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Trek Travel Tuscany, Italy Luxury Cycling Vacation
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Ride along vineyards on a Tuscany bike tour
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Ride through Tuscany on a Tuscany luxury bike tour
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Trek Travel Tuscany, Italy Luxury Cycling Vacation TCSG_ValDOrcia_CANVA_1600x670 Ride along vineyards on a Tuscany bike tour TCSG_ValDOrcia_CANVA_1600x670 (2) (1) 22TC-TuscanyReserve-Banner--EDITS-IMG2386-1600X670 TCSG_ValDOrcia_CANVA_1600x670 (4) (1) TCSG_ValDOrcia_CANVA_1600x670 (11) (1) Ride through Tuscany on a Tuscany luxury bike tour TCSG_ValDOrcia_CANVA_1600x670 (9) (1) 16TCL0612_bjoy_-125 - 1600x670

Tuscany Self-Guided Bike Tour

Val d'Orcia: the beating heart of a postcard-like Tuscany

Tuscany is more beautiful than you can imagine. As you ride along winding cypress-lined roads, the famous golden rolling hills reveal their gentle majesty before you. Ancient farms, vineyards, and valleys bask quietly in natural sun-kissed splendor. Tranquil hilltop villages await discovery behind medieval walls. With a cuisine as simple and fresh as it is delicious, a proud tradition producing some of the world’s finest wines, and a people blessed with profoundly friendly hospitality, Tuscany has a magic that instantly allows you to relax and savor every precious moment. If you are seeking adventure but don't want to worry about how to make it happen, Trek Travel's self-guided bike tour in Tuscany offers an incredible itinerary to discover the wonders of this truly magnificent land at your own pace. Book your trip with confidence »Learn more about Self-Guided trips and if they're right for you » Also see our classic Tuscany bike tour »
Join Trek Travel for a Tuscany Self-Guided Bike Tour
From:
$1999 Per Person
Duration:
5 Days & 4 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Self-Guided
Hotel Level: ?
Explorer
Reviews:
From $1999 per person View All Details
Trip Wows
Ride along quiet roads lined with cypress trees in the beautiful Tuscan landscape
Stay in a historic building which has been transformed into an elegant and charming hotel
Explore the unique cultural landscape of Val d'Orcia designated a UNESCO World Heritage Site
Pamper yourself with the world-famous Brunello di Montalcino wine and the noble "vino nobile" di Montepulciano
Indulge in the fresh pasta dishes of the Tuscan cuisine and discover local pecorino cheese
Tuscany Self-Guided Bike Tour
All was great. Traveling without the hassle of bikes was worth every penny. Having the routes pre-loaded made for ease when unsure where to go ride safely.
- Liz Baugher, Trek Travel Guest

Dates & Prices

Choosing the Best Time to Book

Our Tuscany Self-Guided bike tour is available in April, May, and September through to mid-October so that you may enjoy the best riding conditions.
Guaranteed 
to run
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Sold Out/
Waitlist
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Private/
Reserved
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Limited 
Availability
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Single Occupancy from: +$1200
?
Apr 4 – Apr 8 
$1999 / Person, Double Occupancy Book this date
Apr 11 – Apr 15 
$1999 / Person, Double Occupancy Book this date
Apr 18 – Apr 22 
$1999 / Person, Double Occupancy Book this date
Apr 25 – Apr 29 
$1999 / Person, Double Occupancy Book this date
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:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 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.

Meet your Trek Travel host at the boutique hotel Palazzo del Capitano, located in the heart of the medieval village of San Quirico d’Orcia. Your host will give you a brief orientation of the adventures ahead and will fit you to your Trek bike, ensuring your comfort on your bike for the week. Then, it's off on your first self-guided adventure in the enchanting landscape offered by the Val d’Orcia, famous for the unique and pristine views where cypress-lined country roads have become the worldwide representative image of the Tuscan countryside. Your first stop is the tiny medieval spa town of Bagno Vignoni, where you can dip your toes in the famous thermal springs and take pictures of the Roman baths located right at its center. Continue this scenic loop with a gentle climb up to Pienza, a UNESCO Site renowned for its Pecorino cheese and considered one of the symbols of the Italian Renaissance. Wander through its streets and grab the best gelato at “Buon Gusto” before cycling back to your hotel at your leisure. Take some time to relax perhaps with a glass of wine and afterward we suggest you walk to our favorite restaurant in the heart of San Quirico to enjoy your first Tuscan dinner!

