- 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*
A one-hour shuttle will deliver you to your starting point for today's ride, a countryside trattoria set among the rich vineyards of Chianti. After a delicious lunch of handmade pizza and salads, your Trek Travel guides will ensure that you have an excellent fit to your Trek bicycle while offering specific cycling tips for riding in Italy. We’ll then start with a rolling, scenic loop ride among the vine-covered slopes and olive groves of the Chianti region. This evening, you and your companions will gather for an Italian aperitif on the hotel terrace as our chef prepares seasonal delights for tonight’s Tuscan feast.
La Cantoniera to Vescine
Approximately 19 miles with 1,900 feet of climbing
Il Borgo di Vescine
Lunch | Social Hour | Dinner
Don’t forget your camera today as you descend into the valley where vines and olive trees give way to shady chestnut trees as the landscape subtly shifts and changes. Stop to visit the Castello di Brolio and its famous L’eroica café, home to great espresso and cool cycling memorabilia. For lunch we'll stop at Bar Dante in Radda in Chianti. Our hosts, Fabrizio and Carolyn pride themselves on serving the best bruschetta in Radda, washed down with a glass of local Chianti. Following lunch continue your ride to the tiny village of Lucarelli and join the locals for the ritual of mid-afternoon espresso. Alternatively, choose to wander the tiny streets of Radda. Buy a local bike jersey or some delicious Tuscan olive oil before shuttling back to the hotel to relax and enjoy the pool. This evening is yours to explore Castellina in Chianti: wander the medieval cobblestone streets before discovering the “Via della Volte”, an impressive, historic, underground tunnel which is now a fascinating walkway filled with artisan boutiques and restaurants. Enjoy a family-style dinner in town on the piazza, or perhaps something a little more romantic, while savoring the picturesque views and unique atmosphere of this charming village.
Vescine to Radda in Chianti Loop
Approximately 32 miles with 2,800 feet of climbing
Vescine to Radda in Chianti
Approximately 22 miles with 2,000 feet of climbing
Vescine to Radda in Chianti with San Donato Loop
Approximately 49 miles with 4,500 feet of climbing
Il Borgo di Vescine
Breakfast | Lunch
This morning, you'll climb high up above the vineyards, where you'll be rewarded by rich panoramic views of rolling Tuscan hills discreetly chaperoned by the ubiquitous cypress. Spin your wheels surrounded by ancient stone walls, wildflowers and the scent and shade of the forest as you leave the 21st century far behind. Pause for lunch at a local trattoria along the way before arriving at this afternoon’s destination, the 18th-century manor house Casabianca. Enjoy the afternoon, take a dip in the pool or enjoy a cocktail on the terrace overlooking the hotel's beautiful gardens. This evening, join your fellow travelers for a fun-filled pizza making session at the hotel. You will learn how to prepare a perfect Italian pizza, paired of course with the regions local wines, under the guidance of an Italian pizza master, using the original wood oven of the hotel, still functioning since the times when the hotel was itself a small village.
Vescine to Casabianca
Approximately 52 miles with 4,400 feet of climbing
Vescine to Castelnuovo Berandenga with shuttle
Approximately 26 miles with 2,000 feet of climbing
Vescine to Casabianca with Monteluco Climb
Approximately 55 miles with 5,500 feet of climbing
Il Borgo Casabianca
Breakfast | Lunch | Dinner
Today you’ll head north into one of Italy’s most dramatic regions, the Crete Senesi, following winding ribbons of road into southern Tuscany’s gently undulating terrain into the hills, distinguished by the dramatic colors of the soil and blessed with some of the most stunning views in Tuscany. Along the way, visit Monte Oliveto Maggiore, a 12th-century Benedictine abbey. Soak up its austere beauty before venturing on toward the town of Montisi. Here you will relax and enjoy a delicious farm to table lunch prepared by our friend and local chef Roberto, who is both passionate and faithful to the traditions of the slow food movement. Choose to either jump in the van or return to your bike and ride along cypress-lined ridges to this afternoon’s destination, the medieval village of San Quirico d’Orcia and our boutique hotel the Villa del Capitano. The evening is yours to explore the cobbled streets of the town and to enjoy dinner at one of the many small bistros on your own.
Casabianca to San Quirico
Approximately 40 miles with 3,900 feet of climbing
Casabianca to Montisi with shuttle
Approximately 27 miles with 2,400 feet of climbing
Casabianca to San Quirico with Abbazia Monte Oliveto
Approximately 46 miles with 4,500 feet of climbing
Villa del Capitano
Breakfast | Lunch
This morning’s route lifts you high above the Val d’Orcia, a vista dotted with rolling hills blanketed with vines and rows of cypress. Your first stop is a tiny Roman spa town of Bagno Vignoni, known for its hot sulfurous springs. The town plaza is filled with a pool built by the Medici family centuries ago where you can refresh your feet before you continue on your ride to Abbazia di Sant’Antimo, a stunning 12th century Romanesque abbey, if you're lucky you may arrive to the haunting choral harmonies of the monks' Gregorian chants—magical! Our lunch destination today is the walled village of Montalcino, its 14th century fortress and steep cobblestone streets dominate the surrounding countryside. Here you can discover the delights of Brunello wine, one of the finest Italian varietals and enjoy lunch at your leisure at one of Montalcino’s many trattorias. Cycle back along winding roads or reward yourself with a shuttle and more time to relax back at the hotel. This evening you will experience an exceptional dinner at our favorite restaurant in the heart of San Quirico. Enjoy a selection of traditional dishes with a modern twist, paired with a unique selection of regional wines. We will toast to a week of great riding, warm fellowship, and truly phenomenal food!
San Quirico to Montalcino Loop
Approximately 34 miles with 3,100 feet of climbing
San Quirico to Montalcino with shuttle
Approximately 23 miles with 2,100 feet of climbing
San Quirico to Montalcino with Pienza Loop
Approximately 52 miles with 5,200 feet of climbing
Villa del Capitano
Breakfast | Social Hour | Dinner
It’s sadly time to bid farewell today. Get up bright and early this morning to make the most of the stunning light and watch a bright new day unfurl over the classic Tuscan countryside. Or linger awhile over a hot cappuccino and enjoy a more leisurely paced morning in the hotel. However you say goodbye to Tuscany, you’re sure to take a little of this destination with you.
San Quirico to Bagno Vignoni Loop
Approximately 17 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
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
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
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 the Florence Airport (FLR).The 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.
You can also fly into Rome or Milan and take a train or flight from either city. 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 1.5 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. For information about travel through Milan’s Malpensa Airport (MXP), consult the website www.airportmalpensa.com.
Your Trek Travel guides will meet you at the Hotel Home Florence (Piazza Piave, 3 - 50122 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 (subject to availability). 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 starts with their names and contact details. If you cannot reach them, please call our first hotel, Il Borgo di Vescine (+39 0577 741 144) and leave a message with your expected arrival time and contact details. You may take a taxi to the first night’s hotel in Vescine, Il Borgo di Vescine, 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 Villa del Capitano, San Quirico. You’ll depart by private shuttle for Hotel Palazzo Vecchio, Florence, arriving at around 12:30 PM. The hotel is a 5-minute walk 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.com for train information.View our post hotel recommendations
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 warmer with warm daytime temperatures (80F-95F). 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:
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:
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.