USA · SAILING

15 Sailing Trips in the USA, Ranked by What You Get

32 tours  ·  from $41

The good sailing trips fill weeks ahead and the best ones go first. Below: the 15 to book early, what each includes and where they differ.

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time - The catamaran ride across Gulf waters
Boat Tours in the Florida Panhandle, Cruises & Boat Tours, Dolphin Tours in the Florida Panhandle, Dolphin Watching, Florida Panhandle Tours, Florida Tours, Sailing, Snorkeling, Tour Reviews

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

1.Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

★★★★★★★★★★5.0 · 4,362 reviews · 3 hours (approx.) · from $57Our pick

Sail from Panama City Beach to Shell Island aboard Island Time’s roomy catamaran. Look for wild dolphins, snorkel in St. Andrews Bay, collect shells, paddleboard, or use the waterslide. The crew provides gear and life jackets, with drinks available to buy. Allow about three hours and check in 30 minutes early.

“shell Island was beautiful seeing dolphins on the way was fun. We also snorkeled and collected shells.”

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Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - Leaving Honokohau Marina on the power catamaran
Big Island of Hawaii Tours, Boat Tours in Big Island of Hawaii, Cruises & Boat Tours, Hawaii Tours, Sailing, Snorkeling, Snorkeling Trips in Big Island of Hawaii, Tour Reviews

Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch

2.Captain Cook Snorkel On A Power Catamaran With Lunch

★★★★★★★★★★5.0 · 2,232 reviews · 4 hours (approx.) · from $85

Cruise Kona’s volcanic coast to historic Kealakekua Bay with Hang Loose Boat Tours. Captains Aiden or Bryce and the crew provide snorkel gear, flotation devices, lunch, history, and plenty of time in the water. Expect coral, reef fish, possible dolphins and winter humpback whales, plus a boat slide and rinse-off shower.

“A great morning trip to a perfect snorkeling experience on the big island of Hawaii. The bay next to the captain Cook Memorial is about a 40 minute boat ride from the harbor. We spent two hours snorkeling playing on the boat slides and jumping off the boat and enjoying lunch. there was good equipment for everybody and the boat was comfortable.”

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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed - Waikiki and Diamond Head from the water
Boat Tours in Oahu, Cruises & Boat Tours, Hawaii Tours, Oahu Tours, Sailing, Sailing Trips in Oahu, Sea Turtle Tours, Sea Turtle Tours in Oahu, Snorkeling, Snorkeling Trips in Oahu, Tour Reviews

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

3.Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

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

From Kewalo Basin, you cruise past Waikiki and Diamond Head to Turtle Canyon for guided snorkeling with green sea turtles. The midday trip includes lunch, beer, wine, and cocktails, while the morning sailing offers soft drinks. The crew, including guides such as Chris, Natalie, Greta, and Joey, provides gear and water safety help.

“Bathroom before departing is far from the slip. Better to park near restrooms under the tree if you’re driving. Parking was cheap and easy. The trip was awesome. Captain and crew were so friendly answered all of our questions and saw 6 or 7 turtles.”

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Sunset & Dolphin Catamaran Cruise with Island Time - Setting Out From 5201 North Lagoon Drive
Boat Tours in the Florida Panhandle, Cruises & Boat Tours, Dolphin Tours in the Florida Panhandle, Dolphin Watching, Florida Panhandle Tours, Florida Tours, Sailing, Tour Reviews

Sunset & Dolphin Catamaran Cruise with Island Time

4.Sunset & Dolphin Catamaran Cruise with Island Time

★★★★★★★★★★5.0 · 1,867 reviews · 2 hours (approx.) · from $57

Spend about two hours on Island Time Sailing’s catamaran from Panama City Beach. You’ll cruise Grand Lagoon, pass St. Andrews State Park, look for dolphins, and watch the sun set. Captain Clay and crew members including Christo, Sara, Audra, Carter, and Emma have helped create lively sailings, with onboard drinks, music, photos, games, and dancing at the dock.

“Relaxing, beautiful, fun, friendly informative staff..loved the sails going up and coming down...great boat ride”

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San Francisco Bay Sunset Cruise by Luxury Catamaran - Alcatraz and the Pier 39 sea lions
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San Francisco Bay Sunset Cruise by Luxury Catamaran

5.San Francisco Bay Sunset Cruise by Luxury Catamaran

★★★★★★★★★★4.8 · 1,097 reviews · 1h 30m · from $90

Set out from Pier 39 on a 90-minute sunset sail with Adventure Cat Sailing Charters. You’ll pass Alcatraz, Sausalito, and the Golden Gate Bridge, with a chance to see sea lions and other wildlife. A drink is included, and the 55- or 65-foot catamaran offers indoor seating, 360-degree views, and open-air trampoline nets.