Today's Ride:

San Quirico to Bagno Vignoni to Pienza Loop
Approximately 19 mi | 30 km and 1,458 ft | 444 m

Hotel:

Palazzo del Capitano

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 trees. After passing by the spa town of Bagno Vignoni, you will ride up to Castiglione d’Orcia, admiring the remains of what was once the mighty Rocca Aldobrandesca, a fortress that dominates the village. Your first stop today will be the renowned Abbazia di Sant’Antimo, a monumental 12th-century Romanesque abbey, where if you're lucky, you may arrive to the haunting choral harmonies of the monks' Gregorian chants—magical! Your lunch destination is the walled village of Montalcino with its 14th-century fortress and steep cobblestone streets that 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. When you're ready, cycle back to San Quirico along winding roads and relax at the hotel before selecting a local bistro in town from the list of Trek Travel recommendations.

Today's Ride:

San Quirico to Montalcino Loop
Approximately 34 mi | 54 and 3,927 ft | 1,196 m

Avid Option:

San Quirico to Montalcino Loop with Monticchiello
Approximately 54 mi | 86 km and 5,421 ft | 1,652 m

Hotel:

Palazzo del Capitano

Included Meals:

Breakfast

Today you’ll head north into one of Italy’s most dramatic regions, the Crete Senesi, following winding ribbons of road into gently undulating terrain. Here vineyards and olive trees give way to cultivated fields crossed occasionally by rows of cypress trees and a few solitary farmhouses. The particular dry grey terrain forms a sort of badlands typical of this area, which appears almost lunar, and are distinguished by the dramatic colors of the clay-dense soil. At the same time a barren landscape yet also some of the most stunning views in Tuscany. Riding here gives you a feeling of peace and, if you feel like adding some more mileage and elevation, take the avid route to Asciano, pedaling through meandering roads overlooking the surrounding ridges on an other-worldly route. We recommend you stop for lunch at our favourite restaurant in the tiny village of Montisi, Taverna da Roberto. Please, remember to make a reservation ahead of time because our friend and local chef Roberto only works with reservations. You'll be amazed by the passion and love he puts into preparing a delicious farm to table lunch for his guests! After lunch, continue your loop back to the medieval village of San Quirico d’Orcia where you can relax, perhaps with a spa session. The evening is yours to explore the cobbled streets of the town and to enjoy dinner at one of the many small bistros recommended by our local experts.

Today's Ride:

San Quirico to San Giovanni d'Asso Loop
Approximately 25 mi | 40 km and 2,465 ft | 751 m

Avid Option:

San Quirico to San Giovanni d'Asso to Asciano Loop
Approximately 43 mi | 69 km and 4,377 ft | 1,334 m

Hotel:

Palazzo del Capitano

Included Meals:

Breakfast

Enjoy your morning cappuccino and venture on a spectacular ride through the Val d'Orcia. Your destination today is one of Tuscany's prettiest towns, strung along a ridge at 605 meters above sea level and surrounded by walls and fortifications. Montepulciano is well known for its Renaissance buildings and lovely churches, but it is especially renowned for its noble wine called “Vino Nobile di Montepulciano", simply divine! Stop for lunch in this elegant town and don't miss the opportunity of tasting its high-level vintage made from Tuscan Sangiovese grapes. There are plenty of wineries where you can sample it. After lunch, continue your ride at your own pace surrounded by idyllic cultivated hills. Back at the hotel in San Quirico, take some time to relax with a stroll in town soaking up the tranquil atmosphere of this ancient medieval village. Tonight, we suggest you dine at the local trattoria Il Vecchio Forno to celebrate a trip of a lifetime in a magical region of Italy!

