The 15 Best USA Sailing Tours

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

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

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

Spend about two hours sailing from Key West with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and chef-prepared hors d’oeuvres. A local musician provides live entertainment while you pass Mallory Square, Fort Zachary Taylor, Sunset Key, and the Key West harbor. Arrive 30 minutes early and bring a sweater.

“Wonderful experience, drinks food and music all terrific and the sunset was breathtaking. Bring a sweater”

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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

2.Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

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

Join the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a barefoot sunset sail along Waikiki and past Diamond Head. Your first premium drink is included, with more available for $8. The crew, including staff such as Viv and Eli, serves drinks while you watch for dolphins, humpback whales from November to May, and changing sunset colors.

“Great experience, great crew, very satisfied. The positive attitude of the crew made for a very enjoyable and relaxing trip. They were very attentive, boat is clean and well kept. They went to extra efforts to see a whale off of Diamond Head and we were successful at capturing whale flukes with a gorgeous sunset in the background”

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Waikiki Turtle Snorkel and Sail on Hawea Catamaran

3.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 catamaran trip to Turtle Canyon. Snorkel with green sea turtles, tropical fish, octopuses, and reef life in relatively shallow water, then sail along Waikiki. Guides such as Jenna, Julia, Claire, and Dez have been praised for attentive safety help, though you must know how to swim.

“Awesome trip with great sea life including whales, dolphins and sea turtles. The captain and staff were terrific and made sure everyone had a good time.”

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Key West Afternoon Snorkel Sail with Unlimited Cocktails!

4.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 provides gear, safety instruction, and time to snorkel in shallow reef water. After swimming, enjoy included beer, wine, soft drinks, and cocktails on the return trip. The boat has restrooms and a freshwater rinse.

“The boat was great as well as the captain and mates! I didn't see a lot of fish that was a bit disappointing. Other than that it was fun!”

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

5.Key West Small-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 Street for a two-hour sunset sail with up to eight wines, five beers, soft drinks, and wine-paired hors d’oeuvres. Crews including Mary, James, Connor, and Molly are known for warm service, stories, blankets on cool evenings, and a relaxed small-boat setting.

“Great crew, excellent wine, delicious hors d’oeuvres, beautiful sunset ~ perfect evening! Plus, the limited number of guests was definitely preferred.”

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Key West Sunset Sail with Live Music, Drinks and Appetizers

6.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Spend about two hours aboard Fury’s 65-foot catamaran as local musicians play popular cover songs, crew serve unlimited margaritas, beer, wine, champagne, soda, and seasonal appetizers. You can dance, sit in the shade, or watch the sunset near Mallory Square and Fort Zachary Taylor. Arrive early for a better seat.

“Great fun! Drinks flowed freely, great apps, but mostly awesome band & dancing under the beauty of Gods Key West sunset!!!”

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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

7.Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

★★★★★★★★★★4.5 · 936 reviews · 2 hours 30 minutes (approx.) · from $76

Sail from Kewalo Basin Harbor to Turtle Canyon for a guided snorkel with provided gear, lifeguards, and a secured raft for beginners and children. You may see turtles, tropical fish, octopuses, starfish, dolphins, or even a monk seal. The 2.5-hour trip ends with a complimentary first drink from the full bar.

“We had a great time. The staff was very nice and courteous. Water was beautiful, so relaxing so worth it.”

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Sunset Sail in Key West with Beverages Included

8.Sunset Sail in Key West with Beverages Included

★★★★★★★★★★5.0 · 907 reviews · 1 hour 30 minutes (approx.) · from $79

Sail Key West Harbor aboard Floridays’ 54-foot sailboat for about 90 minutes, with champagne, wine, margaritas, beer, and soft drinks included. The crew, including Eric, Carlo, Hunter, Chuck, Lori, and Janet, keeps the mood relaxed and personal. Expect sunset views, room to move around, and a chance of spotting dolphins.

“The boat was nice and clean. The crew was very friendly and accommodating. We had a percext view of the sunset. We enjoyed every minute of the ride.”

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2 Hour Sailing Cruise on Lake Tahoe

9.2 Hour Sailing Cruise on Lake Tahoe

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

Sail Tahoe Blue takes you from South Lake Tahoe on a two-hour cruise aboard the 40-foot Blue. The public sailing carries up to 14 people, with Coast Guard-licensed captains, local beer and wine, soft drinks, water, and an onboard restroom. Captains such as Justin, Nellie, David, and Kyle are known for friendly service and lake facts.

