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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:
Rome Fiumicino (FCO)
Pick-up location:
Assisi Train Station, Italy
Pick-up time:
12:00 PM
Where to Depart
Airport:
Florence Airport (FLR)
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 and Umbria 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 Rome’s Fiumicino Airport (FCO), then take a direct train, shuttle bus or taxi to Rome’s central station called Roma Termini. From Roma Termini there are frequent direct trains to Assisi and the ride takes about two and a half hours. We recommend purchasing your ticket in advance online at www.TrenItalia.com or at the train station from a Biglietteria (ticket) office or one of the ticket machines available there. All paper tickets must be validated before boarding the train; you can do this by stamping your ticket at the yellow machines located near the platforms.
Your Trek Travel guides will meet you at the Assisi train station (06081 Santa Maria degli Angeli, Province of Perugia, Italy) at 12:00 PM 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€.
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 online at www.TrenItalia.com or at 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 and Umbria bike adventure! Meet your Trek Travel guides at the Assisi Train Station at 12:00 PM. 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 where you can enjoy a relaxing afternoon by the pool. In the evening, gather with your fellow travelers for an Italian aperitif on the hotel terrace, followed by a family-style dinner featuring Umbrian specialties and estate wines. And get ready for more exciting cycling adventures ahead!
Hotel
Valle di Assisi Resort & Spa
Meals included
Lunch | Social Hour | Dinner
Highlight of the Day
Valle di Assisi Resort & Spa
Relax and soak up views of olive groves, vineyards, and rolling hills that stretch endlessly across the Umbrian region.
Ride Options
Ride Option 1
TODAY'S RIDE:
Valle di Assisi to Collemancio Loop - Approximately 20 mi | 32 km and 1,230 ft | 375 m
Experience Bevagna, Montelfalco, Spello and the authentic allure of Umbria
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 wine. Enjoy the sweeping descent and head to Spello, a delightful village famous for being one of the most flowery towns in Italy. Enjoy a well-earned lunch of your choice in this picture-postcard town characterized by its warren of narrow, cobbled streets that are a triumph of verdant balconies and colorful flowers. Afterward, relish a pleasant flat section of your ride back to the hotel. Later in the afternoon we'll shuttle you to Assisi to explore the cobbled streets of this medieval town on a delightful walking tour that ends at the celebrated Basilica of Saint Francis, a UNESCO World Heritage Site. Tonight is yours to find the perfect dinner in town, armed with the best recommendations from your guides.
Hotel
Valle di Assisi Resort & Spa
Meals included
Breakfast
Highlight of the Day
Assisi in Umbria
Uncover St. Francis’s birthplace, a UNESCO-listed city of art and architecture where the Basilica showcases Italy’s finest masterpieces.
Ride Options
Ride Option 1
TODAY'S RIDE:
Valle di Assisi to Bevagna-Montefalco-Spello Loop - Approximately 41 mi | 66 km and 1,813 ft | 553 m
Ride Option 2
SHORT OPTION:
Valle di Assisi to Bevagna-Montefalco-Spello with Shuttle - Approximately 29 mi | 46 km and 1,589 ft | 484 m
Ride Option 3
AVID OPTION:
Valle di Assisi to Bevagna-Montefalco-Spello Loop with Collepino Climb - Approximately 49 mi | 80 km and 2.912 ft | 888 m
Explore Lake Trasimeno's beauty before entering the distinctive landscapes of Tuscany
Overview
After your morning cappuccino, you'll ride through the rural countryside, passing cultivated fields and olive groves that characterize the Umbrian landscape. Our lunch destination today is San Feliciano, an inviting village on the shore of the Trasimeno lake, where you'll enjoy a casual lunch while admiring the views of this idyllic lake, a hidden gem that captivates with its beauty and rich history. From here, you'll continue riding by the lake until you reach 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. In the evening a 30-minute shuttle will take you to the fascinating hilltop town of Cortona, a fairytale village where the famous movie 'Under the Tuscan Sun' was filmed, attracting a stream of international tourists. This evening we'll enjoy a traditional Tuscan dinner in Cortona before making our way back to the hotel.
Hotel
Borgo Tre Rose
Meals included
Breakfast | Lunch | Dinner
Highlight of the Day
The scenic Trasimeno lake
Ride the hills south of Perugia to Lake Trasimeno, a serene lake encircled by rolling hills and among Europe’s most scenic cycling routes.
Ride Options
Ride Option 1
TODAY'S RIDE:
Valle di Assisi to Borgo Tre Rose - Approximately 53 mi | 86 km and 2,415 ft | 736 m
Ride Option 2
SHORT OPTION:
Valle di Assisi to San Feliciano with Shuttle - Approximately 31 mi | 51 km and 1,552 ft | 473 m
Discover the hilltop town of Pienza and be seduced by the eternal charm of Val d'Orcia
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 will lead you to the charming hilltop town of Pienza, where your guides will be ready with a casual lunch of fresh sandwiches and a van full of ride snacks and drinks to keep you fueled. Prepare to be mesmerized by breathtaking panoramas that resemble masterpieces paintings. This evening we'll raise a toast to our unforgettable Tuscany bike tour tasting 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.
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 lined with cypress trees and soft ochre hues to Pienza, a UNESCO World Heritage jewel of Tuscany.
Ride Options
Ride Option 1
TODAY'S RIDE:
Borgo Tre Rose to Pienza Loop - Approximately 43 mi | 70 km and 3,300 ft | 1,000 m
Ride Option 2
SHORT OPTION:
Borgo Tre Rose to Pienza with Shuttle - Approximately 21 mi | 34 km and 1,970 ft | 600 m
Ride Option 3
AVID OPTION:
Borgo Tre Rose to Pienza Loop via Montisi - Approximately 53 mi | 85 km and 4,650 ft | 1,400 m
One last spin through the rolling Tuscan hills
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. Or simply linger over a hot cappuccino as you watch the sunrise creeping over the classic Tuscan landscape. 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.
Hotel
Borgo Tre Rose
Meals included
Breakfast
Highlight of the Day
Sunrise ride
Savor your final sunrise ride as golden light fills the region, embracing the tranquility and beauty of the Tuscan hills.
Ride Options
Ride Option 1
TODAY'S RIDE:
Borgo Tre Rose to Ferretto Loop - Approximately 13 mi | 22 km and 694 ft | 212 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
Trek Travel offers three hotel levels to match your style. Luxury hotels provide elegant, thoughtful touches with exceptional hospitality. Explorer hotels blend modern amenities with local charm in unique settings. Comfort hotels are casual and conveniently located near Trek Travel activities.
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).
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.
Venture off the beaten path to unforgettable places, with fully-supported routes that combine gravel and paved roads in classic Trek Travel style.
Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.
See the pros in action at the biggest cycling events of the year.
Step into adventure with carefully designed routes, unparalleled hospitality, and deep-routed local connections.
Train like the pros in some of their favorite riding destinations.
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