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Super Tuscan: The Finest of the Region

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Take in the very best wine, food, scenery, people--everything magnificent Tuscany has to offer on this stellar small group biking trip. Choose an E-bike if it adds to your pleasure!

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Italy: Drink It In

Our Super Tuscan has been finely crafted for the traveler who delights in truly exquisite accommodation, exceptional wine and wants to suss out the idyllic countryside through a well-structured blend of activity—pedaling past hilltop hamlets, ambling among vines tended by generations of winemakers and (optionally!) rising to salute the famous Tuscan sun on a yoga mat. In between you’ll savor traditional cuisine made from the freshest ingredients. It’s a robust build. Fancy a taste? (E-bikes available.)
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Travel Curator’s Insights:

    • Optional yoga classes available every morning in the rising Tuscan sun. Start your beautiful day on the mat!
    • Discover stunning wilderness plus abandoned medieval forts and abbeys as you peddle across the Val di Merse and its nature reserves.
    • End each day in stylish 5-star accommodations sampling the tastes Tuscany is famous for. This operator is passionate about offering you the very best of the best.


From $9,695 per person
Policies and protocols provided before you book.

Oct 6-11, 2024
May 11-16, 2025
June 1-6, 2025
June 22-27, 2025
Sept 14-19, 2025
Sept 28 - Oct 3, 2025
Oct 12-17, 2025

Ask us about later dates or custom dates.

April, May, June & September
Hover here for specific dates


Trip Sustainability Awards 



Fantastic advances in minimizing carbon footprints at locations.



On the East African Energy Renewal Board



Runs local educational facilities for children.


Day 1: Chianti Classico

Meet your guides in Florence and then head straight to the heart of the Chianti Classico region! Ride through gently rolling hills and breathtaking scenery arriving to a stunning lunch.

Accommodation: Belmond Castello Di Casole, Casole d'Elsa

Belmond Castello Di Casole: Like a postcard from another time, Belmond's Castello di Casole places you in the heart of rural Italy. With delightful interior detailing--wood beamed ceilings, reclaimed antiques, stone walls--the hotel artfully blends comfort with historic charm. When tasked with restoring the property, the overarching theme was clear: honor the natural wonders of the hotel and the iconic countryside. Arriving to the main building via the grand cypress-lined lane re-enforces the message; this hotel is timeless.

Day 2: Chianti Classico

Join an optional sunrise yoga class before a morning walk through finely curated vineyards arriving to an intimate farm and winery tucked into the hills. The in-house chef teaches us a few tricks of the Italian pizza-making trade.

Accommodation: Belmond Castello Di Casole, Casole d'Elsa


Day 3: Montalcino

Consider morning yoga or initiate the day by bike leaving directly from the hotel and down toward the open countryside. Tonight, an energetic historian gives us an overview of Tuscany's historical significance, with a splash of politics.

Accommodation: Rosewood Casriglion del Bosco, Montalcino

Rosewood Casriglion del Bosco: Simply stunning and overlooking a quiet corner of Tuscany's Montalcino area, the beautifully restored 800-year-old Tuscan estate boasts Brunello di Montalcino winery, two restaurants, a spa and more on its 4000-plus acres. The stylish touch of Massimo Ferragamo and his wife Chiara is apparent in all aspects of the design and layout of the property ensuring an elegant yet authentically Tuscan experience.

Day 4: Montalcino

Leave directly from the hotel pedaling through the crete, part of the expansive Val di Merse and one of the most stunning rides on the trip. Pause for a gourmet picnic courtesy of a local friend then return to the hotel to take advantage of the exceptional spa.

Accommodation: Rosewood Casriglion del Bosco, Montalcino

Day 5: Tavernelle Val di Pesa

Today's walk is pure heaven as you cruise through the Sienese countryside. On return, an al fresco feast awaits. This evening you'll explore an exclusive winery on a hillside overlooking Montalcino. Salute!

