8-Nights Italy Tuscany & Cinque Terre Walking from $6,595

Itinerary Details

MT Sobek: Italy Tuscany & Cinque Terre Walking

Day 1 Arrive in Florence & Journey to Tavarnelle
1-hour private van transfer
2 hours/2-3 miles hiking
Welcome to Italy! Arrive in Florence this afternoon and meet your trip leader for an orientation. Explore the Benedictine church of San Miniato al Monte, with its splendid Romanesque architecture and sweeping views of the city, before heading south to the hilltop town of Tavarnelle. Enjoy a scenic drive on the Via Cassia, an ancient Roman road, then set off on a hike past olive orchards and vineyards to a 12th-century family estate. Here you'll sample olive oils and savor a delicious country dinner.
Accommodation: The Hotel Executive
(D)

Day 2 Chianti Wines & Walks
1-hour private van transfer
3-4 hours/5 miles hiking
Rise for a journey through bucolic rolling hills to Greve, the wine capital of Chianti. Take a picturesque hike to the hilltop village of Lamole. Lunch on local delights and continue on foot to Volpaia, a medieval hamlet famed for its Chianti Classico wine. Here you'll sample some of the region's most celebrated reds. Rest up tonight in your charming hotel in the historic town of Radda.
Accommodation: Hotel Palazzo Leopoldo
(B, L, D)

Day 3 Vineyard Trails to San Polo in Rosso
20-minute private van transfer
3-4 hours/4 miles hiking
Begin the day with a short transfer to Galenda, a tiny medieval village just south of Radda in Chianti. From here, you'll follow vineyard trails to the fortified medieval estate of San Polo in Rosso, where lunch awaits. Continue walking via enchanting rural villages to San Giusto in Salcio, a pretty Romanesque church. Return by van to Radda and sample more Chianti wines before exploring the town at leisure. Tonight, dinner is on your own at the hotel or local restaurant.
Accommodation: Hotel Palazzo Leopoldo
(B, L)

Day 4 Explore Enchanting Siena
1-hour private van transfer
4 hours/2-3 miles hiking
Journey to the captivating city of Siena for a special guided tour of its historical wonders, including UNESCO-listed Piazza del Campo and the Duomo. Next, enjoy free time to explore the city's beautiful cobblestone streets and charming restaurants. In the afternoon, visit the walled city of Monteriggioni, known as the "Gateway to the Middle Ages" for its fortified ramparts and watchtowers. Later, transfer to your hotel set in a 15th-century villa in Poggibonsi.
Accommodation: Hotel Villa San Lucchese
(B, D)

Day 5 Hike to San Gimignano
30-minute private van transfer
4-5 hours/8 miles hiking
Start the day with a drive to Colle Val d'Elsa, known for its fine Italian crystal, then follow scenic trails to the romantic hill town of San Gimignano. This UNESCO World Heritage wonder, known as "medieval Manhattan," is beloved for its 11th-century towers, labyrinthine streets, and fresco-adorned Duomo. Explore town before heading back to your hotel.
Accommodation: Hotel Villa San Lucchese
(B, L, D)

Day 6 Journey from Carrara to Cinque Terre
2.75-hour private van transfer
Rise for a drive to Carrara, world famous for its ancient marble quarries that rise like snow-capped peaks above the town. After lunch, breathtaking coastal scenery awaits in the UNESCO-listed Cinque Terre and the pretty seaside town of Levanto. Enjoy a tasty dinner in town and get ready to explore the Italian Riviera over the next two days.
Accommodation: Hotel La Giada del Mesco
(B, L, D)

Day 7 Explore Trails in Cinque Terre
5 hours/5-6 miles hiking
Take a short train ride to Monterosso al Mare, one of the five towns that make up the Cinque Terre. Perched on cliffs above the Ligurian Sea, these breathtakingly beautiful seaside villages are a bucket-list must — and perfect for hikers. Take in amazing coastal scenery on a stunning trail that links the neighboring villages of Vernazza, Corniglia, Manarola, and Riomaggiore. Alternatively, you can enjoy a scenic train and boat ride from village to village. Return to Levanto for dinner on your own tonight.
Accommodation: Hotel La Giada del Mesco
(B, L)

Day 8 Coastal Path to Monterosso
3-4 hours/3-4 miles hiking
Starting at the hotel, follow a meandering coastal trail back to Monterosso. Along the way you'll pass lemon groves and old hilltop farmhouses, and enjoy splendid views of the Ligurian Sea. Perhaps reward yourself with a refreshing gelato and explore the town at leisure. Take a train back to Levanto and celebrate your Italian adventure with a farewell dinner in town.

(B, D)

Day 9 Depart from Pisa
1.5-hour private van transfer
Bid farewell to Italy as you transfer to the airport in Pisa.

(B)