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Stay at the luxury hotel Castello di Casole on a Tuscany luxury bike tour
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22TC-TuscanyReserve-Banner--EDITS-IMG2386-1600X670
Enjoy Toscana wines and local cuisine on a Tuscany bike tour
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Trek Travel Tuscany, Italy Luxury Cycling Vacation
Stay at the luxury hotel Castello di Casole on a Tuscany luxury bike tour
22TC-TuscanyReserve-16BO0821_ChelseaMurray042-1600X670
21TCL-HOTELBorgoSanFelice3-1600X670
Trek Travel Tuscany, Italy Luxury Cycling Vacation
Stay at the luxury hotel Castello di Casole on a Tuscany luxury bike tour 21TCL-HOTELBorgoSanFelice-1600X670 22TC-TuscanyReserve-Banner--EDITS-IMG2386-1600X670 Enjoy Toscana wines and local cuisine on a Tuscany bike tour 21TCL-Siena3-CANVA-1600X670 Trek Travel Tuscany, Italy Luxury Cycling Vacation Stay at the luxury hotel Castello di Casole on a Tuscany luxury bike tour 22TC-TuscanyReserve-16BO0821_ChelseaMurray042-1600X670 21TCL-HOTELBorgoSanFelice3-1600X670 Trek Travel Tuscany, Italy Luxury Cycling Vacation

Tuscany Wine Country Bike Tour

Quintessential Luxury of Chianti’s Famous Castles and Wines


Book now to guarantee the best prices and your preferred dates before September 27th!

Allegria. This is how Italians describe the feelings of contentment and joy that sweep over them when something is just perfect, and it's in no short supply in Tuscany. If you can imagine your perfect luxurious bike tour in Tuscany, then you’ve pictured traveling to Italy with us. We’ve scoured every olive grove, vineyard, and sun-drenched landscape to bring you the best this region has to offer. Here you'll savor the revered wines and intimate hospitality of the Mascheroni Stianti family at their private Castello di Volpaia wine estate. You’ll feast on exquisite Michelin-starred Tuscan cuisine and perfect your pizza spin with our expert pizzaiolo at a private cooking class. And all while resting your head each night in hidden hotels known for centuries and now are the pinnacle of luxury. Every detail has been planned, down to the last chocolate on your pillow before turn down. Every moment is magical, from the fiery sunrise peeking above the trees to the last sip of Chianti straight from the vineyards right in your backyard. It’s more than just the ultimate Tuscany bike and wine tour, it's a revelation on what allegria truly can be. Book your trip with confidence » Learn more about a Perfect Day on our Tuscany Wine Country Bike Tour»
From:
$6799 Per Person
Duration:
6 Days & 5 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Reserve
Hotel Level: ?
Ultimate Luxury
From $6799 per person View All Details
Trip Wows
Toast the day from Travel + Leisure’s #1 European hotel resort Belmond Castello di Casole, on a sprawling 4,200 acres
Enjoy your spectacular 5-star hotel, Borgo San Felice or Castel Monastero — Medieval hamlets that have been transformed into the ultimate in luxury properties.
Visit San Gimignano, where you’ll be met with vibrant colors, sights, and sounds of the open-air market
Experience an intimate gathering with the Mascheroni Stianti family at a gourmet lunch paired with an exquisite wine tasting at their hidden estate, Castello di Volpaia
Take part in a private pizza-making class and sip local wines with perfect dessert pairings
Tuscany Wine Country Bike Tour
Another spectacular adventure! After an incredible trip to Napa with Trek Travel, we were excited to explore yet another amazing area with you. Tuscany was absolutely awesome, and we are already debating where we should go with Trek Travel next. Thanks for all that you do – we can’t imagine anyone doing it better.
-Melissa, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price is guaranteed.
Guaranteed 
to run
?
Sold Out/
Waitlist
?
Private/
Reserved
?
Limited 
Availability
?

