Skip to main content

Italy Hiking: Tuscany & Cinque Terre

10 days  |  12 days with Florence extension

Physical activity
Group size
10–24 travelers

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

Italy is always a good idea, but why limit yourself to just one stretch of such a stunning country when you can combine the best hikes on a two-part trip through the Tuscan countryside and Cinque Terre? Begin in Tuscany, where rolling hills and vineyards unfold like a Renaissance painting. Wander from the UNESCO-listed Val d'Orcia to San Gimignano's medieval towers, sipping world-class Chianti along the way. Then, transition to the dramatic coast of the Italian Riviera in Cinque Terre, where colorful fishing villages cling to cliffs above the Mediterranean. Hike breathtaking coastal trails connecting towns that feel frozen in time and cool off in hidden coves. Get ready for the perfect mix of adrenaline-pumping hikes and leisurely exploration, allowing you to fully immerse yourself in these beautiful regions—and justify all the focaccia and wine you’ll be enjoying, too.

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 Portofino to Rapallo
  • 8 breakfasts
  • 2 lunches
  • 4 dinners with wine or beer
  • 1 Pecorino cheese tasting, 1 coffee and cookie tasting, 1 focaccia tasting & 2 wine tastings
  • Local licensed guides for select hikes
  • Select guided sightseeing tours

Why you'll love it

  • Hike 8.6 miles from Pienza to Montepulciano, ending with a wine tasting
  • Sip Chianti in its birthplace over a leisurely vineyard lunch & pairing in Greve in Chianti
  • Visit medieval towns like San Gimignano and hilltop hamlets like Bagno Vignoni
  • Ascend Portovenere's cliffside trail to Campiglia Tramonti for sweeping sea views
  • Explore Corniglia, Manarola & Riomaggiore on Cinque Terre's stunning coastal paths
  • Journey from Camogli's coast to San Fruttuoso Abbey en route to chic Portofino

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 2 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: Transfer from the airport to the hotel is only available to travelers who book round-trip flights with EF Adventures.

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.

Skip to end of carousel

Val d'Orcia region - Albergo le Terme

Tradition meets modern comfort in the heart of Val d'Orcia. Albergo le Terme occupies a 15th-century palace with a remarkable history and overlooks Bagno Vignoni's famous Piazza delle Sorgenti, a thermal pool dating back to...

San Gimignano region - Borgo San Luigi

Spread across 60,000 square meters of Tuscan countryside, Borgo San Luigi is more than just a hotel—it's a sanctuary for relaxation. This oasis offers rooms that blend medieval village charm with modern comforts. Lounge by the...

Italian Riviera - Grand Hotel Torre Fara

Located on the Italian Riviera, Grand Hotel Torre Fara in Chiavari serves up luxury with a side of sea breeze. This unique tower-turned-hotel boasts rooms with postcard-worthy views of the Gulf of Tigullio and Portofino. You...

Florence - Grand Hotel Adriatico (Extension)

Steps from Florence's iconic sights, Grand Hotel Adriatico welcomes you with its comfortable rooms, on-site restaurant, and garden bar (a quiet retreat from the city buzz). Unique perks include a 24/7 gym and in-room massages....

Skip to start of carousel

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.

Add our airfare and you’ll get:

  • Round-trip flight for your tour
  • Airport transfers at your destination
  • A great price locked in today
  • 24/7 support from our dedicated service team
  • Options for requesting an upgrade
  • Flexible rebooking options if your tour itinerary changes

Know before you go

Loading your quote