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. Hike past terraced vineyards and lemon groves overlooking the Mediterranean, and experience the region’s distinct culture.


Trip Highlights

  • Hike to hilltop towns perched above Chianti’s vineyard-laced valleys, and stay at picturesque farmhouses and villas.

  • Discover San Gimignano’s soaring towers and Siena’s Gothic architecture, and soak up the charm of these UNESCO World Heritage sites.

  • Embark on one of Italy’s most dramatic hikes to the coastal villages of the Cinque Terre.

  • Sample Tuscany’s famed wines and cuisine and the specialties of Liguria.

Activity Level: Easy and Moderate

We will be hiking 2 to 5 hours per day (2 to 6 miles), on moderate to steep grades at low elevations. During hikes, vehicle support is provided at various points along the way, except while hiking in Cinque Terre (which is a car-free zone). Participants always have the option to rest a day and ride to the next hotel.


Itinerary - 9 Days

Day 1 — Florence, Italy/San Casciano in Val di Pesa
Arrive in Florence and meet your trip leader this afternoon. Travel south along the ancient Roman road, Via Cassia, through the countryside to the hilltop town of San Casciano. Set out on our first hike past olive orchards and vineyards to the 15th-century home of a local Tuscan family, where we’ll enjoy an olive oil tasting and a hearty country dinner. (3–4 miles hiking, 2 hours) Hotel Executive (D)


Day 2 — Florence/Greve in Chianti/Volpaia
After breakfast, visit the Benedictine church of San Miniato al Monte perched above Florence with sweeping views of the city’s red-tiled roofs and Duomo. Then drive into the vineyard-laced hills of Chianti and stop at Greve in Chianti, where we’ll sample the region’s celebrated wines. Set off on a scenic hike to the fortified village of Lamole. After a lunch of local specialties, take a short drive to Volpaia, home to a winery that produces the famed Chianti Classico. From here, depending on the terrain, we’ll continue on foot to the Romanesque church of Santa Maria Novella. Then transfer to our charming hotel in Radda in Chianti’s historic center. (4–5 miles hiking, 3 hours) Palazzo Leopoldo Radda (B,L,D)


Day 3 — Chianti
Transfer by van near Gaiole in Chianti, a beautiful, medieval fortified town built around the Pieve di Santa Maria a Spaltenna, a Romanesque parish church. Our hiking destination is the Badia a Coltibuono, a Vallombrosian Abbey transformed into a spectacular “wine resort” owned by Lorenza dè Medici. We will visit the complex known the world over for its hospitality, and wine and olive oil production. We’ll then head back to Radda for a tasting of Chianti wines, then follow it up with a delicious dinner at the one restaurant in town. (4-5 miles hiking, 3 hours) 
Palazzo Leopoldo Radda (B,L,D)


Day 4 — Siena
Spend the morning exploring this enchanting city, once a historic rival to Florence and graced today with winding red-brick lanes, Gothic churches and elegant palaces. Learn about the city’s competitive contrade, or districts, and have lunch on your own at the great central square, Il Campo. Then visit the fortified village of Monteriggioni, known for its well-preserved walls and towers which Dante wrote about in Inferno. Later, transfer to our hotel set in a 15th-century villa. (2–3 miles walking, 4 hours) Hotel Villa San Lucchese (B,D)


Day 5 — Colle di Val d’Elsa/San Gimignano
Begin the day at Colle di Val d’Elsa where crystal and glassware have been produced since the 17th century. Then hit the trails on a spectacular hike to San Gimignano — one of Tuscany’s most beautiful hill towns and a UNESCO World Heritage site. Of the 72 medieval towers that once soared above the rooftops, 14 towers remain. Explore the city’s maze-like streets and fresco-adorned Duomo or climb one of the towers. (6 miles hiking, 4-5 hours) Hotel Villa San Lucchese (B,L,D)


Day 6 — Carrara/Levanto
At the Tuscan town of Carrara, discover the ancient quarries where sculptors, including Michelangelo, have sourced marble for centuries. After lunch, a two-hour drive takes us to the seaside town of Levanto, our launching point for exploring the Riviera di Levante. Unwind with a seafood dinner by the waterfront. Hotel La Giada del Mesco (B,L,D)


Day 7 — Cinque Terre
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. Embark on a more challenging hike along the trail that links the neighboring villages of Vernazza, Corniglia, Manarola and Riomaggiore. Climb steep hillsides past terraced vineyards and olive groves with stunning views of the coast. (5–6 miles hiking, 5 hours) Hotel La Giada del Mesco (B,L)


Day 8 — Cinque Terre
Set out from our hotel on a coastal trail to Monterosso that meanders past fragrant lemon groves and hilltop farmhouses. Enjoy a refreshing gelato or lunch on your own in the main square. Return to Levanto by train, and celebrate our adventure with a farewell dinner in town. (3–4 miles hiking, 3–4 hours) Hotel La Giada del Mesco (B,D)


Day 9 — Pisa/U.S.
After breakfast and a final cappuccino, transfer to Pisa and connect to your return flight home. (B)



Pricing starts at $5,700 per person, double occupancy. For a single room, add $1,000. International airfare to Florence and return from Pisa is not included in the adventure cost.

Group Size: 8–16


Solo Travelers

Accommodations (hotels, tents and cruise cabins) are based on double occupancy. If you prefer single accommodations, and if such are available, you can pay a single supplement fee. If you are traveling alone and wish to share accommodations, we can assign a roommate of the same gender. If there is no one with whom you can share, a single supplement fee will apply.


See special terms and conditions for this adventure.

Tuscany and Cinque Terre Hiking

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Group or Custom Journeys

Starting at $5,700 Per Person