Single Occupancy from: +$3100
Single Occupancy from: +$2599
?
Sep 24 – Sep 29 
Guaranteed Limited Availability
$7399 / Person, Double Occupancy / Hotel Variation: Castel Monastero Book this date
May 19 – May 24 
$6799 / Person, Double Occupancy Book this date
May 26 – May 31 
$6899 / Person, Double Occupancy Book this date
Jun 2 – Jun 7 
Guaranteed
$7299 / Person, Double Occupancy Book this date
Sep 22 – Sep 27 
Guaranteed Limited Availability
$7699 / Person, Double Occupancy Book this date
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*


Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Your Trek Travel guides will meet you at the Hotel Montebello Splendid at 11:00 AM on the first day of your luxury bike tour in Tuscany. After a one-hour shuttle, you will arrive at the quiet and historic Badia a Coltibuono, or "Abbey of the Good Harvest," to have a delicious local lunch with stunning views of the Chianti hills. Your Trek Travel guides will then spend some time familiarizing you with your Trek bicycle and ensuring you have an excellent fit. A warm up ride will take you along picturesque, winding roads through woodlands and ancient olive groves, before you make your way to the small, quintessential village of San Felice, magically transformed into a lavish hotel, where you will be hosted for the next three nights. This evening, you'll enjoy a warm welcome to your Tuscany Wine Country bike tour as we gather for drinks on the terrace overlooking the hotel's own Sangiovese vineyards before enjoying the first of many exquisite meals together, this one expertly prepared at the hotel's convivial osteria.

Today's Ride:

La Badia di Coltibuono to San Felice
Approximately 14 mi | 22 km and 1,250 ft | 381 m

Hotel:

Borgo San Felice

Included Meals:

Lunch | Social Hour | Dinner

Following a relaxing breakfast, this morning you’ll cruise through the Chianti vineyards where you'll be rewarded by rich panoramic views of rolling, sun-drenched Tuscan hills. Choose to stop and explore the Castello di Brolio, the oldest castle and winery in the area, which has belonged to the Ricasoli family for nearly 800 years. Stop for an espresso at their Eroica Caffè, named after L’Eroica, the local cycling event on the strade bianche with contestants riding vintage bikes in full vintage regalia. Then choose to climb up into the hills to Monteluco, one of the highest points in Chianti, or continue on to the quaint village of Villa a Sesta, our lunch destination. Enjoy true Tuscan hospitality as you savor the cuisine of Osteria alla Villa, a small bistro that serves up fresh and creative dishes. This afternoon indulge yourself with some free time at the hotel; enjoy their restorative spa or lounge by the pool with an Aperol spritz in hand. This evening, an exquisite Michelin-starred dinner awaits you at Poggio Rosso. Surrender your taste buds to the innovative cuisine of our Chef Juan Camilo Quintero who prides himself on crafting gourmet cuisine from all locally sourced ingredients, harmoniously paired with the hotel’s best vintages from their own vineyards.

Please note: For guests staying at the Castel Monastero hotel variation, dinner will be at the celebrated La Bottega del 30, a restaurant nestled in the heart of Chianti that has held a Michelin star for over 25 years.

Today's Ride:

San Felice to Villa Sesta Loop
Approximately 29 mi | 46 km and 2,800 ft | 853 m

Short Option:

San Felice to Castello di Brolio Loop
Approximately 21 mi | 33 km and 2,050 ft | 624 m

Avid Option:

San Felice to Monteluco to Villa Sesta Loop
Approximately 38 mi | 61 km and 4,100 ft | 1,249 m

Hotel:

Borgo San Felice

Included Meals:

