Where to Go Island Hopping by Sailboat: 15 Trips Worldwide

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly - Hotel pickup can make or break the day

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

Review of Cancun’s Isla Mujeres luxury sailing tour, with snorkeling, lunch, open bar, hotel pickup, costs, family notes, and honest drawbacks.

“This Isla Mujeres catamaran tour was hands down one of the best experiences of our trip. The crew was incredible—attentive, fun, and made the whole day feel effortless. The catamaran was clean and spacious, the snorkeling spot was beautiful, and the drinks and music kept the energy up the entire time. Isla Mujeres was breathtaking and we had plenty of time to explore and relax. If you’re in Cancun and considering this trip, DO IT. You won’t regret it.Christina was great!”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

2.Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion to protected Dia Island for swimming, snorkeling, a Mediterranean meal, unlimited drinks, and sunset sea views.

“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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Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

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

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

Review of Turtle Cove Catamaran Snorkel at Little Buck Island, with turtle sightings, sailing details, price, tips, and practical advice.

“By far our favorite thing we did on the island! Saw several turtles, unique fish, and pretty coral! Plenty of drinks and snacks were good! Plenty of free time to snorkel and swim on our own time. Definitely would do it again!”

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Icacos Island Catamaran Day Sail from Fajardo

4.Icacos Island Catamaran Day Sail from Fajardo

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

Review of the Icacos catamaran sail from Fajardo, with snorkeling, lunch, rum drinks, beach time, costs, tips, and honest drawbacks.

“Crew was amazing I loved the beach/island I loved everything about this day and the hospitality was greats”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

5.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Review of Crete’s Dia Island sailing trip from Heraklion, with yacht views, swimming, snorkeling, lunch, drinks, costs, and practical tips.

“A very choppy crossing to the island. Very well handled by the skipper though The boat was comfortable and safety was well looked after Food was very good. Would have been nice to have beer as an option perhaps Time went very quickly”

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Sailboat tour from PALAU to the Maddalena Archipelago.

6.Sailboat tour from PALAU to the Maddalena Archipelago.

★★★★★★★★★★5.0 · 952 reviews · 7 to 8 hours (approx.) · from $107

Review of a small-group sailing tour from Palau to La Maddalena, with Sardinian food, wine, swimming, snorkeling, and pink beach views.

“We had a wonderful experience with the best captains, Alberto and Augustine. They really made our trip fun and memorable. The food was delicious and the views were gorgeous even on a cloudy day. All four of us left very happy and we would go again in a heartbeat. Thank you!!”

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From Palau or La Maddalena: Archipelago Sailing Ship Tour

7.From Palau or La Maddalena: Archipelago Sailing Ship Tour

★★★★★★★★★★4.4 · 903 reviews · 7 hours · from $77

Sail La Maddalena’s turquoise waters from Palau or Maddalena, with Budelli, Santa Maria, Spargi, beach time, swimming, and a vintage boat.

“Really enjoyed our day on this tour! It was one of the only tours we could find that started from La Maddalena island at a reasonable price. The boat is not too big which meant we didn’t have too many people on board. I liked that we could bring our own food on board but the food they served looked delicious too. All the destinations we went to were unbelievable, such stunning water and landscape. We had 3 swim spots, 2 beaches and one dive spot. I would recommend bringing a sun umbrella for the last beach as we spent 2 hours there and there was little shade. Also bring…”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

8.Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Review of Corfu’s Gouvia sailing trip, with small groups, clear-water swims, cliff jumping, snacks, drinks, and Blue Cave views.

“Fantastic day out!! Definitely would recommend booking! We had booked for a hen party with 11 girls and we had the best time! Ari, our skipper, was second to none and joined in on the fun, taking pictures and tailoring our stops to suit us. we had plenty of time on each stop to jump in, swim or to stay on board and enjoy a drink. We were able to buy alcohol on-board and the prices were very reasonable! Ari made us a light lunch also which was perfect! 10/10 would recommend!!!”

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4-Hour Sailing Tour of Lobos Island from Fuerteventura

9.4-Hour Sailing Tour of Lobos Island from Fuerteventura

★★★★★★★★★★5.0 · 785 reviews · from $75

Review of Fuerteventura’s 4-hour Lobos Island sailing tour, with catamaran views, water sports, paella, drinks, pickup, and practical tips.

“Gorgeous trip to Isla de los Lobos with a really lovely crew who were so kind and attentive and funny. Paella great and snorkeling but the highlight was the island and sailing.”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

10.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Review of Sailing Grace’s six-hour cruise from Heraklion to Dia Island, with swimming, snorkeling, SUP, lunch, drinks, and sunset views.

“This was truly an incredible day! So relaxing in such a beautiful place. They made lunch on the boat and it was amazing. Swimming, walking the beach and soaking up the sun on the deck - absolute perfection.”

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2-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar

11.2-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar

★★★★★★★★★★4.5 · 771 reviews · from $466

Review of the 2-night Avatar trimaran sailing trip from Airlie Beach, with snorkeling, Whitehaven Beach, meals, cabins, costs, and practical tips.

“The tour guides were relatively friendly. The pickup point map was incorrect, you need to ensure you go to the address and ignore the map as it was contradictory. The tour left fairly promptly after 11am. It was fairly expensive for you got, conRead more”

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Heraklion: Dia Island Sailing Cruise with Snorkeling

12.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island for swimming, snorkeling, paddleboarding, Greek food, wine, and clear-water bays.

“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”

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Shared Mykonos Sail Cruise to Delos and Rhenia Islands

13.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151

Review of Mykonos sailing to Delos and Rhenia, with ruins, swimming, snorkeling, barbecue lunch, drinks, costs, and practical tips.

“The sailing trip to Delos and Renia was maybe our favorite activity of our time in Mykonos. It was a good mix of relaxation and activity — enjoying a relaxing drink and lunch on the boat, exploring on our own in Delos, and a refreshing swim at Renia. I would have liked a little bit more time on Delos, but other than that, it was perfect. Staff/crew was very attentive to the needs of all passengers.”

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St John & Surrounding Cays – Full-Day Sail/Snorkel, 6 Guests Max

14.St John & Surrounding Cays – Full-Day Sail/Snorkel, 6 Guests Max

★★★★★★★★★★5.0 · 635 reviews · from $245

Review of a six-person St John sailing and snorkeling tour from St Thomas, with lunch, open bar, turtles, coral reefs, and practical booking tips.

“Captain Mark and Rusty did a great job Beautiful boat, lunch was amazing and Michelle loved swimming with the turtles. If you'd like to go snorkeling but don't want to deal with the crowds on the big catamarans, we highly recommend taking this day trip! Great music as well.”

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Sailing boat from Santa Teresa di Gallura to the Maddalena Archipelago

15.Sailing boat from Santa Teresa di Gallura to the Maddalena Archipelago

★★★★★★★★★★5.0 · 628 reviews · 7 to 8 hours (approx.) · from $119

Review of the Santa Teresa sailing trip to La Maddalena, with swimming stops, lunch, snorkeling, practical tips, and honest drawbacks.

“Fantastic cruise to the islands of the Maddalena archipelago. WhatsApp messages the night before giving clear directions of where to park at the marina and how to find the pier. Marco and Lorenzo our crew were brilliant. Such lovely guys with a great attitude making sure everyone had the best time. Stopped at 3 beautiful bays for swimming. Were served food and drink several times between stops. Such a great day out. Highly recommend this excursion!”

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