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Trip Itinerary
Discover two of Italy's top cycling destinations: lush Umbria, renowned for its fine olive oil, and the noble Montepulciano wine region.
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Where to Arrive
Airport:
Florence Airport (FLR)
Pick-up location:
Assisi Train Station, Italy
Pick-up time:
11:30 AM
Where to Depart
Airport:
Florence Airport (FLR) or Rome Fiumicino (FCO)
Drop-off location:
Santa Maria Novella train station, Florence Italy
Drop-off time:
12:30 PM
Additional Arrival Information
We suggest that you arrive at least one day prior to the start of your Tuscany Countryside bike tour, 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 three miles from the center of Florence. You can take a taxi (approximately 20 euros) directly to Santa Novella train station, or a bus which departs hourly. There are frequent direct trains from Firenze S.M. Novella to Assisi and the ride takes two and a half hours. We recommend you purchase your ticket in advance on the Trenitalia website at www.TrenItalia.com or at a Biglietteria office or from ticket machines available at the train station.
You can also fly into Rome and take a train to Assisi. 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. There are frequent direct trains from Roma Termini to Assisi and the ride takes about two hours. Tickets can be purchased on the Trenitalia website at www.TrenItalia.com or at a Biglietteria office or from ticket machines available at the train station.
All tickets must be validated before getting on the train: do this by stamping your ticket at the yellow boxes near the platform.
Your Trek Travel guides will meet you at the Assisi train station at 11:30 AM on the first day of the trip. Please wait here to meet your Trek Travel guide, who will be visible and dressed in Trek Travel attire. Together you'll shuttle 5 minutes to the hotel Valle di Assisi, your home for the next two days. Here you will be welcomed by a casual buffet-style lunch while your guides fit and familiarize your group with your Trek bike for the week. Please have your first day's cycling clothes easily accessible, separate from your luggage, to facilitate the bike fitting and ride. After a brief orientation and a safety talk, saddle up to begin the day's ride through the Umbrian countryside.
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, Valle di Assisi (+39 075 804 4580) and leave a message with your expected arrival time and contact details. You may take a taxi from Assisi to to the first night’s hotel for approximately 20 euros.
Additional Departure Information
You will say farewell to your guides at 11:00 AM at the Borgo Tre Rose in Montepulciano. You’ll depart by private shuttle for the Florence train station, arriving at around 12:30 PM. Please, do not reserve a seat prior to 1:30 PM, allowing adequate connection time for any ongoing travel or possible traffic delays. Train schedules, fares and bookings can be made on the Trenitalia website at www.TrenItalia.com, or www.thetrainline.com, for other European destinations.
Welcome ride in the green hills of Umbria to Assisi, a UNESCO World Heritage site
Overview
Welcome to the start of your Tuscany Countryside bike adventure! Meet your Trek Travel guides at the Assisi Train Station at 11:30 AM. A quick 5-minute shuttle ride takes you to your hotel near Assisi, a peaceful property surrounded by vineyards, olive groves, and fruit trees. After a short round of introductions, get fitted to your Trek bicycle and enjoy a casual buffet-style lunch at the hotel. Begin your first scenic ride and, as you familiarise yourself with you... Welcome to the start of your Tuscany Countryside bike adventure! Meet your Trek Travel guides at the Assisi Train Station at 11:30 AM. A quick 5-minute shuttle ride takes you to your hotel near Assisi, a peaceful property surrounded by vineyards, olive groves, and fruit trees. After a short round of introductions, get fitted to your Trek bicycle and enjoy a casual buffet-style lunch at the hotel. Begin your first scenic ride and, as you familiarise yourself with your bike, explore the quiet roads up to Collemancio. Take in the breathtaking views from the top before descending to the valley to return to the hotel. In the evening, gather with your fellow travelers for an Italian aperitif on the hotel terrace, followed by a gourmet dinner featuring Umbrian specialties and estate wines. And get ready for more exciting cycling adventures ahead! Read More
Hotel
Valle di Assisi Resort & Spa
Meals included
Lunch | Social Hour | Dinner
Highlight of the Day
Valle di Assisi Resort & Spa
Relax and take in the breathtaking views of the surrounding olive groves and vineyards, with rolling hills that stretch as far as the eye ca... Relax and take in the breathtaking views of the surrounding olive groves and vineyards, with rolling hills that stretch as far as the eye can see. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Valle di Assisi to Collemancio Loop - Approximately 19 mi | 22 km and 1,180 ft | 360 m
