Sailing trips · ISLAND HOPPING SAILING TRIPS

The 15 Best Island Hopping Sailing Trips

120 trips  ·  from $11 a head

Three anchorages and no road between them. These 15 island-hopping sails are compared on how many stops they make, how long the crossings take and whether lunch is served on board or ashore.

Hurghada: 3 Islands, Dolphins & Snorkel Yacht Trip w/ Lunch - Morning pickup and the ride to the harbor
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Hurghada: 3 Islands, Dolphins & Snorkel Yacht Trip w/ Lunch

1.3 Islands, Dolphins & Snorkel Yacht Trip w/ Lunch

★★★★★★★★★★4.7 · 4,609 reviews · 8 hours · from $47Our pick

Join Go Shalabi for an 8-hour yacht trip from Hurghada to Orange Bay, Giftun, and Magawish. You get two snorkeling stops, dolphin watching, breakfast, seafood lunch, fruit, and unlimited drinks. Guides such as Fouad, Ahmed, Saef, and Ashraf help beginners feel safe in the water.

“Despite having picked a day of strong winds, our boat still sailed and it ended up being one of the nicest experiences we've had in Hurghada. Warm clothes and big towels are a must. We stopped first on Orange Bay, took some photos, then sailed to the first snorkeling stop near Giftun island. Although the water in February is colder, snorkeling was worth it, seeing the corals and the many different color fish made my day. Seafood lunch on board was delicious. Finally, we stopped on Magawish for another round of snorkeling in less deep waters and sunbathing. Our guides Fouad, Ahmed and Saef expertly coordinated the group and ensured…”

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Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time - Dolphin Watching Works Best When You Treat It as Wildlife Viewing
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Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

2.Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

★★★★★★★★★★5.0 · 4,362 reviews · 3 hours (approx.) · from $57Top rated

Sail from Panama City Beach aboard Island Time’s broad, stable catamaran, with time to search for wild dolphins, snorkel at Shell Island and St. Andrews Bay, paddleboard, swim, or use the waterslide. Captain Heath, Clay, Keith, Sarah, Emma, and other crew members have earned strong praise for friendly service and practical help on board.

“This was absolutely so much fun, such an amazing group of staff. Soooo cool- saved it for our last little extravaganza & it was absolutely worth it.”

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Punta Cana: Catamaran Boat to Saona Island with Buffet Lunch - The early pickup and drive south
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Punta Cana: Catamaran Boat to Saona Island with Buffet Lunch

3.Catamaran Boat to Saona Island with Buffet Lunch

★★★★★★★★★★4.4 · 3,822 reviews · 8 hours · from $82

Travel by bus, speedboat, and catamaran from Punta Cana to Saona Island. Swim in a starfish-filled natural pool, enjoy a Dominican buffet, relax on white sand, and return with music and dancing. Guides may include Christian, Alex, Eduardo, or Juan. The day is fun but often lasts 12 hours.

“christian was an amazing tour guide who provides an amazing vibe to the trip. very versatile in both english and french. the bus ride was a little long but the bus had ac and pit stop for the washroom. The bathrooms on saona was disgusting but other then that you definitely get your moneys worth with the lunch buffet and open bar. My favourite part of the trip was the dancing girls on the catamaran.”

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Isla Mujeres Luxury Sailing: Adults Only or Family Friendly - Snorkeling near Cancun, with weather in charge
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Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

4.Adults Only or Family Friendly

★★★★★★★★★★4.5 · 3,418 reviews · 5 hours 30 minutes (approx.) · from $129

Sail from Cancun to Isla Mujeres on a catamaran with lunch, an open bar, snorkeling when conditions allow, and free island time. Choose a family-friendly or adults-only departure, but confirm the exact boat and pickup details. Guides such as Enrique, Christina, Judy, and Abraham have earned praise for attentive service.

