- Hike to hilltop towns perched above Chianti’s vineyard-laced valleys, and stay at a picturesque 14th-century palace.
- Discover San Gimignano’s soaring towers and Siena’s Gothic architecture, and soak up the charm of these UNESCO World Heritage sites.
- Get an in-depth look at Florence’s Palazzo Vecchio—site of a National Geographic–funded search for Leonardo da Vinci’s lost masterpiece, The Battle of Anghiari.
- Wind your way through the terraced vineyards and olive groves that link the colorful coastal villages of the Cinque Terre.
Set off on a hiking adventure in two of Italy’s most scenic regions: the lush countryside of Tuscany and the rugged coast of Liguria. In the heart of Chianti, wind your way through vineyards and cypress-dotted valleys, exploring hilltop towns and historic abbeys that have changed little over the centuries. Sample the region’s famed wines, and explore the medieval treasures of Siena and San Gimignano. Then travel to the Italian Riviera to climb the spectacular coastal trails linking the colorful hamlets of the Cinque Terre.
Arrive in Florence and drive to our 14th-century palace in Radda in Chianti, a medieval town tucked among vineyard-laced landscapes. Begin hiking through gentle hills and vineyards to Castellina in Chianti, stopping along the way at a panoramic spot to enjoy Chianti wine and local cheese. Drive back to Radda for a welcome dinner. (4 miles hiking, 3 hours)
Set out from our hotel for a walk amid vineyards and olive groves to the renowned Badia a Coltibuono winery, a fortified abbey where a wine tasting and lunch await. Continue through pristine oak and spruce woods to the idyllic village of Gaiole in Chianti. (8 miles hiking, 6 hours)
Spend the morning exploring the enchanting city of Siena, once a historic rival to Florence and graced today with winding red-brick lanes, an impressive Gothic cathedral, and elegant palaces. Learn about the city’s competitive contrade, or districts, and have lunch on your own at the great central square, Piazza del Campo. Later, meet a local artisan in Colle di Val d’Elsa, where crystal and glassware have been produced for hundreds of years. (5 miles hiking, 3 hours)
Rise early to explore the stunning hill town of San Gimignano before the crowds descend on this World Heritage site. Of the 72 medieval towers that once soared above the rooftops, 14 towers remain. Explore the city’s mazelike streets and fresco-adorned Duomo, or climb one of the towers. Drive to Campiglia dei Foci, where a scenic walk takes us alongside the ancient Via Francigena route and through the striking Isola Abbey, before reaching Monteriggioni and its unmistakable crown of fortified walls and towers. (12 miles hiking, 8 hours)
Set off for a bicycle ride along the Renaissance-era walls of Lucca, a Tuscan town rich in historical and artistic treasures. Join a local guide on a tour of the town’s striking cathedral and secluded Palazzo Pfanner, then proceed to Sestri Levante—our launch point for exploring the Italian Riviera. Unwind with a seafood dinner by the waterfront. (4 miles cycling, 2 hours)
Hike along the rugged Ligurian coast towards Moneglia and get a glimpse of this region’s historic peasant identity. Pass Mediterranean scrub that gives way to steep cliffs tumbling to the sea, century-old cork trees, and holm oak and maritime pine forests. Take in spectacular views that stretch from the coast of Tuscany to the French Riviera. (10 miles hiking, 7 hours)
Take a short train ride to Monterosso al Mare, one of the five villages that make up the Cinque Terre, or “five lands.” Clinging to cliffs above the Mediterranean, these hamlets dazzle with clusters of pastel-hued homes overlooking harbors dotted with fishing skiffs. Depending on trail conditions, hike along the paths that link the neighboring villages of Vernazza, Corniglia, Manarola, and Riomaggiore; or enjoy a scenic train and boat ride from village to village. (5–6 miles hiking, 5 hours)
Return to Tuscany and drive to the hilltop town of San Casciano in Val di Pesa, near Florence. Set out on a hike to the 15th-century home of a local Tuscan family, and enjoy an olive oil tasting and a hearty country lunch. This afternoon, explore the fascinating city center of Florence on an urban hike with an art historian. Get an in-depth look at Florence’s Palazzo Vecchio—site of a National Geographic–funded search for Leonardo da Vinci’s lost masterpiece, The Battle of Anghiari. Toast your adventures over a farewell dinner. (3 miles hiking, 3 hours)
After breakfast and a final cappuccino, transfer to the Florence airport for your flight home.