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Italy Biking: Tuscany

9 days  |  11 days with Florence extension  |  Loading prices

Equipment
Group size
6–16 travelers

A ride to remember through Tuscan wine country

Get ready to live out your Italian cycling fantasies on the ultimate trip through Tuscany. With five days of stunning rides—including sections of the historic Via Francigena, an ancient route that’s connected Canterbury to Rome for over 1,000 years—you know you’re in for quite the adventure. You'll cruise through picturesque pastures and hillsides in the Val d'Orcia region, ride to wine tastings at vineyards in Chianti, and conquer tough—yet rewarding—climbs around San Gimignano. Along the way, numerous medieval towns and walled cities await, as well as food so spectacular, it’s what put Tuscany on the map as a culinary hotspot. This is the land of pecorino cheese and pappa al pomodoro (Tuscan tomato and bread soup), after all. We’ve got all the gear and professional cyclist-curated routes waiting—all you need to do is take the plunge and jet over to Tuscany.

Special departures

What's included

  • 7 nights in handpicked hotels
  • Private local transfers
  • Support van for bike rides
  • 7 breakfasts
  • 2 lunches
  • 4 dinners with beer or wine
  • 1 coffee tasting, 1 pasta tasting, 1 ricciarelli tasting & 2 wine tastings
  • Two expert European Tour Directors/bike guides
  • Choice between performance road bike and e-touring bike (Road racing bike and e-road bike available for a fee)
  • Helmets, GPS tracking devices, and other biking equipment
  • 5 days of guided bike ride options through Tuscany
  • Select guided sightseeing tours

Why you'll love it

  • Pedal through Val d’Orcia’s wine country en route to a pasta factory for a tour and lunch
  • Conquer steep hills and descents on a scenic loop to Montalcino
  • Tour a Chianti estate's cellars and vineyards, then enjoy an elegant wine-paired dinner
  • Bike to Radda in Chianti, heart of the renowned Chianti Classico wine zone
  • Savor local cuisine at dinner in hilltop San Gimignano, where medieval meets magical
  • Tackle a challenging ride to the walled town of Monteriggioni

Itinerary

Overnight flight

Day 1: Fly to Florence

Your action-packed trip is about to kick off! Head to the airport and board your overnight flight to Italy.

Val d'Orcia region

Day 2: Arrival in Florence and transfer to Val d’Orcia region

Included meal: Welcome dinner

After landing in Florence, you’ll set off to your first region of the trip: Val d’Orcia, known for its characteristic green hillsides blanketed with vineyards and olive groves. Named after the Orcia river running throughout the region, Val d’Orcia is a heavily photographed stretch of Tuscany thanks to its typical medieval villages like Pienza and Montalcino. Try to get some sleep tonight—the adventure starts bright and early tomorrow.

Today’s highlights
  • Meet an EF representative at the airport.
  • Transfer 1–1.5 hours to your hotel in the Val d’Orcia region to check in and settle into Italian time.
  • Get fitted for your bike and gear up with the appropriate equipment.
  • Raise a glass of beer or wine during a meet-and-greet with your fellow bikers during a Welcome Orientation with your Tour Directors.
  • Get your first taste of Tuscan cuisine at a Welcome Dinner nearby.

Note: Airport transfers are included for travelers who book flights with EF Adventures. If you book your own flights, airport transfers may be available for a fee upon request.

Florence extension

Arrive early and give yourself two nights in Florence before the biking begins. The capital of Tuscany is a culinary and art mecca that's home to masterpieces like Michelangelo's David sculpture. While the city can seem like a living museum, there's plenty to do when you're ready for an art break—from browsing the Mercato Centrale food hall to sampling the city's best gelato and traditional Florentine desserts like zuccotto, a semi-frozen, dome-shaped cake. It's not a bad way to shake off jet lag before the biking begins.

Overnight flight

Day 1: Fly to Florence

Your adventure starts before the main tour does. Head to the airport and board your flight to Florence—two days in one of Italy’s most storied cities await before the biking begins.

Florence

Day 2: Arrival in Florence

Touch down in Florence and transfer to your hotel in the city center. The evening is yours—settle in with a welcome drink at the hotel or a nearby bar, then set out to explore Florence at your own pace.

Today’s highlights
  • Transfer 30–60 minutes from the Florence airport to your hotel in the city center.
  • Enjoy a welcome drink at the hotel with your fellow travelers.
  • Spend the evening exploring Florence on your own.

Day 3: Florence walking tour & optional visit to Pitti Palace & Boboli Gardens

Included meals: Breakfast, Tasting

Join a local guide for a walking tour of the city’s greatest hits—the Duomo, Ponte Vecchio, the Uffizi Gallery courtyard, and Piazza della Signoria—ending with a gelato tasting that’s as much a Florence tradition as anything else you’ll see. If you’d like, join the optional afternoon visit to the Pitti Palace and Boboli Gardens, the Medici family’s 16th-century residence-turned-art museum, where Renaissance and Baroque masterworks by Raphael, Titian, and Caravaggio line the walls before the gardens open up into sweeping views over the city.