“Enrique and the crew made our Isla Mujeres trip unforgettable on 2/9/26! From drink service to local tips, they waited on us hand and foot. Great food, even better vibes—pure paradise. 10/10, ask for this team! 🌊🍹🌞”

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Isla Mujeres: Catamaran with Open Bar, Snorkeling and Lunch - Getting to Marina Las Perlas
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Isla Mujeres: Catamaran with Open Bar, Snorkeling and Lunch

5.Catamaran with Open Bar, Snorkeling and Lunch

★★★★★★★★★★4.1 · 2,848 reviews · 8 - 10 hours · from $59

Sail from Cancun to Isla Mujeres with a lively crew, national open bar, a short reef snorkel, Playa Norte time, and optional buffet lunch. Guides such as Juam, Ivet, Luis, and Romando have earned praise for keeping the day friendly and well organized, though the dock fee and crowded snorkel stop deserve attention.

“A really fun day out. The staff are very friendly and welcoming. Really fun vibe. Would highly recommend.”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Dia Island from the water, not from the beach
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

6.Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion’s Venetian Harbour to protected Dia Island aboard a comfortable yacht with a maximum of 14 people. Swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. Afternoon departures can include a beautiful sunset sail back.

“It was amazing experience. Definitely a highlight of my vacation. Mariana and Manos was fun and helpful. Good food and beautiful views.”

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Cartagena: Rosario Islands Catamaran with Lunch and Snorkel - Settling in with fruit, shade, and open water
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Cartagena: Rosario Islands Catamaran with Lunch and Snorkel

7.Rosario Islands Catamaran with Lunch and Snorkel

★★★★★★★★★★4.5 · 2,479 reviews · 7h 30m · from $107

Sail from Cartagena’s Bodeguita Dock to the Rosario Islands on a roomy catamaran with shaded and sunny seating. You’ll get a fruit welcome drink, snacks, lunch, free soft drinks, two swim or snorkel stops, onboard bathrooms, and a relaxed return with music. This is a boat day, not an island walking tour.

“I loved this activity! The catamaran sailing was amazing and so much fun. We were able to swim at two different spots, and the lunch was delicious. Sailing back to Cartagena was such a highlight! 100% recommend.”

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Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - The boat ride from Honokohau Marina
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Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch

8.Captain Cook Snorkel On A Power Catamaran With Lunch

★★★★★★★★★★5.0 · 2,232 reviews · 4 hours (approx.) · from $85

Cruise from Honokohau Marina to historic Kealakekua Bay on a power catamaran with Captain Aiden, Bryce, Jordan, or Kiwami. Snorkel among coral and fish, watch for dolphins and winter humpback whales, then enjoy sandwiches, fruit, snacks, and drinks before the coastal ride home.

“Super fun and knowledgeable! Very informative about the reef and marine animals. Staff was super friendly! Will definitely be coming back!”

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All Inclusive Isla Mujeres Catamaran - The catamaran ride and onboard atmosphere
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All Inclusive Isla Mujeres Catamaran

9.All Inclusive Isla Mujeres Catamaran

★★★★★★★★★★4.5 · 2,232 reviews · 8 hours (approx.) · from $83

Spend about eight hours sailing from Cancun to Isla Mujeres with Caribean Golden Tours. You get drinks, snacks, snorkeling gear, a buffet lunch, Playa Norte, island free time, and a sunset return. Expect lively music and a party-boat mood, plus a $20 dock fee per person.

“We were told to arrive at 9.30 for 10am trip. It was like a cattle market and we didn't leave until nearer 11. Uncomfortable trip. Not enough seating, netting damaged so couldn't sit on it. Spent hours sitting on hard deck. On the way back we decided we would sit inside to be comfortable but there were children sat there even though we booked adult only. On the plus side the staff were very friendly and constantly asking if you want drinks. Edwardo was very friendly and knowledgeable. It was not the experience we were hoping for lack of seating our backs were hurting very uncomfortable even if they supplied…”

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Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise - Icacos beach, swimming, and shell hunting
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Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise

10.Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise

★★★★★★★★★★5.0 · 2,202 reviews · from $138

Sail from Fajardo to Cayo Icacos aboard the Barefoot IV Catamaran, with crew members such as Captain Robert, Luis, Matthew, and Edgar. You get beach time, snorkeling gear, floating devices, a sandwich buffet, tropical drinks, and about five and a half hours on the water.