Accommodation: COMO Castello Del Nero, Tavernelle Val di Pesa

COMO Castello Del Ner: With 740 acres shored up around it, Castello del Nero is an enchanting vestige of the 12thC recently refreshed to perfectly suit the au courant travel set. Featuring 50 intimate rooms and suites, a Michelin-starred restaurant, an extensive wine cellar and numerous amenities--you'll experience the best of antiquity and modernity.


Day 6: Florence, Depart

Enjoy a final breakfast at the hotel before the drive to the Florence train station. Buon Viaggo!

Activity Level: Active. You will cover hilly terrain, but this operator has kept the average daily distance to a moderate 40 km (25 miles). As much as possible, the recommended routes avoid the steepest climbs, but please be aware that Tuscany is hilly! E-bikes also available.


Custom Road Bike: High Performance | Drop Bar

Custom-designed in partnership with this operator, this bike features sporty geometry with an aluminum frame and carbon fork, as well as powerful disc brakes, making it perfect for flats and hills alike. The bike is comfortable, lightweight and equipped with top-end Shimano Ultegra components.

Who is this bike for? This bike is a great option for intermediate to experienced riders with good cycling and fitness levels. The sporty positioning and drop bars are perfect for the cyclist who prefers to ride fast, climb hills and loves a good challenge. (Connect with your Travel Advisor on recommendations per region.)

Custom Hybrid Bike: The Perfect Touring Bike | Flat Bar

Custom-designed by this operator, the hybrid bike tends to be the most popular choice. The bike performs like a road bike, but offers the comfort and stability of a hybrid—it features the same Shimano Ultegra R8000 group set and brakes as our road bike but offers more relaxed geometry and flat bars. The adjustable stem allows the handlebars to be raised and lowered for the perfect fit, and the ergonomic grip keeps hands comfortable over a long day of riding.

Who is this bike for? This bike is a great option for a recreational to intermediate rider with average cycling and fitness levels. The more upright position and flat handlebars are geared toward the traveller who loves to cycle but also wants to see the sights! If you don’t cycle a road bike regularly, we recommend the hybrid. (Connect with your Travel Advisor on recommendations per region.)

Moustache E-Bike: Electric Assistance Whenever it’s Needed

These e-bikes are regular pedal bikes that provide electric assistance whenever you want it. Designed by French e-bike brand, Moustache Bikes, the new fleet boasts a sporty, road-focused e-bike with skinny tires, a low-step frame and a very efficient e-system. The bike is incredibly light-weight (for an e-bike) and its clever design makes it extremely comfortable to ride.

Who is this bike for? This is a bike that both novice and professional cyclists can enjoy. Generally, though, it's a great option for a recreational to intermediate rider with average cycling and fitness levels, or someone who may be more interested in seeing the sights than squeezing in a workout. The more relaxed positioning and helpful e-system make for a comfortable and versatile ride, while its sporty tires and lightweight frame make it a great option for any traveler at any skill level.

Please Note: Unless you are on an e-bike specific Small Group departure, there will be a modest upgrade fee (US$200).




Image by David Maunsell


Two people traveling in a room together. Rate is per person.

From in USD:


Image by David Maunsell


As a solo traveler, a cost supplement will be added to your trip.

From in USD:


For active people, this creative and much-loved operator is offering off-the-beaten path experiences combined with super decadence. I say go for it!

Joy Martinello, Founder



What’s Included & Cancellation Policy:

Everything you need. Plus everything you’d want. Plus a few things you never knew you wanted ‘til you got them. In a word: everything. In ninety words? Signature guides; local experts; unique, unforgettable biking and walking routes; private tours; authentic local cuisine; lessons and demonstrations; local artisanal wines; wine tastings; all victuals and libations; all the endorphins you can handle; new insight; interesting, fun and like-minded travel companions; a feeling of total freedom. In short: an extraordinary, hassle-free journey of discovery.

• All hotel accommodation
• All breakfasts, 4 lunches and 4 dinners, including local wine
• Services of guide(s)
• Detailed maps, route suggestions and water bottle and walking sticks
• All special events and private tours
• All indicated transportation from rendezvous to drop-off
• All baggage transportation


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