Walking in Tuscany and the Riviera

September 30- October 10, 2024

From $6,795 Per Person Based on Double Occupancy.

Join us on an Italian walking tour of Tuscany and the Riviera. This tour permits the traveler not only to see the sites but to visit "into the lives of others." Walking permits the traveler to slow down and savor the exquisite tranquility of the Italian hill towns many skip, to relish the camaraderie of fellow Vanderbilt hikers reaching a common destination, and to catch a glimpse into the lives of the local populace. We'll first gather in Florence for a brief orientation and welcome reception before departing the next day to the medieval village of San Quirico in the hills of southern Tuscany. From here we'll make our first memories on a panoramic hike from Vignoni Alto to Bagno Vignoni before reaching the Tuscan hill town of Montalcino. From the lofty ridge on which our hotel sits you will be able to enjoy the views of the bucolic contours of the Tuscan landscape and rusticated terracotta roofs of the pale limestone houses below. Our walks will continue past silvery clouds of olive groves and the patchwork quilt of vineyards where we'll enjoy a respite of a lunch at a farmhouse or dine alfresco before reaching other towns, such as the city of Pienza, a World Heritage Site in the heart of the region of Val d'Orcia. From Val d'Orcia we'll travel to the city of Siena, once a historical rival to Florence to learn about its competitive contrade or districts.

From Siena, we move north to Colle di Val d'Elsa, where crystal and glassware have been produced since the 17th century. Departing early the next morning to avoid the crowds, we'll stroll through nearby San Gimignano, one of the most beautiful hill towns and also a World Heritage Site. Our steady perambulations will take us alongside the Via Francigena, one of the oldest pilgrimage routes in Europe, through the striking Abbey of Isola before reaching the unmistakable crown of towers of Monteriggioni, one of Italy's best known walled towns. In the city of Lucca, we'll have the opportunity to enjoy a bicycle ride along its unique medieval walls to explore its historical and artistic treasures. From here, we proceed to the seaside town of Sestri Levante, our home to explore the Riviera di Levante. Here we hike the Ligurian coast toward Moneglia. On our walks, experience the peace, scents, and colors of this area. Forest of holm oak, centenary specimens of cork, Mediterranean scrub, and stunning maritime pines grace the coast. As we walk, the views are striking and span from the coast of Tuscany to the French Riviera. Our visit to Cinque Terre is a highlight and includes a short train ride to Monterosso al Mare, one of the five villages perched high on the Italian Riviera that make up the Cinque Terre. We hike along the trail that links the neighboring villages or others may instead opt for a scenic train and boat ride from village to village taking in the amazing scenery and spectacular views of the coast. On our last day, we take a train ride to Santa Margherita Ligure and walk the coastal path to stunning Portofino, a picturesque harbor and fishing village with a romantic and affluent aura.

Pre-trip extension to Florence and Post-trip extension to Rome are available.

Call (615) 322-3673 or contact us to learn more and register.

  • Accommodations


  • Program Inclusions
    • All activities per itinerary
    • Professional English speaking guides and tour director throughout
    • Professional expert guide in Florence, Siena, and Lucca
    • Transportation by private motorcoach
    • Airport transfers for group flights
    • All local train tickets in the Riviera
    • Ferry boat tickets in the Riviera
    • Cinque Terra Card
    • Bicycles in Lucca (e-bikes available on request)
    • Tips to local guides and drivers
    • Service charges and taxes
    • Baggage handling
    • Entrance fees