USA · SAILING

15 Sailing Trips in the USA Worth Booking

40 tours  ·  from $41

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 - Shell Island: the main stop
Cruises & Boat Tours, Panama City Beach Tours, Sailing, 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. You can watch for wild dolphins, snorkel in St. Andrews Bay, paddle board, ride the waterslide, or walk the beach. Crew members including Captain Clay, Keith, Heath, Sarah, and Emma have helped make trips lively and well organized.

“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 - Kealakekua Bay and its difficult history
Big Island of Hawaii Tours, Boat Tours in the Big Island, Cruises & Boat Tours, Lunch Experiences, Sailing, 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 from Kona to historic Kealakekua Bay aboard a power catamaran, with snorkeling gear, flotation aids, lunch, and a crew led by captains such as Aiden or Bryce. Expect clear water, reef fish, possible dolphins and winter whales, plus a slide and rinse shower on the boat.

“We had a great time, everything ran very smooth. Guides are funny and knowledgeable about the island. Saw dolphins, humpbacks and plenty of different reef fish and coral. Boat is very comfortable and lunch was delicious. Highly recommend doing this experience. Friendly for all ages.”

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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed - Snorkeling at the one-hour Turtle Canyon stop
Boat Tours in Oahu, Cruises & Boat Tours, Lunch Experiences, Oahu Tours, Sailing, 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

Join Hawaii Nautical’s 40-person Honu Lani from Kewalo Basin for a 2 to 3-hour cruise to Turtle Canyon. Guides such as Chris, Natalie, Greta, and Captain JoJo provide safety help, premium gear, lunch, and drinks on the midday trip, with a free re-ride if turtles do not appear.

“Only saw one turtle and very few fish. Water was overcrowded and hard to see anything. Would not recommend”

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Sunset & Dolphin Catamaran Cruise with Island Time - Key points to know before you sail
Cruises & Boat Tours, Evening Experiences, Panama City Beach 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

Set sail from 5201 N Lagoon Dr for a two-hour sunset cruise through Grand Lagoon. Island Time Sailing’s crew, including Captain Clay and Christo on some departures, looks for dolphins, raises the sails, serves drinks for purchase, and ends with dockside music, games, and dancing.

“Fantastic! The crew was incredibly nice and welcoming. I thought it was nice that they came around and took pictures for us! We saw plenty of dolphins. The amount of time on the water was appropriate. I liked that there was a bar onboard!”

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Waikiki Turtle Snorkel and Sail on Hawea Catamaran - Safety help in the water
Boat Tours in Oahu, Cruises & Boat Tours, Oahu Tours, Sailing, Tour Reviews

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

5.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. Crew members such as Jenna, Julia, Claire, and Dez help you spot turtles, fish, octopuses, and reef life. Snorkel gear, drinks, cold brew, snacks, and a scenic sail are included.

“Best snorkel tour! For someone who hasn’t done a snorkel tour in awhile this was perfect. The staff was excellent fun and so helpful. They all made the experience amazing. We saw 3 turtles and some fish. On the return ride tried to see whales but none some saw flying fish! Next time I come with fam I will book this tour. Smooth and way from booking to end of tour. Def worth it!”

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Manhattan Architecture Yacht Cruise - Boarding at Pier 62 in Chelsea
Boat Tours in New York City, Cruises & Boat Tours, New York City Tours, Sailing, Tour Reviews

Manhattan Architecture Yacht Cruise

6.Manhattan Architecture Yacht Cruise

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

Spend about 2 hours 45 minutes circling Manhattan aboard a classic 1920s-style yacht. An American Institute of Architects New York guide, including hosts such as Jenny, Ginny, Doug, and John on recent departures, explains landmark buildings, bridges, neighborhoods, and waterfront design. Indoor seating, open-air views, and one free drink are included.

“We had such a wonderful experience! Our tour guide John, was incredibly knowledgeable. When he was asked questions about other places on the tour that he had not yet described, he was immediately able to provide a very thorough and detailed description. And the team on the boat servicing us were absolutely delightful! I would not hesitate to do this again and again. I was on this trip celebrating my birthday with my sister. It was so very special! Don’t hesitate to book this. You won’t regret it!”

