- 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*
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.
La Badia di Coltibuono to Gaiole in Chainti
Approximately 19 miles with 1,300 feet of climbing
Castello di Spaltenna
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. Afterwards, 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.
Gaiole in Chianti to Volpaia Loop
Approximately 30 miles with 3,400 feet of climbing
Gaiole in Chianti to Volpaia with shuttle
Approximately 20 miles with 2,700 feet of climbing
Gaiole in Chianti to Monte Luco to Volpaia Loop
Approximately 37 miles with 4,500 feet of climbing
Castello di Spaltenna
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.
Gaiole in Chianti to Villa Sesta Loop
Approximately 32 miles with 2,700 feet of climbing
Gaiole in Chianti to Villa Sesta with shuttle
Approximately 25 miles with 2,100 feet of climbing
Gaiole in Chianti to Villa a Sesta Loop with Vico Arbia Loop
Approximately 40 miles with 3,400 feet of climbing
Castello di Spaltenna
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. Afterwards, 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.
Gaiole in Chianti to Castello di Casole
Approximately 36 miles with 2,700 feet of climbing
Gaiole to Castello di Casole with Simignano climb
Approximately 44 miles with 3,700 feet of climbing
Evening masterclass, perfecting your pizza spin with our expert pizzaiolo
Belmond Castello di Casole
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.
Castello di Casole to San Gimignano Return
Approximately 40 miles with 4400 feet of climbing
Castello di Casole to San Gimignano w/shuttle to hotel
Approximately 20 miles with 2,100 feet of climbing
Castello di Casole to San Gimignano to San Benedetto Return
Approximately 53 miles with 5,500 feet of climbing
Belmond Castello di Casole
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.
Castello di Casole to Mensanello Loop
Approximately 15 miles with 1,200 feet of climbing
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.
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
It’s lightweight and equipped with an adjustable pedal-assist motor that helps riders of all skill levels stay together, play together and make some great memories together. Included at no additional cost, these bikes will be available on a first-come, first-served basis, so reserve yours when you book today. Learn More
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.
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
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
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.
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.
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 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.
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.