SWIMMING AND BEACH SAILING TRIPS

Swim-Stop Sailing Trips: the 15 Best Worldwide

129 sailings  ·  from $20 a head

The whole point is the ladder going over the side. These 15 sailings are compared on how many stops they make, how long you get in the water and whether the beach at the end is one you could otherwise walk to.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why 14 people changes the feel of the cruise
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion’s Old Venetian Harbour to Dia Island aboard a small yacht with up to 14 people. You’ll swim, snorkel, paddleboard, and eat shrimp linguini, Greek salad, and Cretan appetizers. English-speaking crew members such as Mariana, Manos, Sofia, Giannis, and Captain Petros have earned warm praise for friendly service, with afternoon trips offering sunset views.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

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Malaga: Catamaran Sailing Cruise with Swimming & Optional DJ - The first 30 minutes: leaving the pier and finding your seat
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Malaga: Catamaran Sailing Cruise with Swimming & Optional DJ

2.Catamaran Sailing Cruise with Swimming & Optional DJ

★★★★★★★★★★4.2 · 2,022 reviews · 1.5 hours · from $23Best value

Sail Malaga Bay aboard the Mundo Marino catamaran for 1.5 hours of coastline views, music, bar service, and a possible swim stop. Choose the DJ option for a livelier ride. Routes change with wind and sea conditions, and swimming is allowed only when it is safe.

“The whole trip, the staff members who were very attentive and friendly. It was a very pleasant day as well for sailing .”

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Valencia: Sailing Catamaran with Swimming & Optional DJ - The catamaran itself: space, music, and the front net
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Valencia: Sailing Catamaran with Swimming & Optional DJ

3.Sailing Catamaran with Swimming & Optional DJ

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

Spend 90 minutes aboard a spacious catamaran off Valencia’s marina, stretching out on the front net, watching the coast, and stopping to swim in the sea. The boat offers music, drinks for purchase, and an optional DJ. English and Spanish are available, and the trip suits families, couples, and anyone wanting a short break from the beach.

“Good atmosphere with beautiful location for a nice swim. Thoroughly enjoyed!”

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Airlie Beach: Whitsundays Full-Day Camira Sailing Adventure - From Port of Airlie to the Whitsunday Islands
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Airlie Beach: Whitsundays Full-Day Camira Sailing Adventure

4.Whitsundays Full-Day Camira Sailing Adventure

★★★★★★★★★★4.7 · 1,307 reviews · 10 hours · from $183

Spend 10 hours aboard Cruise Whitsundays’ fast Camira catamaran, sailing from Airlie Beach to Whitehaven Beach and Hill Inlet. Walk with a guide to the lookout, swim, snorkel a fringing reef, and enjoy morning tea, BBQ lunch, afternoon tea, beer, wine, cider, soft drinks, and water. Guides such as Dakota, Joel, and Mossi have earned praise for warm, helpful service.

“Such a great trip! The staff were so friendly and helpful, creating a great atmosphere. There was snacks and food available throughout the day. And what an experience seeing Whitehaven beach in person! Definitely recommend.”

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Blue Lagoon, Beaches and Bays Catamaran Sailing Tour - Blue Lagoon: the main event
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Blue Lagoon, Beaches and Bays Catamaran Sailing Tour

5.Blue Lagoon, Beaches and Bays Catamaran Sailing Tour

★★★★★★★★★★4.5 · 1,269 reviews · 6 hours (approx.) · from $66

Sail from St. Paul’s Bay aboard the Sea Breeze, a large catamaran with sunbeds, lounging nets, a bar, restrooms, and some snorkeling gear. Spend about six hours swimming near Malta’s Blue Lagoon and possibly Crystal Lagoon, Popeye Village, Mellieha Beach, Ramla Bay, or Ghajn Tuffieha. The €15 barbecue is optional.

“Great experience. This is the second time I've been on this trip. The first experience was slightly better due to the total number of stopoffs the first boat trip had. I do realise that the number of stops is dictated by the weather but it was a slight shame we didn't experience more of the coast line on our recent trip.”

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2-Night Whitsundays Sailing Cruise incl. Whitehaven Beach & Great Barrier Reef - Snorkeling around Hook, Hayman, and Border islands
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2-Night Whitsundays Sailing Cruise incl. Whitehaven Beach & Great Barrier Reef

6.2-Night Whitsundays Sailing Cruise incl. Whitehaven Beach & Great Barrier Reef

★★★★★★★★★★5.0 · 752 reviews · from $466Top rated

Spend two nights aboard the 82-foot sailing yacht Spank Me, visiting Whitehaven Beach and snorkeling around Hook, Hayman, Border, and Whitsunday islands. Captain Alex and crew handle meals, gear, sailing, and the route. Expect shared bunks, basic marine facilities, limited fresh water, and a social group of up to 27 people.

“We loved going snorkling, swimming, camping one night on an island. Food was good and crew was very nice. A lot of people on the boat but everyone was friendly.”

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Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea - Hāwea, a catamaran built for the job
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Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

7.Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

★★★★★★★★★★4.7 · 656 reviews · 2h 30m · from $84

Board Hāwea behind the Duke Kahanamoku Statue for a 2.5-hour Turtle Canyon trip. You’ll snorkel with green sea turtles and reef fish, then sail along Waikiki with Diamond Head views. The crew provides gear, safety help, non-alcoholic drinks, and morning cold brew with Anahola Granola.

“Wonderful crew made for a very relaxing and exciting time snorkelling. Felt safe and saw plenty of fish and luckily had a large turtle surface right next to us and watched young ones being cleaned by the local fish. Great time and worth the money. Highly recommended.”

