15 Sunset Sailing Cruises in the USA to Book

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

3.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

4.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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Sunset Sail in Key West with Beverages Included

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

6.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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Sunset Dolphin Sail Aboard the Privateer Catamaran

7.Sunset Dolphin Sail Aboard the Privateer Catamaran

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

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

8.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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Sightseeing and Sunset Catamaran Sailing Excursion

9.Sightseeing and Sunset Catamaran Sailing Excursion

★★★★★★★★★★5.0 · 617 reviews · 2 hours 30 minutes (approx.) · from $80

Sail from Capri Boulevard aboard Cool Beans, a 20-passenger catamaran with Captain Dan, Patrick, or Kyle and their crew. Choose a 2.5-hour day sail with swimming and shelling, or a two-hour sunset cruise with beer, wine, soda, water, and a champagne toast. Expect wildlife, Gulf views, limited motoring, and a relaxed pace.

“The captain and 1st Mate were great. Our weather wasn’t the best but they did everything to make sure all guests were taken care of”

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Sunset Sail Along the San Diego Skyline

10.Sunset Sail Along the San Diego Skyline

★★★★★★★★★★5.0 · 603 reviews · 2 hours (approx.) · from $109

Sail San Diego Bay for about two hours with no more than six people aboard. Captains such as Aaron, Patrick, Derek, Adam, and Maggie share the helm as you pass the USS Midway and Maritime Museum. Expect bean bags, blankets, a bathroom, sunset views, and room to bring your own food and drinks.

“Excellent sail with beautiful sunset views! Our Captain was great and informed us of everything we needed to know!”

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Evening Colors Sunset Sail Tour in Seattle

11.Evening Colors Sunset Sail Tour in Seattle

★★★★★★★★★★5.0 · 593 reviews · 2 hours (approx.) · from $59

Join Seattle’s Tall Ship for a roughly two-hour evening sail from Bell Harbor Marina. Help raise the sails, glide across Puget Sound with the engine off, and watch the Space Needle, Mount Rainier, Olympic Mountains, and sunset from the deck. Drinks are available for purchase, and a cannon salute may mark the end of the day.

“I loved the sunset sailing! Laid back and unique. Great staff. Would absolutely recommend to anyone!”

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Small-Group San Diego Sunset Sailing Excursion

12.Small-Group San Diego Sunset Sailing Excursion

★★★★★★★★★★5.0 · 592 reviews · 3 hours (approx.) · from $127

Sail San Diego’s Catalina-style boat for about three hours with no more than six people aboard. Expect sunset views of the skyline, Point Loma, Coronado Island, the USS Midway, and the bridge, plus beer, soft drinks, snacks, blankets, binoculars, and Bluetooth music. Captains such as Dave, Greg, and Reese add local insight when asked.

“We had a great time on Captain Dave’s sunset sail, he was very knowledgeable about the landmarks around San Diego harbor and was more than willing to step in and snap a photo for our group. Definitely enjoyed the complimentary snacks and beverages as well!”

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Waikiki Sunset Cocktail Sail with Open Bar

13.Waikiki Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.5 · 554 reviews · 1 hour 30 minutes (approx.) · from $84

Set sail from Waikiki aboard the Holokai Catamaran for 90 minutes of sunset views, conversation, and unlimited drinks. Choose wine, champagne, beer, soda, juice, or the signature Holokai Hooch. Crew members including Ryan, Chase, Kevin, Kayla, Bridget, and Alec have been praised for keeping the mood friendly and the bar moving.

“I would definitely recommend thus to everyone, no matter the age! Our entire family loved it! The crew were all extremely friendly and the sunset was beautiful! Will definitely do this again the next time we come back!”

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Kauai: Leila Na Pali Sunset Dinner Sail

14.Kauai: Leila Na Pali Sunset Dinner Sail

★★★★★★★★★★4.5 · 524 reviews · 5 hours (approx.) · from $263

Spend about five hours sailing from Port Allen along Kauai’s Na Pali Coast aboard the 50-foot Leila. Expect cliffs, waterfalls, marine life, dinner, mai tais, beer, wine, and a sunset toast. The crew may include captains such as Kevin, Max, or Mike, with routes shaped by ocean conditions.

“The crew was professional and courteous they took amazing care of my bride and ii. Unfortunately Mother Nature beat us up pretty good the sea was heavy! However feeing as poorly as I was the north coast was amazingly beautiful. We highly recommend holo holo they were outstanding.”

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Oahu: Waikiki Sunset Catamaran Sail and Swim

15.Oahu: Waikiki Sunset Catamaran Sail and Swim

★★★★★★★★★★4.7 · 519 reviews · from $44

Join Pink Sails Waikiki for a two-hour sunset catamaran trip from Waikiki. You can swim in the Pacific before sunset, then watch Diamond Head and Waikiki’s lights glow from the water. English-speaking crew members such as Jamie, Alex, John, and Morgan have helped with photos, drinks, and swim support, though boats and crew can change.