8-Nights Italy Tuscany & Cinque Terre Walking — CALL

MT Sobek

OFFER ID 1479527

Immerse yourself in two of Italy's most enchanting regions on this perfectly paced walking adventure from Tuscany to the Italian Riviera. Follow scenic trails through Tuscan vineyards and cypress-dotted valleys, exploring historic hill towns and sampling fine Chianti wines. Marvel at the medieval wonders of Siena and San Gimignano with their ancient ramparts and towers. Then journey to Liguria's spectacular coast to hike cliff-side paths that connect the Cinque Terre's picturesque seaside towns. With fragrant lemon groves and stunning sea views, this is la dolce vita at its best!

Highlights:

  • Explore hilltop towns in the heart of Chianti and follow dramatic coastal trails in the Cinque Terre
  • Experience a "Gateway to the Middle Ages" through the splendor of Siena, San Gimignano, and Monteriggioni
  • Sip fine wines, feast on regional culinary delights, and enjoy tranquil stays at charming hotels

Important Trip Details:
Easy to moderate walking and hiking for 3-5 hours per day on gently rolling terrain, vineyards and cliffside trails. Cultural touring of historic sites includes walking on cobblestone streets.

Minimum Age: 16

8 nights | Call for pricing

Itinerary

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 the 15th-century home of a local Tuscan family. 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/5 miles hiking
Begin the day with a short transfer to San Giusto in Salcio, a pretty Romanesque church 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 back to San Giusto in Salcio. 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/6 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)

Featured Destinations
Levanto
Poggibonsi
Pisa
Cinque Terre
Radda in Chianti
San Cassiano
Florence

Vacation Details

Valid Date Ranges
04/22/2025 - 04/30/2025
Call for pricing
05/20/2025 - 05/28/2025
Call for pricing
09/02/2025 - 09/10/2025
Call for pricing
09/16/2025 - 09/24/2025
Call for pricing
09/30/2025 - 10/08/2025
Call for pricing


* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.
Prices Start At
Call for pricing
Length
8 Nights
Air City
Call for airfares from your city.
Vacation Rating
Deluxe
Fine dining, on-site bars or lounges and room service with extended hours are characteristic of deluxe establishments. Guest services usually include valet parking, concierge services, baggage assistance and laundry services. Other on-site facilities often include shops and boutiques, full service spas, full fitness facilities with pools and tennis courts. Business amenities may include available up-to-date technology and support staffs available for services. Attention to detail is apparent in the guestrooms which typically have stylish furnishings, quality bedding and bath products and often provide an evening turn down service.
Remarks
Prices subject to availability and change without notice. Some restrictions may apply.

All fares are quoted in US Dollars.

OFFER ID
1479527

Reference this number when contacting our agency so we may better serve you. Also keeping this number handy will allow you to locate this document again quickly.

Let's Travel SM

21021 Ventura Blvd. Suite 300
Woodland Hills, CA 91364
USA

(310) 451-5805