Today's Ride:

San Quirico to Montepulciano Loop
Approximately 37 mi | 59 km and 3,111 ft | 948 m

Avid Option:

San Quirico to Montepulciano to Sarteano Loop
Approximately 48 mi | 77 km and 4,072 ft | 1,241 m

Hotel:

Palazzo del Capitano

Included Meals:

Breakfast

If you're up for it, close out your Tuscany self-guided bike tour by rising early for a final bike ride to Monticchiello as you watch the sunrise creeping over the classic Tuscan countryside. Or simply linger over a hot cappuccino and walk into town at your leisure, enjoying your final moments in this enchanting region. Your Trek Travel contact will meet you at the hotel at 11:00 AM to take your bike and say farewell before you leave for Florence or other destinations.

Today's Ride:

San Quirico to Monticchiello return
Approximately 20 mi | 32 km and 1,494 ft | 455 m

Included Meals:

Breakfast

Hotels

hotel image

Palazzo del Capitano

San Quirico d’Orcia, Italy

Explorer Accommodation | Nestled in the heart of the charming village of San Quirico d'Orcia, Palazzo del Capitano is a charming 15th-century building transformed into an elegant 4-star hotel, joining tradition with modern comforts. Boasting its own traditional trattoria - Al Vecchio Forno, the property is surrounded by olive groves and Mediterranean gardens where you will find plenty of opportunity to lounge in the sun. This historic palazzo features newly renovated rooms, an indulgent YON-KA SPA, a fantastic outdoor pool, tranquil gardens, and an ideal location. Its mix of modern details and rich history is sure to enchant you.

What's Included

For us, the details matter most

Every moment of a Trek Travel self-guided bike trip has more than you could have ever dreamed. More experiences. 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.

bike

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

bike

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

WHAT'S INCLUDED

  • Four nights of accommodation at one handpicked hotel
  • Daily breakfast
  • Daily lunch and dinner recommendations
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Trek Travel water bottles to keep
  • Each bike is equipped with a flat pack containing one tube, two tire levers, CO2 cartridge with inflator, and a patch kit (the flat pack is only large enough for these items so if additional gear is needed, please plan to bring your own bar bag or small backpack for daily rides)
  • A mini frame pump, phone mount, front and rear lights
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager saddle (we suggest you bring your own for the most comfortable fit)
  • Shimano clipless pedals or flat pedals (optional if you do not bring your own)
  • All luggage transfers during your trip
  • A bike lock, all necessary chargers, and a floor pump
  • Bike fit on the first day to help you find your optimal riding position, with recreational or avid set-up along with saddle preference
  • Ride With GPS app on your phone to navigate and get all the information you need on your self-guided adventure

GEAR

  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, or flat pedals (optional if you do not bring your own)
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • Each bike is equipped with a flat pack containing one tube, two tire levers, CO2 cartridge with inflator, and a patch kit (the flat pack is only large enough for these items so if additional gear is needed, please plan to bring your own bar bag or small backpack for daily rides)
  • A mini frame pump and phone mount
  • A bike lock, all necessary chargers, and a floor pump
  • 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 Trek Travel host will install your gear on the first day during your bike fit.

WHAT'S NOT INCLUDED

Gratuities for your Trek Travel host are not included in your trip price. We recommend tipping 7.5-10% of your trip price, preferably in the local currency. Please tip your host at your discretion, based on their level of professionalism, guest care, and service.
  • Airfare and transportation to and from the trip meeting/departing locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • While we provide daily breakfast, the other meals are not included. On self-guided trips, Trek Travel provides restaurant recommendations and invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

AVERAGE DAILY MILEAGE:
41 kilometers / 26 miles
TOTAL MILES:
212 kilometers / 132 miles
AVERAGE DAILY ELEVATION:
736 meters / 2,415 feet
TOTAL ELEVATION:
3,680 meters / 12,074 feet
TERRAIN: HILLY
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 Tuscany self-guided bike tour is best suited for our Type 3 Riders. 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.
NON-RIDING ACTIVITIES:
There are a variety of non-riding options on this trip 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. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options on this trip are:
  • Shop and explore the medieval villages of Pienza, San Quirico, Montalcino, and Montepulciano
  • Relax by the pool
  • Enjoy a stroll through medieval villages
  • Enjoy a wine tasting of the renowned Brunello wine in the heart of Montalcino
  • Enjoy an olive oil tasting
  • Take a cooking class

See itinerary for specific daily ride distances and elevation options. On all of our 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 Trek Travel's local experts to improve the trip experience.