Breakfast | Lunch | Dinner

Slowly awaken in your opulent surroundings to another perfect day in Tuscany! Today’s ride traverses the forested hills and olive groves of the celebrated Chianti region. Pedal through the village of Lecchi and enjoy an espresso with the locals before continuing up to Radda, the ancient capital of the League of Chianti. Take time to explore this vibrant village, filled with art galleries, gourmet food and wine shops—the perfect place to pick up some mementos to take home. Your midday destination is Castello di Volpaia, where the Mascheroni Stianti family personally welcomes you for a spectacular wine-paired lunch in their villa. Afterward, enjoy an exclusive visit of the castle’s cellars and olive oil press. From here, shuttle back to our hotel for a dip in the pool or hop back on your bike to return through the rolling vineyards. This evening, we’ll shuttle into the medieval town of Siena where you'll learn the secrets of this historic city from our local guide and see the world-famous Duomo and the Piazza del Campo. Afterward, we’ll wander the cobbled streets as an array of Tuscan specialties unfold before our eyes, to arrive at tonight’s spectacular trattoria. Surrender your tastebuds to culinary favorites like wood-fired pizza or a bowl of cinghiale (wild boar) pasta accompanied by a glass of the finest Brunello and we’ll be sure to finish our fabulous day with a world-class gelato!

Today's Ride:

San Felice to Volpaia with Shuttle
Approximately 18 mi | 29 km and 2,600 ft | 792 m

Short Option:

San Felice to Lecchi with Shuttle
Approximately 8 mi | 12 km and 900 ft | 274 m

Avid Option:

San Felice to Volpaia Loop
Approximately 33 mi | 53 km and 3,850 ft | 1,173 m

Hotel:

Borgo San Felice

Included Meals:

Breakfast | Lunch | Dinner

The breathtaking Elsa Valley awaits you today. The quiet roads offer rich, colorful vistas of golden hills dappled with silver olive groves, framed by dark green cypress trees. After a beautiful morning ride descending from the hills of Chianti, you will pedal on quiet country lanes and observe a landscape change as we journey to the stunning 5-star Castello di Casole. This incomparably resplendent hotel is one of Italy's most impressive destination hotels—and formerly an estate to the 10th-century nobility. Along the way, you’ll pause to enjoy a farm to table picnic lunch, featuring hand-cured prosciutto and local cheeses accompanied by delicious Frantoio olive oil. Afterward, choose to climb up to the medieval village of Simignano or pedal directly to your castle hotel to relax with a cocktail on the hotel terrace and enjoy the spectacular views over timeless Tuscan scenery. Tonight, enjoy a private pizza-making class, where you'll learn how to spin your own pizza dough and make the pie of your choice with a trained pizzaiolo!

Today's Ride:

San Felice to Castello di Casole
Approximately 42 mi | 67 km and 3,200 ft | 975 m

Short Option:

San Felice to Scorgiano
Approximately 35 mi | 56 km and 2,700 ft | 822 m

Avid Option:

San Felice to Castello di Casole with Simignano Climb
Approximately 50 mi | 80 km and 4,200 ft | 1,280 m

Hotel:

Belmond Castello di Casole

Included Meals:

Breakfast | Lunch | Dinner

It's pure extravagance to awake at Castello di Casole, and after a leisurely breakfast, you'll mount your bike for one last amazing day on the rolling hills of Tuscany. You will start with a descent from the hotel into the valley below, across vine-covered slopes, and up to the medieval town of San Gimignano, where you're welcomed by the vibrant colors, sights, and sounds of the legendary open-air market. Taste fresh regional olives and take a stroll through the stalls of the local artisans before savoring the famous picci pasta at our favorite local osteria. This afternoon, spin back to the hotel to relax by the infinity pool overlooking the gorgeous Elsa Valley. Or, choose one of the many activities available at the hotel including a ceramics lesson or a watercolor class, or indulge yourself at their destination spa. Tonight, you'll savor the trip's final gastronomic delight: a perfectly timed aperitif on the hotel’s panoramic terrace as the sun dips below the horizon, followed by a magnificent meal at the hotel's renowned restaurant, La Tosca. Soak in the magical atmosphere of this elegant retreat and raise your glass to an unforgettable luxury bike tour in Tuscany.

