15 Island-Hopping Sailing Trips Worth Flying For

Sailboat tour from PALAU to the Maddalena Archipelago. - La Maddalena National Park and the natural swimming pool

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

Set out from Palau at 9:30 a.m. for a 7 to 8 hour sailing day through La Maddalena National Park. With a maximum of 12 people, your crew, which may include Giuseppe, Simone, Claudia, Alberto, or other Sardinia Sailing Tour skippers, serves Sardinian snacks, pasta, wine, and drinks between swimming stops. The route changes with the weather.

“Sailing with Gaetano and Max was fun. I enjoyed watching them work to get sails up. Water and beaches were beautiful. Lunch was delicious. Safety was of great importance to them. My friend's first time on a boat. She was very nervous and hesitant about going. By the end of the trip, she was relaxed with a big smile. Forget the big crowded boats. Spend a little more and do this. Thanks for a memorable day!”

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From Palau or La Maddalena: Archipelago Sailing Ship Tour

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

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

Join a multilingual crew, often led by Letizia, for a seven-hour motorsailer trip from Palau or La Maddalena. See Budelli’s pink beach from the water, swim near Santa Maria, and visit Cala Corsara on Spargi. Bring lunch or buy pasta and drinks aboard. Expect limited shade, boat transfers, and some climbing.

“Loved it! Amazing islands! Leticia was super nice and making sure everyone was Ok”

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2-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar

3.2-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar

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

Sail from Coral Sea Marina aboard Avatar, the Whitsundays’ only commercial trimaran, for two nights among island beaches and reef waters. You’ll snorkel, visit Whitehaven Beach, and share meals with up to 26 people. Crew members such as Alex, Ella, Dave, Tyler, Casper, Sammy, and Ella have been praised for warm hosting and strong local guidance.

“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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Shared Mykonos Sail Cruise to Delos and Rhenia Islands

4.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

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

Spend about six hours aboard a spacious gulet from Agios Ioannis, sailing to UNESCO-listed Delos and the clear swimming waters of Rhenia. You can explore Delos on your own or prebook a guided tour, then enjoy a BBQ buffet, drinks, snorkeling gear, and attentive crew care. Hotel transfers cost extra.

“The experience was amazing, once in a lifetime. We are so happy we decided to book this tour. The crew and food were excellent!”

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

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

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

Sail from Sapphire Beach Marina with a maximum of six people, heading toward St. John National Park and nearby cays. Your captain chooses two or three snorkel stops based on wind, weather, and crowds. Expect provided gear, grilled lunch, soft drinks, an open bar, and possible sightings of turtles, rays, coral, and tropical fish.

“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

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

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

Set out at 9:30 a.m. from Santa Teresa di Gallura aboard a small sailing boat for a full day around La Maddalena. With up to 12 people, you’ll visit protected Pink Beach, Port Madonna, Spargi, and Cala Santa Maria, with swimming, snorkeling, lunch, wine, coffee, and soft drinks included. The crew may include Carlo, Andrea, Marco, Lorenzo, or other Sardinia Sailing Tour staff.

“Marco and Lorenzo were great hosts, lots of drinks available, food was great and the boat in good shape. The itinerary is too much for sailing most of the time however if that is what you are looking for. We did get of engine with the sails up for a little bit which was appreciated as two of us are keen sailors.”

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Airlie Beach: Whitsunday Islands 2-Day Sailing Tour

7.Airlie Beach: Whitsunday Islands 2-Day Sailing Tour

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

Sail from Airlie Beach aboard Matador, a racing yacht operated by OzSail Whitsunday. You will snorkel reef sites, reach Whitehaven Beach early, eat fresh meals, and sleep onboard beneath the stars. Crew members such as Tony, Chris, Ruby, and Dave have been praised for warm service and strong local knowledge. Expect simple sleeping quarters, shared facilities, and an active boat routine.

“We had the best time! Did snorkeling on the best places you could have and there was no one else! We went to white heaven beach with no other people on the island! We saw stingrays, lemon sharks and the best views! Couldn’t recommend more! Ruby, Tony and Kate were the best! Had some incredible information from ruby during the night about the coral reefs, was so interesting! Thanks for the great experience!!”

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Camira Sailing Adventure through Whitsunday Islands

8.Camira Sailing Adventure through Whitsunday Islands

★★★★★★★★★★4.5 · 452 reviews · from $185

Spend about 10 hours aboard the Camira from Airlie Beach, sailing to Whitehaven Beach and Hill Inlet. Walk to the lookout with a guide, swim, snorkel the fringing reef, and enjoy barbecue lunch, snacks, soft drinks, and alcohol after snorkeling. The boat carries up to 60 people, with hotel transfers available as an upgrade.

“Amazing staff, very experienced, friendly and helpful. Adventure Was amazing even had some personal time to explore. Food was lovely with heaps of Variety.”

