Sailing Yacht Charters Worldwide: 15 Boats Worth the Fee

Lisbon Sunset Sailing Tour on Luxury Sailing Yacht with 2 Drinks

1.Lisbon Sunset Sailing Tour on Luxury Sailing Yacht with 2 Drinks

★★★★★★★★★★5.0 · 1,109 reviews · 2 hours (approx.) · from $61Top of the fleet

Sail the Tagus for about two hours aboard a 50 to 58 foot yacht from Belém. A captain and host explain Lisbon landmarks in English and other languages, while you enjoy two drinks, Portuguese cheese, chouriço, and sunset views. Sebastian, Tiago, and Christina are among the guides who may lead the cruise.

“Very enjoyable. Knowledgeable and friendly captain. Kept us all informed on the sights and was very entertaining”

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Lisbon Sailing Tour on a Luxury Sailing Yacht with 2 Drinks

2.Lisbon Sailing Tour on a Luxury Sailing Yacht with 2 Drinks

★★★★★★★★★★5.0 · 703 reviews · 2 hours (approx.) · from $46

Spend about two hours sailing from Belém on a 50-foot yacht with up to 14 people. The captain and host point out Belém Tower, the 25th of April Bridge, Christ the King, Alfama, and more. Two drinks per person, Portuguese cheese, and chouriço are included, with guidance in English and other languages.

“Very friendly, knowledgeable & attentive. Lovely river cruise with great local & historical information, without being intrusive”

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America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head

3.America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head

★★★★★★★★★★4.5 · 504 reviews · 1 hour 30 minutes (approx.) · from $55

Join Captain Peter and the Vagabond Cruise crew for a 90-minute sail aboard the 39-foot Stars & Stripes, an America's Cup 12-Meter yacht. You can help raise the mainsail, try the wheel, and view Harbour Town Lighthouse, the marina, and the Intracoastal Waterway. Cushioned deck seating, paid drinks, and weather-dependent sailing are part of the deal.

“Just a great day on the water with some friendly, knowledgeable people! I would go back in a heartbeat!”

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Private Luxury Yacht Charters, BYOB & Dolphins

4.Private Luxury Yacht Charters, BYOB & Dolphins

★★★★★★★★★★5.0 · 395 reviews · 2 hours 30 minutes (approx.)

Book a private 2.5-hour yacht charter from 33 Lockwood Drive for up to six people. Your captain and first mate sail Charleston Harbor past downtown, Fort Sumter, and the Ravenel Bridge. Bring your own drinks and snacks, request catering, and choose a departure time, including sunset. Captains such as Holly, Brian, Will, and Glenn add local stories and careful sailing.

“No parking at the marina. Other than that, get ready for a super chill time at sea with a more than capable crew. Brian and Judd were a pleasure”

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Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

5.Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

★★★★★★★★★★5.0 · 386 reviews

Spend up to seven hours aboard Pisces, a 47-foot private Leopard catamaran from Havensight. Your captain, often AnneMarie, JP, or another Seas the Day crew member, helps shape the day around sailing, snorkeling, turtle watching, beach time, and island views. Drinks, floats, snorkel gear, music, and a restroom are included.

“I’ve never reviewed anything in my life. This was amazing. The captain was great and the person helping was fantastic as well.”

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Sunset on a Luxury Sailing Yacht from Vilamoura (Max 12 Guests)

6.Sunset on a Luxury Sailing Yacht from Vilamoura (Max 12 Guests)

★★★★★★★★★★5.0 · 383 reviews · 2 hours 30 minutes (approx.) · from $60

Set sail from Vilamoura for about 2.5 hours aboard a yacht limited to 12 people. Your crew points out Falésia’s clay cliffs, a small sea-access beach, and Albufeira’s coastline. Enjoy one welcome drink, Portuguese cheese, chouriço, toast, music, and possible swimming when conditions allow.

“It was a lovely relaxed atmosphere.. sunset was beautiful and the 2 boatmen were gentlemen . We had cheese and wine .chatted and had a good laugh.”

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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

7.San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

★★★★★★★★★★5.0 · 331 reviews · 2 hours 30 minutes (approx.) · from $115

Join Captain Phillip aboard Liberty, a hand-restored reproduction of a 1904 sailboat, for a two-and-a-half-hour San Diego Bay cruise. With no more than six passengers, you can help sail the boat, sip beer or white wine, spot sea lions and dolphins, and watch the skyline glow near sunset.

“The sunset sail with Captain Phillip is the highlight of our trip so far. Well worth every penny and highly recommend”

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Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

8.Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef

★★★★★★★★★★4.5 · 290 reviews · 3 hours (approx.) · from $199

Sail from Cabo Marina at 5:00 pm aboard a shared yacht for about three hours. You’ll pass Land’s End, the Arch, and Lovers Beach, then enjoy cocktails, appetizers, and a dinner of shrimp and beef with dessert. The cruise is adults-only, relaxed, and capped at 40 people, not a private charter.

