Sailing trips · USA SAILING TRIPS

The 15 Best Sailing Trips in the USA

110 trips  ·  from $18 a head

Key West sunsets, Hawaiian snorkel catamarans, San Diego bay sails and the Newport schooners. The 15 below are priced and timed, with a note on which run all year and which stop with the season.

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time - Dolphin Watching Works Best When You Treat It as Wildlife Viewing
Catamaran Cruises, Catamaran Cruises in the USA, Island Hopping Sailing Trips, Panama City Beach Sailing Trips, Sailing & Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Tour Reviews, USA Sailing Trips, Whale & Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

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 aboard Island Time’s broad, stable catamaran, with time to search for wild dolphins, snorkel at Shell Island and St. Andrews Bay, paddleboard, swim, or use the waterslide. Captain Heath, Clay, Keith, Sarah, Emma, and other crew members have earned strong praise for friendly service and practical help on board.

“This was absolutely so much fun, such an amazing group of staff. Soooo cool- saved it for our last little extravaganza & it was absolutely worth it.”

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Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - The Key West sights from the water
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Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

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

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

Sail from Key West for about two hours aboard a spacious catamaran with sunset views, live local music, an open bar, shrimp, antipasti, mini tarts, and soft drinks. Arrive 30 minutes early, claim a good bow seat, and bring a sweater for breezy evenings.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

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City Cruises Boston Whale Watching Cruise by High-Speed Boat - Why Stellwagen Bank matters
City Tours, Tour Reviews, USA Sailing Trips, Whale & Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

City Cruises Boston Whale Watching Cruise by High-Speed Boat

3.City Cruises Boston Whale Watching Cruise by High-Speed Boat

★★★★★★★★★★4.5 · 3,115 reviews · 3 hours 30 minutes (approx.) · from $85

From Long Wharf, you’ll ride a high-speed catamaran to Stellwagen Bank with a naturalist guide, watching for humpback, fin, minke, and pilot whales, dolphins, and seabirds. Expect about 3.5 hours on the water, indoor seating, restrooms, and snacks for purchase.

“Saw a humpback blow and dive several times, including one up close. The narrator was great and enthusiastic.”

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Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - The boat ride from Honokohau Marina
Big Island of Hawaii Sailing Trips, Catamaran Cruises, Catamaran Cruises in the USA, Island Hopping Sailing Trips, Lunch Experiences, Sailing & Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Trips with Lunch & BBQ, Tour Reviews, USA Sailing Trips

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

4.Captain Cook Snorkel On A Power Catamaran With Lunch

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

Cruise from Honokohau Marina to historic Kealakekua Bay on a power catamaran with Captain Aiden, Bryce, Jordan, or Kiwami. Snorkel among coral and fish, watch for dolphins and winter humpback whales, then enjoy sandwiches, fruit, snacks, and drinks before the coastal ride home.

“Super fun and knowledgeable! Very informative about the reef and marine animals. Staff was super friendly! Will definitely be coming back!”

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Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - A two-hour route along Waikiki and Diamond Head
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

5.Moana’s Sunset Cocktail Sail

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

Set sail from Kewalo Basin Harbor for two hours along Waikiki and past Diamond Head. The Moana Catamaran offers a barefoot cruise, a premium full bar with your first drink included, and a chance to spot dolphins or humpback whales. Crew members such as Vivian help keep the mood warm and relaxed.

“The crew were very attentive and made the trip enjoyable despite the rough seas and some people suffering from sea sickness. Drinks were plentiful with a good variety.”

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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed - Waikiki and Diamond Head from the water
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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

6.Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

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

Sail from Kewalo Basin to Turtle Canyon aboard the 40-passenger Honu Lani. Snorkel with green sea turtles under crew guidance, then enjoy lunch and drinks on the midday trip. Chris, Natalie, Greta, Joey, and other crew members have earned praise for calm, attentive service.

“Great experience!! Joey and crew did a great job giving us the turtle/snorkeling experience! Hawaii on a catamaran is definitely a must!! Get out there with them and experience this thrilling adventure! The dolphins were also so beautiful! My tik tok will definitely be awesome with these shots! 100% guys!!!”