“It was very fun. The crew was exceptionally helpful. My 45 year old son is in a wheelchair and the crew helped him up and down the stairs. The walk to the loading pier is about a half mile… long for handicapped person. The sail was excellent. Going under the Golden Gate Bridge was a life time experience. I would love to do this again”

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Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - Boarding at Ma’alaea Harbor
Boat Tours in Maui, Cruises & Boat Tours, Hawaii Tours, Maui Tours, Sailing, Tour Reviews, Tours, Whale Watching, Whale Watching in Maui

Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

6.Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

★★★★★★★★★★4.6 · 979 reviews · 2 hours · from $49

Cruise Ma’alaea Bay aboard Quicksilver’s double-deck power catamaran during Maui’s whale season. Captain Kiwi, Captain Carlos, and other crew members have led trips with clear whale narration, hydrophone songs, drinks, restrooms, and wide viewing areas. The $49 fare is a strong value, though parking and alcohol cost extra.

“This was a great experience. We saw lots of whales relatively closely. The crew was informative and friendly.”

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Waikiki Signature Sunset Catamaran Sail - Snack Boxes and Drinks on the Water
Boat Tours in Oahu, Cruises & Boat Tours, Hawaii Tours, Oahu Tours, Sailing, Sailing Trips in Oahu, Sunset Cruises, Sunset Cruises in Oahu, Tour Reviews

Waikiki Signature Sunset Catamaran Sail

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 for about 90 minutes. You’ll get a bento-style snack box, two alcoholic drinks, unlimited nonalcoholic beverages, and views of Waikiki at sunset. Crew members including Chris, Phil, and Keoni have been praised for friendly service and marine-life tips.

“It was a beautiful sunset views, and we saw a bunch of rainbow. It wasn’t the best, but the views were amazing.”

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2 Hour Sailing Cruise on Lake Tahoe - The first hour: leaving shore and finding the wind
2-Hour Experiences, Cruises & Boat Tours, Sailing, Tour Reviews

2 Hour Sailing Cruise on Lake Tahoe

8.2 Hour Sailing Cruise on Lake Tahoe

★★★★★★★★★★5.0 · 886 reviews · 2 hours (approx.) · from $140

Sail Tahoe Blue takes you onto Lake Tahoe aboard Blue, a Coast Guard-certified 40-foot yacht with public departures capped at 14 people. Captains such as Justin lead the wind-powered cruise, while the crew serves local beer, wine, water, and soft drinks. The route changes with the wind, and the boat returns to Ski Run Boulevard after about two hours.

“The captain and crew was very nice and polite and provided information about the lake and area. Well worth the money !!”

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Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona - Breakfast with the Kona coast sliding past
Big Island of Hawaii Tours, Boat Tours in Big Island of Hawaii, Cruises & Boat Tours, Dolphin Watching, Hawaii Tours, Sailing, Snorkeling, Snorkeling Trips in Big Island of Hawaii, Tour Reviews, VIP

Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

9.Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

★★★★★★★★★★5.0 · 797 reviews · 4 hours 30 minutes (approx.) · from $183

Set out from Kailua Pier aboard Body Glove’s spacious catamaran for a four-and-a-half-hour Kona coast cruise. Look for dolphins and seasonal whales, snorkel at Red Hill for about two hours, then enjoy breakfast, a barbecue lunch, paddleboards, a slide, and a high-jump platform. Captain Erica and crew members such as Adam, Brianna, and Taylor have been singled out for attentive service.

“My family and I had the best time on the Body Glove Catamaran! The crew and Captain were professional, personable, and always watching for the safety of the guests. There’s something for entire on this boat. Everyone enjoyed snorkeling while my husband, teen daughter, and I enjoyed the slide, high jump, and paddle boarding. My parents enjoyed the beautiful scenery and beverages handcrafted by our gorgeous bartender. This boat has everything!!”

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Seward: Kenai Fjords National Park Catamaran Cruise w/Lunch - Wildlife watching in a working fjord
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Seward: Kenai Fjords National Park Catamaran Cruise w/Lunch

10.Seward: Kenai Fjords National Park Catamaran Cruise w/Lunch

★★★★★★★★★★4.8 · 736 reviews · from $265

From Seward, you will cruise Resurrection Bay and Kenai Fjords National Park aboard a fast, stable catamaran. Captain Laura and other skilled captains point out whales, sea otters, puffins, seals, sea lions, and calving glaciers. A deli lunch, hot drinks, binoculars, and an onboard bar make this a well-equipped six-hour outing.

“We enjoyed the captain and crew’s hospitality and their knowledge of running the tour. The sealife and park shore as well as Holgate glacier were breathtaking.”

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Sunset Catamaran Cruise in Ft. Lauderdale - Millionaires Row and Fort Lauderdale’s canal-side mansions
Boat Tours in Fort Lauderdale, Cruises & Boat Tours, Florida Tours, Fort Lauderdale Tours, Sailing, Sunset Cruises, Tour Reviews

Sunset Catamaran Cruise in Ft. Lauderdale

11.Sunset Catamaran Cruise in Ft. Lauderdale

★★★★★★★★★★5.0 · 692 reviews · 2 hours (approx.) · from $99

Set out from Spirit of Lauderdale at 5 pm for a two-hour catamaran ride past waterfront mansions, Port Everglades, and Fort Lauderdale Beach. The boat motors through the canals, then raises its sails offshore. You get a complimentary glass of champagne, shaded seating, a restroom, music, and a cash bar. Recent sailings have featured Captains Jim, Joe, and John, with crew such as Justin and Marcos.

