15 Guided Sailing Trips, Coast by Coast

1.Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

★★★★★★★★★★4.5 · 936 reviews · 2 hours 30 minutes (approx.) · from $76Our pick

Sail from Kewalo Harbor to Turtle Canyon for a guided family snorkel with provided gear, certified lifeguards, and a secured raft for children and beginners. You may see turtles, tropical fish, starfish, octopuses, dolphins, or even a monk seal. The first drink from the premium bar is included.

“Such a great experience even with 2 kids.We saw 2 turtles and tons of fish. Everyone who worked the boat was very knowledgeable and sweet. One even swam down and brought up a sea urchin for my son to hold. Great adventure!!”

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2.Sailboat Tour w/ Local Guide and Open Bar Green Wine

★★★★★★★★★★4.9 · 625 reviews · 2 hours · from $35

Cruise the Tagus on a 33-foot sailboat limited to eight passengers. Local guides such as Andre, Mariana, Francisco, and Felipe share Lisbon stories in English, Portuguese, or Spanish while you enjoy Portuguese Vinho Verde, music, sofas, and views of Belém Tower, the Discoveries Monument, Almada, Alfama, and Commerce Square. Sunset departures are the best choice.

“The guides were beautiful people that gave a beautiful experience. Extremely thoughtful, courteous, and very kind. Very skilled sailor and gave the absolute best tour. I am so thankful to have found these people beautiful. It was a very nice highlight to my first trip to Portugal! Highly recommended!”

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3.Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

★★★★★★★★★★4.5 · 608 reviews · 6 hours (approx.) · from $145

Sail from Mykonos to Rhenia and Delos on a six-hour yacht trip with an English-speaking guide, lunch, wine, soft drinks, Wi-Fi, and snorkeling gear. Swim from the yacht in a clear Rhenia cove, then explore Apollo’s legendary birthplace with a licensed guide. Delos admission and optional transfers cost extra.

“Overall, the experience was great. The Delos tour was a little long - especially given the temperature. The guide was very knowledgeable though. The time swimming at Rhenia was lovely. The water was so clear and refreshing. There were 14 people on our boat, which was too many to be comfortable. The crew was professional and provided great service.”

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4.Sailing and Self-Guided Walk

★★★★★★★★★★4.8 · 238 reviews · 8 hours · from $80

Start with a morning transfer from Marahau to Kaiteriteri, then sail a catamaran along Abel Tasman’s golden coast with an English-speaking skipper. After lunch and a swim at Anchorage Bay, walk 3.5 to 4 hours through native bush and along beaches back to Marahau. Bring food, water, layers, and sturdy shoes.

“Such a fantastic way to experience Abel Tasman, our guide Claudia was great and the sailboat ride was fantastic. I recommend getting lined up to board early so you can get one of the seats out front for the best experience. The hike from the beach our boat dropped us off at back to our car was a moderate hike with a few steep sections, well marked and with multiple beaches to stop at on the way!”

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5.2.5-hour Guided Sailboat Tour

★★★★★★★★★★5.0 · 181 reviews · 2 hours to 2 hours 30 minutes (approx.) · from $118Top rated

Join Brooklyn Sail for a 2 to 2.5-hour small-group sail from Pier 5 in Brooklyn. With Captain Ian, Andrew, or Tyler at the helm, you will pass the Statue of Liberty, Ellis Island, Governors Island, Brooklyn Bridge, and One World Trade Center. The boat holds no more than six passengers, keeping the outing personal and quiet.

“Great option for seeing the NYC sites (Brooklyn Bridge, skyline, Statue of Liberty, etc.) with a smaller group. Definitely worth the money & recommend over a larger boat tour that holds hundreds of people.”

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6.Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco

★★★★★★★★★★5.0 · 177 reviews · 4 hours 30 minutes (approx.) · from $156

Spend 4.5 hours aboard Honest Eco’s 42-foot sailing catamaran, kayaking through shallow mangrove channels, snorkeling at the day’s best calm-water site, and watching for dolphins, turtles, rays, and birds. A small group of up to 16, organic snacks, flotation gear, and instruction make this a relaxed choice for families and first-timers.

“Captain Libby and 1st Mate Brian were great, despite the fact that Brian's a Maine Black Bear ;) They were able to check off all the boxes for this trip starting off with a lucky manatee sighting just as we were preparing to leave the dock. kayaking at Cottrell Key, and as we were transiting to our snorkel spot by Archer Key we happened upon a pod of 8 dolphins. Brian is a wealth of knowledge about the mangroves, the Keys and the wildlife proving he learned something at UMaine. Snorkeling was okay by Archer Key. There are probably better snorkel spots on the Atlantic reef side of Key West.…”

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7.Mexico Rocks Day Sail Shared Guided Tour

★★★★★★★★★★5.0 · 69 reviews · 6 hours (approx.) · from $134

Join Catamaran Belize from Palapa Bar in San Pedro for a six-hour Mexico Rocks sailing trip with guides such as Raoul and Anna. Snorkel among coral, rays, turtles, lobster, and colorful fish, then enjoy a Belizean buffet, open bar, music, and a calm natural pool stop. The boat uses its motor for most of the route.