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Sunset & Dolphin Catamaran Cruise with Island Time - Key points at a glance
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Sunset & Dolphin Catamaran Cruise with Island Time

7.Sunset & Dolphin Catamaran Cruise with Island Time

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

Spend about two hours aboard Island Time Sailing’s catamaran from Panama City Beach. Cruise Grand Lagoon, watch for dolphins near St. Andrews State Park, enjoy sunset views, music, and drinks from the onboard bar. The crew, including Captain Clay and Cristo, may also invite you to dance and play games at the dock.

“This is an incredible experience! Crew was excellent and friendly! Dolphins and sunset was amazing. Highly recommend!”

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Waikiki Turtle Snorkel and Sail on Hawea Catamaran - Snorkeling gear and crew support reduce the fuss
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Waikiki Turtle Snorkel and Sail on Hawea Catamaran

8.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

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

Join the Hawea catamaran from the Duke Kahanamoku Statue for a 2.5-hour Waikiki sail and snorkel at Turtle Canyon. You’ll get gear, flotation support, snacks, drinks, and guidance from crew such as Jenna, Julia, Claire, and Kapono. Swimming ability is required, and the group can reach 45 people.

“The crew made this an awesome, safe, and fun experience! The bar onboard was a great bonus after snorkeling :-)”

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Key West Afternoon Snorkel Sail with Unlimited Cocktails! - What the snorkeling time is really like
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Key West Afternoon Snorkel Sail with Unlimited Cocktails!

9.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. You’ll get gear, a safety briefing, and time to snorkel before the open bar begins on the ride home. Captain Brett and the Sebago crew are known for a safety-first approach, though the boat can feel busy.

“The boat, the trip and the crew were all amazing. Recommend this highly. Will definitely go on this excursion with the same company again!”

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Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed - What the two-hour schedule feels like
Catamaran Cruises, Catamaran Cruises in Oahu, Catamaran Cruises in the USA, Oahu Sailing Trips, Sailing & Snorkeling Trips, Sailing and Snorkeling Trips in Oahu, Sailing and Snorkeling Trips in the USA, Tour Reviews, Tours, USA Sailing Trips, Whale & Dolphin Watching Sails, Whale and Dolphin Watching Sails in Oahu, Whale and Dolphin Watching Sails in the USA

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

10.See Turtles 100% Guaranteed

★★★★★★★★★★5.0 · 1,420 reviews · 2 hours (approx.) · from $49

Join Oahu Catamarans for a two-hour catamaran trip from Honolulu to Turtle Canyon. Swim with Hawaiian green sea turtles and tropical fish while guides such as Lucy, Shannon, and Krash help in the water. The boat carries no more than 28 people, with gear, drinks, snacks, and turtle sightings included.

“Very exhilarating experience - thecrew - Greg, Shannon & Haley - were wonderful!! Would definitely recommend’”

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Manhattan Architecture Yacht Cruise - Woolworth Building and Lower Manhattan’s Older Towers
Luxury Yacht Cruises, Luxury Yacht Cruises in New York City, Luxury Yacht Cruises in the USA, New York City Sailing Trips, Tour Reviews, USA Sailing Trips

Manhattan Architecture Yacht Cruise

11.Manhattan Architecture Yacht Cruise

★★★★★★★★★★5.0 · 1,395 reviews · 2 hours 45 minutes (approx.) · from $113

Board a 1920s-style yacht at Pier 62 for a 2-hour-45-minute cruise around Manhattan. An American Institute of Architects guide explains landmark buildings, bridges, neighborhoods, and waterfront design. You get an assigned table, one beer, wine, or soft drink, indoor seating, and open-air photo spots.

“The lecturer from the AIA was extremely interesting and informative about the history of the buildings and the events in different periods. It was a relaxed atmosphere, and questions were welcomed. Also, the captain and boat crew were friendly and professional.”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Checking in at 255 Front Street
Evening Experiences, Key West Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips, Wine Tours

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

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

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

Board Danger Charters at 255 Front Street for a two-hour sunset sail limited to 26 people. Crew members such as Mary, Connor, Lexi, Tony, and Molly have served wines, beer, small bites, stories, and blankets while the boat heads offshore for sunset.

