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Tuscany Luxury Bike Tour

Quintessential Luxury of Chianti and the Val d'elsa

Imagine your perfect luxury vacation, and your mind is already halfway to Tuscany with us. Allegria. Contentment. Joy. This is how Italians describe the feeling that comes over them when something is just perfect, and it's in no short supply in Tuscany. We’ve scoured every olive grove, every vineyard and every 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 estate. You’ll feast on exquisite Michelin-starred Tuscan cuisine and perfect your pizza spin with our expert pizzaiolo at a private cooking class. While resting your head each night in hidden hotels known for centuries as the pinnacle of luxury. It’s more than our vision of the perfect Italian luxury holiday. It’s a revelation on what allegria truly can be.Learn more about your Perfect Day in Tuscany»
$4999 Per Person
6 Days & 5 Nights
Rider Type: ?
3 - Active Non-riders Welcome
From $4999 per person View All Details
Trip Wows
Toast the day from Travel + Leisure’s #1 European hotel resort on a sprawling 4,200 acres
Enjoy your 5-star hotel in Gaiole, a castle perched above the village, and transcendentally above the fray
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
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 and date are guaranteed.
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Single Occupancy from: +$1600
Apr 19 – Apr 24 
$5099 / Person, Double Occupancy Book this date
Apr 26 – May 1 
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May 3 – May 8 
$5099 / Person, Double Occupancy Book this date
May 10 – May 15 
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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. All you need to do is pick any open 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 +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
*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 the trip. After a 60-minute 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 Chianti hills. Your Trek Travel guides will then spend some time familiarizing you to your Trek bicycle and ensuring you have an excellent fit. A warm up ride will take you along winding roads through woodlands and the tiny village of San Sano with its locally-famous frog fountain before making your way to the small village of Gaiole in Chianti where our luxurious hotel for the next three nights, Castello di Spaltenna, awaits. This evening you'll gather for drinks on the terrace overlooking the hotel's own Sangiovese vineyards before we enjoy our first gourmet meal together.

Today's Ride:

La Badia di Coltibuono to Gaiole in Chainti
Approximately 19 miles with 1,300 feet of climbing


Castello di Spaltenna

Included Meals:

Lunch | Social Hour | Dinner

Today’s ride traverses the forested hills and olive groves of the 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. You'll have time to explore this vibrant village, filled with bustling shops and galleries—the perfect place to pick up some mementos to bring home. Your midday destination is Castello di Volpaia, where the Mascheroni Stianti family personally welcomes you for a wine-paired lunch in their villa. Afterward, enjoy an exclusive visit of the castle’s cellars and olive oil press. From here, continue to our hotel for an afternoon of relaxation, or hop back on your bike to spin back through the rolling vineyards. This evening we’ll shuttle into the medieval town of Siena, home of the "Palio" horse race and the storied Mangia Tower. Here, you'll learn the secrets of this historic city from a local guide and see the world-famous Duomo. Afterward, wander the cobbled streets as an array of Tuscan specialties unfold before your eyes. Your guides will have plenty of suggestions on where to find culinary favorites like wood-fired pizza or a bowl of Cinghiale (wild boar) pasta accompanied by a glass of Brunello.

Today's Ride:

Gaiole in Chianti to Volpaia Loop
Approximately 30 miles with 3,400 feet of climbing

Short Option:

Gaiole in Chianti to Volpaia with shuttle
Approximately 20 miles with 2,700 feet of climbing

Avid Option:

Gaiole in Chianti to Monte Luco to Volpaia Loop
Approximately 37 miles with 4,600 feet of climbing


Castello di Spaltenna

Included Meals:

Breakfast | Lunch

This morning, you will cruise through lush 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 coffee at their Eroica Caffè and learn about the history of the heroic Eroica race contested on “strade bianche” (gravel roads) with contestants on vintage bikes and in full vintage regalia. Your lunch destination is the quaint village of Villa Sesta. Enjoy true Tuscan hospitality as you savor the cuisine of Osteria alla Villa, a small bistro that serves up fresh, local, and creative dishes. Return to our hotel for an afternoon of relaxation or hop back on your bike to spin back through the rolling vineyards. This evening, an exquisite Michelin starred dinner awaits you at Castello di Spaltenna.

