The World’s 15 Best Sailing Trips with a Swim Stop

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Dia Island from a protected bay

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Top of the fleet

Sail from Heraklion’s Venetian Harbour to protected Dia Island aboard a yacht limited to 14 people. You’ll swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. English-speaking crew members may include Mariana, Manos, Sofia, Giannis, or Captain Petros, with morning and sunset departures available.

“This was a top notch experience: I strongly recommend this sunset boat trip!”

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Malaga: Catamaran Sailing Cruise with Swimming & Optional DJ

2.Malaga: Catamaran Sailing Cruise with Swimming & Optional DJ

★★★★★★★★★★4.2 · 2,022 reviews · 1.5 hours · from $23Lowest fare aboard

Join Mundo Marino at Malaga’s pier for a relaxed 1.5-hour catamaran ride along the bay. You’ll see Malaga from the water, buy drinks at the onboard bar, and, if sea conditions allow, stop for a short swim. Choose the DJ option for music and dancing. Crew members named Leo and Carlos have been praised for friendly service.

“Great boat, cool people and delicious drinks and bbq! But the boat was very crowded.”

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Valencia: Sailing Catamaran with Swimming & Optional DJ

3.Valencia: Sailing Catamaran with Swimming & Optional DJ

★★★★★★★★★★4.2 · 1,310 reviews · 1h 30m · from $25

Spend 90 minutes on a spacious catamaran off Valencia, stretching out on the suspended nets, enjoying coastal views, and stopping for a swim. Music plays onboard, with a DJ option on selected departures. Drinks are available to buy, but food, hotel transfers, and refreshments are not included.

“It was a lovely boat, the sangria was yum and only 3 euro a cup, but it is so short! You only get out there and then turn around. Not enough time to fully get in the groove and settle in. We did muck up our booking time and they made accommodation for us to adjust the time and get on a different boat, so was very grateful for that!”

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Bacalar: Group Sailing Trip with Swimming and Drinks

4.Bacalar: Group Sailing Trip with Swimming and Drinks

★★★★★★★★★★4.8 · 585 reviews · 3 hours · from $40

Join DayTour Bacalar for a three-hour sailing trip across Bacalar Lagoon, with bilingual guides such as Hugo, Angelo, Nami, and David. You will pass Cenote Esmeralda, Cenote Negro, Pirate Canal, and Bird Island, stopping to swim in clear water. Fruit, natural drinks, and three beers are included, with no sunscreen allowed.

“Sebastian and Daniel were very nice and did explain Everything we asked. The Location/lagoon is Like a dream.”

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Malaga: Sailing Catamaran with Swimming and Paella Lunch

5.Malaga: Sailing Catamaran with Swimming and Paella Lunch

★★★★★★★★★★4.1 · 578 reviews · 3 hours · from $53

Spend three hours sailing off Malaga on the Catamaran Shooting Star. You can relax on deck or pay extra for the front nets, swim during open-water stops, and enjoy pork paella with salad, bread, fruit, and one drink. Spanish and English-speaking staff are on hand, and the boat is wheelchair accessible.

“Amazing trip!! Great staff. So so clean. Great food! Cannot recommend more. Loved this trip so much!!”

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Oahu: Waikiki Sunset Catamaran Sail and Swim

6.Oahu: Waikiki Sunset Catamaran Sail and Swim

★★★★★★★★★★4.7 · 519 reviews · from $44

Join Pink Sails Waikiki for a two-hour sunset catamaran trip from Waikiki. You can swim in the Pacific before sunset, then watch Diamond Head and Waikiki’s lights glow from the water. English-speaking crew members such as Jamie, Alex, John, and Morgan have helped with photos, drinks, and swim support, though boats and crew can change.

“Incredible crew from the captain to Alex and John were all friendly and entertaining. Lovely sunset”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

7.Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Sail six nautical miles from Heraklion to Dia Island with a maximum of 10 people. Captains George, Panos, and Vaso bring local stories and easygoing Cretan hospitality, while you swim, snorkel, paddleboard, fish, and eat shrimp or vegetarian pasta with unlimited drinks.

“George and Marco were friendly and informative and made the trip very enjoyable. We spent a good amount of time snorkelling using the equipment they provided and enjoyed a nice lunch of pasta, salad and fruit. It’s a small group of 10 so the boat isn’t overcrowded and you get to know the people well. Highly recommend”

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Whale and Dolphin Watching Sailing Boat with Drinks, Snacks and Swimming Time

8.Whale and Dolphin Watching Sailing Boat with Drinks, Snacks and Swimming Time

★★★★★★★★★★4.5 · 511 reviews · 3 hours (approx.) · from $78

Cruise from Puerto Colón in Costa Adeje on a sailing boat limited to 11 people. Your captain searches for pilot whales and dolphins, explains local marine life, then stops for swimming and snorkeling. Guy, Alex, Dani, and Maximilian have led departures. Champagne, sandwiches, snacks, beer, wine, and soft drinks are included.