“The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!”

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San Francisco Bay Sunset Catamaran Cruise - Alcatraz at twilight and the changing San Francisco skyline
Bay, Harbour & Coastal Sailing, Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, San Francisco Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

San Francisco Bay Sunset Catamaran Cruise

13.San Francisco Bay Sunset Catamaran Cruise

★★★★★★★★★★5.0 · 1,342 reviews · 1 hour 35 minutes (approx.) · from $88

Board Adventure Cat at Pier 39 for a 1-hour-35-minute sunset sail past Alcatraz and beneath the Golden Gate Bridge. Choose a sheltered seat or the open trampoline, enjoy one beer, wine, or soft drink, and bring a jacket for the chilly bay air.

“It was freezing and so windy I thought I would go overboard. The opportunities for photos were not many so it felt like a bit of a waste of $$$. I would check the weather before hand the fog rolled in and the bridge was barely visible. They did have jackets but like if you can’t even walk up outside onto the deck cause it’s so windy what’s the point. Also too many people.”

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San Francisco Bay Sunset Cruise by Luxury Catamaran - A 90-minute route through the heart of the bay
Bay, Harbour & Coastal Sailing, Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, San Francisco Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips, VIP

San Francisco Bay Sunset Cruise by Luxury Catamaran

14.San Francisco Bay Sunset Cruise by Luxury Catamaran

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

Board Adventure Cat Sailing Charters at Pier 39 for a 90-minute sunset sail past Alcatraz, Sausalito, and the Golden Gate Bridge. You get one complimentary drink, open-air trampoline nets, sheltered seating, and audio commentary in several languages. Bring warm layers for the cool, sometimes wet bay air.

“Liked being with a small group as opposed to a large group on a bigger boat, getting up in the captain’s chair was really cool!”

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Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - Boarding the spacious Quicksilver catamaran
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Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

15.Whale Watching Tour Aboard Power Catamaran

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

Cruise Maalaea Bay with Quicksilver Charters from December through April. Your captain and crew explain whale behavior while you watch for breaches, tail slaps, spy-hops, mothers, and calves. The double-deck catamaran has open and shaded seating, restrooms, drinks, and underwater hydrophones.

“The tour was wonderful! We saw so many whales. Worth the $$. Dave was amazing and super attentive. The Captain (forgot his name but an Aussie and fr New Zealand) was very informative and the perfect host. There was a 3rd gentleman on the tour who was at the bar. Also, great!”

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New in USA Sailing Trips

★ 5.0Statue of Liberty Cruise aboard a Classic SailboatFrom $60129 reviews
★ 5.0Deluxe Sunset & Day Sail Small GroupFrom $119245 reviews
★ 5.02.5-Hour Small-Group Catamaran Sunset Sail with DrinksFrom $119223 reviews
★ 5.0New York City Sunset Cruise on a YachtFrom $113331 reviews
★ 4.9Sunset Sail Aboard Schooner AdirondackFrom $90283 reviews
★ 4.9Sunset Sail Aboard a SchoonerFrom $101344 reviews
★ 4.5Sunset Sail from Ma’alaea HarborFrom $151207 reviews
★ 4.8Ka’anapali Luxury Sunset Dinner SailFrom $169123 reviews
★ 4.7Ka’anapali Luxury Sunset Cocktail Sail with Open BarFrom $134150 reviews
★ 5.0Seattle Sunset Sail BYOBFrom $71187 reviews
★ 5.0San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine IncludedFrom $115331 reviews
★ 4.8Tall Sailboat Sunset Harbor CruiseFrom $79223 reviews
★ 5.0Waikiki 3pm Tradewind Sail – Open Bar IncludedFrom $53246 reviews
★ 4.7Waikiki Sunset Catamaran Cocktail CruiseFrom $99348 reviews
★ 5.0Molokini Snorkel and Performance Sail: Mā’alaea HarborFrom $200214 reviews

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