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Chianti, Florence & Seaside Villages

Tuscany & the Cinque Terre Cultural Walking Tour

7 DaysStarting at $6,495
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Overview

Drinking in the sunset and the Chianti at our friend Marco's farmhouse, we decided that a Tuscany walking tour couldn't be improved upon. Since he's a staunch Tuscan, he surprised us by saying, "Then you've never been to the Cinque Terre." So we went. They're not far, these five once almost unreachable villages that grow out of rock along the Ligurian Sea. For centuries, a connecting footpath was their lifeline, but for us it's the scenic route into a remote and vibrant coastal culture. Beforehand, we spend three nights in the parts of Tuscany we love best…complete with hilltowns that rise out of silver-green olive groves, homemade prosciutto and potato ravioli and the sunny vineyards of Chianti. Throughout, we'll explore the art history, and savor the food and wine. But in the end, will you prefer walking tours in Tuscany or the Cinque Terre? The good news is that because this trip gives you both, you don't have to decide.

Classic Journeys’ tour to Tuscany and the Cinque Terre is our favorite luxury walking experience.”
Forbes Magazine

Itinerary Highlights

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• Gather in Florence, where a short journey into Chianti leads to a private visit and tasting at one of the famed wineries, followed by a scenic walk to our hotel, a historic villa that dates to the 16th century and is owned by a count and countess.

• Walk past silvery olive groves to visit a shepherd who shows how he makes sheep's-milk cheeses…and a chance to sample some of the traditional specialties.

• Follow a footpath in the lovely Chianti hills, to a vineyard walk that ends with a home-cooked lunch and wine-tasting in the private cellars of Castello della Paneretta.

• Spot San Gimignano, fortified with more than a dozen medieval towers, shimmering in the near distance as we approach along a rural footpath.

• Journey along the Apuane mountains to Santa Margherita, where our hotel overlooks the Ligurian Sea.

• Walk to the colorful, isolated villages of the Cinque Terre — Monterosso, Vernazza, Corniglia, Manarola and Rio Maggiore — with time out for shopping or a picnic. (Or skip the walking, and take a little coastal train that runs between the villages.)

• Explore the tiny monastery of San Fruttuoso reachable only by foot or boat after visiting iconic Portofino.

• Cap off an evening in Florence with a memorable dinner at our favorite trattoria, where in one meal we enjoy the whole tapestry of Tuscan cuisine.

• Skip the lines to see Michelangelo's David as part of a guided walk in Florence that provides an insider's view of the famed Renaissance city.

• Wandering the ancient streets to see and learn about Brunelleschi's incredible dome, the Ponte Vecchio, and Piazza della Signoria.

• Graze through San Lorenzo, the Florentine's main market, with its pyramids of produce, olives, breads, meats and more.

Download Full Daily Itinerary

Map

  • Starting Point:

    Florence – 1:00 pm – Lobby of Antica Torre Di Via Tornabuoni Hotel

  • Ending Point:

    Florence – 1:00 pm – Lobby of Antica Torre Di Via Tornabuoni Hotel
Itinerary Map

Click map to enlarge

Walking Level

  • Daily Mileage Options: 2-8 miles

  • Route Notes:

    The terrain on this trip includes a mix of paved and cobblestone streets in Florence, Santa Margherita, Portofino and the Chianti villages, as well as well-maintained countryside and coastal trails, vineyard and shepherds’ paths of compressed dirt and stone, and even sections of the famed Camino de Santiago de Compostela. Generally, the walking paths through the Chianti countryside and to Portofino are mostly level or gently rolling; along the coast among the villages of the Cinque Terre there will be some elevation gain and loss.
To See Mileage Daily, Download Full Itinerary

Dates & Prices

The earlier you book, the more options you’ll have and the lower your price. Secure your spot with a deposit of just $500 per person at the time of reservation. Plus, you can always change your mind — there’s no fee to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

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Family Departure

Select our “Family Departure” to travel with other families.

Hotels

We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour. 

Villa Le Barone

This historic home dates to the 16th century, and your hosts are a count and countess. Its rooms have wood-beamed ceilings and antiques. The property boasts lovely gardens, a new saltwater infinity pool, and a terrace for sunning and Chianti sipping.

Grand Hotel Miramare pool

Grand Hotel Miramare

One of the first grand hotels in the region, this property is a Leading Hotel of the World. It offers all of the luxurious comfort you expect…plus a pool that overlooks the scenic promenade to Portofino.

Antica Torre Di Via Tornabuoni

Originally a palace of the Guelf family, this historic hotel in the heart of Florence is known for its attentive service. The rooftop terraces offer remarkable views of the entire city. Rooms are decorated in elegantly understated Florentine style.

