Coastal and Harbour Sailing: the 15 Best Short Trips

1.Oslo Fjord Sightseeing Cruise by Sailing Ship

★★★★★★★★★★4.5 · 5,790 reviews · 2 hours · from $39Our pick

Cruise Oslo Fjord for two hours on a traditional heated sailing ship with blankets, a bar, and multilingual audio commentary. You’ll pass Hovedøya, Dyna Lighthouse, the Opera House, Munch Museum, and Bygdøy. Disembark at Bygdøy at 12:20 PM and return at 2:50 PM if you want time for the Fram or Maritime Museum. Guides such as Karen add lively local color.

“The weather was awful, it was raining all the time and it was just +13 and windy - but we managed to enjoy the trip (the boat is protected from rain + they gave us warm blankets)”

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2.Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89Top rated

Board the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a two-hour sunset sail along Waikiki and past Diamond Head. Your captain and crew serve a complimentary first drink from the premium bar, with more available for $8. Look for dolphins, and humpback whales from November through May. Shoes are collected before boarding.

“A really wonderful expierence, we did the VIP which we liked to board early and get the free drinks included. Lovely hosts and weather was amazing!”

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

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

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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4.4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

★★★★★★★★★★5.0 · 1,465 reviews · from $145

Spend four hours sailing from Grace Bay aboard a 48-foot catamaran, with crew members such as Captain Mike, Ross, Jay, and Reggie helping with snorkeling, photos, and island stops. You’ll swim over tropical fish and coral, visit Half Moon Bay or Little Water Cay, and enjoy sandwiches, fruit, beer, soft drinks, and rum punch.

“My FAVORITE activity during my stay at Turks & Caicos! Got to snorkel, see iguanas, go to secluded beaches, eat sandwiches and fruits, open bar, and all the hosts were so friendly and funny. I'm definitely booking this again next time I'm back!”

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5.Indochina Sails Halong Bay

★★★★★★★★★★5.0 · 1,393 reviews · from $190

Spend one night aboard Indochina Sails, a classic junk with air-conditioned en-suite cabins, fresh meals, and a small group capped at eight. Visit Surprise Cave, Titop Island, and famous bay landmarks from Tuan Chau Island. Expect attentive service from staff such as Emily, Jane, Ruby Jane, and Mee, but bring a warm layer for the evening.

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6.Blue Lagoon, Beaches and Bays Catamaran Sailing Tour

★★★★★★★★★★4.5 · 1,269 reviews · 6 hours (approx.) · from $66

Sail from St. Paul’s Bay aboard the Sea Breeze, a large catamaran with sunbeds, lounging nets, a bar, restrooms, and some snorkeling gear. Spend about six hours swimming near Malta’s Blue Lagoon and possibly Crystal Lagoon, Popeye Village, Mellieha Beach, Ramla Bay, or Ghajn Tuffieha. The €15 barbecue is optional.

“Great experience. This is the second time I've been on this trip. The first experience was slightly better due to the total number of stopoffs the first boat trip had. I do realise that the number of stops is dictated by the weather but it was a slight shame we didn't experience more of the coast line on our recent trip.”

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7.Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s Cove

★★★★★★★★★★5.0 · 1,176 reviews · from $119

Sail St. Thomas aboard the 54-foot VI Cat from Marriott Frenchman’s Cove. You’ll enjoy a two-hour evening cruise toward Little Buck Island and Charlotte Amalie, with an open bar, tacos on Tuesdays or barbecue on select nights, sunset views, and harbor lights. Arrive 30 minutes early, and request vegetarian or vegan food 48 hours ahead.

“Beautiful experience! We sat at the front of the boat and drank cocktails through the night. The good was good and we met some great people on the boat.”

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8.Sailing Tour through the Lagoon of the 7 Colors

★★★★★★★★★★5.0 · 1,161 reviews · 3 hours (approx.) · from $37

Spend about three hours on Bacalar Lagoon with a bilingual captain and a small group of up to 16 people. You’ll visit several cenotes, Bird Island, and the old Pirate Canal, with time to swim in clear freshwater. Snorkeling gear, fruit drinks, three beers per adult, and snacks are included. Captains such as David, Angelo, Hugo, and Valentin are praised for friendly guidance.