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San Francisco Bay Sunset Cruise by Luxury Catamaran - Finding Gate J at Pier 39
Boat Tours in San Francisco, Cruises & Boat Tours, Evening Experiences, Sailing, San Francisco Tours, Sunset Cruises, Tour Reviews, VIP

San Francisco Bay Sunset Cruise by Luxury Catamaran

7.San Francisco Bay Sunset Cruise by Luxury Catamaran

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

You’ll spend 90 minutes aboard Adventure Cat Sailing Charters, leaving from Pier 39 with a friendly English-speaking crew. Expect Alcatraz, Sausalito, the Golden Gate Bridge, skyline views, sea lions, canvas trampoline nets, a protected cabin, and one complimentary drink.

“I highly recommend doing this activity. There are breathtaking views and what we most liked was the service. The crew and staff are pretty friendly ;)”

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Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - Boarding at Boss Frog’s near the harbor
Boat Tours in Maui, Cruises & Boat Tours, Maui Tours, Sailing, Tour Reviews, Tours, Whale Watching, Whale Watching in Maui

Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

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

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

Cruise Maui’s Ma'alaea Bay aboard Quicksilver’s double-deck power catamaran during whale season. Captain and crew explain humpback behavior, while underwater hydrophones let you hear whale songs. Choose shaded or open-air seating, with drinks, restrooms, and wide viewing areas on board.

“We took our daughter on a whale-watching excursion for her ninth birthday. She was thrilled to observe the whales jumping. She counted nearly 20 of them. The tour guide was extremely knowledgeable and provided us with a wealth of information about the whales and their migration. Sandy Palmer”

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Miami: 2 Hour Private Yacht Cruise - Star Island and the famous homes route
2-Hour Experiences, Boat Tours in Miami, Cruises & Boat Tours, Miami Tours, Private, Sailing, Tour Reviews

Miami: 2 Hour Private Yacht Cruise

9.2 Hour Private Yacht Cruise

★★★★★★★★★★5.0 · 899 reviews · 2 hours (approx.) · from $98

Spend two hours on a private Miami yacht with your own group, passing Bayside Marketplace, Star Island, and celebrity homes. Bring food and drinks, use the onboard cooler and Bluetooth speaker, and choose a captain such as Jorge, Alex, or Eduardo. Expect extra captain and fuel charges.

“Worst Experience. Not at all satisfied and captain is not at all friendly. He is in a rush and not at all explained anything about the place. Money waste.”

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2 Hour Sailing Cruise on Lake Tahoe - The two-hour route changes with the wind
2-Hour Experiences, Cruises & Boat Tours, Sailing, Tour Reviews

2 Hour Sailing Cruise on Lake Tahoe

10.2 Hour Sailing Cruise on Lake Tahoe

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

Spend two hours sailing South Lake Tahoe aboard Blue, a Coast Guard-certified 40-foot yacht limited to 14 public-cruise passengers. Captains such as Justin and crew members including Nellie, David, and Kyle may share lake facts while you enjoy complimentary beer, wine, water, and non-alcoholic drinks. The route changes with the wind.

“Had a great time. The crew was outstanding and full of great information and both were outstandingly personable. Would book agsin.”

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Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona - Breakfast first, then the open Kona water
Big Island of Hawaii Tours, Boat Tours in the Big Island, Cruises & Boat Tours, Sailing, Tour Reviews, VIP

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

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

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

Spend 4.5 hours aboard Body Glove’s spacious catamaran from Kailua-Kona. Expect a coastal cruise, dolphin and seasonal whale sightings, about two hours in the Red Hill snorkeling area, breakfast, barbecue lunch, slides, paddleboards, and attentive water safety staff.

“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 - A fast, steady ride through Resurrection Bay
Alaska Tours, Boat Tours in Alaska, Cruises & Boat Tours, Lunch Experiences, National Park Tours, National Parks, Sailing, Tour Reviews

Seward: Kenai Fjords National Park Catamaran Cruise w/Lunch

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

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

From Seward, cruise Resurrection Bay and Kenai Fjords National Park on a stable catamaran with captains such as Laura, Nicole, and Chris. Watch for whales, puffins, sea otters, sea lions, and seals, pause at a tidewater glacier, and eat a deli lunch onboard.

