The 15 Sailing Trips in the USA That Earn Their Price

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Spend about two hours aboard Sebago’s large Key West catamaran, sailing past Mallory Square, Fort Zachary Taylor, and Sunset Key. Your ticket includes an open liquor bar, champagne, wine, sangria, premium beer, soft drinks, chef-selected hors d’oeuvres, and live music from local performers. Arrive early for a good bow seat, and bring a sweater for cool or windy evenings.

“Fun crew and drinks were plenty. There is enough room for everyone and the boat was well handled. Highly recommend this one.”

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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

Sail the Waikiki coast aboard the Hawaii-built Moana Catamaran for sunset views, Diamond Head, and a premium cocktail. The crew, including Vivian, keeps service friendly and attentive. From November through May, you may spot humpback whales, and dolphins are possible year-round. Shoes come off before boarding.

“Great trip. Saw humpback whales and a fantastic sunset. Crew was attentive and we all had a lovely time.”

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3.Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

★★★★★★★★★★4.5 · 2,109 reviews · 2 to 3 hours (approx.) · from $134

Sail from Kewalo Basin aboard the Honu Lani to Turtle Canyon for guided snorkeling with green sea turtles. The crew provides gear, safety help, lunch, and drinks on the midday trip. Guides may include Chris, Natalie, Greta, Joey, or Whitney. Turtles are guaranteed, with a free return cruise if none appear.

“This was a highlight of our Hawaii vacation! I most definitely recommend this excursion. The crew was amazing and the snorkeling experience was incredible! We saw the spectacular turtles and sea life. It was amazing!”

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4.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

★★★★★★★★★★5.0 · 1,655 reviews · 2 hours 30 minutes (approx.) · from $89

Meet near the Duke Kahanamoku Statue for a 2.5-hour catamaran trip to Turtle Canyon. The crew provides gear, flotation support, snacks, drinks, and marine-life guidance. Expect shallow reef water, green sea turtles, tropical fish, and a relaxed sail back toward Waikiki.

“Great crew! Fun day, very friendly and informative staff. Catamaran was well equipped. Team did a great job ensuring everyone was safe in the water. Reminder…this is a trip for participants who know how to swim and are comfortable in the water.”

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5.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59

Join Sebago Key West aboard the 69-foot catamaran Marquesa for a roughly three-hour afternoon sail from the historic seaport. After the hour-long ride to the Florida Reef, the crew provides gear, safety guidance, and time to snorkel among coral and tropical fish. Once you are back aboard, enjoy unlimited beer, wine, cocktails, and soft drinks on the return sail.

“The weather was perfect on our snorkeling day trip to the reefs. The boat ride was about an hour to get 8 miles offshore. The catamaran was smaller than usual and it was crowded but we still fit and had fun. We couldn't drink until after snorkeling and returning back to the docks. Safety precautions were paramount and the captain and crew instructed everyone on the proper way to snorkel. I saw the reefs and took video down below. A nurse shark crossed my path which wasn't too bothered by us humans but it was incredible experience. I'm an expert snorkeler and diver but this was fun. Good selection of…”

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6.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125

Sail from 255 Front Street for about two hours with a maximum of 26 people. The crew pours up to eight wines, offers beer and soft drinks, and serves small plates such as cheese, fruit, and skewers while you watch the Key West sunset. Crews may include Mary, James, Connor, Molly, or Tony.

“Our sunset sail was perfect from start to finish. We absolutely loved the wine tasting and appetizers — you never know what you’re going to get on these types of excursions, and sometimes you brace yourself for cheap wine and sad snacks… but this was the total opposite. The wines were genuinely great bottles, and the cheese apps were delicious and beautifully done. We also adored our all-women crew. They were fun, warm, and made the whole experience feel extra special — the perfect vibe for a girls trip celebrating our 40ths. Would 100% recommend this sail to anyone looking for something elevated, relaxing, and unforgettable.”

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7.Waikiki Signature Sunset Catamaran Sail

★★★★★★★★★★4.5 · 890 reviews · 1 hour 30 minutes (approx.) · from $89

Sail from Honolulu toward Diamond Head aboard a 53-foot catamaran with a light bento box, two alcoholic drinks, and unlimited nonalcoholic beverages. Crew members such as Chris, Phil, Keoni, Kelley, Andrea, and Captain Flynn have been praised for friendly service, while the sunset, sea life, and glittering Waikiki return make this a relaxed 90-minute outing.

“Great boat; great crew; great views. Will definitely do this again. Probably will bring off-island friends, too. The lights coming up in Honolulu were spectacular.”