“Fantastic sail! Lovely Lake Tahoe is spectacular and our hosts Justin and Nellie were awesome. We will be back next year for another sail with family or friends.”

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Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

10.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122

Board the replica 1851 schooner America 2.0 at Key West Bight Marina for a relaxed two-hour sunset sail. Captains such as Janet, Rae, and Dan have guided recent trips, while the crew serves beer, wine, Champagne, soda, and plated hors d’oeuvres. You’ll pass Fort Zachary, Sunset Pier, and Sand Key Lighthouse before returning to the marina.

“Sunset was enchanting and the crew was super accommodating! Captain Dan also added historical tid bits that enhanced the Key west experience. Great trip!”

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Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

11.Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

★★★★★★★★★★5.0 · 767 reviews · 6 hours 30 minutes (approx.) · from $152

Spend 6.5 hours aboard a 65-foot schooner with guides such as Daniel, Brian, Joe, or Captain Janet. Sail through the Key West National Wildlife Refuge, snorkel in Florida Keys waters, paddle through mangroves, and enjoy a buffet lunch with unlimited beer, wine, and soft drinks. The group is limited to 20 people.

“We really enjoyed our experience with this day excursion. The captain and the deck hands were so friendly and knowledgeable. We love that it was more intimate experience. Each of the crew members took the time to talk to all the couples on board and getting to know us . Conversation with everyone was enjoyable. Loved that it wasn’t over crowded, there was enough room for everyone to sit in the boat. The light brunch was unexpected surprise. The lunch was perfect for a day trip on the sailboat. We will definitely be coming back and booking with this company again. Well worth it. We give them 5 stars all…”

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Afternoon Sail & Snorkel to the Captain Cook Monument

12.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 722 reviews · 3 hours (approx.) · from $136

From Keauhou Bay, you’ll cruise along Kona’s lava-lined coast to Kealakekua Bay, where a guide leads a one-hour snorkel near the Captain Cook Monument. Sea Paradise supplies masks, fins, flotation noodles, reef-safe sunscreen, snacks, and drinks. Expect a 44-person maximum, afternoon departure, and a crew that shares local history and ocean safety.

“The cruise was a lot of fun and supplied all the equipment needed for a great snorkeling adventure. The crew was informative and regarded safety as a high priority for those on board. We had an added bonus to see a pod of dolphins following the boat as we headed back to the harbor. Definitely recommend!”

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Sunset Dolphin Sail Aboard the Privateer Catamaran

13.Sunset Dolphin Sail Aboard the Privateer Catamaran

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

Set out from 4114 Jan Cooley Drive for a two-hour sunset cruise on the 52-foot Privateer catamaran. Captain Mike, Lamar, Chelsea, and other crew members keep the ride lively while you watch for dolphins, deer, sea turtles, and the Gulf sunset. One drink is included, with snacks and cocktails available for purchase.

“I went with my 8 year old son. So much fun!!! We would go back. We saw so many dolphins. There was music playing and it was so relaxing and beautiful.”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

14.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Set out from Key West’s Historic Seaport for a 2.5-hour catamaran cruise past Mallory Square, Fort Zachary Taylor, and Sunset Key. The crew, including captains such as Daniel and hosts such as Jordan or Gracie, serves wine, champagne, beer, soda, and small bites. Dolphins are possible, not promised.

“Wonderful experience, excellent hors d’oevres, drinks, beautiful sunset, well worth the price - would have liked to be under sail instead of engine for the trip”

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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

15.Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

★★★★★★★★★★5.0 · 695 reviews · 4 hours (approx.) · from $189

Sail Kona’s coast aboard a 50-foot catamaran with a crew that may include Captains Dan, Jacques, or Nick. Enjoy Kona coffee and pastries, watch for dolphins and seasonal whales, then snorkel for about an hour at Kealakekua Bay. A water staircase, flotation noodles, lunch, and non-alcoholic drinks are included.

“My spouse and I booked this activity for our first trip to Hawaii's Big Island. We had a great time and the crew is awesome! It was the perfect size group (around 24 folks) and there is a lot to do and see on Big Island, so the half day worked great.”

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