“It was nice :) despite strong wind, we had a great time. The dolphins were swimming quite close to our boat.”

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Los Gigantes: Sailing Excursion with Swimming, Drink & Tapas

9.Los Gigantes: Sailing Excursion with Swimming, Drink & Tapas

★★★★★★★★★★4.8 · 471 reviews · 3 hours · from $82

Set sail from Puerto de Los Gigantes aboard the Sangría for a three-hour coastal trip with up to 10 people. You’ll search for whales and dolphins, stop for swimming or snorkeling near the cliffs, and enjoy tapas with an alcoholic or soft drink. Guides speak Spanish, English, and French. Some departures are led by Luis and Moises.

“It was in line with our expectations. We did see whatever we wanted to see, but would have liked to stay in the whale and dolphin locations just longer. Now it was slightly too much sailing and less watching which was a pity in our view.”

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Puerto Morelos Secret Sandbar Catamaran Sail

10.Puerto Morelos Secret Sandbar Catamaran Sail

★★★★★★★★★★4.5 · 396 reviews · 4 hours (approx.) · from $140

Board the Adelita at Marina La Bonita for a four-hour sail through Puerto Morelos National Reef Park. Crew members such as Jose, Martin, Arturo, and Ulises may keep drinks flowing while you reach a shallow sandbar suited to children and nervous swimmers. Swim, paddleboard, float, or relax aboard with lunch and music.

“We have taken many catamaran excursions over the years and this was my favorite! The boat was very clean and well-kept, the drinks and food were good and the music was fun. The staff is what made it so special. They were very helpful and attentive, bringing us pillows, drinks, snacks, and letting me seven year old son steer the ship. Would highly recommend - I am so grateful for this experience!”

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Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

11.Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

★★★★★★★★★★5.0 · 236 reviews · 2 hours (approx.) · from $34Best loved

Leave Waikiki Beach behind on a two-hour catamaran cruise from Kewalo Basin Harbor. Sail toward Diamond Head, watch for turtles, dolphins, fish, and whales, then swim from the boat or stay aboard with a cocktail. The crew keeps things relaxed, and the small-group setting, capped at 47 people, feels far calmer than the beach.

“We had such an amazing experience✨ 100% recommend this for everyone. The crew was amazing and did their best to make sure everyone was safe and satisfied.”

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Barcelona Badalona : Sailboat Tour, Snacks, Drinks, Swimming

12.Barcelona Badalona : Sailboat Tour, Snacks, Drinks, Swimming

★★★★★★★★★★4.9 · 225 reviews · 2 hours · from $45

Join skipper Jean aboard a rare 36-foot Breton sailboat for two relaxed hours off Barcelona. You’ll enjoy seasonal snacks, cava, beer, vermouth, or soft drinks, then choose between swimming, paddleboarding, skyline watching, or simply relaxing on deck. Groups are limited to nine, with English, French, and Spanish spoken.

“What a great experience! This was the best thing we did in Barcelona.”

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Sail, Swim & Tapas

13.Sail, Swim & Tapas

★★★★★★★★★★5.0 · 209 reviews · 2 hours 30 minutes (approx.) · from $42

Set out from Lagos Marina on a traditional Portuguese sailing ship, cruise toward Ponta da Piedade, then transfer to a smaller boat for a close look at the caves. Your multilingual crew explains the rock formations and local history, with time for swimming and Portuguese tapas. Drinks cost extra, and the tour returns to the marina after about 2.5 hours.

“Lovely day on the water. The guides were so nice. My husband and I really enjoyed it! Price was great!”

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Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

14.Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

★★★★★★★★★★5.0 · 191 reviews · 2 hours (approx.) · from $71

Spend about two hours sailing from Honolulu past Diamond Head, the Royal Hawaiian Hotel, and Magic Island, with a swim stop off Waikiki before sunset. Three Tiki Sailing keeps the boat relaxed and BYOB, so bring drinks, cups, ice, snacks, and your own towel. Music plays onboard, and the crew handles the sailing and safety.

“This is relaxing, amazing staff, great views and easily accessible. You cannot go wrong with an amazing staff while watching a gorgeous sunset”

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Barcelona: Sailing Tour + Food, Drinks, Swim & Sunset Option

15.Barcelona: Sailing Tour + Food, Drinks, Swim & Sunset Option

★★★★★★★★★★4.8 · 185 reviews · 2 hours · from $55

Join a small yacht at Port Vela for a two-hour Barcelona sailing trip with pinchos, cold cuts, two drinks, harbor views, and a Mediterranean swim stop when conditions allow. English or Spanish-speaking hosts such as Ivy, Maria, Connor, and Miguel guide the outing, with sunset departures available.