Best Private Sailing Charters: Our Top 15

★★★★★★★★★★5.0 · 662 reviews · 8 hours 30 minutes (approx.) Top of the fleet

Set out from Kalkara Marina with a private skipper such as David, Terry, Nick, or Maurizio. Sail toward Comino, stopping at Crystal Lagoon, Blue Lagoon, St. Paul’s Bay, and quieter coves chosen around the weather and your wishes. Swim, snorkel, paddleboard, or simply enjoy the boat. Lunch is optional, and you may bring your own food and drinks.

“The boat was in good condition and our captain was wonderful. We enjoyed the scenery, getting in the water and had a great lunch. I would definitely recommend this for larger families (4-8 people).”

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Los Gigantes Whale Watching Charter by Sail Boat

2.Los Gigantes Whale Watching Charter by Sail Boat

★★★★★★★★★★5.0 · 608 reviews · 3 hours (approx.) · from $90

Sail along Tenerife’s Los Gigantes coast aboard a 45-foot Bavaria Cruiser with no more than 10 people. Guides such as Jaime, Eileen, and David explain the marine life, then anchor near the cliffs for swimming and snorkeling. Expect fruit, snacks, custom sandwiches, drinks, and about three hours on the water.

“We saw a pod of pilotwhales and dolphins. Had a lovely snorkel, fab views. Crew were excellent, very knowledgeable and helpfull. 😀”

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Private Sailboat + Captain for a Day Experience

3.Private Sailboat + Captain for a Day Experience

★★★★★★★★★★5.0 · 582 reviews · 3 hours (approx.)

Spend about three hours on a private sailboat in Bacalar Lagoon with a bilingual crew. Take an optional sailing lesson, swim at Cenote Cocalitos and Cenote de la Bruja, look for birds and stromatolites, or simply enjoy a quiet, motor-free ride. The boat carries up to six people and includes fruit, drinks, beer for adults, safety gear, and kayak use.

“Amazing experience on the private charter with Hugo and David. Their knowledge and experience was second to none. Would highly recommend!”

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Barcelona Private Sailing with Open Bar & Snacks (max 9)

4.Barcelona Private Sailing with Open Bar & Snacks (max 9)

★★★★★★★★★★5.0 · 440 reviews · 1 to 10 hours (approx.)

Set sail from Port Olimpic on a private yacht for up to nine people. Your skipper handles the boat while you enjoy Barcelona’s skyline, cold drinks, light snacks, music, and a possible swim in the Mediterranean. Choose a short morning sail, a longer afternoon outing, or a sunset trip, with captains such as Daniel, Marie, Pau, and Luigi.

“Great experience, we had a great time with the music on board, chatting with the skippers and bathing in the beautiful sea. We really enjoyed the trip thanks to the rich snacks and drinks on board. Recommended”

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Private sailing tour of Bacalar Lagoon

5.Private sailing tour of Bacalar Lagoon

★★★★★★★★★★5.0 · 403 reviews · 3 hours (approx.)

Board a private sailboat at Casa Sirena dock with a captain and crew such as Flor, Karla, Leandro, or Maria. Over about three hours, you’ll sail Bacalar Lagoon, pause at Cenote Negro, swim at Pirate Canal and Bird Island, and enjoy fresh fruit, beer, and water. The boat holds up to seven people.

“Superbe tour, capitaine Leandro au top, très sympa et avenant ! Nous avons passé une moment totalement parfait avec mon épouse, vous pouvez y aller sans hésiter !”

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Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

6.Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

★★★★★★★★★★5.0 · 402 reviews

Spend seven hours aboard a private catamaran with Captain Mike and host Elmira, cruising St. Maarten’s coast, snorkeling at Long Bay and Little Bay, and stopping near Tintamarre when weather allows. Coffee, snacks, BBQ lunch, snorkeling gear, paddleboarding, and an open bar are included. Bring towels and non-spray sunscreen.

“Mike and Elmira were down to earth amazing hosts who made us feel welcome from the start. They were very attentive from beginning to end making sure everyone was well taken care of. The food was homemade and delicious. They both Read more”

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Barcelona Private Sailing Tour with Drinks for Family and Friends

7.Barcelona Private Sailing Tour with Drinks for Family and Friends

★★★★★★★★★★5.0 · 389 reviews · 2 hours (approx.) · from $151

Set out from Port Olímpic with a private captain such as Fiona, Marc, David, or Alessio. You’ll see Barcelona’s coast from the water, enjoy beer or sparkling wine, local-style snacks, music, and time for swimming or water toys when conditions allow. The two-hour sail suits families, friends, and small celebrations.

