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Italy Hiking: Tuscany & Cinque Terre

10 days  |  Loading prices

Group size
6–20 travelers

Riviera glamour, cliffside hikes, and a whole lot of dolce vita.

Italy is always a good idea, and this trip pairs two of its best stretches. Begin in Tuscany, where rolling hills and vineyards unfold like a Renaissance painting. In the UNESCO-listed Val d’Orcia you’ll walk from the steaming thermal pool of Bagno Vignoni to San Quirico d’Orcia, then follow vineyard-lined farm roads from Monticchiello to Pienza, where a winery lunch is waiting. Then head to the Italian Riviera and Cinque Terre, where colorful fishing villages cling to cliffs above the Mediterranean. You’ll follow the coast from Manarola to Riomaggiore, sail to Monterosso, and finish with a forest trail from Portofino to a hidden abbey cove—plenty of reason to enjoy all the focaccia and wine.

What's included

  • 8 nights in handpicked hotels
  • Private bus for local transfers
  • Train tickets in Cinque Terre and the Italian Riviera
  • Ferry tickets from Manarola to Monterosso, from Rapallo to Portofino, and from San Fruttuoso Abbey back to Portofino
  • An expert local Tour Director
  • 8 breakfasts
  • 1 lunch
  • 5 dinners with wine or beer
  • 1 Pecorino cheese tasting, 1 cookie tasting, 1 focaccia tasting & 2 wine tastings
  • Local licensed guides for select hikes
  • Select guided sightseeing tours

Why you'll love it

  • Wander Montepulciano’s Piazza Grande and Bagno Vignoni’s thermal pool
  • Hike from Monticchiello to Pienza, ending with a wine tasting
  • Walk Monteriggioni’s intact medieval ramparts after a hike from Strove
  • Discover Portovenere’s clifftop church, harbor front, and Byron’s Grotto
  • Follow Cinque Terre’s coastal path from Manarola to Riomaggiore
  • Hike through Mediterranean forest from Portofino to San Fruttuoso Abbey

Itinerary

Overnight flight

Day 1: Fly to Florence

The day is finally here—you’re off to Italy! Head to the airport and board your overnight flight to Florence. We know you’re excited—there are plenty of surprises awaiting in Tuscany and the Italian Riviera. Stretch your legs on the flight for the days of hiking ahead and have your sleep mask ready—you’ll want to arrive feeling rested for the adventure-packed trip.

Val D'Orcia region

Day 2: Arrival in Florence & travel to Val d’Orcia region

Included meal: Welcome dinner

Benvenuto in Italia! Don’t worry if your Italian is rusty—you can brush up on the basics while taking in the scenery on the stunning drive from the Florence airport. You’ll be whisked off to the Val d’Orcia region in southern Tuscany, known for its rolling vineyards, postcard-perfect villages, medieval castles, and trails so gorgeous they’ve appeared as backdrops in films like Gladiator.

Today’s highlights
  • Meet an EF representative at the airport.
  • Transfer 1–1.5 hours to your hotel in the Val d’Orcia region.
  • Toast with a glass of wine, beer, or a soft drink while you get to know your fellow hikers and Tour Director during a Welcome Orientation.
  • Enjoy a Welcome Dinner and keep the bonding going with the group.

Note: Airport transfers are included for travelers who book flights with EF Adventures. If you book your own flights, airport transfers may be available for a fee upon request.

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Handpicked accommodations

From boutique hotels to 5-star luxury retreats, our accommodations are curated with the expert eye and attention to detail that come from 60 years of travel experience, always prioritizing authenticity. We select high-quality properties that balance comfort, location, sustainability, and local charm. From bustling city centers to serene countryside and picturesque small towns, each hotel is chosen to complement your adventure’s unique style. While the specific accommodations may vary based on your travel dates, you can always count on staying at fantastic properties that meet our standards for quality and character.

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Val d'Orcia region - Albergo le Terme

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Outdoor pool area with a central fire pit surrounded by red chairs. Lush greenery and umbrellas in the background create a serene atmosphere.

San Gimignano region - Borgo San Luigi

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Italian Riviera - Grand Hotel Torre Fara

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Customize with excursions

Enhance your experience with hand-picked optional excursions—designed to add adventure, culture, and unforgettable moments to your journey.

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Flights

Round-trip flights are one more thing we handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate, thanks to our partnerships with top airlines.

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Weather

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Porto Venere, Italy

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53°54°57°62°69°77°83°83°77°70°63°56°45°45°47°51°56°64°69°70°66°60°54°48°53°54°57°62°69°77°83°83°77°70°63°56°45°45°47°51°56°64°69°70°66°60°54°48°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Genoa, Italy

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48°50°56°63°69°78°83°83°75°66°56°50°37°39°42°48°53°61°66°66°60°53°46°39°48°50°56°63°69°78°83°83°75°66°56°50°37°39°42°48°53°61°66°66°60°53°46°39°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Montepulciano, Italy

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46°49°54°61°67°78°85°85°75°66°56°49°34°35°38°43°48°57°63°63°56°50°43°37°46°49°54°61°67°78°85°85°75°66°56°49°34°35°38°43°48°57°63°63°56°50°43°37°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Monticchiello, Italy

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46°49°54°61°67°78°85°85°75°66°56°49°34°35°38°43°48°57°63°63°56°50°43°37°46°49°54°61°67°78°85°85°75°66°56°49°34°35°38°43°48°57°63°63°56°50°43°37°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Siena, Italy

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48°51°57°64°70°81°88°88°78°68°57°50°35°37°39°45°50°59°64°64°57°51°44°38°48°51°57°64°70°81°88°88°78°68°57°50°35°37°39°45°50°59°64°64°57°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

San Gimignano, Italy

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48°52°58°65°71°82°88°89°78°68°57°49°36°37°41°46°51°60°65°65°58°51°44°38°48°52°58°65°71°82°88°89°78°68°57°49°36°37°41°46°51°60°65°65°58°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND

Florence, Italy

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Temperature scale

48°52°58°65°71°82°88°88°78°68°58°50°36°37°40°45°50°58°64°64°58°51°44°38°48°52°58°65°71°82°88°88°78°68°58°50°36°37°40°45°50°58°64°64°58°51°44°38°JanFebMarAprMayJunJulAugSepOctNovDecJFMAMJJASOND
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Round-trip flights are one more thing we can handle to make your journey as smooth as possible. Our team of travel experts will find the best flight itinerary for you at a competitive rate. Rates shown in cart.