USA · SAILING

15 Sailing Trips in the USA Worth Booking

31 tours  ·  from $41 a head

Good sailing trips fill up weeks ahead and the great ones go first. Below: the 15 to book early, what each includes and how they differ.

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time - Watching wild dolphins from a sailing catamaran
Cruises & Boat Tours, Dolphin & Manatee Tours, Sailing, Snorkeling, Shark & Manta Ray Tours, Tour Reviews, Tours in Panama City Beach

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 on Island Time’s spacious catamaran to Shell Island, watching for wild dolphins along the way. At the island, use provided snorkel gear and paddleboards, ride the waterslide, or walk the beach for shells. A crew including Captain Clay, Heath, Sarah, Emma, and Carter may vary by departure.

“The captain, Keith and his crew were very informative and helpful. Their goal was to help us have a wonderful trip and it met our expectations and more. The attention to detail including doing everything to assure we saw loads of schools of dolphins up close! It was a cold and windy day and they offered us to stay below deck to keep the wind and cold blocked as much as possible! If their were 10 stars we would rate them 10 out of 10! We highly recommend this trip!”

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Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - Snorkeling, flotation, and getting back aboard
Cruises & Boat Tours, Lunch Experiences, Sailing, Snorkeling Tours in Big Island of Hawaii, Snorkeling, Shark & Manta Ray Tours, Tour Reviews, Tours in Big Island of Hawaii

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 from Honokohau Harbor to historic Kealakekua Bay aboard a power catamaran with Hang Loose Boat Tours. Captain Aiden, Captain Bryce, Jordan, Kiwami, and the crew may share local history, search for dolphins and winter humpback whales, and guide you to clear water filled with reef fish. Snorkel gear, lunch, drinks, a rinse shower, and boat slides are included.

“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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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed - Waikiki and Diamond Head from the water
Cruises & Boat Tours, Lunch Experiences, Sailing, Snorkeling Tours in Oahu, Snorkeling, Shark & Manta Ray Tours, Tour Reviews, Tours in Oahu

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

Sail from Kewalo Basin aboard the power catamaran Honu Lani, then snorkel with green sea turtles at Turtle Canyon. A guide joins you in the water, and the crew provides premium gear, flotation devices, drinks, and lunch on the midday trip. Watch for dolphins and seasonal whales along the Waikiki coast.

“Great experience! The crew was very experienced and made sure we all felt safe and secure. They were very knowledgeable and made out adventure that much more intriguing.”

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Sunset & Dolphin Catamaran Cruise with Island Time - Key points to know before you book
Cruises & Boat Tours, Dolphin & Manatee Tours, Evening Experiences, Sailing, Tour Reviews, Tours in Panama City Beach

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

Join Island Time Sailing at 5201 N Lagoon Drive for a 2-hour sunset catamaran cruise through Grand Lagoon. Look for dolphins near St. Andrews State Park, enjoy music and sunset views, and buy drinks from the onboard bar. The cruise ends with games and dancing at the dock, weather permitting.

“My daughter and I went and had so much fun watching the dolphins! I’ve been on a lot of tours with different companies and Christo was the best at getting us wonderful views of dolphins jumping out of the water. It was absolutely incredible! The girls working were so attentive making sure everyone on the boat was well taken care of. Thank you Sara and Audra for taking pics and getting our drinks! And yes, even “fishing” something out of the water that a guest dropped. We will book with them again!”

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San Francisco Bay Sunset Cruise by Luxury Catamaran - A 90-minute route with San Francisco in every direction
Cruises & Boat Tours, Dinner & Sunset Cruises, Evening Experiences, Sailing, Tour Reviews, Tours in San Francisco, VIP

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

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, 360-degree views, and access to open trampoline nets or a protected viewing area. Bring a jacket, since wind and spray can make the bay feel cold.

“such a cool experience sailing under the Golden Gate Bridge on a Catamaran. I was thankful that they had coats for us to use as I underestimated the cold and wet while on the boat. Highly recommend to anyone that wants some good ole fun and beautiful sight seeing”

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Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - Boarding the double-deck power catamaran
Cruises & Boat Tours, Sailing, Tour Reviews, Tours, Tours in Maui, Whale Watching

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 from Ma'alaea Harbor aboard Quicksilver's double-deck power catamaran during Maui's December to April whale season. Captain Kiwi, Carlos, Paul, and other crew members have provided lively whale narration, while hydrophones let you hear whale songs. Expect open views, shaded seating, drinks, restrooms, and a chance to see breaching calves.

