Take to the hills of Tuscany and Cinque Terre with your camera in hand and capture stunning scenes of the countryside, villages and everyday life in two of Italy’s most beautiful regions. Frame cypress-topped hills and silvery olive groves as we hike through Chianti, and photograph the exquisite details of medieval and Renaissance architecture in hilltop towns like Siena and San Gimignano. Then head to the seaside slopes of Cinque Terre to photograph stunning views of terraced vineyards and orchards stacked high above the colorful hamlets that cling to the Mediterranean shores.


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.


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 photo hike, capturing the shimmer of olive orchards against hills striped with vineyards. Our destination is the 15th-century home of a local Tuscan family, where we’ll enjoy an olive oil tasting and a hearty dinner — and a great chance to photograph a centuries-old country house and its surroundings in the evening light. (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 picturesquely above Florence. Take advantage of this bird’s-eye view of the city to capture the sweep of red-tiled roofs and the iconic dome designed by Brunelleschi. Then drive through the hills to Greve in Chianti, where we’ll wander with our cameras through vineyards dangling with ripening grapes and sample the region’s celebrated wines. Set off on a photo hike to the fortified village of Lamole. After a lunch of local specialties, take a short drive to Volpaia, a fortified village where the famed Chianti Classico wine is produced. From here, depending on the terrain, we’ll continue on foot to the Romanesque church of Santa Maria Novella and photograph the historic site in the golden light of late afternoon. Our home for the next two nights is a charming hotel in Radda in Chianti’s 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
With its winding lanes, Gothic churches and red-brick palaces, Siena begs to be photographed. Spend the morning exploring with your camera. Capture the jarring contrast of black and white marble in the cathedral, and frame the graceful curves of the great central piazza, Il Campo, known for the medieval horserace that continues today: il Palio. Then visit Monteriggioni, a well-preserved walled village mentioned in Dante’s Inferno, and photograph its evocative ramparts and towers. 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. Try out different angles on this much-photographed town, and explore its maze-like streets. View the frescos in the Duomo, or climb one of the towers to photograph a vista of rolling hills speckled with pointed cypress trees. (2–3 miles hiking, 3 hours) Hotel Villa San Lucchese (B,L,D)


Day 6 — Carrara/Levanto
At the Tuscan town of Carrara, photograph 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 and a photo walk along 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 are incredibly picturesque, with dazzling clusters of pastel-hued homes overlooking harbors dotted with fishing skiffs. After time to photograph the village, 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 your camera in hand, capturing 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, offering spectacular photographic opportunities. 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 $6,800 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: 8–15


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 Photo Adventure

Learn More

Group or Custom Journeys

Starting at $6,800 Per Person