“Loved every aspect of this tour! One of the best on our trip. Definitely recommend this tour to anyone visiting Bacalar!”

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9.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115

Spend about two hours sailing San Juan Bay aboard a 30-foot J30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect views of El Morro, harbor traffic, sunset photos, local stories, and complimentary beer, sangria, rum and Coke, water, and light refreshments. This is an authentic sailing trip, not a yacht party or catamaran cruise.

“It was such a great sailing experience with Captain Ivan. He told us a lot of history about the island and great spots to go to after the tour was over.”

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10.Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

★★★★★★★★★★5.0 · 695 reviews · 4 hours (approx.) · from $189

Set sail from Kailua-Kona aboard a 50-foot catamaran with a friendly crew such as Captain Dan and Captain Jacques. Enjoy Kona coffee and pastries, snorkel for about an hour at Kealakekua Bay, then build a deli lunch before sailing home. Instruction, gear, flotation noodles, drinks, and reef guidance are included.

“Amazing snorkeling trip. Friendly and helpful crew, amazing boat and snorkeling gear and the fish and coral are incredible!”

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11.2-Hour Oslo Fjord Sightseeing Cruise by Sailing Ship

★★★★★★★★★★4.0 · 694 reviews · 2 hours (approx.) · from $40

Spend two hours aboard an authentic sailing ship from Oslo City Hall, passing Hovedøya, Dyna Lighthouse, sheltered bays, summer cabins, and the Opera House. Choose from several departure times, use the free Oslo Fjord Guide app, and warm up with blankets or a drink from the onboard bar. Some departures may include guide John.

“Nice way to see Oslo by water. Well taken care of ship with character. Lots of seating. We were there on a cruise and had spare time so easily for into our schedule. Walkable from the other cruise terminal.”

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12.San Francisco Bay Sailing Cruise

★★★★★★★★★★5.0 · 629 reviews · 1 hour 30 minutes (approx.) · from $72

Set out from Pier 39 on Adventure Cat, a 55- or 65-foot catamaran carrying up to 42 people. You’ll sail past Alcatraz, under the Golden Gate Bridge, and toward Sausalito, with covered seating, trampoline nets, onboard drinks, and multilingual audio guides. Crew members have included Captain Mike, Wolfgang, Chad, and Lisa.

“The sailing catamaran was amazing! We scored with the best weather and minimal passengers onboard. The best staff and service 10/10 🙌🏻”

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13.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

★★★★★★★★★★4.5 · 620 reviews · 1 hour 30 minutes (approx.) · from $45

Spend 90 minutes aboard the 84-foot Schooner Pride, a real sailing ship that uses wind power when conditions allow. The crew raises the sails, answers questions, and may let you help with the lines. Look for dolphins, Fort Sumter, the USS Yorktown, the Battery, and the Ravenel Bridge. Snacks are welcome, but drinks must be purchased on board.

“It was so fun! They really give you the experience you signed up for. We saw dolphins and they provided drinks and a few snacks as well.”

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14.Classic Tall Ship Cruise in Boston Harbor

★★★★★★★★★★4.5 · 615 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $35Best value

Board Liberty Fleet of Tall Ships at Marina Overlook for a 90-minute sail aboard the Liberty Star. Captain Fredo and crew may invite you to help raise the sails while sharing harbor commentary. Bring a bagged lunch, buy drinks onboard, and enjoy skyline and Constitution views from the water.

“I enjoyed it. even go to help pull up the main sail!! Would love to do it again, actually go to get involved and do some of the tasks.”

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15.Sail Tour of Cyclops Coast with Sicilian Aperitif

★★★★★★★★★★4.7 · 548 reviews · 4 hours · from $69

Spend four hours sailing from Catania to Aci Trezza aboard a small boat with up to 10 people. Your English or Italian guide points out lava rocks and Aci Castello, then gives you time to swim, snorkel, or use the SUP. Finish with sparkling wine, local cheese, tomatoes, cold cuts, bread, and pesto.

“Fantastic guide! The trip was really nice with plenty of time to swimm, eat and relax! Also we had enough space for each of us. The tour guide was so friendly and nice, explaining us about the sights”

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