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8.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 722 reviews · 3 hours (approx.) · from $136

You’ll leave Keauhou Bay at 1:45 pm for a three-hour sail along Kona’s lava coast, then snorkel near the Captain Cook Monument in protected Kealakekua Bay. Sea Paradise supplies masks, fins, flotation noodles, reef-safe sunscreen, snacks, and drinks. Guides such as Captain Eddie and Shannon’s crew add safety tips, local stories, and cultural context.

“Supercalifragilistic! The best crew to make every person confident and comfortable. Small group of 12 with plenty of personal attention. Good for everyone even non swimmers and all ages.”

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9.Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

★★★★★★★★★★5.0 · 668 reviews · 1 hour 30 minutes (approx.) · from $47

Meet the crew at Harbour Town and board the Black Dagger for a 90-minute pirate adventure. Kids receive pirate names, costumes, face paint, tattoos, and lessons before following a map, battling Stinky Pete with water cannons, and sharing the treasure. Shade is limited, there is no restroom aboard, and a $10 cash Sea Pines gate fee applies.

“We just returned from the pirate adventure! We all said it was our most fun experience on our trip. Our grandchildren were 8, 11 and 13 and even though most of the kids were younger everyone was face painted and had tattoos. They learned to be a pirate and shot water at stinky Pete. They involved the parents too which was great fun. I can’t see how you could not have fun with the kids on this experience.”

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10.Waikiki Sunset Catamaran Sail and Swim

★★★★★★★★★★4.7 · 519 reviews · from $44Best value

Spend two hours on a Pink Sails Waikiki catamaran with an English-speaking crew, sunset views of Diamond Head, and time for an ocean swim. The crew, including captains Jamie and Nick on some departures, keeps the mood lively and helps with photos. Boat type and departure time can change with weather and availability.

“The crew is just amazing and super funny! We had an amazing time after a tour we hated 🤣 so our expectations were low. But thank God this was everything we needed. Cool vibes, good ambiente and an amazing crew! I forgot the names of them but all of them were so nice! I would totally recommend this activity!”

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11.America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head

★★★★★★★★★★4.5 · 504 reviews · 1 hour 30 minutes (approx.) · from $55

Spend 90 minutes aboard the 39-foot Stars & Stripes, an America's Cup 12-Meter yacht sailing from Harbour Town. Captain Peter and his crew may invite you to raise the mainsail, grind lines, or take the wheel while you enjoy views of the lighthouse, marina, Intracoastal Waterway, and Hilton Head coast. Cushioned deck seating, paid drinks, and weather-dependent departures are part of the deal.

“It was such a fabulous experience and Captain Peter is quite an interesting person. He was so friendly and eager to take your picture and make sure you had a nice sail.”

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12.From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

★★★★★★★★★★4.8 · 348 reviews · from $114

Join Sail Maui aboard the Alihilani from Ma’alaea Harbor for a two-hour sunset sail in the Au’au Channel. Sip drinks, enjoy cold hors d’oeuvres, and settle on the forward trampolines or under the cabin. Crew members such as James, Kevin, Jess, and Nicholas have earned praise for warm service, music, and expert handling.

“Captain and crew were on point and greatly appreciated their kindness and hospitality.”

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13.Sunset Sail Aboard a Schooner

★★★★★★★★★★4.9 · 344 reviews · 2 hours · from $101

Board the 105-foot Schooner America at Pier 62 for a two-hour sunset sail past Chelsea, Battery Park, Ellis Island, and the Statue of Liberty. The professional crew serves one beer, wine, or Champagne to guests 21 and older. Bring a photo ID, arrive early, and pack a warm layer for the river breeze.

“I’ve been to New York many times but me and a few friends decided to book this spur of the moment and it is one of the best experiences I’ve had here! Amazing! I’ll do it again”

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14.Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Board the America 2.0 behind Schooner Wharf Bar for a two-hour sunset sail with complimentary drinks and a personal hors d’oeuvres plate. You’ll pass Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier while the crew handles the sails. Captains including Janet and Amber have led highly praised departures.

“This was a wonderful experience with an excellent crew.”

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15.Harbor Champagne Sunset Sail from Rowes Wharf

★★★★★★★★★★4.8 · 299 reviews · 2 hours · from $82

Spend two hours aboard Schooner Adirondack III or IV, sailing from Rowes Wharf around Boston Harbor at sunset. You will pass the Fish Pier, Castle Island, Fan Pier, the Inner Harbor Islands, and Charlestown Navy Yard. The crew, including hosts such as Steve and Therese on some departures, shares local stories while you relax with a drink from the onboard bar.

“Out of everything we've done in Boston, this by far was one of the best. Everyone was extremely polite and personable, full of knowledge about various places, and made sure to check in with us while doing their duties aboard. Make sure to tip when once it's all over because it's well worth it! 1000% recommend and hope to do again in the future!”

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