The 15 Best Sailing Trips in the USA

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

Board Sebago’s spacious catamaran at 205 Elizabeth Street for a two-hour Key West sunset sail. Expect live local music, peel-and-eat shrimp, wine, sangria, beer, cocktails, and soft drinks as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Bring a sweater and arrive 30 minutes early.

“Very well done. Great attitude from the crew which made for a great rise in morale for all the guests.”

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2.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 about two hours. You’ll get a complimentary first drink from the premium bar, then pay $8 per drink. Look for Diamond Head, dolphins, and seasonal humpback whales, with crew members such as Viv helping make the evening run smoothly.

“We would definitely do this again. The crew was professional and made it a very fantastic experience.”

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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 40-person Honu Lani for a guided Turtle Canyon snorkel. Look for green sea turtles, reef fish, dolphins, and winter whales. The midday trip includes a deli lunch, beer, wine, and cocktails. Morning departures include unlimited soft drinks.

“The catamaran sail was very enjoyable but the snorkeling was very crowded. Lunch was simply a deli wrap.”

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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 at the Duke Paoa Kahanamoku Statue for a 2.5-hour Hawea catamaran trip to Turtle Canyon. Your crew provides gear, points out turtles, fish, octopus, and reef life, then raises the sails for a scenic ride back toward Waikiki. Swimming ability is required.

“Awesome and Safe! They were very attentive, polite, experienced and they knew how to keep everyone safe and entertained in and out of the water. 10 out of 10.”

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5.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

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

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew supplies gear and instruction, then serves beer, wine, cocktails, and soft drinks after snorkeling. Captain Brett has earned special praise for his safety-minded approach.

“Not cruise ship friendly. If you're traveling on a cruise ship, they dropped us off far from our port and made it a difficult boarding. At least let me know, so I can plan accordingly. Because I would not have selected this experience.”

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6.Group Sunset Sail with Wine and Hors d’oeuvres

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

Join Danger Charters at 255 Front St for a roughly two-hour sunset sail limited to 26 passengers. Expect wines from around the world, beer, soft drinks, and easy-to-eat hors d'oeuvres, with crew members such as Mary, Connor, Lexi, or Tony sharing stories and keeping the glasses moving.

“Just do it! The crew is wonderful. The wine & appetizers were delicious. It was a chilly and windy sail, but the crew had blankets ready and it was picture perfect. And, a couple got MARRIED during the sail!”

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7.Waikiki Signature Sunset Catamaran Sail

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

Board Hawaii Nautical’s 53-foot catamaran in Honolulu for a 90-minute sunset sail toward Diamond Head. You’ll receive a light bento box, two alcoholic drinks, and unlimited nonalcoholic beverages while the crew shares local wildlife tips. Pickup is available from selected Waikiki hotels for an added fare.

“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

From Keauhou Bay, you’ll cruise the Kona coast to Kealakekua Bay, then snorkel near the Captain Cook Monument with masks, fins, flotation noodles, and reef-safe sunscreen. The crew shares island history and ocean lore, with snacks and drinks included.

“Lovely afternoon sail to Kealakekua bay for snorkeling. Fun, friendly crew, well organized boat, clean gear, yummy snacks and drinks. Great excursion!”

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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

Join Scurvy and the crew aboard the Black Dagger for a 90-minute Hilton Head treasure hunt. Kids receive pirate names, face paint, tattoos, costumes, and lessons before battling Stinky Pete with water cannons. Expect shade, sun, dolphins if you are lucky, and treasure to take home.

“We loved it all! It was very interactive, and the kids had a great time! Ever did a great job, thank you guys!”

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10.Waikiki Sunset Catamaran Sail and Swim

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

Join Pink Sails Waikiki for a two-hour sunset cruise from Waikiki. Expect views of Diamond Head, city lights, music, a friendly English-speaking crew, and time to swim in the open ocean. Boat type and departure time can change with weather, repairs, and availability.

“The crew were funny and informative. Loved having time to swim and then enjoy the sunset. Great experience!!”

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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

Sail for 90 minutes aboard the 39-foot Stars & Stripes from Harbour Town. Captain Peter and crew may invite you to raise the mainsail, grind lines, or take the wheel while you pass the lighthouse, marina, and Lowcountry shoreline. Cushioned deck seating, drinks for purchase, and a maximum of 20 people keep it personal.

“Outstanding! The boat was amazing. We saw more dolphins than we had seen on any previous dolphin tours which was great for the kids on board. Great first mate!! He explained things well and shared his knowledge on the area. It was a really fun afternoon.”

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12.‘Alihilani Sunset Sail Catamaran Tour

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

Sail Maui’s Alihilani carries you from Maalaea Harbor into the Auau Channel for a two-hour sunset cruise. Expect open-deck seating, forward trampolines, cold appetizers, drinks, live English commentary, and possible dolphins or humpback whales from December through March.

“The crew were phenomenal! The people on board were such a pleasure to talk to, and great music.”

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13.Sunset Sail Aboard a Schooner

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

Spend two hours aboard the 105-foot Schooner America, sailing from Chelsea Piers toward the Statue of Liberty. You’ll see Ellis Island, Battery Park, Lower Manhattan, and possibly Governors Island, with one beer, wine, or Champagne for guests 21 and older. Bring a photo ID and a warm layer.

“We loved our trip on Harbor Line America 2.0 - staff are really friendly, the views you get from the water are incredible. We had a perfect night weather wise, and when we got a little chilly the staff brought out blankets for us all. Drinks flowed for the 2 hours. Would highly recommend this trip to see New York like no other way.”

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14.Schooner Sunset Sail with Food & Drinks

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

Set sail from 202 William Street aboard the America 2.0, a handsome schooner with teak decks and mahogany trim. During this two-hour cruise, you’ll enjoy drinks, a personal hors d’oeuvres plate, views of Fort Zachary Taylor and Sand Key Reef, and a sunset guided by captains such as Janet and Amber.

“Excellent tour! Top quality staff, captain, boat, snacks and drinks. This adventure was first class. It was not a booze-cruise run by idiots. I would highly recommend this company if you enjoy a peaceful and relaxing time.”

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15.Harbor Champagne Sunset Sail from Rowes Wharf

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

Spend two hours sailing Boston Harbor aboard Schooner Adirondack III or IV. From Rowes Wharf, you’ll pass the Fish Pier, Castle Island, Fan Pier, the Navy Yard, and Inner Harbor Islands while the crew explains local sights. Bring a picnic, dress warmly, and buy champagne, wine, beer, or soft drinks by credit card.

“Highlight of our trip to Boston! This was so much fun. Highly recommend.”

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