Today's Ride:

Castello di Casole to San Gimignano with Shuttle to Hotel
Approximately 21 mi | 33 km and 2,200 ft | 670 m

Short Option:

Castello di Casole to Castel San Gimignano
Approximately 14 mi | 22 km and 1,300 ft | 396 m

Avid Option:

Castello di Casole to San Gimignano Return
Approximately 42 mi | 67 km and 4,500 ft | 1,371 m

Hotel:

Belmond Castello di Casole

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

While by now this region is surely starting to feel like home, this morning you'll arise early for a final bike loop through the Tuscan countryside as the sunrise washes over the captivating Elsa Valley. If you’d rather, simply linger over a hot cappuccino and enjoy a leisurely morning soaking in the gorgeous views from the breakfast patio before you bid your farewells and board a private shuttle, taking you to Florence and further adventures.

Today's Ride:

Castello di Casole to Mensano Loop
Approximately 15 mi | 24 km and 1,400 ft | 426 m

Included Meals:

Breakfast

Your Trek Travel guides will meet you at the Hotel Montebello Splendid at 11:00 AM on the first day of your luxury bike tour in Tuscany. After a one-hour shuttle, you will arrive at the quiet and historic Badia a Coltibuono, or "Abbey of the Good Harvest," to have a delicious local lunch with stunning views of the Chianti hills. Your Trek Travel guides will then spend some time familiarizing you with your Trek bicycle and ensuring you have an excellent fit. A warmup ride will take you along picturesque, winding roads through woodlands and ancient olive groves, before you make your way to the medieval Castel Monastero, magically transformed into a lavish hotel, where you will be hosted for the next three nights. This evening, you'll enjoy a warm welcome to your Tuscany Wine Country bike tour as we gather for drinks on the terrace overlooking Tuscan vineyards before enjoying the first of many exquisite meals together, this one expertly prepared at the hotel's convivial osteria, La Cantina.

Today's Ride:

La Badia di Coltibuono to Monastero
Approximately 24 mi | 39 km and 1,825 ft | 559 m

Hotel:

Castel Monastero

Included Meals:

Lunch | Social Hour | Dinner

Following a relaxing breakfast, this morning you’ll cruise through the Chianti vineyards where you'll be rewarded by rich panoramic views of rolling, sun-drenched Tuscan hills. Choose to stop and explore the Castello di Brolio, the oldest castle and winery in the area, which has belonged to the Ricasoli family for nearly 800 years. Stop for an espresso at their Eroica Caffè, named after L’Eroica, the local cycling event on the strade bianche with contestants riding vintage bikes in full vintage regalia. Then choose to climb up into the hills to Monteluco, one of the highest points in Chianti, or continue on to the quaint village of Villa a Sesta, our lunch destination. Enjoy true Tuscan hospitality as you savor the cuisine of Osteria alla Villa, a small bistro that serves up fresh and creative dishes. This afternoon indulge yourself with some free time at the hotel; enjoy their restorative spa or lounge by the pool with an Aperol Spritz in hand. This evening, an exquisite Michelin-starred dinner awaits you at be at the celebrated La Bottega del 30, a restaurant nestled in the heart of Chianti that has held a Michelin star for over 25 years.

Today's Ride:

Monastero to Castello di Brolio Loop
Approximately 37 mi | 60 km and 2,910 ft | 888 m

Short Option:

Monastero to Castello di Brolio with Shuttle
Approximately 31 mi | 50 km and 2,220 ft | 860 m

Avid Option:

Monastero to Monteluco Loop
Approximately 40 mi | 65 km and 3,350 ft | 1,021 m

Hotel:

Castel Monastero

Included Meals:

