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Tuscany Luxury 4-Day Bike Tour

Quintessential luxury of Chianti’s famous castles and wines

Escape to the Tuscan countryside to discover allegria, the feeling Italians express when something is just perfect. Whether lounging by the pool, riding through vineyards, or sipping regional wines, you'll quickly discover the feeling is 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 on a delightful 4-day trip. Here, you'll savor the revered wines and intimate hospitality of the Mascheroni Stianti family at their private Castello di Volpaia estate and feast on exquisite Michelin-starred Tuscan cuisine all while resting your head each night in a charming hotel with centuries of history and now the pinnacle of luxury. It’s more than just the ultimate Tuscany getaway. It’s a revelation on what allegria truly can be. Book your trip with confidence »

Learn more about a Perfect Day on our Luxury Bike Tour in Tuscany»
$4099 Per Person
6 Days & 5 Nights
Rider Type: ?
3 - Active Non-riders Welcome
From $4099 per person View All Details
Trip Wows
Enjoy your 5-star hotel, Borgo San Felice; an entire medieval hamlet has been transformed into the ultimate Relais & Chateaux luxury property.
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
Visit Radda in Chianti, where you’ll be met with vibrant colors, sights, and sounds of a classic Chianti village life
Experience a private walking tour of Siena and learn about the Palio di Siena, a famous horse race
Ride along quiet roads lined with cypress trees in the beautiful Tuscan landscape
Tuscany Luxury 4-Day Bike Tour
The design for the rides was a perfect mix linking all of the important points of interest with the countryside of Tuscany.  The camaraderie and challenge all combined to create a close knit group of newly found friends.
-Tom, 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.
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Single Occupancy from: +$1400
Aug 29 – Sep 1 
$4099 / Person, Double Occupancy Book this date
Sep 5 – Sep 8 
$4099 / Person, Double Occupancy Book this date
Sep 12 – Sep 15 
$4099 / Person, Double Occupancy Book this date
Sep 19 – Sep 22 
$4099 / Person, Double Occupancy Book this date
Would you like to get early access to next year’s dates?
Please contact us to join our exclusive waitlist for first notice about new dates.
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:

2021 and 2022 DEPARTURES:
  • 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 +$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 4-day 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 where our luxurious hotel for the next three nights, awaits you. This evening, you'll enjoy a warm welcome to your Tuscany bike and wine tour as we gather for drinks on the terrace overlooking the hotel's own Sangiovese vineyards before enjoying our first gourmet meal together.

Today's Ride:

La Badia di Coltibuono to San Felice
Approximately 14 miles with 1,250 feet of climbing


Borgo San Felice

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. Take time to explore this vibrant village, filled with wine shops and art galleries—the perfect place to pick up some mementos to take home-—or choose to climb up to the medieval village of Lucarelli on our avid option. 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, 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, home of the "Palio" horse race and the storied Mangia Tower. Here, 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, 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. Be sure to finish your fabulous day with a world-class gelato!

Today's Ride:

San Felice to Volpaia Loop
Approximately 33 miles with 3,850 feet of climbing

Short Option:

San Felice to Volpaia with shuttle
Approximately 18 miles with 2,600 feet of climbing

Avid Option:

San Felice to Lucarelli to Volpaia Loop
Approximately 48 miles with 5,400 feet of climbing


Borgo San Felice

Included Meals:

Breakfast | Lunch

This morning you will 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 coffee at their Eroica Caffè, named after L’Eroica, the local cycling event on the “strade bianche” (white gravel roads) with contestants riding vintage bikes and 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 relax with some free time at the hotel; enjoy the 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 tastebuds to the innovative cuisine of our Chef Juan Camilo Quintero who prides himself on crafting gourmet cuisine from all locally sourced ingredients, perfectly paired with the hotel’s best vintages from their own vineyards.

Today's Ride:

San Felice to Villa Sesta Loop
Approximately 29 miles with 2,800 feet of climbing

Short Option:

San Felice to Castello di Brolio Loop
Approximately 21 miles with 2,050 feet of climbing

Avid Option:

San Felice to Monteluco to Villa Sesta Loop
Approximately 38 miles with 4,100 feet of climbing


Borgo San Felice

Included Meals:

Breakfast | Lunch | Dinner

Rise early this morning and witness the sunrise creeping over the stunning Chianti countryside for a final time, surely by now it's starting to feel like your second home. 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 your private shuttle at 9:00 AM. It's been a great Tuscan getaway!

Today's Activity:

Private shuttle to Florence

Included Meals:



hotel image

Borgo San Felice

San Felice, Italy

Relais & Chateaux Logo 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.

What's Included

For us, the details matter most

Every moment of a Trek Travel luxury bike tour 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 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. Upgrade to the Domane+ LT on this trip for $500. 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


  • Three 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, three lunches, and two dinners
  • One 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 luxury bike tour in Tuscany
  • A personalized digital 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
81 miles
2,200 feet
7,500 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 five kilometers long. Our Chianti 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.
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 4-day Tuscany cycling 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

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

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 start of your 4-day bike tour in Chianti, 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 (~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 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 ~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, Borgo San Felice (+39 0577 3964) 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 9:00 AM at Borgo San Felice, in San Felice. You’ll depart by private shuttle for Hotel Montebello Splendid, Florence, arriving close to 10:30 AM. The hotel is a 10-minute taxi ride from Santa Maria Novella train station where trains connect to many European cities. Please do not book seats before 12:00 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. 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) 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 Chianti bike tour. 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. If you are looking to discover the bustling city of Rome after your trip, 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 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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