Today’s highlights
  • Meet your local guide for a walking tour of Florence, taking in the Duomo, Ponte Vecchio, Uffizi Gallery courtyard, and Piazza della Signoria.
  • Sample gelato at the end of the tour—a well-earned reward for all that cobblestone walking.
  • Opt to join a visit to the Pitti Palace and Boboli Gardens for an afternoon of Renaissance art and sweeping city views—or stay back and enjoy more of Florence on your own.

Day 4: Travel to Val d’Orcia region

Included meals: Breakfast, Welcome dinner

Your time in Florence has been short and sweet. Cross off any final bucket list items in the early morning before meeting the rest of your group en route to the Val d’Orcia region—where the riding begins tomorrow. 

Today’s highlights
  • Join the rest of your group en route to the Val d’Orcia region.
  • Raise a glass of beer or wine during a meet-and-greet with your fellow bikers during a Welcome Orientation with your Tour Directors.
  • Get a taste of Tuscan cuisine at a Welcome Dinner nearby.

Note: While today is officially Day 4 of your pre-extension, when you meet up with the rest of the Tuscany Biking group, they will be on Day 2. For consistency, once you join the group, you will also be on Day 2.

Handpicked accommodations

From boutique hotels to 5-star luxury retreats, our accommodations are curated with the expert eye and attention to detail that come from 60 years of travel experience, always prioritizing authenticity. We select high-quality properties that balance comfort, location, sustainability, and local charm. From bustling city centers to serene countryside and picturesque small towns, each hotel is chosen to complement your adventure’s unique style. While the specific accommodations may vary based on your travel dates, you can always count on staying at fantastic properties that meet our standards for quality and character.

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Val d'Orcia region - Albergo le Terme

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Rustic spa room with stone walls, lounge chairs, and a large window overlooking a lush garden. Soft lighting creates a tranquil atmosphere.

Chianti region - Villa Campomaggio

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Outdoor pool area with a central fire pit surrounded by red chairs. Lush greenery and umbrellas in the background create a serene atmosphere.

San Gimignano region - Borgo San Luigi

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Elegant hotel room with a large bed, warm lighting, abstract wall art, desk, and window with heavy curtains. A robe and towels are on the bed.

Florence - Grand Hotel Adriatico (Pre-Extension)

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Customize with excursions

Enhance your experience with hand-picked optional excursions—designed to add adventure, culture, and unforgettable moments to your journey.

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Equipment

We've partnered with EF Pro Cycling and Cannondale to offer four exceptional Cannondale bikes for you to choose from. You'll be able to select your preferred bike in your online account after you book.

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Flights

Round-trip flights are one more thing we handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate, thanks to our partnerships with top airlines.

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  • Flexible rebooking options if your tour itinerary changes

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Weather

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Monteriggioni, Italy

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Temperature scale

48°51°57°64°70°81°88°88°78°68°57°50°35°37°39°45°50°59°64°64°57°51°44°38°48°51°57°64°70°81°88°88°78°68°57°50°35°37°39°45°50°59°64°64°57°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Greve, Italy

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48°52°58°65°71°82°88°88°78°68°58°50°36°37°40°45°50°58°64°64°58°51°44°38°48°52°58°65°71°82°88°88°78°68°58°50°36°37°40°45°50°58°64°64°58°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Siena, Italy

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Temperature scale

48°51°57°64°70°81°88°88°78°68°57°50°35°37°39°45°50°59°64°64°57°51°44°38°48°51°57°64°70°81°88°88°78°68°57°50°35°37°39°45°50°59°64°64°57°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Montalcino, Italy

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Temperature scale

46°49°54°61°67°78°85°85°75°66°56°49°34°35°38°43°48°57°63°63°56°50°43°37°46°49°54°61°67°78°85°85°75°66°56°49°34°35°38°43°48°57°63°63°56°50°43°37°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

San Gimignano, Italy

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Temperature scale

48°52°58°65°71°82°88°88°78°68°57°49°36°37°41°46°51°60°65°65°58°51°44°38°48°52°58°65°71°82°88°88°78°68°57°49°36°37°41°46°51°60°65°65°58°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Florence, Italy

Weather averages

Temperature scale

48°52°58°65°71°82°88°88°78°68°58°50°36°37°40°45°50°58°64°64°58°51°44°38°48°52°58°65°71°82°88°88°78°68°58°50°36°37°40°45°50°58°64°64°58°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND
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Round-trip flights are one more thing we can handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate. Rates shown in cart.