Breakfast | Lunch | Dinner

Slowly awaken in your opulent surroundings to another perfect day in Tuscany! Today’s ride traverses the forested hills and olive groves of the celebrated Chianti region. Pedal through the village of Lecchi and enjoy an espresso with the locals before continuing up to Radda, the ancient capital of the League of Chianti. Take time to explore this vibrant village, filled with art galleries, gourmet food and wine shops—the perfect place to pick up some mementos to take home. Your midday destination is Castello di Volpaia, where the Mascheroni Stianti family personally welcomes you for a spectacular wine-paired lunch in their villa. Afterward, enjoy an exclusive visit of the castle’s cellars and olive oil press. From here, shuttle back to our hotel for a dip in the pool or hop back on your bike to return through the rolling vineyards. This evening, we’ll shuttle into the medieval town of Siena where you'll learn the secrets of this historic city from our local guide and see the world-famous Duomo and the Piazza del Campo. Afterward, we’ll wander the cobbled streets as an array of Tuscan specialties unfold before our eyes, to arrive at tonight’s spectacular trattoria. Surrender your tastebuds to culinary favorites like wood-fired pizza or a bowl of cinghiale (wild boar) pasta accompanied by a glass of the finest Brunello and we’ll be sure to finish our fabulous day with a world-class gelato!

Today's Ride:

Monastero to Volpaia with Shuttle
Approximately 29 mi | 46 km and 3,553 ft | 1,083 m

Short Option:

Monastero to Radda with Shuttle
Approximately 23 mi | 38 km and 900 ft | 274 m

Avid Option:

Monastero to Volpaia Loop
Approximately 53 mi | 86 km and 5,341 ft | 1,628 m

Hotel:

Castel Monastero

Included Meals:

Breakfast | Lunch | Dinner

The breathtaking Elsa Valley awaits you today. The quiet roads offer rich, colorful vistas of golden hills dappled with silver olive groves, framed by dark green cypress trees. After a beautiful morning ride descending from the hills of Chianti, you will pedal on quiet country lanes and observe a landscape change as we journey to the stunning 5-star Castello di Casole. This incomparably resplendent hotel is one of Italy's most impressive destination hotels—and formerly an estate to the 10th-century nobility. Along the way, you’ll pause to enjoy a farm to table picnic lunch, featuring hand-cured prosciutto and local cheeses accompanied by delicious Frantoio olive oil. Afterward, choose to climb up to the medieval village of Simignano or pedal directly to your castle hotel to relax with a cocktail on the hotel terrace and enjoy the spectacular views over timeless Tuscan scenery. Tonight, enjoy a private pizza-making class, where you'll learn how to spin your own pizza dough and make the pie of your choice with a trained pizzaiolo!

Today's Ride:

Monastero to Castello di Casole
Approximately 41 mi | 66 km and 3,860 ft | 1,175 m

Short Option:

Monastero to Scorgiano
Approximately 34 mi | 55 km and 3,510 ft | 1,070 m

Avid Option:

Monastero to Castello di Casole with Simignano Climb
Approximately 50 mi | 80 km and 4,200 ft | 1,280 m

Hotel:

Belmond Castello di Casole

Included Meals:

Breakfast | Lunch | Dinner

It's pure extravagance to awake at Castello di Casole, and after a leisurely breakfast, you'll mount your bike for one last amazing day on the rolling hills of Tuscany. You will start with a descent from the hotel into the valley below, across vine-covered slopes, and up to the medieval town of San Gimignano, where you're welcomed by the vibrant colors, sights, and sounds of the legendary open-air market. Taste fresh regional olives and take a stroll through the stalls of the local artisans before savoring the famous picci pasta at our favorite local osteria. This afternoon, spin back to the hotel to relax by the infinity pool overlooking the gorgeous Elsa Valley. Or, choose one of the many activities available at the hotel including a ceramics lesson or a watercolor class, or indulge yourself at their destination spa. Tonight, you'll savor the trip's final gastronomic delight: a perfectly timed aperitif on the hotel’s panoramic terrace as the sun dips below the horizon, followed by a magnificent meal at the hotel's renowned restaurant, La Tosca. Soak in the magical atmosphere of this elegant retreat and raise your glass to an unforgettable luxury bike tour in Tuscany.