Experience Montelfalco and the authentic allure of the Umbrian countryside
Overview
Today's route takes you through the beautiful Val'Umbra, Umbria's largest and most prolific valley awash in vineyards and olive groves. A leisurely ride leads you to Bevagna, a celebrated town with two of Italy's oldest Romanesque churches in its central cobblestone piazza. Wander the narrow streets and enjoy its enotecas and art galleries. Then gear up for a rewarding climb to reach the hilltop town of Montefalco, synonymous with world-renowned Sagrantino ... Today's route takes you through the beautiful Val'Umbra, Umbria's largest and most prolific valley awash in vineyards and olive groves. A leisurely ride leads you to Bevagna, a celebrated town with two of Italy's oldest Romanesque churches in its central cobblestone piazza. Wander the narrow streets and enjoy its enotecas and art galleries. Then gear up for a rewarding climb to reach the hilltop town of Montefalco, synonymous with world-renowned Sagrantino wine. Enjoy a well-earned lunch of your choice in this picture-postcard town characterized by its warren of narrow, cobbled streets within its ancient walls. Afterward, relish a pleasant flat section of your ride before ascending to Assisi. You'll take in the panoramic views of this magical medieval town before heading back to the hotel for a relaxing afternoon by the pool. This evening we'll shuttle you to Assisi to explore the cobbled streets of this medieval town. Enjoy dinner of your choice at one of the many small bistros. Be sure to visit Assisi's celebrated Basilica of Saint Francis, a UNESCO World Heritage Site. Read More
Hotel
Valle di Assisi Resort & Spa
Meals included
Breakfast
Highlight of the Day
Assisi
Discover St. Francis’s birthplace, a city of art and exquisite architecture. The historic center and Basilica, home to Italy’s finest ma... Discover St. Francis’s birthplace, a city of art and exquisite architecture. The historic center and Basilica, home to Italy’s finest masterpieces, are highlights of this UNESCO-listed borgo in Umbria. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Bevagna to Montefalco to Assisi Loop - Approximately 42 mi | 68 km and 2,520 ft | 760 m
Ride Option 2
AVID OPTION:
Bevagna to Montefalco to Assisi Loop with Collemancio Climb - Approximately 55 mi | 90 km and 3,600 ft | 1100 m
Explore Lake Trasimeno's beauty before entering the distinctive landscapes of Tuscany
Overview
After your morning cappuccino, prepare to say arrivederci to Umbria. A 30 minute shuttle ride will take you to your ride start in Solomeo, a fascinating medieval village characterised by narrow streets covered by tiled bricks. Here you'll saddle up and ride along quiet secondary roads, winding through rolling hills and olive groves. The climb up Castel Rigone will challenge your legs, but the panoramic descent towards the Trasimeno lake will make all the ef... After your morning cappuccino, prepare to say arrivederci to Umbria. A 30 minute shuttle ride will take you to your ride start in Solomeo, a fascinating medieval village characterised by narrow streets covered by tiled bricks. Here you'll saddle up and ride along quiet secondary roads, winding through rolling hills and olive groves. The climb up Castel Rigone will challenge your legs, but the panoramic descent towards the Trasimeno lake will make all the efforts worthwhile. Your lunch destination is Passignano, an inviting village on the northern shore of Lake Trasimeno, where your guides will be ready with casual lunch of fresh sandwiches and a van full of ride snacks and drinks to keep you fueled! Enjoy the views of the lake, the largest in Umbria and home to wild ducks, cormorants, and more. From here, continue riding the last 12 miles (20 km) all the way to our lovely country hotel, perched on a hilltop amidst picturesque vineyards. Spend the rest of the afternoon relaxing by the pool or strolling through the estate. You'll spend this evening in Cortona. A short shuttle will take you to this fascinating Tuscan hilltop town. Tonight is yours to find the perfect dinner in this historic town, armed with the best recommendations from your guides. Read More
Hotel
Borgo Tre Rose
Meals included
Breakfast | Lunch
Highlight of the Day
The scenic Trasimeno lake
Traverse the hills south of Perugia on one of Europe's most beautiful cycling routes. Reach Lake Trasimeno, a picturesque lake surrounded by... Traverse the hills south of Perugia on one of Europe's most beautiful cycling routes. Reach Lake Trasimeno, a picturesque lake surrounded by rolling hills, offering a unique and captivating landscape. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Solomeo to Borgo Tre Rose - Approximately 35 mi | 56.7 km and 2,620 ft | 800 m
Ride Option 2
AVID OPTION:
