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.
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.
Explore the coastal villages of the Cinque Terre on a
series of spectacular walks and hikes.
Sample Tuscany’s famed wines and cuisine and the specialties of Liguria.
Itinerary - 9 Days
Day 1 — Florence, Italy/San Casciano in Val di Pesa
Arrive in Florence and meet your trip leader this afternoon. Right after presentation, a short stop to the Benedictine church of San Miniato al Monte, perched above Florence with sweeping views of the city’s red-tiled roofs and Duomo. After the last view of Florence, we will 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 enjoy an olive oil tasting and a hearty country dinner. (2-3 miles hiking, 2 hours) Hotel Executive (D)
Day 2 — Florence/Greve in Chianti/Volpaia
After breakfast, we 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, we approach, on foot, Volpaia, home to a winery that produces the famed Chianti Classico. From Volpaia, a transfer to our charming hotel in Radda in Chianti’s historic center. (5 miles hiking, 3-4 hours) Palazzo Leopoldo Radda (B,L,D)
Day 3 — Chianti
A short transfer to San Giusto in Salcio, an exquisite medieval church just south of Radda. From there, we walk along prestigious vineyards surrounding the capital of Chianti wine. Our trail takes us to San Polo in Rosso, one of the many powerful castles built by Florence to defend its territory against Siena. After picnic lunch, we continue our walk through more unspoiled medieval villages and then back to San Giusto in Salcio. Return by van to Radda for a tasting of Chianti wines, then follow it up with a dinner on your own at the hotel or a restaurant in town. (5 miles hiking, 3-4 hours) Palazzo Leopoldo Radda (B,L)
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. Depending on trail conditions, we hike along the trail that links the neighboring villages of Vernazza, Corniglia, Manarola, and Riomaggiore, or enjoy a scenic train and boat ride from village to village. Take in the amazing scenery of 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)
National Geographic Active Expeditions are unique, active itineraries for intrepid travelers that combine spectacular places, cultural interaction, and physical challenge. You'll explore fascinating, off-the-beaten-path places with top guides, and wherever possible, meet National Geographic experts in the field.
We will be hiking 2–5 hours per day (2–6 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).
Click here for a description of all activity levels.
What To Expect
We will stay 8 nights in comfortable,
ideally located hotels.
Contact Us: 1-888-689-2557
Call to speak with an Adventure specialist about this trip.