SUNSET SAILING CRUISES IN THE USA

The 15 Sunset Sailing Cruises in the USA We Would Step Aboard

118 sailings  ·  from $40 a head

The 15 best sunset sailing cruises in the USA you can get aboard today, with what each costs, how long it stays out and who it suits. Number one is first for a reason; start there.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Fort Zachary Taylor and the open-water turn
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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 $79Our pick

Sail from Key West for about two hours aboard a spacious catamaran with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and hors d’oeuvres. Local musicians provide live music as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Arrive 30 minutes early and bring a sweater for cool or windy 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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Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - What the Moana Catamaran feels like underway
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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 $89Top rated

Board the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a two-hour sunset sail along Waikiki and past Diamond Head. Your captain and crew serve a complimentary first drink from the premium bar, with more available for $8. Look for dolphins, and humpback whales from November through May. Shoes are collected before boarding.

“A really wonderful expierence, we did the VIP which we liked to board early and get the free drinks included. Lovely hosts and weather was amazing!”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Setting sail with wine and small plates
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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

Spend about two hours sailing from 255 Front Street with a group capped at 26 people. The crew serves up to eight wines, five beers, soft drinks, and easy-to-eat hors d’oeuvres while sharing stories and tending to the boat. Recent sailings have featured crew members including Mary, James, Connor, Lexi, Tony, and Molly.

“Our sunset sail was perfect from start to finish. We absolutely loved the wine tasting and appetizers — you never know what you’re going to get on these types of excursions, and sometimes you brace yourself for cheap wine and sad snacks… but this was the total opposite. The wines were genuinely great bottles, and the cheese apps were delicious and beautifully done. We also adored our all-women crew. They were fun, warm, and made the whole experience feel extra special — the perfect vibe for a girls trip celebrating our 40ths. Would 100% recommend this sail to anyone looking for something elevated, relaxing, and unforgettable.”

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Key West Sunset Sail with Live Music, Drinks and Appetizers - A 65-foot catamaran with room to move
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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, with live local musicians, unlimited margaritas, champagne, beer, wine, soda, and seasonal appetizers. You can dance, sit on the sundeck, or watch the sunset from shaded decks. The cruise returns to Greene Street in time for dinner.

“Sunset was amazing. Staff were great and very engaging. Service was great. Lots to eat & drink. It was a beautiful night.”

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Sunset Sail in Key West with Beverages Included - Watching Key West’s Sunset Celebration from offshore
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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 from the Hyatt Centric Key West Resort aboard Floridays for about 90 minutes, with champagne, wine, margaritas, beer, and soft drinks included. The crew, including Eric, Carlo, Hunter, Chuck, Lori, and Janet on various departures, keeps the mood relaxed while you watch the sunset and the nightly waterfront celebration from the water.

“This is a great cruise. We did not want a loud and loaded up party boat. Instead we wanted a nice and quiet cruise. Our boat was a 54 ft sailboat and we had about a dozen people on the boat (I think it holds twice that). The captain and mate were very nice and informative. Plenty of wine, prosecco and beer on board. If you want a peaceful and pleasurable sunset cruise, this is the one.”

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Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - The marina meeting point and boarding routine
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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 America 2.0 at Key West Bight Marina for a two-hour sunset sail past Fort Zachary, Sunset Pier, and Sand Key Lighthouse. Captain Janet, Captain Rae, Captain Dan, and their crews have been praised for friendly service, clear sailing explanations, and hands-on moments such as raising the sails. Beer, wine, Champagne, soda, and plated hors d’oeuvres are included.

“This was our first time sailing on a schooner and it was amazing. Our captain Dan and his crew were all so nice and welcoming. We had such a wonderful evening. We will definitely be back aboard the America 2.0 next year.”

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Sunset Dolphin Sail Aboard the Privateer Catamaran - Boarding a 52-foot catamaran
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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

Sail the Gulf of Mexico from Panama City Beach aboard the 52-foot Privateer catamaran for about two hours. You get one drink, tropical music, sunset views, and a chance to spot dolphins, deer, and sometimes sea turtles. Captain Mike, Lamar, Chelsea, Teagan, Jess, and Jeff are among the crew members you may meet, depending on the evening.

