Southern Tuscany and western Umbria combine two of the most beautiful and photographed landscapes in Italy. Imagine a gentle rolling terrain of hilltop villages surrounded by fertile green meadows with grazing sheep, fields of ripening grain, lush oak forests, olive groves shimmering in the sunlight and gentle breezes coming off its undiscovered lakes. Starting in the countryside just south of Siena, we'll discover Medieval monasteries and pre-Roman Etruscan settlements. We'll visit villages renowned for their cheeses, their wines and their small town hospitality. In Umbria, we'll ride along the shores of Lake Trasimeno where the Romans met their match in Hannibal, and we'll discover that Assisi is much more than just the city of San Francesco. Follow the quiet sideroads from Tuscany to Umbria, and discover their ever changing landscapes in one of Italy's most enjoyable and refreshing biking destinations.

Day 1 - The Sienese Landscapes - Rendezvous in Florence or Siena. Private transfer to the 14th-century monastery of Abbazia di Monte Oliveto Maggiore for an introductory lunch and a visit into its hallowed cloisters to view its frescos by Signorelli and Sodoma. Cycle into the open clay landscapes of Le Crete and its undulating hills with isolated brick villas and farmhouses surrounded by tall cypress trees.

Day 2 - Pienza and the Val d'Orcia - Follow quiet roads past forgotten hilltop villages dotting stunning landscapes of grazing sheep and Tuscany's prized oxen. Discover Pienza, a perfectly designed Renaissance village that overlooks the spectacular Orcia Valley. Cruise its main village street with shops stuffed with Pienza's favorite food item, Pecorino cheese. Why not do a taste testing from mild to aged. An afternoon ride will take us past small villages, monasteries, fortified villas and castles.

Day 3 - Montepulciano and Lake Trasimeno - Bike to Montepulciano, a hilltop town with a pedestrian street lined with Renaissance palaces. Discover its ancient underground wine cellars and sample its prized Nobile di Montepulciano red wines, regarded as some of the finest in Italy. Continue into the flat Chiana Valley and the border between Tuscany and Umbria. Follow quiet sideroads with grain fields flowing in the wind. Pass by abandoned 17th-century brick farmhouses. Follow along a panoramic ridge overlooking Lake Trasimeno in the distance. Dine tonight at a favorite trattoria, specializing in local produce including Trasimeno's delicious lake fish.

Day 4 - Torgiano & Deruta - Start your biking day with one of the nicest biking routes in Italy. Follow a panoramic ridge past untouristed farm villages. Continue around shallow Lake Trasimeno, scene of a Roman defeat during Hannibal's march on Rome, today, a much quieter place with silvery green olive groves covering its lakeside slopes. Venture into the vibrant green landscapes of the Umbria plain. Take in a Club Toscana picnic in a sleepy Umbrian hilltop village before passing along the fertile slopes of the Tiber Valley, past a patchwork of olive groves, vineyards and small farms. Visit Deruta, home to Italy's finest ceramic shops and discover one of its most illustrious producers to see ceramic production from raw clay to finished product. Follow along the Tiber River to Torgiano, Umbria's wine capital and our home for the next two nights.

Day 5 - Valle Umbra & Assisi - Take a casual visit of the Lungarotti Wine and Olive Oil Museums before biking across the flat Valle Umbra to the town of Assisi. This ancient town of pink and white stone, flowing up the base of Mount Subasio has something for everyone, from the festival of Renaissance frescoes in the Basilica to the sweeping views from the Rocca Maggiore fortress high above the town. Take a casual tour of the Basilica of San Francesco, walk Assisi's medieval streets and discover its vibrant history.

Day 6 - Perugia - Homeward bound. Bid a final farewell to the green landscapes of Umbria and take a private transfer to your post-trip hotel or other travel connections in Perugia. As always, we would be more than pleased to help you with any of your post-trip travel planning.
Arrivederci and Buon Viaggio !

NEED MORE TRIP INFORMATION? E-mail or call our professional travel advisers at Club Toscana Reservations at 1-866-563-4248 toll free 8:30 am to 5:30 pm (EST) Mon. to Fri., 8:30 am to 1:00 pm Sat. They are ready to answer your trip questions and arrange all your pre and post-trip travel needs for a truly all-inclusive European Active Vacation.

Please note that the above itinerary is typical for this trip and can be adjusted to accommodate optional route daily distances & effort levels, your daily biking pace and interests, and special local events. Weather conditions and road repairs, etc. can also alter the routes.
In an effort to enhance this itinerary to help you get the most out this destination and your traveling experiences with Club Toscana, we are always in the process of researching additional local routes, accommodations and interesting places to visit.

Pienza - (2 nights) - a family run boutique hotel with modern amenities and spectacular views of the Val d'Orcia from their terraced gardens, all located just footsteps from the historic village walls of Renaissance Pienza.
Cittą della Pieve - (1 night) - Hotel Vannucci was built in 1887 by King Vittorio Emanuele II as the elegant Villa Mirafiori. Its ornate iron gates open into private landscaped gardens overlooking medieval churches and the verdant Umbrian countryside.
Torgiano - (2 nights) - once a village townhouse built in the 1700s with original wood beam ceilings and terra cotta floors, this charming hotel offers wonderful views of Assisi and the Umbrian Valley from its garden pool.

Note: The above Michelin rated hotels are subject to accommodations availability upon trip request. Alternative accommodations meet or excede the above selection in ratings, settings, amenities and views.