“Great relaxing sailboat ride with beautiful views. However, some of the Viator information was incorrect so call the company to confirm times and address.”

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1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain - What sailing conditions change
Cruises & Boat Tours, Portland & Bar Harbor Tours, Sailing, Tour Reviews

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

12.1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

★★★★★★★★★★4.0 · 601 reviews · 2 hours (approx.) · from $70

Sail Frenchman Bay aboard the Schooner Margaret Todd with a licensed captain and crew. You’ll pass the Porcupine Islands, view Acadia National Park from the water, watch for seals and bald eagles, and relax on spacious decks. Bring a jacket, arrive 45 minutes early, and expect a group of up to 150 people.

“Overall, a nice ride around the harbor. Could have had a little more narration to make it more interesting, but still quite enjoyable.”

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Key West Champagne Sunset Catamaran Cruise - Seeing Mallory Square from the water
Boat Tours in Key West, Cruises & Boat Tours, Florida Tours, Key West Tours, Sailing, Sunset Cruises, Sunset Cruises in Key West, Tour Reviews, Wine Tours

Key West Champagne Sunset Catamaran Cruise

13.Key West Champagne Sunset Catamaran Cruise

★★★★★★★★★★4.5 · 586 reviews · 1 hour 30 minutes (approx.) · from $59

Sail from Key West Historic Harbor on a 90-minute catamaran cruise timed for sunset. Sip champagne, wine, beer, sangria, margaritas, soft drinks, or water while watching the island from offshore. The crew shares the best sunset viewpoints, and you may spot birds, fish, dolphins, or other marine life.

“This was an awesome cruise! The crew were attentive and very polite. The view was incredible and the food was great! Not dinner but light appetizers. A must do for any Key West visit!”

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Boston: Harbor Sunset Yacht Cruise - The Northern Lights: Choose Your View
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Boston: Harbor Sunset Yacht Cruise

14.Harbor Sunset Yacht Cruise

★★★★★★★★★★4.6 · 570 reviews · 2 hours · from $54

Spend two hours aboard the 115-foot Northern Lights, a 1920s-style New England yacht sailing from Rowes Wharf. Choose the climate-controlled cabin or open deck, buy drinks and snacks by credit card, and watch Boston light up at sunset. The route includes Castle Island, the inner harbor, and a cannon firing from the USS Constitution.

“We enjoyed the cruise. It rained on our cruise but it wasn't a deal breaker. We were able to see the USS Constitution shoot its cannon off at sunset which was cool.”

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NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols - From Chelsea Piers to the lower harbor
Boat Tours in New York City, Cruises & Boat Tours, Jazz & Live Music, Live Music Tours in New York City, New York City Tours, Sailing, Tour Reviews

NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols

15.Holiday Yacht Cruise with Jazz, Cocoa & Carols

★★★★★★★★★★4.7 · 568 reviews · 1h 30m · from $134

Spend 90 festive minutes aboard the classic yacht Manhattan or Manhattan II, sailing from Chelsea Piers past Battery Park, the Seaport, Governor’s Island, Ellis Island, and the Statue of Liberty. Enjoy a heated salon, assigned seating, cookies, cocoa, carols, live jazz, and one included champagne, wine, or beer.

“Fantastic live jazz band on board doing all the Christmas classics. Thoroughly enjoyed! Beautiful to see skyline and Statue of Liberty all lit up! Yummy cocktails and cookies too. Highly recommend.”

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New in Sailing

★ 4.5Dry Tortugas National Park Day Trip by Catamaran from Key WestFrom $220433 reviews
★ 5.0Kalapaki Kai Sunset Catamaran CruiseFrom $109349 reviews
★ 5.0Na Pali Coast Power CatamaranFrom $274403 reviews
★ 5.0Fort Lauderdale Sailing CharterFrom $150387 reviews
★ 5.0Private tour for 12 people on a 40 ft Yacht, Ft Lauderdale bayFrom $184341 reviews
★ 5.0Private Luxury Yacht Charters, BYOB & Dolphins395 reviews
★ 4.5Sunset Sailing Cruise on a Tall Ship in Boston HarborFrom $68414 reviews
★ 4.5Waikoloa Signature Catamaran Sunset SailFrom $159396 reviews
★ 4.7Waikiki Sunset Catamaran Cocktail CruiseFrom $99348 reviews
★ 4.8From Ma’alaea: ‘Alihilani Sunset Sail Catamaran TourFrom $114348 reviews
★ 4.9Sunset Yacht CruiseFrom $113461 reviews

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