Private
If a date is marked as Private, it is reserved for a private group.
Don’t see exactly what you are looking for or looking for a custom date?
Call our trip consultants at 866-464-8735
Tailwind on every ride? – See e-bike trips
European Classic booking fast – see the trips
Trip Itinerary
If you’ve imagined your perfect luxury bike tour in Italy, then you’ve envisioned traveling to the heart of Tuscany's wine country with us.
Print Tip: For wider content, set Margins to 'Minimum' in the print window settings.
Where to Arrive
Airport:
Amerigo Vespucci Airport (FLR)
Pick-up location:
Palazzo Montebello, Florence, Italy
Pick-up time:
11:00 AM
Where to Depart
Airport:
Amerigo Vespucci Airport (FLR)
Drop-off location:
Palazzo Montebello, Florence, Italy
Drop-off time:
12:30 PM
Additional Arrival Information
We suggest that you arrive at least one day prior to the start of your Tuscany Wine Country bike tour, 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€) 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€ 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€.
Your Trek Travel guides will meet you at the Palazzo Montebello (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 bike 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. If you cannot reach them, please call your first hotel, 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€. The trip takes over an hour from the center of Florence.
Additional Departure Information
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 Palazzo Montebello, 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.
Enjoy a warm up ride through ancient olive groves
Overview
Your Trek Travel guides will meet you at the Palazzo Montebello at 11:00 AM on the first day of your luxurious 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 rid... Your Trek Travel guides will meet you at the Palazzo Montebello at 11:00 AM on the first day of your luxurious 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. Read More
Hotel
Castel Monastero
Meals included
Lunch | Social Hour | Dinner
Highlight of the Day
Scenic Warm-Up Ride
Warm up on picturesque, winding roads through woodlands and ancient olive groves to the medieval Castel Monastero, now a lavish hotel, where... Warm up on picturesque, winding roads through woodlands and ancient olive groves to the medieval Castel Monastero, now a lavish hotel, where you'll stay for the next three nights. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
La Badia di Coltibuono to Monastero - Approximately 24 mi | 39 km and 1,825 ft | 559 m
Wine tasting at Castello di Volpaia followed by a Michelin-starred dinner
Overview
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... 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, 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. Read More
Hotel
Castel Monastero
Meals included
Breakfast | Lunch | Dinner
Highlight of the Day
Michelin-starred dinner at La Bottega del 30
Surrender your taste buds to the innovative cuisine of La Bottega del 30, a restaurant nestled in the heart of Chianti that has held a Miche... Surrender your taste buds to the innovative cuisine of La Bottega del 30, a restaurant nestled in the heart of Chianti that has held a Michelin star for over 25 years. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Monastero to Volpaia with Shuttle - Approximately 29 mi | 46 km and 3,553 ft | 1,083 m
Ride Option 2
SHORT OPTION:
Monastero to Radda with Shuttle - Approximately 23 mi | 38 km and 900 ft | 274 m
Ride Option 3
AVID OPTION:
Monastero to Volpaia Loop - Approximately 53 mi | 86 km and 5,341 ft | 1,628 m
Discover the history of Castello di Brolio followed and an evening exploring Siena
Overview
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 cont... 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 on the white gravel roads 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, 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! Read More
Hotel
Castel Monastero
Meals included
Breakfast | Lunch | Dinner
Highlight of the Day
Magnificent Siena
This evening, we’ll shuttle to the medieval town of Siena, where you'll learn the secrets of this historic city from our local guide and s... This evening, we’ll shuttle to 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 Piazza del Campo. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Monastero to Castello di Brolio Loop - Approximately 37 mi | 60 km and 2,910 ft | 888 m
Ride Option 2
SHORT OPTION:
Monastero to Castello di Brolio with Shuttle - Approximately 31 mi | 50 km and 2,220 ft | 860 m
Ride Option 3
AVID OPTION:
Monastero to Monteluco Loop - Approximately 40 mi | 65 km and 3,350 ft | 1,021 m
Ride through the breathtaking Elsa Valley and spin your own pizza dough with a trained pizzaiolo
Overview
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 for... 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. 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! Read More
Hotel
Belmond Castello di Casole
Meals included
Breakfast | Lunch | Dinner
Highlight of the Day
Private pizza-making class
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 trai... 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! Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Monastero to Castello di Casole - Approximately 41 mi | 66 km and 3,860 ft | 1,175 m
Ride Option 2
SHORT OPTION:
Monastero to Scorgiano - Approximately 34 mi | 55 km and 3,510 ft | 1,070 m
Ride Option 3
AVID OPTION:
Monastero to Castello di Casole with Simignano Climb - Approximately 50 mi | 80 km and 4,200 ft | 1,280 m
Explore the medieval market town of San Gimignano
Overview
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 sta... 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. You may wish to 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. Read More
Hotel
Belmond Castello di Casole
Meals included
Breakfast | Lunch | Social Hour | Dinner
Highlight of the Day
Featured Meal | La Tosca
Indulge in a gastronomic delight at La Tosca, where exquisite meals use the finest local ingredients. Enjoy beautifully presented dishes tha... Indulge in a gastronomic delight at La Tosca, where exquisite meals use the finest local ingredients. Enjoy beautifully presented dishes that pay homage to farm traditions. Soak in the magical atmosphere of this elegant restaurant and toast to the unforgettable cuisine of Tuscany. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Castello di Casole to San Gimignano with Shuttle to Hotel - Approximately 21 mi | 33 km and 2,200 ft | 670 m
Ride Option 2
SHORT OPTION:
Castello di Casole to Castel San Gimignano - Approximately 14 mi | 22 km and 1,300 ft | 396 m
Ride Option 3
AVID OPTION:
Castello di Casole to San Gimignano Return - Approximately 42 mi | 67 km and 4,500 ft | 1,371 m
Witness the sunrise creeping over the stunning Val d'Elsa
Overview
While by now this region is surely starting to feel like home, this morning you'll arise early for your 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.
Meals included
Breakfast
Highlight of the Day
Ride Options
Ride Option 1
TODAY'S RIDE:
Castello di Casole to Mensano Loop - Approximately 15 mi | 24 km and 1,400 ft | 426 m
If a date is marked as Private, it is reserved for a private group.
Don’t see exactly what you are looking for or looking for a custom date?
Call our trip consultants at 866-464-8735
Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.
Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.
These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.
On select cycling vacations, you’ll stay at a mix of Explorer and Luxury hotels. Rest assured, no matter which hotel level you’re at, our trip designers carefully select every accommodation.
Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).
Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).
Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).
Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).
Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).
Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).
Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).
Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).
Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).
Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).
Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).
Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).
Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.
Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.
Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.
Train like the pros in some of their favorite riding destinations.
See the pros in action at the biggest cycling events of the year.
Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.
Enjoy a bike tour on your schedule with just your chosen travel companions.
Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself