The 9 Best Sailing Trips Worldwide

1.Private Catamaran Swim sail snorkel cliff jumping SUP

★★★★★★★★★★5.0 · 232 reviews Our pick

Spend three flexible hours on a private Bermuda catamaran with Captain Mark, Alex, Georgia, or Matt and crew. Sail around West Bermuda, stop for snorkeling and swimming, try cliff jumping, use the SUP and crystal kayak, and play your own music. The boat has a restroom and space for 15.

“We had a fantastic afternoon with Captain Alex and his first mate, Georgia. They were so accommodating, and made us all feel at home on the catamaran. They gave us suggestions on how to best spend the afternoon, even though the harbRead more”

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2.Lérins Islands Sailing Discovery, snorkeling and paddle SUP

★★★★★★★★★★4.7 · 110 reviews · 3h 30m · from $100

Sail from Antibes with a French or English-speaking skipper, often Valentin, toward Île Sainte-Marguerite and Fort Royal. You’ll learn basic sailing, stop for snorkeling and paddleboarding, admire Riviera yachts, and enjoy a comfortable 9-person boat. Swimming stops run May 15 to September 15.

“This activity was INCREDIBLE! The water was so blue and a perfect temperature for exploring and relaxing. However, there were some unhappy people on board, which was a bummer! Part of the group couldn’t swim and thought that they’d be able to explore the island while others snorkel/swim. (Obviously not!) And then others weren’t strong swimmers and were upset that the boat didn’t dock in shallow water (Obviously, it can’t!). If you’re looking for an island-hopping on-land activities, this isn’t for you! All this to say — this activity is amazing! You’re on a sailboat in the Mediterranean and sailing along the coast — and then jumping off the boat…”

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3.Airlie Beach: Whitsunday Islands Sailing, SUP & Snorkel Tour

★★★★★★★★★★4.8 · 90 reviews · 6 hours · from $162

Spend six hours aboard the air-conditioned Wings III, a 60-foot sailing catamaran with a jacuzzi, shaded decks, and space for 29 people. Sail near Hook Island and Hayman Island, snorkel fringing reefs, paddle at Langford Island, and enjoy fresh morning tea and lunch. Bring your own drinks.

“what a relaxing day! the team really looked after us, and the sailing was amazing. thanks so much 🙏🏼😊”

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4.Private Yacht Cruise 4 Hour- Snorkeling & Paddle Boarding

★★★★★★★★★★5.0 · 74 reviews · 4 hours (approx.)

Spend four hours on a private yacht with crew members such as Lewis, Leo, or Sergio, depending on availability. Cruise past Cabo’s Arch, watch sea lions, then swim, snorkel, fish, and paddle board at Santa Maria or Chileno Bay. Drinks, snacks, gear, towels, and water are included.

“Absolutely amazing! We had a private yacht and felt like royalty! Our captain and crew was phenomenal and met needs we didn’t even knew we had. They were always ready with drinks and snack (beautiful cheese/meat/fruit trays, nuts/snack mix, and fresh caught fish). They also had rigorous cleaning and sanitizing policies that made us feel much safer during the pandemic. They even had a warm rinse following our snorkeling adventure! Weather was perfect and we even saw the rays flying out of the water (mating season). One hundred thumbs up!”

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5.Milos: Full-Day Catamaran Cruise with Paddle Board

★★★★★★★★★★5.0 · 62 reviews · 8 hours · from $235

Join a small-group, all-inclusive catamaran cruise from Adamas with an English-speaking crew. Swim at remote coves, ride a dinghy into Sykia and Kleftiko caves, paddleboard, enjoy Greek food and drinks, and receive GoPro photos after your day at sea.

“Our boat day in Milos was incredible—by far our favorite day on the island! The crew was absolutely amazing—so warm, welcoming, and knowledgeable. They made us feel completely at home from the moment we stepped on board, and they truly went above and beyond to maximize our experience. Exploring the caves, swimming in the crystal-clear water, and soaking up the beauty of the coastline was unforgettable. We can’t recommend this experience highly enough—an absolute must if you’re visiting Milos!”

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6.2-Hour Sailboat Tour with Paddle Boarding

★★★★★★★★★★4.9 · 44 reviews · 2 hours · from $65Best value

Sail from Port Olimpic for two hours, with views of Sagrada Familia, Torre Agbar, Tibidabo, and Montjuic. Your guide handles the boat, explains sailing basics, and may let you steer. Stop for a swim, paddle boarding, floating toys, snacks, soft drinks, and one glass of cava.

“A great experience for an excellent price! You can play music on the boat, enjoy sailing, explore all parts of the ship, and drinks are free. There is also food and snacks. At one point, they provide water gear, so you can swim and jump off the boat as many times as you like. The guide even lets you steer the boat on the way back. Highly recommended for everyone!”

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7.Afternoon yacht charter in lagos with drinks, tapas, paddle boards and kayak

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

Cruise Lagos aboard Karma with a private group of up to eight. The crew handles the route while you enjoy Ponta da Piedade, local wine, tapas, snorkeling, two paddleboards, and a two-person kayak.

“Wonderful afternoon out on the water with Ze and Lucas. Fun stories and information about the history of Lagos and the rock formations. We were fortunate to have calm weather which allowed for mooring at a deserted beach for paddle boarding and kayaking. Very nice charcuterie and wine service as well! The boat is beautiful and well maintained. Highly recommend!”

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8.Private tour on a sailboat Swim and stand up paddle Antibes cape

★★★★★★★★★★5.0 · 24 reviews

Join Nicolas for a private sailboat outing from Port Vauban in Antibes. Cruise around Cap d’Antibes, stop near Billionaires Bay or La Garoupe, then swim, snorkel, and use the paddleboard. Drinks, water, soda, masks, and snorkels are included. The boat carries groups of up to eight.

“This was a fantastic experience with a friendly and competent crew. We enjoyed a swim and paddleboarding in a beautiful bay following a short trip along the coast. The access, instructions and ease of boarding made this very hassle free with two small children.”

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9.Paros: Private Catamaran Cruise with Lunch, Drinks & SUP

★★★★★★★★★★5.0 · 7 reviews · 6 hours

Spend six hours on a private catamaran from Piso Livadi with a captain and crew member, sailing near Paros and Naxos. Swim, snorkel, use the SUP and underwater scooter, then enjoy Greek food, fruit, coffee, beer, wine, and soft drinks.

“The pace of the day was excellent. Sail. Stop for swim and snacks. Sail. Stop for swim and lunch. The 6 hours flew by and was very relaxed and enjoyable.”

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