“Everything was great!! We seen whales! The sun was shining it was a good day. The captain was very friendly and knowledgeable about the whales. The staff were polite and friendly served drinks . We would highly recommend this whale tour!!!”

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Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona - Breakfast, Kona views, and the search for dolphins
Cruises & Boat Tours, Dolphin & Manatee Tours, Sailing, Snorkeling Tours in Big Island of Hawaii, Snorkeling, Shark & Manta Ray Tours, Tour Reviews, Tours in Big Island of Hawaii, VIP

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

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

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

Spend about 4.5 hours aboard Body Glove’s large catamaran from Kailua Pier. You’ll cruise Kona’s coast, watch for dolphins and whales, snorkel near Red Hill for about two hours, and enjoy breakfast, BBQ lunch, slides, a high-jump platform, paddleboards, and floating mats. Captain Erica and crew members such as Adam, Brianna, and Taylor have earned special praise for their care and service.

“There were many snorkeling companies, but I never regret choosing this.The staff were super kind and the breakfast and lunch they provided were so delicious with fresh ingredients. On the way to the snorkeling spot, we could see a group of dolphins. Besides snorkeling, they provided various swimming equipment for children to enjoy. It was a very satisfying experience and I want to do it again!!”

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Seward: Kenai Fjords National Park Catamaran Cruise w/Lunch - Searching Resurrection Bay for wildlife
Cruises & Boat Tours, Lunch Experiences, National Parks, Sailing, Tour Reviews, Tours in Seward

Seward: Kenai Fjords National Park Catamaran Cruise w/Lunch

8.Kenai Fjords National Park Catamaran Cruise w/Lunch

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

Board Major Marine Tours’ catamaran in Seward for a six-hour Kenai Fjords cruise through Resurrection Bay. Your captain points out whales, puffins, sea otters, seals, sea lions, and calving glaciers, while you enjoy a deli sandwich, warm drinks, and wide ocean views. Captains including Laura, Nicole, and Chris have earned praise for their wildlife spotting and clear narration.

“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 Dolphin Sail Aboard the Privateer Catamaran - Finding Paradise Adventures at 4114 Jan Cooley Drive
Cruises & Boat Tours, Dolphin & Manatee Tours, Evening Experiences, Sailing, Tour Reviews, Tours in Panama City Beach

Sunset Dolphin Sail Aboard the Privateer Catamaran

9.Sunset Dolphin Sail Aboard the Privateer Catamaran

★★★★★★★★★★5.0 · 709 reviews · 2 hours (approx.) · from $45

Spend about two hours aboard Paradise Adventures’ Privateer catamaran, watching for dolphins and deer as the sun drops over the Gulf. Captain Mike, Lamar, and other crew members keep the trip friendly and informative. Your ticket includes one beverage, music on selected evenings, and access to a cashless bar selling cocktails and snacks.

“Beautiful evening on the water—saw lots of dolphins and even two large sea turtles. A young musician provided some great live music and the crew was very attentive to every guest. Captain Mike & the brother & sister first mates were lots of fun and very engaging! We saw a gorgeous sunset and wrapped up our cruise with sone great party tunes!”

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Sunset Catamaran Cruise in Ft. Lauderdale - Millionaires Row from the water
Cruises & Boat Tours, Evening Experiences, Sailing, Tour Reviews, Tours in Fort Lauderdale

Sunset Catamaran Cruise in Ft. Lauderdale

10.Sunset Catamaran Cruise in Ft. Lauderdale

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

Sail from Spirit of Lauderdale past waterfront mansions and Port Everglades, then head into the Atlantic for sunset. Your roughly two-hour catamaran cruise includes one glass of champagne, shaded seating, restrooms, light snacks, and a cash bar. Captains and crew such as Jim, Joe, Justin, Maria, and Marcos are known for friendly service and useful narration.

“Very cooperative and considerate crew. Professional and safe voyage. Would definitely go again as well recommend to others.”