What’s Included

  • Meals: All breakfasts, one lunch and five dinners.
  • Hotels: Award-winning boutique properties, thoughtfully selected for their exceptional location, design, history, and regional character.
  • Tour Leader(s): Expert guides who are your well-connected local friends and provide you access to people and places you wouldn’t find on your own.
  • Supplemental Experts: Additional regional guides and specialists on select tours.
  • Transportation: All land transportation as listed in the daily itinerary, including fares for trains, ferries, and other modes of travel.
  • Privileged Access Events: One-of-a-kind access to remarkable people, places, and experiences arranged just for you, as noted in the daily itinerary.
  • Admissions & Entry Fees: Entry to tastings, historic sites, and other scheduled activities listed in the daily itinerary.
  • Baggage Transfers:: Upon arrival, we whisk you and your bags directly to your room—no waiting, no tipping.
  • Gratuities: All gratuities at hotels, restaurants, and for baggage handling.
  • Dedicated Guest Services Coordinator: Your pre-trip concierge and tour expert, available to answer questions and ensure you’re fully ready to get the most out of your tour.
  • Perfect Pairings Dinner: A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.
Not Included: Tour Leader gratuities, travel to and from your trip’s start and end points, and any meals or activities taken independently.

Why Choose Classic Journeys

Travel + Leisure has awarded Classic Journeys the #1 World’s Best Tour Operator multiple times and says, “Classic Journeys provides unbeatable access to experiences around the globe.” Here’s what that access means for you.
  • Experience the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in Tuscany and along the coastal towns of Cinque Terre.
  • Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, sharing their lifelong connections as well as engaging anecdotes about Italian history and culture.
  • Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like skipping the lines to see Michelangelo’s David in Florence, visiting with a shepherd and tasting his sheep’s-milk cheeses and strolling through a vineyard with the owners in Tuscany.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you’re exploring, including a historic villa that dates to the 16th century and is owned by a count and countess.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us. From gourmet picnics to coveted local restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
  • Handcrafted itineraries with all activities included. With our long-term friendships, we know our walking tour regions more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
  • Sustainable travel that supports the places you’re visiting. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.

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FAQs

How many days do you need in Cinque Terre?
You only need about 2–3 days to see Cinque Terre on your own—but with Classic Journeys you enjoy six full days that blend the best of the five cliffside villages with the relaxed pace of Tuscany. You walk along the iconic coastal trails, savor fresh seafood and local wine, and still have time for vineyard walks and hill town discoveries without rushing or getting lost in the crowds.
How long does it take to walk the 5 villages of Cinque Terre?
Walking all five Cinque Terre villages in one stretch takes about 5–6 hours. With Classic Journeys, you’ll savor the best sections of the path—the most scenic and less crowded stretches—while also hopping by boat or train when it makes sense. With your expert local guide, every walk is at a pace that leaves you free to linger over breathtaking sea views and take photos of the iconic colorful villages.
Is Tuscany good for walking?
Tuscany is one of the world’s dream destinations for walking. On tour, you’ll stroll through rolling vineyards, olive groves, and medieval towns that look pulled from a Renaissance painting. With Classic Journeys, these cinematic walks lead to vineyard tastings, family kitchens, and artisan encounters that bring Tuscany to life in unforgettable ways.
What is Tuscany best known for?
Tuscany is best known for its wine, Renaissance art, hill towns, and farm-to-table cuisine. On a Classic Journeys tour, you taste Chianti in centuries-old cellars, wander through Florence’s dazzling piazzas, and discover historic walled towns like San Gimignano—all while enjoying relaxed walks that connect the cultural landmarks with everyday Tuscan life.
How many days in Tuscany are enough?
While you can sample Tuscany in 3–4 days, six days is ideal to relax into its rhythm and appreciate all it has to offer. With Classic Journeys, six days means morning walks through vineyards, afternoons in hidden piazzas, and evenings lingering over meals at boutique hotels. With your expert guide, you also slip away from the crowds to discover villages most visitors miss.
Is Tuscany a walkable city?
Tuscany isn’t a city—it’s a region of Italy known for its rolling countryside and historic towns. Places like Lucca and Florence are wonderfully walkable on foot, but Classic Journeys makes it richer by combining these strolls with guided countryside walks through Chianti vineyards and olive groves, where daily life still unfolds just as it has for centuries.
What to do in Tuscany Italy?
In Tuscany, you’ll explore medieval towns, visit vineyards, learn culinary traditions in a cooking class, and enjoy Renaissance treasures. With Classic Journeys, you don’t just do these things—you’ll meet the winemakers, cook alongside locals, and uncover tucked-away villages that others pass by. Every day in Tuscany is la dolce vita—lived, not just observed.
What to do in Cinque Terre?
In Cinque Terre, you’ll hike the cliffside paths that link all five villages, glide between them by boat, and linger over fresh seafood and local wine. With Classic Journeys, your guide leads you to quieter corners and timing that avoids the crowds, turning this famous stretch of coast into your own insider experience.