ISLAND HOPPING SAILING TRIPS

15 Island-Hopping Sails Around the World

228 sailings  ·  from $13 a head

Islands are the reason sailing exists as a holiday. These 15 trips are compared on how many islands you really land on, how long the crossings take and how much of the day is spent under way rather than at anchor.

Isla Mujeres Luxury Sailing: Adults Only or Family Friendly - What happens on the catamaran
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Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

1.Isla Mujeres Luxury Sailing: Adults Only or Family Friendly

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

Sail from Cancun to Isla Mujeres on a five-and-a-half-hour catamaran trip with hotel pickup, snorkeling for ages 8 to 60, an open bar, light lunch, and free island time. Guides such as Enrique, Christina, Judy, Abraham, and Diego have led recent departures, though boat conditions and schedules can vary.

“Great experience and lots of fun. Staff was great and attentive! Christina and Judy were very friendly and entertaining as well as the rest of the crew!”

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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

2.Dia Island Sailboat Cruise with Swimming and Meal

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

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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Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT - What happens at the dock before departure
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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

Sail from Marriott Frenchman’s Cove aboard the 54-foot VI Cat to Turtle Cove at Little Buck Island. You’ll get snorkel gear, guidance from the crew, and time to see green turtles, coral, and tropical fish. Captain Serena, Captain Dave, Tim, Isaac, Sam, Anders, Adrien, and Nick are among the crew members praised for their care and good humor.

“Great Experience! The crew was very knowledgeable and helpful. I would recommend this to anyone!! I would do it again”

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Icacos Island Catamaran Day Sail from Fajardo - Snorkeling for beginners, with conditions attached
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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

Sail from Puerto del Rey Marina to Cayo Icacos, or Palominitos if weather shifts. East Island Excursions provides snorkel gear, float belts, lunch, rum drinks, and friendly crew support. Expect about six hours, a group of up to 70, and easy water time for beginners, with snorkeling quality shaped by sea conditions.

“We had such a wonderful time on the Icacos Island tour. The boat ride was smooth, the island itself was absolutely stunning, and the water was perfect for swimming and snorkeling. The crew provided great service, delicious drinks, and plenty of good vibes. It was the highlight of our trip—highly recommend!”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island: clear water and limited time ashore
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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

Sail from Heraklion with an English-speaking crew to Dia Island for swimming, snorkeling, paddleboarding, fishing, lunch, and unlimited drinks. Shared trips include the meal, while private cruises let you add one. Stavroula, Dennis, and other crew members are praised for friendly, careful service. A one-hour coastal option skips Dia and water activities.

“Nice shorter activity 4 hr, Friendly crew! Good lunch with plenty of water and wine! Beautiful day! ❤️🥂”

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Sailboat tour from PALAU to the Maddalena Archipelago. - Leaving Palau for La Maddalena National Park
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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

Set sail from Palau for 7 to 8 hours around the La Maddalena Archipelago. Your crew may include skippers such as Giuseppe, Simone, Claudia, or Alberto, depending on the boat. Expect swimming stops, snorkeling, Sardinian snacks, pasta or fish lunch, Vermentino, and time under sail in a small group of no more than 12.

“The most gorgeous day!! Absolutely loved this trip from start to finish! We were so well looked after and so was our little one. Lovely group and the captains couldn't do any more for us the food was exceptional and so was the company. A really relaxing day seeing some stunning sights. You HAVE to book this trip now! You won't regret it!”

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From Palau or La Maddalena: Archipelago Sailing Ship Tour - Budelli and the view of Spiaggia Rosa
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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

Spend seven hours aboard a vintage motorsailer from Palau or La Maddalena, visiting Budelli, Santa Maria, and Spargi. Guide Letizia and the crew explain the archipelago in Italian, English, and French. Swim from the boat, reach beaches by tender, buy pasta and drinks onboard, and bring cash for the landing tax.

“We enjoyed it, the only downside was the guide, I dont think she enjoys her job …., the english translation was 10% of the italian, the spanish was for who ?, on the back of the boat you could not hear anything anyhow. Then again I would go again, even without a guide.”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Barbati Beach and the first clear-water swim
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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

Cruise from Gouvia Marina along Corfu’s northeast coast aboard Ikaria or Eros 2, with a skipper such as Ari, Savvas, or Thassos. You’ll stop at Barbati Beach, Gialiskari, and a blue cave for swimming, snorkeling, and optional cliff jumping. Sandwiches, fruit, and soft drinks are included, while snorkeling gear and alcoholic drinks cost extra.

“This trip was a highlight of our holiday. Our skipper was friendly and informative . The boat was great with plenty of shade but also lots of space up front for sun lovers. Sandwiches and fruit were provided at one of the swimming stops and soft drinks were included. There was plenty of time for swimming at each of the 3 stops. I would do this trip again when next in Corfu.”

