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Italy Hiking: Tuscany & Cinque Terre

10 days  |  12 days with Florence extension  |  Loading prices

Physical activity
Group size
5–22 travelers
Notice:

Save up to $500 through Jan. 31

The best years aren’t counted in days, but in moments. Save up to $500 on this tour when you book by January 31.

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 5.5 miles from Monticchiello 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 to the top of Monte Muzzerone for sweeping sea views before finishing in Portovenere
  • 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: 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.

Florence extension

Sure, hiking through rural Tuscany and coastal Cinque Terre along the Italian Riviera is spectacular on its own. But if you’re looking for a few extra days in Italy, start your adventure early in Florence, a city that offers some of the world’s most impressive Renaissance art and architecture like the Duomo. While the city can seem like a living museum, there’s plenty to do when you’re ready for an art break. From browsing the Mercato Centrale food hall to sampling the city’s best gelato and traditional Florentine desserts like zuccotto (a semi-frozen, dome-shaped cake), it’s not hard to fall head over heels for Florence. A few days here is also a great excuse to get adjusted to the new time zone and rest up before your jam-packed hiking tour kicks off!

Overnight flight

Day 1: Fly to Florence

Head off on your overnight flight to Florence and ease into Italian life in one of Europe’s most charming cities.

Florence

Day 2: Arrival in Florence

Welcome to Firenze, the capital of Italy’s Tuscan region, where masters like Leonardo da Vinci lived and worked. Art and architecture buffs won’t know where to start—landmarks, museums, and artwork here are practically endless (it is the birthplace of the Renaissance, after all). Don’t feel like you need to check everything off at once. A stroll along the city’s symbolic Ponte Vecchio, a medieval stone bridge lined with shops, is enough to shake off jet lag and build up excitement for the days ahead.

Today’s highlights
  • Meet an EF representative at the Florence airport.
  • Transfer to your hotel in Florence (a 30- to 60-minute drive).
  • Toast to the start of your trip with a Welcome Drink before setting out and stretching your legs on a stroll around the city.

Day 3: Walking tour of Florence & optional Pitti Palace & Boboli Gardens excursion

Included meal: Breakfast

On your first full day in Italy, cross many of Florence’s highlights off your list on a guided walking tour. Snap photos of the Florence Cathedral, known locally as the Duomo, and the freestanding Giotto’s Campanile, a bell tower with nearly 400 steps to the top, before continuing to Casa di Dante, a museum dedicated to the life and work of the Italian literary legend. Another highlight: the Baptistery of San Giovanni, with its gilded bronze doors famously dubbed the “Gates of Paradise” by Michelangelo. Within walking distance from your hotel, you can also join an optional excursion to the Pitti Palace and Boboli Gardens, where you’ll stroll through the Grand Dukes’ former living quarters and the Medici’s private collection of art before soaking up sweeping views of Florence from the hilltop gardens.

Today’s highlights
  • Soak up Florence’s history on a walking tour with a local expert.
  • Marvel at the city’s iconic architecture as you stroll along the Arno River through the Uffizi Gallery courtyard to Florence’s main square, Piazza della Signoria.
  • Opt for the excursion to the Pitti Palace & Boboli Gardens, or spend the afternoon continuing to explore on your own before finding some dinner at one of Florence’s fantastic restaurants.

Day 4: Travel from Florence to the Val d'Orcia region

Included meals: Breakfast, Welcome dinner

After a morning cappuccino, it’s time to pack your suitcase and hop on the 2-hour bus ride to Val d’Orcia region to meet your hiking companions and kickstart your tour.

Note: While today is officially Day 4 of your trip, when you meet up with the rest of your Italy Hiking: Tuscany & Cinque Terre group, they will be on Day 2. For consistency, once you join the group, you will also be on Day 2.

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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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Historic stone buildings with lit windows reflecting in a calm river under a deep blue evening sky.

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...

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

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...

Curved modern building with balconies by a lush green lawn, overlooking the sea under a clear blue sky.

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...

Elegant hotel room with a large bed, warm lighting, abstract wall art, desk, and window with heavy curtains. A robe and towels are on the bed.

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....

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Weather

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Porto Venere, Italy

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Genoa, Italy

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Greve, Italy

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Montepulciano, Italy

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Monticchiello, Italy

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Siena, Italy

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San Gimignano, Italy

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Florence, Italy

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