Begin in Florence, Italy, then take a hilly bike ride into the heart of Chianti Classico, famous for beautiful landscapes and superior wines. Explore historic Radda and perhaps walk to nearby medieval Volpaia or bicycle to a few castles. Follow a winding route on the way to fairytale San Gimignano, then on to Siena, with its maze of crooked streets, splendid palaces and museums.


  • Florence: Gem of the Renaissance
    Florence: Gem of the Renaissance
    Arrive in Florence by 3:00 to try out your bike before an optional walking tour of the city. Stroll to an outdoor sculpture gallery featuring Michelangelo’s David, along with the works of Cellini, Donatello, and other Renaissance artists. Cross Ponte Vecchio and stop at the massive Duomo cathedral. Tonight we’ll enjoy our welcome dinner; perhaps you will enjoy the ravioli speckled with black truffles and after dinner a glass of vin santo and cantucci biscuits. Those who wish can explore Florence’s gay night life, or simply relax before beginning our bicycle tour tomorrow.
  • Into Chianti Classico Country
    Into Chianti Classico Country
    Leaving Florence by bike, we soon find ourselves along rural roads, winding past vineyards and orchards. Then it’s time for a picnic lunch in the tiny village of Greti: rusty breads, thin slices of prosciutto, several types of cheese, fresh salads, and an assortment of pastries. Some bicyclists will choose the direct route into Radda, some opt for a longer westward loop that brings a couple of extra hills, a forgotten village, and rewarding scenery. Then, it’s on to Radda-in-Chianti. Spend two nights in the hillside stone villas of Castelvecchi.
  • The Castles
    3 Two castles (Brolio and Meleto) with their gardens and vineyards lie on today’s suggested biking loop. The roadsides are lined with the pastel polka-dots of blue chicory flowers, and shaded by oak and cypress trees. We’ll have lunch at an outdoor cafe we’ll continue cycling to Badia Coltibuono, an abbey founded in the 11th century, set in a picturesque woods. If you’d prefer a day of hiking, you can make an enjoyable loop by walking south, through vineyards and forest, to the center of Radda, then return through Volpaia.
  • The Turrets of San Gimignano
    The Turrets of San Gimignano
    Just 8 miles away lies Castellina in Chianti. From the crenellated castle here, we enjoy sweeping views of the countryside and then a visit to Etruscan tombs dating from the 4th century BC. Our ride takes us through a forest preserve and then we’ll picnic is at a Romanesque chapel atop a hill. We’re headed to San Gimignano known for its well preserved medieval 14 towers. Some cyclists will want to bike directly into town to explore the narrow streets, shops, and rampart walls. Energetic others can bike to charming nearby villages. Dinner tonight is an extravagant Tuscan delight: exotic rabbit flavored with saffron, or sausage made of a wild boar accompanied by flavorful cheeses, savory pastas, fresh greens, and aromatic herbs.
  • Volterra
    The ancient city of Volterra, high on a windswept plateau, was an Etruscan stronghold for five centuries. Ancient stone walls 2500 years old still stand, as do the columns of a Roman theater, built in the first century BC. A converted 12th-century convent houses a museum of alabaster sculptures. The ride to Volterra is an all-day affair, about three hours in each direction, leaving us a few hours in the city itself. If you’d like a break from cycling, you can walk the quiet roads through the countryside, building up an appetite for more Tuscan specialties tonight: Florentine steak (grilled til tender and served with lemon and fresh herbs) and superb gelato (rich chocolate and hazelnut, tart lemon and strawberry, or subtle pear).
  • Two Hilltops
    Two Hilltops
    We begin our descent from San Gimignano for our last full day of biking along the Elsa river valley, with stops at two old villages, both perched on hilltops, yet utterly different. In Colle Alta the graceful stone buildings host modern glassworkers, who create sparkling crystal goblets and brilliant glass flowers. Charming Monteriggioni presents a dramatic silhouette against the blue Tuscan sky. For lunch we propose bruschetta, thin-sliced Italian bread topped with fresh chopped tomatoes, then pasta with truffle sauce, melon and prosciutto, and a fresh salad. We arrive this afternoon in Siena, Florence’s long-time rival, and indisputably one of Italy’s most beautiful cities.
  • Siena, frozen in time
    Siena, frozen in time
    Five centuries ago, Siena and Florence were deadly enemies. When Florence finally defeated its rival, the Florentines banned new buildings in Siena. Today Florence is larger; it’s wealthier; and it has more famous works of art. But many visitors find that Siena, frozen in time, has a mystery and a soul unmatched in Italy. This morning, we offer a guided walking tour of Siena, then the afternoon is free for you to explore this magical city on your own. Tonight’s dinner is a festive affair during which we get one last chance to try new delicacies like pasta with a sauce of walnuts and garlic or chicken with shavings of white truffles. Then, we toast new friendships made over a week that seems to have gone by too fast.
  • Departure Day
    8 The hardest thing about our trips is saying goodbye to new friends, and to a charming region of Italy. If you have extra vacation time, we suggest you save it for after the trip, rather than before: Chances are, others from this weeks’ adventure would like company as they extend their time in Italy.
  • Pricing
  • Testimonials
  • Important Notes
  • Included


Title Description Pricing Notes Price
Standard Price

in a shared room

$3998 pp
Upgrades and single rooms are available $950 pp


“This trip combines outdoor exercise and culinary excellence. It is well planned and executed with perfectly selected accommodations and guides and hosts in every city/town who make you feel welcomed and comfortable. Although my legs smiled when we said goodbye to the bikes, my heart was saddened…I truly did not want it to end!"
Brian P., Trinidad and Tobago
“Flavors of Tuscany featured all the things I’ve come to love about [HE Travel]: great sights, intimate views, action-filled days, and great people. The trips are a good value for the money.”
Dane d’Alessandro, San Francisco, CA

Important Notes

Note: Details File
Activity Level

Tuscany has hills! This is a trip of moderate difficulty, for cyclists who can comfortably bike 35 to 40 miles a day over rolling terrain, and who have basic map-reading skills.

What’s Included

Comfortable hotels each night; Services of two tour guides; Use of 21-speed hybrid bike; All breakfasts, 2 lunches, and 5 dinners, with wine included; Five biking days, and a sightseeing day in Siena; Transportation to get luggage (and tired riders!) to destinations; A wine-tasting; Map of Tuscany and detailed routes. All HE Travel tours include complimentary Medical & Evacuation Insurance.

What’s NOT Included

Travel to Florence and from Siena; 4 lunches; 2 dinners; Souvenirs, snacks, admissions; Gratuities for guides.

  • Highlights


* Stroll along Florence’s picturesque Ponte Vecchio, crammed with leather shops, admire Michelangelo’s David, then check out Tuscany’s nascent gay scene. * Enjoy lunch in a medieval town in the heart of “Chianti Classico”, sampling the red wine that made the region famous. * Watch for the wild boar, pheasants, and occasional wolves that still inhabit the forests of scrub oak and pine. * Sip a cappuchino in Siena’s breathtaking Piazza del Campo, one of the most beautiful public plazas in the world. * Delight in the scents and flavors of Tuscany: Fresh-picked wild mushrooms, robust cheeses, crusty Italian breads, and ruby Chianti wines.

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