Today's Ride:

Castello di Casole to San Gimignano with Shuttle to Hotel
Approximately 21 mi | 33 km and 2,200 ft | 670 m

Short Option:

Castello di Casole to Castel San Gimignano
Approximately 14 mi | 22 km and 1,300 ft | 396 m

Avid Option:

Castello di Casole to San Gimignano Return
Approximately 42 mi | 67 km and 4,500 ft | 1,371 m

Hotel:

Belmond Castello di Casole

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

While by now this region is surely starting to feel like home, this morning you'll arise early for a final bike loop through the Tuscan countryside as the sunrise washes over the captivating Elsa Valley. If you’d rather, simply linger over a hot cappuccino and enjoy a leisurely morning soaking in the gorgeous views from the breakfast patio before you bid your farewells and board a private shuttle, taking you to Florence and further adventures.

Today's Ride:

Castello di Casole to Mensano Loop
Approximately 15 mi | 24 km and 1,400 ft | 426 m

Included Meals:

Breakfast

Hotels

hotel image

Borgo San Felice

San Felice, Italy

Relais & Chateaux Logo Ultimate Luxury Accommodation | This medieval Tuscan village, complete with its own chapel and medicinal herb garden, has been beautifully transformed into an elegant 5-star hotel and is surrounded by its own vineyards. A member of the acclaimed Relais & Châteaux group, luxury abounds at every turn. From refined suites that combine the charm of historical dwellings with a taste for contemporary design and amenities, to the Michelin-starred restaurant using only locally sourced ingredients, you will enjoy all the attention to the finest details. Perfectly situated in the heart of Chianti, this sumptuous hotel defines Tuscan luxury.
hotel image

Belmond Castello di Casole

Casole D'elsa, Italy

Stay at Belmond Castello di Casole on a Tuscany luxury bike tour Ultimate Luxury Accommodation | Part of the exclusive Belmond group and ranked the #1 Resort in Europe by Travel + Leisure magazine, Castello di Casole is a beautifully restored castle set on a 4,200-acre private estate. This five-star boutique hotel boasts an incredible destination spa, both gourmet and relaxed dining, and exquisite suite accommodations that effortlessly combine Old World Tuscan charm with modern luxuries.
hotel image

Hotel Variation | Castel Monastero

Castel Monastero d'Ombrone, Italy

Leading Hotels of the World Logo Ultimate Luxury Accommodation | Castel Monastero is a beautifully restored medieval village and monastery that is nestled among Chianti vineyards and chestnut forests. This truly luxurious Tuscan retreat exudes a feeling of simple refinement and pure elegance. Tantalize your tastebuds at one of their two gourmet restaurants and don’t forget to stop in at the wine bar to sample the most famous labels of Tuscan wines. At the harmonious Renaissance spa, you will enjoy a haven of 5-star service and attention to detail. Please note: You will stay at Castel Monastero instead of Borgo San Felice on select dates in 2023. For all dates in 2024, this is your first hotel.

What's Included

For us, the details matter most

Every moment of your Trek Travel luxury bike tour in Tuscany has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.

bike

Trek Domane SL 7

Experiencing your cycling vacation of a lifetime is not complete without a world-class bike and the Trek Domane is the best way to enjoy the ride. Trek Bikes has launched the all-new Trek Domane and now you can ride it on our trips. It raises the bar to deliver incredible endurance road bike comfort without sacrificing performance and features highly responsive disc brakes and electronic shifting. This new bike is lighter than ever before, and carbon wheels come standard on every bike. The road-smoothing IsoSpeed technology lets you ride as long as you want with less fatigue. The bike you ride on a biking vacation matters. That is why we provide the newest and best bikes in the business. Learn More

bike

Trek Electric-Assist Domane+ SLR 7

Take the tailwind with you and leave your limits behind on the all-new Domane+ SLR 7. With a groundbreaking ratio of ultra-lightweight design and electric assist, Domane+ SLR 7 has everything you love in a road bike, with the extra boost to take you farther than ever before. This performance e-road bike will help you on the climbs, hang with the fast group, and venture further on your cycling vacation. So go ahead – take the long way. With Domane+ SLR 7, there’s always room for more distance, more speed, and more fun! Upgrade to the Domane+ SLR 7 on this trip for $399 (3-6 day trips) or $599 (7+ day trips). Available in limited quantities. Please contact a Trip Consultant to check availability. Learn More

bike

Trek Electric-Assist Verve+

With its Low-Step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain. Learn More

