Classic Biking and Walking among Tuscany's Wine Estates, Villas and Hilltop Villages

Biking and walking the quiet pathways and farm laneways of Tuscany's Chianti Classico wine region, from its hilltop villas, vineyards and olive groves to the historic towers of San Gimignano and the Medieval streets of Siena. Open a bottle of Chianti Classico Reserva and sit back and enjoy the Tuscan way of life. A life where time is taken out to enjoy the simple pleasures of its inspiring wines and delightful local cuisine. The vineyards and olive groves of the Chianti, cascading down slopes crowned with Renaissance villas and Medieval hilltop villages, will enchant you with an irresistible lure. Quiet countryside roads leading past stone farm houses framed in a rainbow of flowers overlook a landscape admired for its bounty and put on canvas by artists since the middle ages. Travel its undulating hills and enjoy its seasonal pleasures, from the fresh scents of spring flowers to its summer's golden hues and the essence of its annual grape harvest. Dine on its wholesome culinary masterpieces and celebrate the Tuscan culture with a glass of your favorite vintage.

Day 1 - Greve & Radda in Chianti - Private transfer to Greve in Chianti, the market town for the Chianti wine producing region.Private tour and wine tasting lesson at a Renaissance villa known for its award winning Chianti Classic wines.Follow countryside laneways overlooking a quintessential Tuscan landscape of vineyards, olive groves and stone farm houses.Visit the quiet fortified borgo of Montefioralle, the birthplace of Amerigo Vespucci, who gave America its name.Enjoy a welcoming lunch in a typical trattoria located among Greve's unique and charming arcaded main square.Discover Radda in Chianti, a hilltop wine village with some of the Chianti's best views from its Medieval walls.(Biking option available)

Day 2 - Brolio & Coltibuono - Roam through the heart of Chianti's quiet and picturesque landscapes to Castello di Brolio, a spectacular castle with striking views all the way to the towers of distant Siena. Tour its grounds and Italianate gardens.Take a dramatic route overlooking vineyards, hilltop villages and tree bordered villas to the 8th-century abbey at Badia a Coltibuono.Take a diversion to a family owned ceramics workshop.Relax at a sidewalk cafe with a glass of the your favorite vintage. (Choose Biking or Walking today)

Day 3 - Castellina & San Gimignano - Ride along quiet scenic ridges overlooking neatly rowed vineyards, silvery green olive groves and lush chestnut forests to the wine village of Castellina in Chianti.Cycle along a route regarded as one of the trip's most memorable, as you travel through undiscovered wine villages and silent hamlets to a landscape reminiscent as the backdrop of countless Renaissance paintings.Arrive overlooking the fascinating 13th-century towers of charming San Gimignano. Wander its Medieval streets, visit an "enoteca" wine shop, try Italy's best "gelato" and relax in one of Tuscany's most unique hilltop villages.

Day 4 - Volterra - Follow a panoramic route through a golden patchwork of open pastures and ripening grain fields to the alabaster workshops and the Etruscan Roman ruins at Volterra, one of Italy's oldest cities.Discover the origins of Volterra and its centuries-old tradition of artistic expression through its work on alabaster. Visit its pre-Roman Etruscan walls and town gates, its Roman amphitheater and baths and its untouched Medieval streets, palaces and churches.Picnic in its archeological park or lunch in its central piazza, regarded as one of the most preserved Medieval squares in Italy.(Biking option available)

Day 5 - Medieval Siena - Casually cycle into the colorful Sienese countryside past Colle di Val d'Elsa, known for centuries for its fine crystal.Pass by quiet countryside villages, noble castles and a near-forgotten abbey to arrive in the hilltop hamlet of Monteriggioni. Once a Sienese fort used to defend Siena against its archenemies, the Florentines, Monteriggioni seems like a large crown sitting on a distance hill.Enter Siena along a panoramic route with views of its marble clad Duomo and bell tower, and the Torre di Mangia, one of Italy's tallest Medieval towers, located in the distance.Take a casual tour through Siena's fascinating Medieval streets to visit the neighborhood of St. Catherine of Siena and the magnificent Duomo with its ornate facade and immaculately decorated interior. Dine on Sienese specialties in the Piazza del Campo, considered Italy's most beautiful piazza, and home to the Palio, an ancient Sienese horse race re-enacted twice a year.(Walking option available)

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