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Trip Itinerary
Enjoy a weekend getaway in Tuscany on this self-guided bike tour for a taste of unparalleled riding and culinary delights in the Val d'Orcia.
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Where to Arrive
Airport:
Amerigo Vespucci (Florence) Airport (FLR)
Pick-up location:
Villa Liberty Boutique Hotel, San Quirico d'Orcia
Pick-up time:
11:00 AM
Where to Depart
Airport:
Amerigo Vespucci (Florence) Airport (FLR)
Drop-off location:
Villa Liberty Boutique Hotel, San Quirico d'Orcia
Drop-off time:
12:30 PM
Additional Arrival Information
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) and rent a car for the duration of the trip. Most major rental car companies are available at FLR. Advance booking is recommended. If you are not renting a car, 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.
From Florence (Santa Maria Novella train station) there are frequent direct trains to Siena. The trip takes about 90 minutes and a one-way ticket costs about ten euros. Italian train schedules can be found on www.TrenItalia.com.
The trip takes place in the Tuscan countryside that is not well served by public transportation. For this reason, if you have not rented a car, 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 €150. 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, you'll begin your 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.
Additional Departure Information
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.
Welcome to the breathtaking landscape of the Val d'Orcia
Overview
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!
Hotel
Villa Liberty
Meals included
Highlight of the Day
Visit Pienza
Stroll through this UNESCO heritage site with a gelato in hand and get a photo of the valley below from one of the amazing viewpoints!
Hiking Options
Hike Option 1
TODAY'S RIDE:
San Quirico to Bagno Vignoni to Pienza Loop - Approximately 19 mi | 30 km and 1,458 ft | 444 m
Activities
Activity 1
TODAY’S ACTIVITY:
Visit a Roman Thermal Spa Town
Montalcino, home of the finest Italian wines, Brunello DOCG
Overview
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.
Hotel
Villa Liberty
Meals included
Breakfast
Highlight of the Day
Discover Brunello wine
Brunello di Montalcino is one of Italy's finest wines. At lunch in the walled village of Montalcino, taste this varietal at a trattoria, either on its own or paired with each course of your meal.
Hiking Options
Hike Option 1
TODAY'S RIDE:
San Quirico to Montalcino Loop - Approximately 33 mi | 53 and 3,886 ft | 1,184 m
Hike Option 2
SHORT OPTION:
San Quirico to Monticchiello Return - Approximately 20 mi | 33 km and 1,494 ft | 455 m
Hike Option 3
AVID OPTION:
San Quirico to Monticchiello to Montalcino Loop - Approximately 48 mi | 77 km and 4,824 ft | 1,470 m
Activities
Activity 1
TODAY’S ACTIVITY:
Visit the Abbazia di Sant’Antimo
Pedal through the moonscape of Crete Senesi and the sun-drenched Tuscan countryside
Overview
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.
Hotel
Villa Liberty
Meals included
Breakfast
Highlight of the Day
Ride in the Crete Senesi moonscape
The Crete Senesi, Tuscany's badlands, offer some of the week's most dramatic views. The clay-dense soil creates an almost lunar landscape, with undulating fields that invite you to stop and marvel at its beauty.
Hiking Options
Hike Option 1
TODAY'S RIDE:
San Quirico to San Giovanni d'Asso Loop - Approximately 26 mi | 42 km and 2,539 ft | 774 m
Hike Option 2
AVID OPTION:
San Quirico to San Giovanni d'Asso to Asciano Loop - Approximately 43 mi | 69 km and 4,425 ft | 1,349 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
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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.
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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).
Classic:
Explore beautiful destinations with a curated blend of guided activities, local cuisine, handpicked accommodations, and itineraries to suit every traveler, from laid-back adventures to luxurious escapes.
Gravel:
Venture off the beaten path to unforgettable places, with fully-supported routes that combine gravel and paved roads in classic Trek Travel style.
Cross Country:
Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.
Pro Race:
See the pros in action at the biggest cycling events of the year.
Hiking & Walking:
Step into adventure with carefully designed routes, unparalleled hospitality, and deep-routed local connections.
Ride Camp:
Train like the pros in some of their favorite riding destinations.
Self-Guided:
Enjoy a bike tour on your schedule with just your chosen travel companions.
Enjoy a casual vacation with fantastic routes and comfortable accommodations.
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