• 6 days/5 nights
  • Next Departure: Jun 02, 2019
  • From $3,298 / person
  • ($680 single supplement)

Experience Tuscany on this Italy Vacation!

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, cycling through vineyards and olive groves 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.

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0/5 (0 Reviews)
  • Europe Vacations
  • Adult only
  • Biking
  • Gourmet Dining
  • Wine Tasting
  • Cultural/History

Activity Level: Difficult (5)

This Tour
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 homemadetorta, washed down with a glass of bold Chianti or crisp Vernaccia di San Gimignano
Group of bikers in Tuscany
Photo: Group of bikers in Tuscany

Traveling with Austin Adventures takes all of the stress out of going on vacation!

Jake B. Austin, TX

We will never travel another way again! Austin Adventures and our guides went above and beyond to make this the most amazing adventure for us.

Caroline R. Milford, MA

The guides were fantastic and very flexible. I had a great time- money well spent!

Tessa J St Louis Park, MN

& Map
Day 1: Siena
Meals Included:  D
We meet in Florence in the morning and begin the day with a transfer to the region of Chianti Classico. Hike in the vineyard-clad hills and continue to famous wine villages just waiting to be discovered by foot. Stop for a wine tasting and a 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 in one of the most breathtaking cities of Italy.

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.
Day 2: Siena
Meals Included:  B, L, D
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. Share another amazing dinner together tonight at one of Siena’s best restaurants, Ristorante da Enzo.
Day 3: Siena
Meals Included:  B, L
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. Tonight offers you more time on  your own to relax or experience more of this amazing city.
Day 4: San Gimignano
Tuscany Region
Meals Included:  B, D
Wooded hills form the backdrop for a picturesque and exhilarating day. We’ll hike in the region of Monteriggioni, surrounded by 14 medieval towers, as a reward at the end of your hike, enjoy some more wine tasting at another one of Italy's fine wineries. Nearing day’s end, everyone will meet in San Gimignano, the “Manhattan of Italy,” and dine on expertly prepared local specialties, with panoramic views from your hilltop hotel.

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.
Day 5: Artimino
Meals Included:  B,L,D
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 on a peaceful location, this hotel offers stupendous views of the surrounding hills while offering the highest level of hospitality.
Day 6: Florence
Tuscany vineyards
Meals Included:  B
Overnight: No Overnight
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.
Dates, Rates
& Details

Stop daydreaming and start planning your adventure today. Confirmed departure dates and rates are listed below. We look forward to seeing you soon!

Not finding what you're looking for? Over 33% of our itineraries are tailored to fit your group or family needs. Feel free to call one of our travel specialists for information on custom trips. Let us plan your next adventure of a lifetime!

  • 6 days/5 nights
  • Next Departure: Jun 02, 2019
  • From $3,298 / person
  • ($680 single supplement)

Confirmed Departures

  • Jun 2, 2019 - Jun 7, 2019
  • Jun 23, 2019 - Jun 28, 2019
  • Sep 1, 2019 - Sep 6, 2019
  • Sep 15, 2019 - Sep 20, 2019

Recommended Travel Months

CALL (800) 575-1540 for details

Additional Trip Information


Prior to the trip, arrive at your own convenience in Florence. On Day 1, we will meet you in the lobby of Grand Hotel Minerva in Florence at 8:30 a.m. After a briefing and a transfer to Castellina in Chianti, the cycling begins. After breakfast on Day 6, we take you to the airport, train station, or the hotel of your choice in Florence (one hour transfer).


Hiking: Day 1 Hiking mileage options: 4/5 Day 4 Hiking mileage options: 6 Cycling: Day 2 bicycle mileage options: 17 / 23 Day 3 bicycle mileage options: 17 / 23 / 34 / 40 Day 5 bicycle mileage options: 31 / 36 Walking: Day 2 walking tour of Siena Discovery: 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. 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. 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. 


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.
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.
Pre-departure Information 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.
With over 20-years of experience in the adventure travel industry, we've perfected the recipe for crafting award-winning small group trips and custom itineraries on all seven continents. On every departure, we aim to exceed your expectations with best-in-class service, expert guides and the finest in regional cuisine and accommodations. From first-time travelers to seasoned alumni, our guests agree that on each Austin Adventures journey , the hardest part truly is going home. We're happy to share that 99.26% of these travelers say they'd join us again...and again...and again. But don't take our word for it. Our guests say it best:
The best experience with our large family we could dream for! ” ” Nancy V., , Pebble Beach, CA
Excellent trip and guides - superb trip. ” Richard P., Westminster, CO
Your team outdid themselves! I told them all that, through 34 years of my travels as an adult, they were the best guides (and concierge, bellmen, chefs, drivers, etc.) that I had ever experienced. ” John Hutchins,
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Regions we visit in Europe: , , ...

A few more reasons why you've gotta go”:
  • 1. The vineyards: the Tuscan region is universally acclaimed for its classic wines and natural beauty.
  • 2. The shopping: The picturesque open air markets are the perfect place to find leather goods, paper goods, stunning jewelry and marvelous art.
  • 3. 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.

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