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Airlie Beach: Providence Whitehaven Day Sail with Snorkeling - Crossing the Whitsunday Passage under sail
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Airlie Beach: Providence Whitehaven Day Sail with Snorkeling

8.Providence Whitehaven Day Sail with Snorkeling

★★★★★★★★★★4.4 · 640 reviews · 9 hours - 1 day · from $137

You spend about nine hours aboard the 62-foot gaff-rigged schooner Providence, sailing toward Whitehaven Beach, walking to Hill Inlet Lookout, and snorkeling a fringing Great Barrier Reef site. Crew members such as Jack, Fin, Harry, and Phone have been praised for friendly help, though wind and sea conditions can change the plan.

“It was a spectacular day thanks to Harry and Phone. Was super relaxing and well run. They kept to the timetable and got back when they said. left at 7:30am, back by 4:30pm. They brought the sails out on the way home and was really cool. We brought our own lunch as 1 of our group is celiac and easy and safe to just bring a lunch. Tons of fresh water, coffee and tea on board. If that's. it your thing, make sure to bring what you need as nowhere to buy. Would def sail with them again.”

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Bacalar: Group Sailing Trip with Swimming and Drinks - Starting at Casa China Bacalar
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Bacalar: Group Sailing Trip with Swimming and Drinks

9.Group Sailing Trip with Swimming and Drinks

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

Join DayTour Bacalar for a three-hour sailing trip with up to 10 people. Guides such as Hugo, Adrian, Angelo, Nami, and David explain the lagoon in English or Spanish while you visit Cenote Esmeralda, Pirate Canal, Cenote Negro, and Bird Island. Swim, enjoy fruit and three beers, and bring swimwear. Sunscreen is not 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 - The swimming stop away from the beach
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Malaga: Sailing Catamaran with Swimming and Paella Lunch

10.Sailing Catamaran with Swimming and Paella Lunch

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

Spend three hours aboard the Catamaran Shooting Star, sailing along Malaga’s coast with an English- or Spanish-speaking crew. You’ll receive a drink, stop for swimming and snorkeling away from the beach crowds, and eat pork paella with salad, bread, and fruit. Front-deck net seating costs extra.

“Very relaxing lying on the nets and a good amount of time spent at swimming stop”

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Oahu: Waikiki Sunset Catamaran Sail and Swim - The swim stop before sunset
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Oahu: Waikiki Sunset Catamaran Sail and Swim

11.Waikiki Sunset Catamaran Sail and Swim

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

Spend two hours on Pink Sails Waikiki’s catamaran, leaving Waikiki for a sunset cruise with views of Diamond Head and the shoreline lights. You can jump into the ocean before sunset or stay aboard. English-speaking crew members such as Jamie, Alexio, Peter, and Morgan have earned praise for friendly service, music, photos, and good humor.

“AWESOME! best thing i did in waikiki!!!!! the crew (alex, nici and mo) was amazing and the vibes were GREAT!”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Meeting at Heraklion Port or using the minivan transfer
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

12.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 provide local stories, swimming time, SUP boards, snorkeling gear, fishing equipment, lunch, and unlimited drinks. Optional minivan pickup makes this a practical half-day escape from much of Crete’s north coast.

“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 - Three hours along Tenerife’s south coast
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Whale and Dolphin Watching Sailing Boat with Drinks, Snacks and Swimming Time

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

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

Sail from Puerto Colón with a captain such as Guy, Alex, Dani, or Maximilian, searching Tenerife’s waters for pilot whales and dolphins. The three-hour trip includes a swim stop, snorkel equipment, a fresh sandwich, snacks, beer, wine, soft drinks, and a glass of Champagne or similar sparkling wine. Groups are limited to 11 people.

“We saw several sets of whales, the food/drink was fun. The guide was great, Guy has a great personality and really wants to share his knowledge of the ocean and marine life.”

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Los Gigantes: Sailing Excursion with Swimming, Drink & Tapas - Sailing beneath the red cliffs
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Los Gigantes: Sailing Excursion with Swimming, Drink & Tapas

14.Sailing Excursion with Swimming, Drink & Tapas

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

From Puerto de Los Gigantes, sail aboard the Sangría with an experienced crew such as Luis and Moises. You will cruise past red cliffs, search for whales and dolphins, stop for snorkeling, and enjoy tapas with an alcoholic or soft drink. The boat holds no more than 10 passengers, making this a calm alternative to a large excursion boat.

“We liked all activity and received what expected. Service provider gave some interesting info, responded to questions.”

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Airlie Beach: Whitsunday Islands 2-Day Sailing Tour - Leaving Airlie Beach aboard Matador
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Airlie Beach: Whitsunday Islands 2-Day Sailing Tour

15.Whitsunday Islands 2-Day Sailing Tour

★★★★★★★★★★4.5 · 452 reviews · 2 days · from $350

Spend two days and one night sailing from Airlie Beach aboard Matador, a racing yacht with an English-speaking crew. You will snorkel coral reefs, reach Whitehaven Beach early, eat fresh meals, watch the sunset, and sleep onboard beneath the stars. Crew members such as Tony, Chris, Dave, Ruby, and Fi have earned praise for their friendly care and local knowledge.

“I had an amazing time on the Matador with Kate, Ash and Arron!! Literally would not change a thing. The boat was really nice and I slept pretty well. I usually get sea sick but didn't feel sick at all on this trip. We were the first on Whitehaven Beach which was really nice before all the other tour companies came in. We saw sharks, sting rays, turtles and dolphins, went snorkelling twice and swimming which was so much fun. We event we on a little sunset walk which was so pretty. Everything is exactly like the pictures so would definitely recommend.”

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Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel. - Planning Your Route Around St. Thomas
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Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.

19★ 5.0Private Luxury Catamaran Yacht. Full or Half Day Charter – Sail, Beach, Snorkel.From $1,495 whole boat, up to 12386 reviews

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