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4-Hour Sailing Tour of Lobos Island from Fuerteventura - Three Hours Around Lobos Island
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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

Join FuerteCharter in Corralejo for a four-hour catamaran trip to Lobos Island. Expect a safety briefing, coastal sailing, swimming, snorkeling, kayaks, paddleboards, seafood paella, and unlimited alcoholic and soft drinks. The crew may also take GoPro photos and run a short speedboat visit near the island.

“enthousiastic young people who know personally some citizens from Lobos. they ensure there is a good mood on board.”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Arriving at Dia Island’s clear-water cove
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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

Sail from Heraklion’s Old Venetian Harbor to Dia Island with a certified crew, often including Captain Nick, Stelios, Celia, Kristina, or Iorgu. Swim, snorkel, fish, paddleboard, hike, and eat a fresh lunch onboard. Choose hotel pickup or meet beside Marina Café, and consider an afternoon departure for sunset.

“We had an amazing trip to Dia island with Stelios and Celia! We decided to try the full day trip over the half day and are so glad we did. Definitely pay the bit more if you can! The pickup from our hotel was right from the door and on time, we were welcomed on board at the harbour and at the island had a chance to try snorkelling and SUP for the first time. Lunch was prepared while we swam and we had plenty of chance to sunbathe without feeling under pressure to do anything to a schedule. The whole experience was so relaxing, we felt like welcomed guests…”

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2-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar - Snorkeling at Mantaray Bay and beyond
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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

Spend two nights aboard Avatar, the Whitsundays’ commercial sailing trimaran, with up to 26 people. You’ll visit Whitehaven Beach, snorkel calm reef waters, eat all meals onboard, and sleep at sea. Crew members such as Alex, Ella, Sammy, Dave, Tyler, and Casper have been praised for their warm service, but cabins are compact and comfort is basic.

“Great trip all round! Awesome welcome from Skipper Sammy and Ella. Nice food, cool snorkel spots and great visit to Whitehaven Beach!”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - Arriving at Dia’s clear-water bays
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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 with a professional crew to Dia Island, about an hour offshore. Swim in clear bays, use the included snorkeling and paddleboard gear, and enjoy drinks with either seafood pasta and Greek salad or a lighter half-day meal. Ernesto and George are among the crew members praised for their care and stories.

“Thank you for the nice sailing trip to Dia Island. We had a really great time, the staff has been super nice and caring! We had some nice food and our glutenfree and vegan wishes were considered. We would really recommend this trip and would love to come again one day.”

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Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Sailing toward Delos, Greece’s ancient island center
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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

Spend about six hours sailing from Agios Ioannis to Delos and Rhenia aboard a spacious gulet with a friendly crew, including Dimitri and Thomas on some departures. Explore Delos for 90 minutes, swim and snorkel in clear water, and enjoy a buffet of grilled meats, vegetables, Greek salad, tzatziki, rice, fruit, and drinks.

“This is a must do / from the pick up to the drop off. It was perfectly executed. I’ve done a lot of boat tours at various destinations and this was by far the best. The crew -Dimitri and Thomas - were stand-up. They helped my mom who had some mobility issues throughout the day. Additionally, they were so patient and helpful with all of the guests. The captain was a class act. We loved the swimming spots -my kids enjoyed the day immensely. The lunch was the best lunch I have had yet in Mykonos, which says a lot.”

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St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max - Sailing toward St John National Park
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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

Leave Sapphire Beach Marina at 9:00 a.m. for a six-and-a-half-hour sail toward St John National Park and nearby cays. Your captain may be Kendall, Addison, Tommy, Mark, or another Virgin Islands Day Sailing skipper. Expect two or three snorkel stops, a fresh grilled lunch, open bar, and gear for a maximum of six people.

“Great excursion. Nice way to see the islands. Mark and Rusty did a fantastic job of telling us about the islands, stopped at two locations to snorkel. Small group of 6 which made it really nice. Highly recommend”

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Sailing boat from Santa Teresa di Gallura to the Maddalena Archipelago - Starting at Santa Teresa di Gallura
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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

Spend 7 to 8 hours aboard a small sailing boat from Santa Teresa di Gallura, visiting Budelli, Razzoli, Santa Maria, and Spargi. Expect swimming, snorkeling, lunch, drinks, and a friendly two-person crew such as Carlo, Andrea, Marco, or Lorenzo. The captain may change the route for wind and sea conditions.

“Wonderful trip. Leonardo and Massimo were very friendly and great hosts. They shared some good info about the islands and made sure we were all comfortable and enjoying the day. Highly recommend them.”

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