“This was the highlight of our trip! The beauty of the Kenai fjords is indescribably beautiful. The catamaran was comfortable and the lunch was great! All the crew was available to all! What an incredible experience. Don’t miss it!!”

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Sunset Dolphin Sail Aboard the Privateer Catamaran - Dolphins, deer, and the western horizon
Cruises & Boat Tours, Evening Experiences, Panama City Beach Tours, Sailing, Tour Reviews

Sunset Dolphin Sail Aboard the Privateer Catamaran

13.Sunset Dolphin Sail Aboard the Privateer Catamaran

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

Spend about two hours on Paradise Adventures’ Privateer catamaran, watching for dolphins and deer as the Gulf sunset fades. Captain Mike, Lamar, Chelsea, and other crew members keep the mood friendly, with tropical music, one included drink, an onboard bar, snacks, and live music on selected evenings.

“The music was great and the crew was amazing ..Got to see a mama deer and baby swimming to shore..Had a amazing dolphin show ❤️ 😍 💕 💖 strongly recommend”

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Sunset Catamaran Cruise in Ft. Lauderdale - The Atlantic sunset and the raised sails
Boat Tours in Fort Lauderdale, Cruises & Boat Tours, Evening Experiences, Fort Lauderdale Tours, Sailing, Tour Reviews

Sunset Catamaran Cruise in Ft. Lauderdale

14.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 cruise past waterfront mansions and Port Everglades. The crew, including captains Jim and Joe and mate Justin, guides you toward open water, where the sails rise and a complimentary champagne toast meets the sunset.

“The cruise was very relaxing and informative, guided by shipmate Justin and Captain Jim. Great views of mansions and narration while heading out to sea. The cruise was motorized until we reached the sea, then sails went up and it was a very peaceful, calm ride. Great views toward the city and the sunset. I would note two things--finding the boat was a bit unclear. We initially overshot the walkway to the boat and ended up several boats further, then had to ask for directions and backtracked to correct boat. Also, the boat was smaller and not as new as we had expected from the photos. However, after leaving the…”

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Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea - What Turtle Canyon offers underwater
Boat Tours in Oahu, Cruises & Boat Tours, Oahu Tours, Sailing, Snorkeling, Snorkeling Trips in Oahu, Tour Reviews

Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

15.Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

★★★★★★★★★★4.7 · 656 reviews · 2h 30m · from $84

Spend 150 minutes aboard Hāwea, a hand-built 50-foot catamaran, snorkeling at Turtle Canyon and sailing past Waikiki. The crew, including captains Jenny, Connie, and Woody on some departures, provides gear, safety guidance, non-alcoholic drinks, and turtle-spotting help.

“Was such an awesome time, the waves crazy, but the crew made sure we were safe, they made sure we could find and see turtles! Would do again forsure!”

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New in Sailing

★ 4.0NEGRIL CATAMARAN CRUISE Sunset Ricks Cafe Adults only ALL HOTELSFrom $88390 reviews
★ 5.0Molokini and Turtles Luxury Yacht SnorkelFrom $263477 reviews
★ 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
★ 4.5America’s Cup 12-Meter Yacht Afternoon Sail from Hilton HeadFrom $55504 reviews
★ 5.0Fort Lauderdale Sailing CharterFrom $150387 reviews
★ 5.0Private tour for 12 people on a 40 ft Yacht, Ft Lauderdale bayFrom $184341 reviews
★ 5.0Ft. Lauderdale Mini Powerboat Rental. Canal, Yacht, Mansion Tour494 reviews
★ 4.5Clearwater Evening Yacht Cruise with Optional DiningFrom $40464 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
★ 4.9Golden Gate Bridge Catamaran CruiseFrom $65499 reviews
★ 4.8Sal: All-Inclusive Half-Day Lounge Catamaran CruiseFrom $81486 reviews

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