WHAT'S INCLUDED

  • Five nights of accommodation at handpicked hotels
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support
  • Group size is limited to 16 people (In 2024, group size will be limited to 18)
  • All meals are included
  • Three social hours including beer and wine selection with hors d'oeuvres
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily ride options
  • Snacks and drinks for each day's ride
  • Post-ride refreshments
  • Trek Travel Bontrager cycling jersey, socks, and Trek Travel luggage tag
  • Trek Travel water bottles and cinch sack day bag
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, a flat pack (containing a tube, levers, and a CO2 cartridge with inflator), front and rear Bontrager Flare R lights, a Bontrager saddle, and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals)
  • Bontrager WaveCel helmets
  • All gratuities for drivers, local experts and hospitality staff
  • All luggage transfers and transportation during your trip
  • A digital photo album of your trip
  • Entrance fees for all activities, private tours, and events

GEAR

  • Upgrade your ride to the Trek Electric-Assist Domane+ SLR 7 (+$399, subject to availability)
  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Trek Travel Bontrager cycling jersey, socks, and Trek Travel luggage tag
  • Trek Travel water bottles
  • Cinch sack day bag
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • Garmin Edge 1030 GPS computer
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.

WHAT'S NOT INCLUDED

Guide gratuities are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this trip, we suggest a tip for your guides between $240-$300 per guest and, of course, you may choose to give more if your guides made your trip an unforgettable experience. While local currency is preferred, there are other options to make tipping easier. Most guides accept gratuity via PayPal or our staff can help before or after the trip. Gratuities will be divided among the guide team, so feel free to leave your gratuity with whomever you choose at the end of your trip.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

AVERAGE DAILY MILEAGE:
40 kilometers / 25 miles
TOTAL MILES:
240 kilometers / 150 miles
AVERAGE DAILY ELEVATION:
670 meters / 2,200 feet
TOTAL ELEVATION:
4,084 meters / 13,400 feet
TERRAIN: HILLY
The terrain is consistently rolling, with quiet, narrow, and winding roads. Many towns sit atop hills and, although the ascents are not exceptionally steep, they are often upwards of five kilometers long. Our Tuscany Wine Country bike tour is best suited for our Type 3 Riders. Our Trek Travel guides can also easily accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option—you still get a workout but can climb alongside even the strongest rider. Type 4+ Riders will enjoy the extra mileage the avid route options offer.
NON-RIDING ACTIVITIES:
On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. Some non-riding options on our Tuscany Wine Country bike tour are:
  • Discover why Tuscan wines are so renowned during our private wine-tasting
  • Visit historic Siena
  • Indulge at the Spa
  • Relax by the pool
  • Take part in a private pizza making cooking class
  • Visit to San Gimignano for market day
  • Hot air balloon ride

See itinerary for specific daily ride distances and elevation options. On all of our cycling vacations, Trek Travel seeks to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times, routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our Today’s Ride options.

Travel Details

How to Get There

FLY INTO:
Amerigo Vespucci Airport (FLR)
MEETING TIME:
11:00 AM
MEETING LOCATION:
Hotel Montebello Splendid, Florence, Italy

Say Farewell

FLY OUT OF:
Amerigo Vespucci Airport (FLR)
DEPARTING TIME:
12:30 PM
DEPARTING LOCATION:
Hotel Montebello Splendid, Florence, Italy

Arriving

We suggest that you arrive at least one day prior to the start of your luxury bike tour in Tuscany, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Florence’s Amerigo Vespucci Airport (FLR). The Florence airport is about three miles from the town center. You can take a taxi directly to the hotel (for approximately 20 euros) or a bus which departs hourly.