“Wonderful sunset dinner cruise! We enjoyed the more laid back vibe over the “party” ships we saw going out. Bartender still had the drinks flowing with an open bar but there was fewer people and more comfortable places to lounge and take in the views! 5 star service!”

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Day sailing Skiathos Skopelos with lunch on Rainbow yacht

9.Day sailing Skiathos Skopelos with lunch on Rainbow yacht

★★★★★★★★★★5.0 · 262 reviews · 7 hours (approx.) · from $163

Join Yannis and Angelica aboard Rainbow yacht for a relaxed 7-hour sailing day from Skiathos. Swim at Tsougria, Panormos, and other island bays, see Mamma Mia filming areas near Skopelos, enjoy Greek food cooked on board, and share the day with the hosts’ friendly dog, Naya.

“Our days sailing with Yanis, Angelica and Naya was the highlight of our holiday. Highly recommend 😊”

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Private Sailing Yacht Charter by Independence from Koh Samui

10.Private Sailing Yacht Charter by Independence from Koh Samui

★★★★★★★★★★5.0 · 215 reviews

Charter the 52-foot Independence yacht for up to six people, with a skipper, hostess, chef, drinks, food, swim and snorkel gear, and hotel transfers. Choose a sunset, half-day, full-day, or Ang Thong National Marine Park cruise. Luca and his crew provide a polished private sailing day, though sea conditions and the selected route shape the experience.

“A wonderful, relaxing experience. We chartered the independence for an excursion to the Ang Thong Marine park. The captain picked us up on our resort beach and took us to the ship. The service was fantastic. They were attentive, caring, Read more”

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Private Sailboat tour in Cabo San Lucas with Papillon Yachts

11.Private Sailboat tour in Cabo San Lucas with Papillon Yachts

★★★★★★★★★★5.0 · 198 reviews · 3 hours (approx.)

Book a private three-hour Papillon Yachts sail for up to six people, with roundtrip transport, an open bar, quesadillas, guacamole, snorkeling, and paddleboards. You’ll cruise by Cabo’s Arch and sea-lion colony, then anchor near Médano Beach. Crews have included Captain Martin, Jessica, and photographer Ali, with time shaped around your group.

“Great crew! Very attentive / flexible to what we wanted to do. Appreciated having a photographer on board so we could just enjoy ourselves”

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Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)

12.Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)

★★★★★★★★★★5.0 · 197 reviews · 6 hours (approx.) · from $120

Spend about six hours sailing or cruising from Rhodes to Anthony Quinn, Traganou, and Ladiko bays. Swim, snorkel, visit a sea cave, and enjoy Greek food, fruit, wine, beer, and soft drinks. Crews may include George, Dimitri, Despina, or Yannis. Hotel pickup is available for an added fee.

“This was our favorite day on the trip. Cruising around was so peaceful and so what we wanted to get from Greece.”

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Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group

13.Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group

★★★★★★★★★★4.5 · 194 reviews · 4 hours (approx.) · from $90

Set sail from Hvar’s Riva for four easygoing hours around the Pakleni Islands. With no more than eight guests on the comfort yacht, you’ll swim and snorkel in two bays, hear local sailing stories, and adjust the route to the weather. Bring lunch and drinks, then keep them cold in the onboard fridge.

“The pickup by the green lantern was smooth and efficient. The instructions were easy to follow. Although there was no wind, the 2 lads made it interesting and were able to adapt and overcome. The little stories of the local places of interest were entertaining. Safety of our group was important to them. Nice choice of music!”

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From Skiathos Marina: Yacht Sailing Day Trip with Lunch

14.From Skiathos Marina: Yacht Sailing Day Trip with Lunch

★★★★★★★★★★4.8 · 180 reviews · 8 hours · from $175

Join Perfect Sailing for an eight-hour yacht trip from Skiathos New Port. Lambros and his crew serve breakfast, drinks, snacks, and lunch at a local taverna, with stops near Lalaria, Tsougria, Kastani, Hovolo, Dasia, and Arkos. Swim, snorkel, paddleboard, fish, and watch for dolphins while cruising between the islands.

“The yacht was beautiful with lots of space. There was of plenty of stops for swimming, paddle boarding or snorkelling with drinks and snacks.”

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Yacht Me Up – Private All-Inclusive Cannes Sailing Fever

15.Yacht Me Up – Private All-Inclusive Cannes Sailing Fever

★★★★★★★★★★5.0 · 175 reviews · 3 hours 30 minutes (approx.)

Spend 3.5 hours aboard a private Dufour 382 with Captain Brice and Ansel. Cruise past the Croisette and Palais des Festivals, anchor near the Lérins Islands, snorkel around underwater sculptures, and use the paddleboard, GoPro, and SeaBob. Snacks, drinks, music, fuel, and selected food are included.

“Outstanding half day with Ansel & Captain Brice. Everything was taken care of for us— from food, to drink, to expert sailing. Stand up paddle, snorkel, sea-bob. Just amazing.”

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