Solomeo to Borgo Tre Rose via Terontola - Approximately 50 mi | 81 km and 3,340 ft | 1020 m
Discover the quintessential Tuscan hilltop towns of Montefollonico, Pienza, and Montepulciano
Overview
Prepare for a fantastic day ahead as you pedal along quiet country roads, with unobstructed views of vast ploughed and sown lands stretching over gentle hills that seamlessly blend with the horizon. These captivating vistas are accentuated by the presence of rows of majestic cypress trees. The consistently rolling terrain unveils three captivating climbs, leading you to the charming hilltop towns of Montefollonico, Pienza, and Montepulciano. This renowned region is ... Prepare for a fantastic day ahead as you pedal along quiet country roads, with unobstructed views of vast ploughed and sown lands stretching over gentle hills that seamlessly blend with the horizon. These captivating vistas are accentuated by the presence of rows of majestic cypress trees. The consistently rolling terrain unveils three captivating climbs, leading you to the charming hilltop towns of Montefollonico, Pienza, and Montepulciano. This renowned region is celebrated for its exceptional extra virgin olive oil and of course its world-famous wines. Prepare to be mesmerized by breathtaking panoramas that resemble masterpieces paintings. This evening we'll raise a toast to our unforgettable Tuscany bike tour during a visit to the hotel's cellar, followed by a delightful wine tasting featuring the estate's own exquisite wines. Indulge in a sensational dinner at the hotel's restaurant, where you will be treated to an array of local specialties, creating a perfect finale to our remarkable Italian adventure. Read More
Hotel
Borgo Tre Rose
Meals included
Breakfast | Lunch | Social Hour | Dinner
Highlight of the Day
Val d'Orcia, the Tuscany of your dreams
Pedal through rolling hills that disappear into the horizon, adorned with cypress trees and soft green and ochre colors. Discover Pienza, a ... Pedal through rolling hills that disappear into the horizon, adorned with cypress trees and soft green and ochre colors. Discover Pienza, a UNESCO World Heritage site and one of Tuscany's most iconic towns. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Borgo Tre Rose to Pienza to Montepulciano Loop - Approximately 37 mi | 60 km and 3,180 ft | 970m
Ride Option 2
AVID OPTION:
Borgo Tre Rose to Pienza to Montepulciano Loop - Approximately 49 mi | 79,4 km and 3,770 ft | 1,150 m
One last spin to the perched village of Cortona
Overview
Rise early this morning for one last spin on the gently rolling hills as you say buongiorno to the locals working in the fields. You'll revisit Cortona, this time by bike, on the eastern slope of the Valdichiana. Arrive in the Piazza della Repubblica, the main square, and observe its unique shape before pedaling back to the hotel. We will bid our farewells, and at 11:00 AM, you’ll depart by private shuttle for the Florence train station, arriving at appro... Rise early this morning for one last spin on the gently rolling hills as you say buongiorno to the locals working in the fields. You'll revisit Cortona, this time by bike, on the eastern slope of the Valdichiana. Arrive in the Piazza della Repubblica, the main square, and observe its unique shape before pedaling back to the hotel. We will bid our farewells, and at 11:00 AM, you’ll depart by private shuttle for the Florence train station, arriving at approximately 12:30 PM, in time to catch connecting trains to other destinations. Read More
Hotel
Borgo Tre Rose
Meals included
Breakfast
Highlight of the Day
Cortona
Visit the fairytale hilltop town of Cortona, where "Under the Tuscan Sun" was filmed. With olive groves and panoramic views from the town wa... Visit the fairytale hilltop town of Cortona, where "Under the Tuscan Sun" was filmed. With olive groves and panoramic views from the town walls, it's easy to see why visitors fall in love with this place. Read More
Ride Options
Ride Option 1
TODAY'S RIDE:
Borgo Tre Rose to Cortona Loop - Approximately 24 mi | 39 km and 1,660 ft | 507 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
Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.
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.
On select cycling vacations, you’ll stay at a mix of Explorer and Luxury hotels. Rest assured, no matter which hotel level you’re at, our trip designers carefully select every accommodation.
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).
Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.
Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.
Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.
Train like the pros in some of their favorite riding destinations.
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Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.
Enjoy a bike tour on your schedule with just your chosen travel companions.
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