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Bay of Islands Tall Ship Sailing on R. Tucker Thompson Including BBQ Lunch

9.Bay of Islands Tall Ship Sailing on R. Tucker Thompson Including BBQ Lunch

★★★★★★★★★★5.0 · 361 reviews · from $111

Spend 5.5 hours aboard the working schooner R. Tucker Thompson, sailing from Russell through the Bay of Islands. Help with ropes, steer the ship, climb the rigging, swim from the boat, and visit an island viewpoint. Morning tea, scones, chicken BBQ lunch, and optional Paihia to Russell ferry transport are included.

“A fantastic experience. Our son loved the wild weather, the ability to help on the boat and the crew where incredibly. Highly recommend for everyone.”

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Tour Sailboat 15 mt. BOARDING FROM LA MADDALENA islands Archipelago

10.Tour Sailboat 15 mt. BOARDING FROM LA MADDALENA islands Archipelago

★★★★★★★★★★5.0 · 306 reviews · 8 hours (approx.) · from $119

Spend about eight hours aboard a 15-meter sailboat from La Maddalena, visiting Spargi, Pink Beach, Port Madonna, and Cala Santa Maria. The English-language crew, often including Giuseppe, Salvatore, Max, Denny, or Ettore, serves Sardinian food, wine, mirto, and drinks while you swim and snorkel. The group is limited to 12 people.

“Max was an incredible skipper! Very knowledgeable, best service with food and drinks. Always made sure everyone on board was happy and getting anything they needed. The weather wasn’t the best but it was still an incredible sail!”

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2 Day & 2 Night Whitsunday Islands Sailing Adventure on Condor

11.2 Day & 2 Night Whitsunday Islands Sailing Adventure on Condor

★★★★★★★★★★5.0 · 302 reviews · from $501

Set sail from Coral Sea Marina for two nights aboard Condor, a social Whitsunday sailing adventure with three crew, onboard beds, all meals, snorkeling gear, and time at Whitehaven Beach and Hill Inlet. You can hike, snorkel, help keep the pace lively, or relax in a hammock. The trip suits active adults, mainly ages 18 to 39.

“The passengers and crew were amazing and as a solo traveler I felt so embraced and comfortable sooner than I would’ve ever expected. I had a lovely time even though we didn’t catch the best conditions. Everyone’s attitude and williRead more”

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Sailing boat tour in the Maddalena Archipelago

12.Sailing boat tour in the Maddalena Archipelago

★★★★★★★★★★5.0 · 217 reviews · 7 hours (approx.) · from $145

Spend about seven hours sailing from La Maddalena or Palau through Sardinia’s island chain. With a skipper and crew such as Samuel, Yuri, Ines, or Antonella, you’ll stop near Budelli and Spargi for swimming, snorkeling, and SUP, then eat a generous onboard lunch with wine, beer, spritz, coffee, and local snacks. The boat holds up to 14 people.

“Sebastian and Antonella were fabulous hosts. We really enjoyed this trip. Comfortable boat with 12 people, plenty of food - we had to pass on the last course because we ate so much. Option to go to beaches or swim off boat . If you have the opportunity, spend the extra $ and do this tour. We loved it!”

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Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group

13.Half Day Sailing on a comfort yacht around Hvar and Pakleni islands- small group

★★★★★★★★★★4.5 · 194 reviews · 4 hours (approx.) · from $90

Set sail from Hvar’s Riva for four easygoing hours around the Pakleni Islands. With no more than eight guests on the comfort yacht, you’ll swim and snorkel in two bays, hear local sailing stories, and adjust the route to the weather. Bring lunch and drinks, then keep them cold in the onboard fridge.

“The pickup by the green lantern was smooth and efficient. The instructions were easy to follow. Although there was no wind, the 2 lads made it interesting and were able to adapt and overcome. The little stories of the local places of interest were entertaining. Safety of our group was important to them. Nice choice of music!”

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Phantom Sailing Bay of Islands

14.Phantom Sailing Bay of Islands

★★★★★★★★★★5.0 · 177 reviews · from $121

Spend about 5.5 hours aboard the Phantom, a live-aboard yacht run by sailors Rick and Robin. With no more than 10 people on board, you can sail through the Bay of Islands, stop for a beach walk and viewpoint, swim or snorkel, enjoy a homemade lunch, and hear local stories from Russell back to Russell.

“A very relaxed day in the sunshine on Phantom with Rick and Robyn. Great hosts, good fun, delicious lunch on deck. Enjoyed the swim to shore and walk up to the viewpoint. A wonderful day…..”

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Bay of Islands: Catamaran Sail, Wildlife Island & Lunch

15.Bay of Islands: Catamaran Sail, Wildlife Island & Lunch

★★★★★★★★★★4.9 · 173 reviews · 6 hours · from $134

Join Barefoot Sailing Adventures in Paihia for six hours aboard a comfortable catamaran. Skippers such as Luke share local wildlife stories while you sail among 144 islands, help at the helm, then spend two hours on a sanctuary island with lunch, hiking, snorkeling, swimming and paddleboarding.

“Thoroughly enjoyable day thank you; sailing, snorkelling and walking were great; Luke was engaging and interesting; communication about the booking was straightforward”

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