Averages and totals are calculated from our Today’s Ride options.

Travel Details

How to Get There

FLY INTO:
Amerigo Vespucci (Florence) Airport (FLR)
MEETING TIME:
11:00 AM
MEETING LOCATION:
Trip hotel in San Quirico d'Orcia

Say Farewell

FLY OUT OF:
Amerigo Vespucci (Florence) Airport (FLR)
DEPARTING TIME:
11:00 AM
DEPARTING LOCATION:
Trip hotel in San Quirico d'Orcia

Arriving

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 three miles from the town center. You can take a taxi (approximately €20) to the centre of town, 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. Taxi service is available from Rome Fiumicino Airport to central Rome for approximately €50. From Roma Termini, transfer to a train for Florence. The Frecciarossa trains depart frequently and are the quickest. The trip takes an hour and a half and costs between €44-62 one way per person.

From Florence there are frequent direct trains to Siena. The trip takes about 90 minutes and a one-way ticket costs about ten euros.

The trip takes place in the Tuscan countryside that is not well served by public transportation. For this reason we suggest you take a taxi ride from Siena to San Quirico d'Orcia. A private transfer from Siena to San Quirico takes about one hour and costs approximately €100. We suggest you contact our local driver ahead of time to arrange the transfer. Our Trip Consultant can provide you with our recommended local contact information.

Your Trek Travel host will meet you at your trip hotel Palazzo del Capitano (Via Poliziano, 18, 53027 San Quirico D'orcia SI) at 11:00 AM on the first day of the trip. After getting a brief orientation of the week ahead, you will be fitted to your Trek bike, ensuring you are comfortable for the week. Following a safety talk, saddle up to begin the day's ride through the Tuscan countryside.

If you will be late for the meeting or are going to miss it altogether, please inform your host. You will receive an email a week before the trip start with their name and contact details. If you cannot reach them, please call our hotel, Palazzo del Capitano (+39 0577 899028) and leave a message with your expected arrival time and contact details.

View our pre hotel recommendations

Leaving

Your Trek Travel host will meet you at 11:00 AM at the trip hotel to take your bike and equipment before your departure. The hotel staff will be happy to reserve a taxi for you for Florence or other destinations. The trip to the airport in Florence takes approximately two hours. Please allow adequate connection time for any ongoing travel to accommodate possible traffic delays.

For all guests returning to the United States, COVID-19 testing can be booked at the end of the trip at a convenient location that allows for proper timing to receive results. Your guides can provide more information on the first day, should you require a test during your trip with us. See our Travel to Europe page for updated information on the latest US re-entry requirements.

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, so be prepared with wet-weather gear in order to best enjoy your vacation. Packing List

Before and After Your Trip

before

Before: Siena, Italy

Siena is likely Italy's loveliest medieval jewel made of red-brick lanes rambling every which way. Siena's heart is its central piazza known as Il Campo, a shell-shaped square dominated by the red Palazzo Pubblico and its tower, Torre del Mangia. Admire it from below or climb up over 500 steps to the top to enjoy a wonderful view, this is one stop you don't want to miss in Siena. Piazza del Campo is known worldwide for the famous Palio run here, a horse race run around the piazza two times every summer. Another unmissable highlight is the stunning Gothic Duomo full of treasures, including its marble pavement, Piccolomini library frescoes, and incredibly ornate interiors. We recommend the following accommodations for your pre-trip hotel:

after

After: 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. Michelangelo's David in the Galleria dell'Accademia 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 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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