Italy | Tuscany | Adult Only
Food, wine, history, and scenery that simply can't be beat
6 days / 5 nights
Activity LevelActivity levels are subjective depending on your general level of fitness and your experience; however, all of our trips are self-paced.
Chic and steeped in culture, Tuscany will charm you with its abundant lush landscapes and mouth-watering cuisine. We’ll bicycle rural roads along gently terraced hills, hike through vineyards, olive groves and forests with plenty of time to appreciate the region’s timeless beauty and historic art treasures. Prior to the trip, be sure to visit Florence: rich in art, history, science and shopping, Florence is truly a Tuscan jewel.
Top-notch wine, rich culture, impressive history, pastoral countryside, and world-renowned cuisine await you on this 6-day bike tour through Tuscany.
Welcome to your classic Tuscan adventure; to six full days of mouth-watering food, rolling vineyards, weathered hillside villas, and vibrant cities brimming with art, history, and old-world charm.
- Hike ancient pilgrim trails through the vineyard-clad hills of Chianti Classico, soaking up a quintessential golden-green Tuscan landscape dotted with sheep, castelli, cypress trees, and olive orchards
- Visit the marbled Duomo in Siena on a guided walk and savor a homemade lunch served by Mamma Licia in the village of Chiusure
- Bike to Monteriggioni, a village surrounded by 14 medieval towers, and explore the quaint streets, art galleries and gelaterie in San Gimignano
- Dine as the Medici family once did on crostini ai funghi porcini (a Tuscan specialty: toast with mushrooms), ossobuco alla Toscana and homemade torta, washed down with a glass of bold Chianti or crisp Vernaccia di San Gimignano
A few more reasons why you've gotta go:
The vineyards: the Tuscan region is universally acclaimed for its classic wines and natural beauty.
The shopping: The picturesque open air markets are the perfect place to find leather goods, paper goods, stunning jewelry and marvelous art.
The gastronomical delights: The finest extra-virgin olive oil comes from Tuscany. It's one of the main ingredients of the region's cuisine as well as beans, herbs, ham and salami.
Florence, Italy FLR
Florence, Italy FLR
We meet in Florence in the morning and begin the day with a transfer to Chianti. Hike in the vineyard-clad hills of Chianti Classico and continue to the famous wine village of Gaiole. Savor a lunch in an old abbey with an olive grove. Stop for a wine tasting and a castle tour and find out why Italy is so well-known for its wine and vineyards. The route is filled with temptations before it leads to the golden hued, sentimental city of Siena. Tonight, we’ll gather for a memorable Florentine welcome feast in Siena.
About Hotel Villa Scacciapensieri
A heaven of greenery and peacefulness, the Hotel Villa Scacciapensieri is located in the city, yet it’s surrounded by its own garden and a luxurious park of oak trees. Its peaceful and traditional setting is ideal for relaxing the mind and body.
Travel back in time on an easy spin to the quiet, medieval villages of Belcaro and Sovicille. Spend the remainder of this day in Siena with a local historian who leads us on a spirited tour of this grand city. Tonight offers you more time on your own to relax or experience more of this amazing city.
Relax and enjoy the scenery as you are transferred from Siena to Sinalunga this morning. Today’s bike ride explores the graceful Tuscan landscape, famous for its sprawling green and sepia-toned farms. Visit the walled town of Asciano and take a group tour of the museum there. Break for lunch before visiting the famous abbey at Monte Oliveto Maggiore. Returning to Siena, delicate cypress trees frame dramatic views of the chalky cliffs of the Crete hills. Share another amazing dinner together tonight.
Wooded hills form the backdrop for a picturesque and exhilarating day. We’ll hike the Pilgrim trail in the region of Monteriggioni, surrounded by 14 medieval towers. After lunch take another stroll past dreamy blue green pools on one of our ‘secret hikes’. That afternoon we’ll explore San Gimignano, stopping for a wine tasting in the “Manhattan of Italy,” and dine on expertly prepared local specialties, with panoramic views. Save room for Gelato as the town boasts one of the world’s best Gelaterias.
About Hotel la Cisterna
Located in San Gimignano, a town of fairy tales with medieval towers, this charming hotel is housed in a stone-walled 14th-century palace. You’ll be surrounded by splendid views and the beautiful Tuscan countryside.
