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Tuscany 3-Day Weekend Self-Guided Bike Tour

A weekend getaway in Val d'Orcia, the beating heart of Tuscany

Discover the incomparable beauty of Tuscany's Val d'Orcia on an enchanting 3-day weekend self-guided bike tour. As you meander along winding cypress-lined roads, the famous golden rolling hills unveil their majestic allure. Amidst the sun-kissed splendor, the ancient farms, vineyards, and valleys exude tranquility. Here you’ll experience some of the world's finest wines and cuisine that is celebrated for its simplicity and freshness. If you crave adventure without the hassle of planning, look no further than Trek Travel's self-guided bike tour in Tuscany and discover the wonders of this truly magnificent land at your own pace. This 3-day getaway promises an unforgettable experience, where each moment becomes a cherished memory. Book your trip with confidence » Learn more about Self-Guided trips and if they're right for you » Also see our 5-day Tuscany Self-Guided bike tour »
Join Trek Travel for a Tuscany Self-Guided Bike Tour
From:
$1199 Per Person
Duration:
3 Days & 2 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Self-Guided
Hotel Level: ?
Explorer
From $1199 per person View All Details
Trip Wows
Ride along quiet roads lined with cypress trees in the beautiful Tuscan landscape
Stay in a historic property 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 3-Day Weekend 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 B., 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 and date are guaranteed.
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Single Occupancy from: +$499
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Apr 20 – Apr 22 
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Apr 27 – Apr 29 
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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 your hotel, Villa Liberty, located in the heart of the medieval village of San Quirico d’Orcia. They'll give you a brief orientation of the adventures ahead and will fit you to your Trek bike, ensuring you total comfort on your bike for the week. Then, it's off on your first self-guided adventure in the enchanting landscape of 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 charming Renaissance architecture and its connection to Pecorino cheese, a traditional Italian cheese with deep roots in the region. Wander through its streets and grab the best gelato at “Buon Gusto” before cycling at your leisure back to your hotel. 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 | 31 km and 1,476 ft | 450 m

Hotel:

Villa Liberty

This morning’s route lifts you high above the Val d’Orcia, a vista dotted with rolling hills blanketed with vines and rows of the ubiquitous cypress trees. There are three riding options of different lengths available for you today, so feel free to choose the one that suits you best. 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 in time to hear the magical yet haunting choral harmonies of the monks' Gregorian chants! 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 curated list of Trek Travel recommendations.

Today's Ride:

San Quirico to Montalcino Loop
Approximately 33 mi | 53 and 3,886 ft | 1,184 m

Short Option:

San Quirico to Monticchiello Return
Approximately 20 mi | 33 km and 1,494 ft | 455 m

Avid Option:

San Quirico to Monticchiello to Montalcino Loop
Approximately 48 mi | 77 km and 4,824 ft | 1,470 m

Hotel:

Villa Liberty

Included Meals:

Breakfast

Close out your Tuscany self-guided bike tour by riding through a truly dramatic landscape called 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. Enjoy the feeling of peace conveyed by this stunning landscape often described as lunar due to the dramatic colors of the clay-dense soil. If time allows, we suggest you take the avid option to Asciano, pedalling through meandering roads overlooking the surrounding ridges on an other-worldly route. A late check-out time (at 12:00 PM noon) will allow you to be back at the hotel in time to take a shower before you bid your farewells. Your Trek Travel host will meet you at the hotel at 12:30 PM to take your bike and say arrivederci before you leave for Florence or other destinations.

Today's Ride:

San Quirico to San Giovanni d'Asso Loop
Approximately 26 mi | 42 km and 2,539 ft | 774 m

Avid Option:

San Quirico to San Giovanni d'Asso to Asciano Loop
Approximately 43 mi | 69 km and 4,425 ft | 1,349 m

Included Meals:

Breakfast

Hotels

hotel image

Villa Liberty (CAPITANO COLLECTION)

San Quirico d’Orcia, Italy

Explorer Accommodation | Villa Liberty is an elegant 4-star boutique hotel set in an ancient Renaissance villa with bright and spacious communal areas. The rooms are a perfect blend of Tuscan tradition and modern luxury, decorated with exclusive works of art. Instead of a fully dedicated wellness area, the spa's features are scattered throughout the property in the heart of charming San Quirico d'Orcia. There is also access to a wonderful outdoor pool surrounded by tranquil gardens where you can relax after the ride. Breakfast is served at the hotel's own traditional trattoria "Al Vecchio Forno" within short walking distance from the accommodation.

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 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

bike

Trek Domane SL 7 Gen 3

Trek’s continuous innovation has led to one of the best bikes on the road - a light weight, stable, and technologically advanced machine to make even the hardest roads seem easy. The Domane SL 7 Gen 3 is a beautiful high-performance endurance road bike with wireless electronic Ultegra Di2 12-speed drivetrain for lightning-fast precision shifting in any conditions. The combination of the carbon frame with front and rear IsoSpeed, carbon wheels that come stock on the bike, and hydraulic disc brakes keep it smooth, safe, fast, and most importantly, fun! Learn More

WHAT'S INCLUDED

  • Two 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 Garmin GPS computer, 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, 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)
  • A bike lock, all necessary chargers and a floor pump
  • Bike fit on the first day to help you find your optimal riding position
  • Ride With GPS Experience on your phone to 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
  • Garmin GPS computer with mount
  • 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
  • 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

For self-guided trips you are welcome to thank your host with a gratuity based on your level of 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:
42 kilometers / 26 miles
TOTAL MILES:
126 kilometers / 78 miles
AVERAGE DAILY ELEVATION:
802 meters / 2,633 feet
TOTAL ELEVATION:
2,408 meters / 7,901 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 3-day 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:
Villa Liberty (Capitano Collection), San Quirico d'Orcia

Say Farewell

FLY OUT OF:
Amerigo Vespucci (Florence) Airport (FLR)
DEPARTING TIME:
12:30 PM
DEPARTING LOCATION:
Villa Liberty (Capitano Collection), 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 Villa Liberty (Via Dante Alighieri, 119, 53027 San Quirico D'orcia SI) at 11:00 AM on the first day of the trip. Depending on the number of guests booked for your departure date, it is possible we will ask you to shift your meeting time by approximately 30 minutes. Please have your riding gear readily accessible to avoid having to unpack your luggage. After a trip overview, you may change into your cycling gear where you will then be fitted to your Trek bike ensuring you will be comfortable for the week. Following a safety talk and a review of the details of the route, 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, Villa Liberty (+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 12:30 PM 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.

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/24-32C) 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/27-35C) 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 its architectural beauty and its particular "shell" form. 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:

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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