Today's Ride:

Gaiole in Chianti to Villa Sesta Loop
Approximately 32 miles with 2,700 feet of climbing

Short Option:

Gaiole in Chianti to Villa Sesta with shuttle
Approximately 25 miles with 2,100 feet of climbing

Avid Option:

Gaiole in Chianti to Villa a Sesta Loop with Vico Arbia Loop
Approximately 37 miles with 3,800 feet of climbing


Castello di Spaltenna

Included Meals:

Breakfast | Lunch | Dinner

The breathtaking Elsa Valley awaits you today. Its 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 five-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. Pause to enjoy a farm to table picnic lunch, featuring hand cured prosciutto, 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 with spectacular views over the 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:

Gaiole in Chianti to Castello di Casole
Approximately 36 miles with 2,700 feet of climbing

Short Option:

Gaiole in Chianti to Scorgiano
Approximately 30 miles with 2,200 feet of climbing

Avid Option:

Gaiole in Chianti to Castello di Casole with Simignano climb
Approximately 45 miles with 3,700 feet of climbing


Belmond Castello di Casole

Included Meals:

Breakfast | Lunch | Dinner

It's pure extravagance to awake at Castello di Casole, and after a leisurely breakfast, we'll mount our bikes for one last amazing day. We start with a descent from Casole 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. Sample fresh regional olives and “picci” pasta before taking a stroll through the stalls of the local artisans. 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 lesson in ceramics, a watercolor class or indulge at the destination spa. Tonight, you'll savor the trip's final gastronomic delight: an exquisite meal at the hotel's renowned restaurant, La Tosca. Soak in the magical atmosphere of this elegant retreat and raise your glass to a week of wonders in Tuscany.

Today's Ride:

Castello di Casole to San Gimignano with Shuttle to hotel
Approximately 21 miles with 2,200 feet of climbing

Short Option:

Castello di Casole to Castel San Gimignano
Approximately 14 miles with 1,300 feet of climbing

Avid Option:

Castello di Casole to San Gimignano return
Approximately 42 miles with 4,500 feet of climbing


Belmond Castello di Casole

Included Meals:

Breakfast | Social Hour | Dinner

Arise early this morning for a final bike loop through the Tuscan countryside and witness the sunrise creeping over the stunning Val d'elsa, surely by now it's starting to feel like home. 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.

Today's Ride:

Castello di Casole to Mensano Loop
Approximately 15 miles with 1,400 feet of climbing

Included Meals:



hotel image

Castello di Spaltenna

Gaiole in Chianti, Italy

Trip Advisor Certificate of Excellence Award This medieval hamlet in the heart of Chianti, a sub-region of Tuscany, complete with castle and church, has been transformed into an elegant hotel surrounded by vineyards and woods. Weaving modern luxuries with its rich history, Castello di Spaltenna offers uniquely decorated rooms, fine dining, a full wine cellar, outdoor and indoor pools and impeccable service.
hotel image

Belmond Castello di Casole

Casole D'elsa, Italy

Stay at Belmond Castello di Casole on a Tuscany luxury bike tour 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, gourmet and relaxed dining and exquisite suite accommodations that effortlessly combine Old World Tuscan charm with modern luxuries.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip 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.


Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019, we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More


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


Trek Electric-Assist Domane+ LT

The Domane+ LT combines the best of the race-built Domane endurance bike with a slight pedal-assist perfect for climbing the toughest hills. This bike primarily functions as a road bike, but on tough hills or in strong headwinds, you can get an extra boost by using the electric assist feature. Learn More


  • 5 nights of accommodation at handpicked hotels
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, 4 lunches and 4 dinners
  • 3 social hours of drinks and hors d'oeuvres
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Bontrager cycling jersey and socks to keep
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, flat pack, 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 personalized photobook of your trip
  • Entrance fees for all activities, private tours and events


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Upgrade your bike to a Trek Electric-Assist Domane+ LT carbon road bike with Shimano Di2 electronic shifting
  • Trek Travel Bontrager cycling jersey and socks to keep
  • Trek Travel water bottles to keep
  • 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 and a flat pack
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Upgrade your bike to include carbon wheels (+$200)
  • 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.


Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.
  • 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?

25 miles
150 miles
2,200 feet
13,400 feet
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 5km long. Tuscany Luxury 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.
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 this trip 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 vacations, Trek Travel strives 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

Amerigo Vespucci Airport (FLR)
11:00 AM
Hotel Montebello Splendid, Florence, Italy

Say Farewell

Amerigo Vespucci Airport (FLR)
12:30 PM
Hotel Montebello Splendid, Florence, Italy


We suggest that you arrive at least one day prior to the trip start, 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 3 miles from the town center. You can take a taxi (~20 euros) directly to the hotel, 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 1-1/2 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 ~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. Should you wish to reserve a room at this hotel pre-or post-trip, please contact your Trip Consultant for a discount code. You’ll then shuttle 90 minutes to your lunch spot for a taste of 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 our first hotel, Castello di Spaltenna (+39 0577 749483) 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


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 3 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. for train information.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Spring and Fall in Tuscany is usually clear and sunny, with warm daytime temperatures (75F-90F) 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) 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: 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. 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: Rome, Italy

In every region we travel, we uncover the area’s best, and most delightful accommodations. On our Tuscany trip, you will stay in a historic palazzo in charming San Quirico, a luxurious country villa surrounded by rolling hills, and a former castle of a medieval hamlet high above Gaiole. We recommend the following accommodations for your post-trip hotel.

Customer Reviews

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

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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