Your destination today is Artimino, home to the famous Medici Villa of the Hundred Chimneys. Passing through orchards and vineyards, you’ll visit traditional towns like Certaldo and Montespertoli before crossing the Arno into Artimino. Your home tonight is a 16th-century villa located beside the famous Medici Villa. A gourmet farewell dinner awaits you as the group reflects on their adventures over the past days.
About Hotel Paggeria Medicea
Rustic style meets maximum comfort at the Hotel Paggeria Medicea. Situated in a peaceful location, this hotel offers stupendous views of the surrounding hills while also offering the highest level of hospitality.
Say “arrivederci” to la dolce vita, and shuttle to Florence after enjoying one last breakfast. Your guide will drop you off at the Florence airport or your hotel at the appropriate times for your departure home or the beginning of your trip extension.
*Trip itineraries are subject to change without notice due to road, weather and other factors outside of our control, for the safety and enjoyment of our guests, as deemed necessary and appropriate by Austin Adventures.
Arrival & Departure
Prior to the trip, arrive at your own convenience in Florence. On Day 1, we will meet you in the lobby of the Grand Hotel Minerva in Florence at 8:30 a.m. After a briefing and a transfer to Gaiole in Chianti, the hiking begins. After breakfast on Day 6, we will take you to the airport, train station, or hotel of your choice in Florence (one hour transfer).
Day 1 Hiking mileage options: 4/5
Day 4 Hiking mileage options: 3/4
Day 2 bicycle mileage options: 17 / 23
Day 3 bicycle mileage options: 17 / 23 / 34 / 40
Day 5 bicycle mileage options: 31 / 36
Day 2 walking tour of Siena
Austin Adventures guides are experienced facilitators and regional experts. They take the time to explain the local history and daily sightseeing and route options. Each route has been carefully planned to include options to please each traveler’s interests. Austin Adventures guides are available to help you select the distance that’s right for you and to offer advice and assistance as you desire.
Ciao Bella! No place brings out the romantic in you like Italy. Learn all about the Palio and the competitive Contrades during our walk in Siena. Find St. Catherine’s dried finger and shrunken head in the church in Siena. And, wonder why the inhabitants of San Gimignano built the many towers. In the evenings we’ll relax at small luxury hotels, perfectly situated in the region’s favorite towns, enjoying inspirational views, gourmet meals and fine local wines, as we embrace the people and the lust for life that makes Italy so unique.
The hallmark of an Austin Adventures vacation is our exceptional dining. All meals: breakfasts, lunches, snacks, dinners, refreshments and receptions are included as indicated by itinerary. (B = Breakfast, L = Lunch, D = Dinner). Alcoholic beverages and related gratuities are not included in the trip price.
After receiving your reservation and deposit, we’ll send you a pre-trip planner with general information about the area you’ll be visiting, a packing list, exercise guidelines, a guest information questionnaire and a liability release agreement for you to sign and return within 10 days.
Included in Trip Price
- Double occupancy rooms with private baths.
- All breakfasts. Lunches and dinners as listed by day. Snacks along the route.
- Fully trained, first-aid certified professional guides and knowledgeable local partners.
- Bikes, helmets and other necessary equipment – all safe and well maintained.
- Vehicle support and land transportation during the trip.
- Austin Adventures T-shirt, water bottle, luggage tags and luggage service.
- Pre-departure and packing information.
- Incidental expenses such as taxes, dining and housekeeping gratuities, local guide and expert gratuities.
Not Included in Trip Price
- Gratuities to Austin Adventures guides.
- Alcoholic beverages and related gratuities.
- Pre-and post-trip accommodations and associated expenses.
- Air and land transportation to/from host cities.
- All types of personal insurance.
- Personal expenses.
- Activity levels are subjective depending on your general level of fitness and your experience; however, all of our trips are self-paced.1 Easy (1)
- Activity levels are subjective depending on your general level of fitness and your experience; however, all of our trips are self-paced.2 Moderately Easy (2)
Want to know how to make fast friends in foreign places and how to get the most out of a destination by experiencing it like a local? Ask Adam, a longtime Austin Adventures guide who now serves as European Operations Manager in Holland. He caught the travel bug during a semester abroad in New Zealand and Australia and quickly discovered he never wanted to stop experiencing—and more importantly, sharing—the wonder of travel. He taught English in China, managed a resort in Mexico, and now lives with his wife and child in Amsterdam, ensuring guests have the best guides and experiences possible on their European adventures.