“Exactly as advertised--the food was great, crew was great--it was a great mix of party on the water and beachsnorkeling experience.”

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Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT - The 54-foot catamaran ride
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Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

11.Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

★★★★★★★★★★5.0 · 2,100 reviews · from $119

Sail The VI Cat from Marriott Frenchman’s Cove to Turtle Cove at Little Buck Island. You’ll get gear, about an hour in the water, sea turtles, reef fish, snacks, and drinks after snorkeling. Captains Serena and Dave, plus guides such as Nick, Tim, and Porscha, have helped make this a friendly, safety-minded outing.

“We had a great time! The crew was very insightful and allowed us to make the most of the experience. I highly recommend this experience.”

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Sunset & Dolphin Catamaran Cruise with Island Time - Key points at a glance
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Sunset & Dolphin Catamaran Cruise with Island Time

12.Sunset & Dolphin Catamaran Cruise with Island Time

★★★★★★★★★★5.0 · 1,867 reviews · 2 hours (approx.) · from $57

Spend about two hours aboard Island Time Sailing’s catamaran from Panama City Beach. Cruise Grand Lagoon, watch for dolphins near St. Andrews State Park, enjoy sunset views, music, and drinks from the onboard bar. The crew, including Captain Clay and Cristo, may also invite you to dance and play games at the dock.

“This is an incredible experience! Crew was excellent and friendly! Dolphins and sunset was amazing. Highly recommend!”

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Phuket: James Bond Island and Phang Nga Bay by Premium Yacht - Getting from Phuket to Ao Por Pier
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Phuket: James Bond Island and Phang Nga Bay by Premium Yacht

13.James Bond Island and Phang Nga Bay by Premium Yacht

★★★★★★★★★★4.6 · 1,656 reviews · 330 minutes - 7 hours · from $120

Cruise from Ao Por Pier to James Bond Island and Hong Island on a comfortable yacht. English-speaking guides such as Coco lead the day, while canoe crews paddle you through caves and lagoons. Expect Thai food, fruit, soft drinks, sunset views, and optional hotel pickup.

“The boat, food and guides were all excellent. Had the best day, unfortunately no sunset but the moon looked amazing.”

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Icacos Island Catamaran Day Sail from Fajardo - Snorkeling for beginners and confident swimmers
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Icacos Island Catamaran Day Sail from Fajardo

14.Icacos Island Catamaran Day Sail from Fajardo

★★★★★★★★★★5.0 · 1,483 reviews · from $140

Spend about six hours aboard an East Island Excursions catamaran from Fajardo. Swim and snorkel near Cayo Icacos, or Palominitos if weather changes the route, then enjoy a deli lunch and rum drinks. Captains Jose and Carlos and crew members such as Luis, Neff, and Andres are known for attentive service.

“We had a great time!! I would love to thank the captain and his crew, they did an amazing job entertaining us and keeping us safe. We laughed alot with the crew especially Carlos he was helpful and knowledgeable. He had us laughing the entire time.”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Arriving at Dia Island
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

15.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35

Choose a shared half-day sail to Dia Island with lunch, wine, soft drinks, snorkeling gear, paddleboards, and fishing equipment, or book a private trip. A one-hour coastal option stays near Heraklion and includes drinks but no lunch or water activities.

“It takes a conciderable while to get to the island and there isn't a lot to look at in the meantime, I wish the boat was faster. The island looks nice upclose, but it's unfortunatelly not allowed to take a look around from a hill - you can only stay on the beach and visit an old... church? On the other hand, staying in the water is perfectly fine, as it's crystall clear, you can see the sea floor and there's a lot of fish around. While I recommend bringing your own snorkel, the equipment is provided. Good thing they also have flippers. Beware the see urchins - the shore…”

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Isla Mujeres Catamaran Tour with Snorkel, Open bar and Transport - Sailing south toward El Meco reef
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Isla Mujeres Catamaran Tour with Snorkel, Open bar and Transport

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