The 12 Best Sailing Trips in Capri

1.Capri Private Yacht Tour from Sorrento, Capri & Positano

★★★★★★★★★★5.0 · 35 reviews · 8 hours (approx.) · from $622Our pick

Review of a private Capri yacht tour from Sorrento, with Blue Grotto, swimming, Anacapri, sea caves, snacks, and practical cost tips.

“A notable highlight was a refreshing swim in the Mediterranean, twice!! Throughout our journey, Captain Raffaele's knowledgeable commentary as a native Italian, enriched our understanding of the region's history, culture, and natural beauty & landmarks, bringing their significance to life. 🧐 Our time to explore Anacapri on our own was perfect enabling us to take the chair lift to Mt Solaro! Another notable highlight was a refreshing swim in the Mediterranean, twice!!”

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2.Capri and Blue Grotto Yacht Tour with Snorkeling

★★★★★★★★★★4.5 · 23 reviews · from $143Best value

Cruise from Sorrento to Capri on a small yacht with grotto visits, snorkeling, swimming, drinks, snacks, and two hours to explore.

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3.Private Cruise to Capri and Amalfi Coast from Sorrento or Capri – yacht 50′

★★★★★★★★★★5.0 · 16 reviews · 8 hours (approx.)

Review of a private 50-foot yacht cruise from Sorrento or Capri, with swimming, snorkeling, Positano, Amalfi, snacks, and a flexible route.

“Our cruise was AMAZING!! Leonardo was our skipper and Bianca our host. Both very attentive and made sure that we enjoyed ourselves. The tour started on time & the 8hrs was plenty for activities. We sailed, swam, & stopped for lunch. The boat was clean and spacious. We requested chauffeur service from our hotel providing door to door service. Everything about the day was seamless! I would definitely recommend this tour!! Enjoy!!”

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4.Private Cruise around Capri – yacht 50′

★★★★★★★★★★5.0 · 12 reviews · 8 hours (approx.)

Spend eight private hours circling Capri by yacht, with swimming, snorkeling, grotto views, Faraglioni Rocks, and a stop in Nerano.

“This cruise was amazing, and the staff were very friendly and knowledgeable. Communication was seamless. Highly recommended.”

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5.Private Cruise to Capri and Amalfi coast from Sorrento or Capri – yacht 40′

★★★★★★★★★★5.0 · 9 reviews · 8 hours (approx.)

Private 40-foot yacht cruise from Sorrento or Capri to Positano, Amalfi, and Capri, with swimming, snorkeling, snacks, and a flexible route.

“We had a private tour on Shamal 40’ boat from Sorrento to Positano, had a lunch break and sailed to Capri and back to Sorrento. During the trip our Captain Roberto and his assistant Enrico could not do enough for us. From showing us around the islands, offering all sorts if refreshments, fruits, snacks, taking our pictures for us while we were snorkeling. Roberto booked us a fantastic restaurant called Ristorante Pappone which was one of the best restaurants we visited while on holiday.”

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6.Capri Private Boat Tour from Sorrento, Positano or Naples – Yacht Klase 50

★★★★★★★★★★5.0 · 8 reviews · 7 to 8 hours (approx.) · from $1,992

Cruise Capri on a private Klase 50 yacht from Sorrento, Positano, or Naples with swimming, grottoes, snacks, and a flexible route.

“Roberta and Marco were great! They were kind enough to wait while we explored Capri, had lunch and shopped. Later taking us to swim off the coast and driving us around to see the coast.”

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7.3 – Day All-Inclusive Sailing Adventure: Capri, Positano & Amalfi

★★★★★★★★★★5.0 · 7 reviews · 3 days (approx.) · from $1,321

Sail from Torre del Greco to Capri, Amalfi, Positano, and Sorrento with meals, swim stops, and a six-person boat group.

“This is a wonderful way to see some of the Amalfi coast’s most beautiful destinations from the sea. Our host was so gracious and thoughtful throughout the trip. We stopped at stunning swim spots along the way each day of sailing. It is important to note that you should be comfortable on a boat and being at sea.”

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8.Private Cruise around Capri – yacht 40′

★★★★★★★★★★5.0 · 6 reviews · 8 hours (approx.)

Review of a private 40-foot yacht cruise around Capri, with caves, swimming stops, snorkeling, drinks, and a flexible route for up to six.

“Roberto! He was the highlight he knew everything about everything he was super attentive kind and absolutely made our trip to Capri and the amalfi coast we booked it for a sunset cruise and had the best views and experiences with him from the floating flamingos to the wine to the champagne the snacks the fruit! The snorkelling the caves the blue lagoon the pictures he really did out do himself this was our honeymoon and we plan to come back every year and will only have Roberto from now on absolute outstanding couldn’t thank him enough! We also recommended some people we met here in Italy to him and…”

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9.Positano Private Yacht tour from Sorrento,Positano or Capri

★★★★★★★★★★4.5 · 6 reviews · 8 hours (approx.) · from $957

Review of a private Capri and Positano yacht tour from Sorrento, with grotto swims, island time, snorkeling, drinks, and practical costs.

“This was an amazing tour and or skipper Gabriele was fantastic. He booked an amazing lunch at the famous lo scoliogo restaurant in nerano. We had plenty of time to swim and enjoy the beautiful views of capri, Postitano, nerano, as well as the beautiful coast along the way. We were here for our honeymoon and we couldn’t have been happier with our private experience.”

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10.Private Cruise to Capri from Sorrento – yacht 50′

★★★★★★★★★★5.0 · 6 reviews · 8 hours (approx.)

Cruise from Sorrento to Capri on a private 50-foot yacht with a local skipper, swimming stops, snorkeling, coastal sights, and a flexible itinerary.

“Absolutely fabulous day out 10 out of 10👍😎 the whole day wea amazing and the crew were so helpful and attentive Bravo!!👍”

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11.Private Cruise to Capri and Amalfi coast from Positano or Amalfi – yacht 50′

★★★★★★★★★★5.0 · 5 reviews · 8 hours (approx.)

Cruise from Positano or Amalfi to Capri on a private 50-foot yacht, with swimming stops, coastal views, onboard commentary, and flexible timing.

“Leonardo and Marco were a wonderful team who did everything possible to make it a superlative experience. We highly recommend this team and this company.”

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12.Private sailing trip along Capri and the Sorrento Coast

★★★★★★★★★★5.0 · 5 reviews · 9 hours (approx.)

Sail from Sorrento to Capri with private stops at Massa Lubrense, the Faraglioni, and the Blue Grotto on a relaxed nine-hour trip.

“Our private sailing tour with Amedeo was the highlight of our nine day trip in the Amalfi Peninsula. We got to see all the major sites around Capri, and a few along the Sorrento coast, well timed to visit at off peak hours and give us a better experience. He was knowledgeable, flexible, and gave us a very specialized and personalized tour. I would absolutely book him again and would recommend his sailing excursion to others!”

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