Rome and Milan also offer flight options. From Rome’s Fiumicino Airport (FCO), you may take a direct train to Rome’s central station, Roma Termini. Follow the “Stazione/Railway Station” signs. Trains depart twice hourly. Tickets can be purchased at a Biglietteria office or from ticket machines. All tickets must be validated before getting on the train: do this by stamping your ticket at the yellow boxes near the platform. The ride takes 30 minutes. From Roma Termini, transfer to a train for Florence. The Eurostar trains depart frequently and are the quickest. The trip takes one and a half hours and costs between 44-62 euros one way per person. In Florence, taxis are available to take you to your hotel. Taxi service is available from Rome Fiumicino Airport to central Rome for approximately 50 euros.

Your Trek Travel guides will meet you at the Hotel Montebello Splendid (Via Giuseppe Garibaldi, 14, 50123 Florence, Italy) at 11:00 AM on the first day of the trip. You’ll then shuttle 90 minutes to your lunch spot for your first taste of delicious Tuscan cuisine. After lunch, your guides will do a bike fitting to ensure your comfort on your Trek Domane this week, before you take your first spin through the countryside. Please have your first day’s riding gear handy and separate from your other luggage to facilitate the bike fitting and ride.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call your first hotel, either Borgo San Felice (+39 0577 3964) or the hotel variation Castel Monastero (+39 0577 570001), and leave a message with your expected arrival time and contact details. You may take a taxi to the first night’s hotel for approximately 200 euros. The trip takes over an hour from the center of Florence.

View our pre hotel recommendations

Leaving

You will say farewell to your guides at 11:00 AM at the Castello di Casole, Casole D'elsa. You’ll depart by private shuttle for Hotel Montebello Splendid, Florence, arriving close to 12:30 PM. The hotel is a 10 minute taxi from Santa Maria Novella train station where trains connect to many European cities. Please do not book seats before 1:30 PM, allowing adequate connection time for any ongoing travel or possible traffic delays. The airport in Florence (FLR) is three miles from the city. You can reach it by train, taxi, or shuttle bus; please do not schedule a flight prior to 4:00 PM. Visit www.TrenItalia.com for train information.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Spring and fall in Tuscany are usually clear and sunny, with warm daytime temperatures (75F-90F/24C-32C) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Summers are hotter with higher daytime temperatures (80F-95F/27C-35C) and evening temperatures 10 degrees cooler. Rain is always a possibility, however, so be prepared with wet-weather gear in order to best enjoy your vacation. Packing List

Before and After Your Trip

before

Before: Florence, Italy

Florence is the majestic heart of Renaissance art and intellect. Several days can be spent wandering the streets in the shadow of Brunelleschi’s Duomo and strolling beside the Arno. Along with the Duomo and Ponte Vecchio, the Uffizi gallery, a pillar of the Renaissance and Medici eras, merits a visit. Michelangeo’s David in the Galleria dell’Arte is not to be missed either. Keep in mind while exploring Florence that opening hours vary and are quite often inconsistent. Different museums are open on different days and lines can be very long. It’s worthwhile to pay a few extra euros and pre-book your tickets—this will enable you to bypass long lines of visitors at the entrances. We recommend the following accommodations for your pre-trip hotel.

after

After: Rome, Italy

Rome is a powerhouse of stunning architecture and ancient history, beautifully told through its ruins and buildings. It seems that every street you walk down provides another unexpected glimpse of ancient times, yet modern bustle and energy abounds as well. The Coliseum, the Forum, Vatican City, and the Pantheon are some of the must-see attractions. Be sure to linger on the Spanish Steps one afternoon and take advantage of great shopping and fantastic cuisine. We recommend the following accommodations for your post-trip hotel:

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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