“We had a great trip to Mexico Rocks for snorkeling, swimming and a day of sun! We would highly recommend this trip! Raoul and Anna were our guides and they were awesome! They took such great care of us and were such good guides for our snorkel. Would highly recommend a day on the water with this group!”

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8.Guided Sunset Sailing Trip with Aperitif & Prosecco

★★★★★★★★★★4.7 · 67 reviews · from $768 whole boat, up to 10

Set out from Catania Nautical Club for three hours along Sicily’s volcanic coast. Your skipper and host team, including crew members such as Giulia, Sergio, Carlo, or Julia, guide you toward the Ulysses Caves, with a swimming stop, sunset views, local appetizers, and prosecco. The listing identifies the experience as a private group tour.

“Great day on the sea watching dolphins and sunset while sipping Prosecco”

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9.Group Sailing Tour with Guide

★★★★★★★★★★4.7 · 66 reviews · 3 hours · from $43

Set sail for three hours on Bacalar Lagoon aboard a catamaran or monohull, depending on availability. Your English or Spanish-speaking guide explains the wildlife and plants around Black Cenote, Birds Island, and Pirates Channel. Two drinks, lifejackets, and insurance are included. The route can change with the weather.

“Super fijne tour gehad met 2 geweldige gidsen en een prettige zeilboot. Raad het iedereen aan!”

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10.2-Hour Sailing Yacht Cruise & Guided Tour w/2 drinks

★★★★★★★★★★5.0 · 62 reviews · 2 hours · from $53

Board near the Discoveries Monument in Belém for a two-hour yacht cruise along the Tagus. A live guide in English, French, Portuguese, or Spanish points out Belém Tower, the April 25 Bridge, Alfama, Praça do Comércio, and the Vasco da Gama Bridge while you enjoy two drinks on board.

“Sebastian, Captain, was extremely helpful, communicated very well, and was a great host.”

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11.Mantua: Guided sailing from the Park to the Port with the water elevator

★★★★★★★★★★4.5 · 50 reviews · 1h 45m · from $21Best value

Start at Red Pier B by Mantua’s Castle of San Giorgio and cruise Lakes Mezzo and Inferiore, the Vallazza wetlands, and the Valdaro water elevator. An Italian-speaking guide explains nature, hydraulics, and local history. Use the QR information in English or German, and watch the boat cross the locks twice.

“The trip gave us another perspective on Mantua. It was amazing to experience technology that has been working for hundreds of years and to see the wildlife. We throughly enjoyed our hour and a half voyage. Although the guide spoke in Italian we received a nice paper with translation to English. In addition we had a conversation with the guide at the conclusion of the trip. In spite of the rainy day we were very glad that we went.”

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12.Private Sail in the mangrove GUIDE in ENGLISH

★★★★★★★★★★4.2 · 32 reviews · 90 minutes - 2 hours · from $25

You’ll paddle a traditional canoe through three mangrove tunnels in the Pantano de la Virgen near La Boquilla and Marlinda. A native English-speaking guide explains the area’s history and wildlife as you look for crabs, fish, herons, pelicans, flamingos, reptiles, and birds. Hotel pick-up is optional, but return transport costs extra.

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13.Self-Guided Walk & Sailing

★★★★★★★★★★4.7 · 30 reviews · 6 hours · from $88

Walk the Abel Tasman coastal track independently from Marahau to Anchorage, then meet your skipper at 1:15 pm for a 1:30 pm sailing trip to Kaiteriteri. Allow 3 to 4 hours for the walk. Tea, coffee, toilets, and a free transfer back to Marahau are included.

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14.Barcelona Guided Sagrada Familia Tour & Sailing Experience

★★★★★★★★★★4.9 · 25 reviews · 3.5 hours · from $187

Meet your English-speaking guide outside the BarcelonaSail shop for a guided Sagrada Familia visit, then travel independently to the marina for a two-hour sailing trip. Guides such as Roger, Christina, and William bring the basilica’s details to life. Choose a daytime or sunset sailing slot, with drinks and appetizers included when you select the sailing option.

“La más rescatable de la actividad fue el paseo en velero, la tripulación con excelente actitud nos hizo pasas un buen rato, en la sangrada familia lamentablemente nos tocó el apagón y muchas desorganización y retrasos y por parte de la guía pues una explicación estándar.”

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15.Guided Sailing Yacht Trip in Corfu Island

★★★★★★★★★★4.5 · 21 reviews · 5 hours (approx.) · from $82

Spend about five hours aboard a sailing yacht from Gouvia Marina, stopping at Barbati, Gialiskari near Agni Beach, and Nisaki’s blue cave. You’ll have time for swimming, snorkeling, and cliff jumping, plus sandwiches, fruit, water, soft drinks, and a restroom onboard. Captains such as Tasos and Ari are known for a friendly touch.

“Fabulous trip. Ari our skipper was the best. Fun and chose a great soundtrack. We had plenty of time to swim and enjoy the scenery. Value for money. Perfect itinerary, lovely snacks. Would 100% recommend. My daughter said if there were 6 stars we’d have given 6 stars!”

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