“Marcos was amazing! He was very kind, patient and understanding with kids. His attention made a huge difference. The boat was wonderful: clean and beautiful.”

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Fort Lauderdale Sailing Charter

8.Fort Lauderdale Sailing Charter

★★★★★★★★★★5.0 · 387 reviews · 4 hours (approx.) · from $150

Sail from 937 Mandarin Isle with Captain Dan, a licensed captain with more than 20 years of local experience. Your private group of up to six cruises the New River, passes waterfront homes and yachts, then may sail the Atlantic, swim, learn basic sailing, or simply relax. Bring your own food and drinks. Water, ice, cups, and plates are supplied.

“Captain Dan & First Mate Tracey went above and beyond to make our trip special! They are incredibly kind, accommodating, and welcoming into their slice of paradise. My boyfriend proposed to me on this trip and I can’t imagine a better place or setup for that amazing experience, which we will both remember forever! We will definitely be returning customers next time we’re in town!”

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

9.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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4-Hour Fort Lauderdale Sailing Charter

10.4-Hour Fort Lauderdale Sailing Charter

★★★★★★★★★★5.0 · 311 reviews · 4 hours (approx.) · from $148

Spend four hours aboard Sailing Daffy with Captain Charlie, cruising Fort Lauderdale’s New River, Intracoastal Waterway, Port Everglades, and the Atlantic. The private charter carries up to six people, lets you bring food and drinks, and may include hands-on sailing, dolphin watching, and views of waterfront mansions and yachts.

“Had a great sail with Captain Charlie. He is an interesting character, has a wealth of sailing experience, and is very welcoming.”

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Ibiza & Formentera Private Catamaran Full-Day Sailing Tour

11.Ibiza & Formentera Private Catamaran Full-Day Sailing Tour

★★★★★★★★★★5.0 · 242 reviews · 8 hours (approx.)

Spend about eight hours on a private catamaran for up to 10 people, sailing from Cala Jondal past Ibiza’s south coast to Formentera. You’ll have snorkeling gear, two paddleboards, Wi-Fi, and a restroom aboard. Lunch is optional and extra, so confirm portions or bring your own food.

“Realmente fue una mala experiencia sentimos que el costo versus el beneficio no se justifica una comida carísima que le recomendamos no pedir es preferible llevar la comida porque cobra €65 por una tabla de jamones que realmente no los vale”

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2 Hours Private Sailing Tour in Lisbon

12.2 Hours Private Sailing Tour in Lisbon

★★★★★★★★★★5.0 · 242 reviews · 2 hours (approx.)

Charter a sailboat for up to 12 people and see Lisbon from the Tagus River. Your skipper guides you past Belém Tower, the Discoveries Monument, 25th of April Bridge, Cristo Rei, and Praça do Comércio. Expect a relaxed private setting, crackers, and one beer or soft drink per person. Sunset departures cost an extra €50.

“Breathtaking! Two families children 9-13. Brilliant captain and crew, charming, engaging and highly motivated to make this unforgettable experience for everyone including the kids. One family from Germany, one from Lisboa. For both it was a new and exciting experience. So glad we took the private tour, as this was also about us getting to know each other. Definitely the highlight of our trip. Absolute value for money to charter the boat for ourselves”

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Private Sailing Yacht Charter by Independence from Koh Samui

13.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 Sailing Experience on Lake Windermere

14.Private Sailing Experience on Lake Windermere

★★★★★★★★★★5.0 · 213 reviews

Meet your skipper at Storrs Hall Hotel for a private two-hour sail on Lake Windermere. Ian, Richard, Alan, Andrew, or another skipper may guide your group, adapting the trip for beginners and experienced sailors. Take the helm under supervision, learn about the lake, or simply relax aboard the yacht.

“Ian was wonderful, patiently taught my daughter and all of us how to navigate and use the sails. It was lovely weather . We were late but he accomadated our request and gave us extra sailing time.”

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Private Sailboat tour in Cabo San Lucas with Papillon Yachts

15.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.