Amalfi Coast: Positano & the Isle of Capri

6 DaysStarting at $5,895


On a launch approaching the Amalfi Coast, you face a startling sight— like oversized rock climbers, gleaming villas cling with no visible foothold to the sheer cliffs. You have to ask yourself how…why? But when you swing open the shutters in your cliffside hotel room, the jaw-dropping view is all the answer you need. Situated on the "ankle" of the Italian boot, Amalfi has a balmy climate. Orange trees line village streets. Breezy seaside footpaths around Positano encourage cinematic walks that are perfect for absorbing the atmosphere. We also settle in for two days on the glorious island of Capri—one of our favorite places in Italy. We make time for Pompeii, and unlike most visitors, you’ll see Amalfi in the best way—in the company of an Italian friend who knows the ins and outs of life on the edge of the sea. See Sicily, too! Our Sicily tour starts the day after Amalfi ends. Pair up the two for an amazing Italian vacation. Call 800.200.3887 for details.

Show more
Classic Journeys provides unbeatable access to experiences around the globe.”
Travel + Leisure


We meet in Naples (1 night), one of Italy's classic cities (not to mention the birthplace of pizza). From here, we make a short journey to Pompeii.  We explore Pompeii with an archeologist friend. Visiting the most famous archaeological site in the world. Buried in volcanic ash in 79 AD, Pompeii is famous for its excavations that reveal a complete city, including streets, shops, buildings and many beautiful villas.

After breakfast, we skim across the bay by ferry to Capri (2 nights). From our luxurious hotel on the island, we've arranged a fascinating array of activities. There's time for shopping in the cobblestone lanes. Memorable walks here include an amble along the coast to the villa where Churchill and Eisenhower managed much of WWII. We'll lunch at the exclusive Marina Piccola and view the 14th-century monastery atop Monte Solaro at the top of the island.

Back to the mainland, en route to Positano, we'll follow the spectacular Amalfi coast to our cliffside hotel built in the 17th century. Our leisurely days here include an incredibly scenic walk through "the valley of the mills" for a private demonstration of medieval papermaking. Our trails also lead to Ravello with stupendous views from Villa Rufolo and to a tiny limoncello factory to see how the local lemon liquor is made. On our final day, we toast our week together with a pizza making instruction overlooking the sea. We say ciao in Naples…or ride the ferry to Palermo for a sunny week in Sicily.

Show more Download itinerary


  • Starting Point:

    Naples – 1:30 pm – Lobby of Grand Hotel Vesuvio
  • Ending Point:

    Naples – 6:30 pm – Train Station

Why Choose Classic Journeys

We believe in creating authentic connections by immersing you into the history and culture of a people and place. So we find the most well-connected local guides who share their relationships and knowledge with us. And with them, we handcraft walking tours in cinematic settings that allow you to see the world on foot and at eye level.

It's why Travel + Leisure magazine has named Classic Journeys as the #1 World's Best Tour Operator multiple times, and the editors of T+L say, "Classic Journeys provides unbeatable access to experiences around the globe." Here's what that access means for you every time you travel with us.

  • Experience the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the region.
  • Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, share their lifelong connections as well as engaging anecdotes about the history and culture of the region.
  • 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 Stonehenge so you experience the stone circle when it's closed to the general public, a guided visit to Zion Narrows that other companies cannot arrange because of larger group sizes, and vineyard walks with a count and countess 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 rainforest lodges, 16th century villas, and award-winning properties that show up on World's Best and Gold lists.
  • 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.
Show more

Dates & Prices

Not ready to book just yet? Talk with one of our travel experts at 800-200-3887.

Talk to an expert
Family Departure

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


Le Agavi

This beautiful 5-star hotel is built into a cliff overlooking the bay of Positano and boasts a sea-view restaurant and private beach. The appointed guest rooms have their own balcony or terrace from where to enjoy wonderful views of Positano and the sea.

Grand Hotel Vesuvio

Built in 1882, the Grand Hotel Vesuvio is centrally located on the waterfront, overlooking Santa Lucia Harbor and the Bay of Naples. The atmosphere of an old-world hotel gracefully combines with all the modern comforts and personalized services.

Grand Hotel Quisisana

The 'Quisi' is THE hotel in Capri. Grand and gracious, it’s been named one of the World’s Top 100 Hotels by both Condé Nast Traveler and Travel + Leisure. Its staid façade on the town square gives way to a hugely glamorous pool overlooking the sea.

What’s Included

  • Award-winning boutique hotels that provide you unlimited access to the people and places, culture and history you came to experience
  • All breakfasts, 1 lunch (cooking instruction), 4 dinners
  • Full-time experienced guide(s) who are with you throughout the trip and handle behind-the-scenes logistics
  • Admissions to tastings, historic sites and other scheduled events as noted in the detailed daily itinerary
  • Gratuities for hotels, meals, and baggage
  • All land transportation during the trip

Above & Beyond Benefits

Wine on Us

  • In many regions, we uncork wonderful local wines at every dinner, compliments of Classic Journeys.

Invisible Check-In

  • When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.

Privileged Access Events

  • One-of-a-kind access to remarkable people, places and activities arranged just for you.

Perfect Pairings Dinners

  • A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.