, and explore the bustling artisanal shops before dinner at a local restaurant we love.
Meals: Breakfast / Lunch / Dinner
Destinations: Val di Chiana, Foiano, Cortona
Accomplished: 22 miles / 36 km, elevation gain: 997 feet / 304 meters
Longer Option: 29 miles / 46 km, elevation gain: 1,994 feet / 608 meters
Accommodations: Il Falconiere Relais - Day 3
Lake Trasimeno
Pedal from Cortona through the olive groves to the blue waters of Lake Trasimeno, site of one of Hannibal’s greatest victories over the Romans. Sample some of Tuscany’s top wines during a tasting lunch at a historic winery dating back to 1385. Afterwards, complete the bike loop back to the hotel or opt for a quick shuttle back to relax and enjoy the pool and spa. This evening we’ll end our journey in style with a final dinner at the hotel’s Michelin-starred restaurant.
Meals: Breakfast / Lunch / Dinner
Destinations: Lake Trasimeno, Petrignano, Barullo
Accomplished: 21 miles / 34 km, elevation gain: 1,335 feet / 407 meters
Longer Option: 34 miles / 55 km, elevation gain: 1,955 feet / 596 meters
Accommodations: Il Falconiere Relais - Day 4
Arrivederci
Say goodbye to Tuscany however you see fit. Sleep in, challenge yourself with an optional morning loop ride, or enjoy a leisurely breakfast on the terrace. Your guides will see you off from the train station in Cortona.
Meals: Breakfast
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: Camucia-Cortona Train Station Drop-Off Time: 12:00 pm
Arrival and departure details for 2025 + 2026 tours may be subject to change.
Dates + Availability
Confirm the hotels on your desired date by speaking with a Travel Specialist.
Single Supplement From: $1,000
- DatesPriceSpecial Events
- Apr 21 – 24$4,095
- Apr 28 – May 1$4,095
- May 5 – 8$4,095
- May 12 – 15$4,095
- May 20 – 23$4,095
- May 27 – 30$4,095
- Jun 24 – 27$4,095
- Sep 8 – 11$4,095
- Sep 15 – 18$4,095
- Sep 22 – 25$4,095
- Sep 29 – Oct 2$4,095
- Oct 6 – 9$4,095
- Oct 13 – 16$4,095
- Oct 20 – 23$4,095
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
- 3 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