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1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain - Sailing past the Porcupine Islands
Cruises & Boat Tours, Sailing, Tour Reviews, Tours in Bar Harbor

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

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

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

Board the Schooner Margaret Todd at Bar Harbor for a roughly two-hour sail through Frenchman Bay. You’ll pass the Porcupine Islands, view Acadia National Park from the water, watch for eagles and seals, and help raise the sails if invited. Bring a jacket, arrive 45 minutes early, and expect a shared sailing with up to 150 people.

“This is an excellent way to get a view of the beauty of the surroundings from the water. A great experience.”

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Evening Yacht Cruise with Optional Dining in St. Petersburg - Key details before you book
Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Sailing, Tour Reviews, Tours in St Petersburg

Evening Yacht Cruise with Optional Dining in St. Petersburg

12.Evening Yacht Cruise with Optional Dining in St. Petersburg

★★★★★★★★★★4.5 · 590 reviews · 2 hours 30 minutes (approx.) · from $40Best value

Board the 113-foot StarLite Sapphire in South Pasadena for about two and a half hours on the Gulf. Enjoy two decks, waterfront lights, live DJ music, dancing, and stargazing. Dinner and drinks cost extra, so you can choose a full meal or simply cruise with a drink and the sea air.

“If you are wanting to enjoy an evening out to relax and vibe, this is the perfect place. Very friendly and welcoming. It was also a little cold for me in the inside so I would recommend a jacket or long dress. Other than that it was a great experience and something the mark off your bucket list.”

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Boston: Harbor Sunset Yacht Cruise - Leaving Rowes Wharf behind the Boston Harbor Hotel
Cruises & Boat Tours, Evening Experiences, Sailing, Tour Reviews, Tours in Boston

Boston: Harbor Sunset Yacht Cruise

13.Harbor Sunset Yacht Cruise

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

Settle aboard the 115-foot Northern Lights for a two-hour sunset cruise from Rowes Wharf. Enjoy Boston skyline views, light commentary, music, open decks, climate-controlled seating, and a full bar selling drinks by credit card. The route passes Castle Island and the USS Constitution, where you may see the traditional sunset cannon firing.

“Very beautiful! We saw a double rainbow completely over the water! Sunset was pretty too. Was cool to see airplanes flying over us when we cruised by the airport. Very picturesque with the Boston skyline. Highly recommended! The meeting point was a little difficult to find though”

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NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols - Inside Manhattan and Manhattan II
Cruises & Boat Tours, Jazz, Gospel & Live Music Tours, Sailing, Tour Reviews, Tours in New York City

NYC: Holiday Yacht Cruise with Jazz, Cocoa & Carols

14.Holiday Yacht Cruise with Jazz, Cocoa & Carols

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

Cruise New York Harbor for 90 minutes aboard the classic yacht Manhattan or Manhattan II. You will have an assigned seat in a heated salon, hear live jazz and carols, enjoy cocoa, cookies, and one included beverage, and pass Battery Park, the Financial District, Governor’s Island, Ellis Island, and the Statue of Liberty.

“This was FABULOUS. I thought there was a 50/50 shot it would be a cheesy waste of time. But it turned out to be one of our favorite experiences in NYC. The staff were all SO kind, always offering photos/refreshments, and the jazz band was great!! My only warning is the hot chocolate is very clove-y, which we would have passed on if we knew. But this was a 10/10 and our photos are amazing to remember the trip!”

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Manhattan: Statue and Skyline Cruise Aboard a Luxury Yacht - Hudson River views and the Manhattan skyline
Cruises & Boat Tours, Sailing, Tour Reviews, Tours in New York City, VIP

Manhattan: Statue and Skyline Cruise Aboard a Luxury Yacht

15.Manhattan: Statue and Skyline Cruise Aboard a Luxury Yacht

★★★★★★★★★★4.8 · 540 reviews · 1h 30m · from $60

Cruise New York Harbor aboard a 1920s-style yacht with teak decks, mahogany trim, and a heated or air-conditioned observatory. You’ll pass the Statue of Liberty, Ellis Island, Battery Park, Governor’s Island, and Lower Manhattan. Captain Levi and crew members such as Jesse, Devon, Conor, and Sarah have helped make this a relaxed, personal cruise with one drink included.

“Crew and boat were fantastic. Scenery was breathtaking. History along the way by captain was a nice touch.”

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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

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