“The captain and crew were really hospital and lively. I enjoyed the dolphins and energy during the cruise. The sunset was beautiful and calming.”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Passing Mallory Square and Key West’s western shore
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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

Sail from Key West’s Historic Seaport on a catamaran with Captain Daniel, John, Jordan, Gracie, and other rotating crew members. Look for wild dolphins, pass Mallory Square, Fort Zachary Taylor, and Sunset Key, then settle in for sunset with wine, champagne, beer, and tapas including shrimp cocktail. Dolphin sightings and sailing under wind are not guaranteed.

“Best couple hours during our entire vacation. Sunset, dolphin, drinks, snacks, romantic,, picture perfect.”

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Sightseeing and Sunset Catamaran Sailing Excursion - Swimming and shelling at a secluded beach
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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

Board the 20-passenger catamaran Cool Beans in Naples for a 2.5-hour day sail or 2-hour sunset cruise. Expect Gulf sailing, dolphins and birds, drinks, and crew members such as Dan, Patrick, Kyle, Toni, or Jack. Day sails may include swimming and shelling at a secluded beach, while sunset trips include a champagne toast.

“Best Sunset sailing in the area. Have tried them all and this is without a doubt the best one. The crew was fantastic.”

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Sunset Sail Along the San Diego Skyline - What the small boat changes
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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 up to six people, passing the USS Midway and Maritime Museum as the sun drops behind the skyline. Captains such as Aaron, Patrick, Adam, Derek, and Maggie keep the mood friendly and safe. Bring drinks or snacks, and pack a jacket for the cool ride home.

“Great service, beautiful and relaxing. Bring a jacket… even if it’s warm when you set sail. Gets cold quickly.”

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Evening Colors Sunset Sail Tour in Seattle - Seattle’s skyline and the Space Needle from the water
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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 relaxed two-hour sunset sail from Bell Harbor Marina. Help raise the sails, watch the Space Needle and Seattle waterfront slip past, and look for Mount Rainier and the Olympic Mountains in clear weather. Drinks are sold aboard, and the crew may fire a cannon salute before returning to the marina.

“Very relaxing. Loved the crew interact with the crowd. We didnt get see the sunset due to fog and smoke.”

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Small-Group San Diego Sunset Sailing Excursion - Leaving Shelter Island before sunset
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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

Set sail from Shelter Island for about three hours aboard a Catalina-style sailboat limited to six passengers. Your captain handles the boat while you enjoy views of Point Loma Lighthouse, the USS Midway, Coronado Island, and the skyline. Beer, hard seltzers, soft drinks, snacks, blankets, binoculars, and Bluetooth speakers are provided.

“I was solo and am grateful that Captain Chris has a great personality and is willing to converse. It was my first time on a sail boat and I loved every second. Everything was smooth sailing!”

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Waikiki Sunset Cocktail Sail with Open Bar - Boarding from 2169 Kālia Road
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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

Join Holokai Catamaran for a 90-minute sunset sail from Waikiki. Drinks include wine, champagne, Maui Brewing beers, rum punch, sodas, juices, and the signature Holokai Hooch. Crew members such as Ryan, Chase, Kevin, Kayla, Bridget, and Alec are known for keeping the mood social. Expect barefoot boarding through shallow water and possible spray.

“Beautiful scenery and vibes !! ✨️ Good drinks at open bar !! Very relaxing, smooth ride to see the sunset 😎 🌺🌇”

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Kauai: Leila Na Pali Sunset Dinner Sail - The ride from Port Allen to the Na Pali Coast
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Kauai: Leila Na Pali Sunset Dinner Sail

14.Leila Na Pali Sunset Dinner Sail

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

Spend about five hours aboard Holo Holo Charters’ 50-foot catamaran Leila, sailing from Port Allen along Kauai’s Na Pali Coast. Expect towering cliffs, waterfalls, marine life, dinner, mai tais, wine, beer, and a sunset Champagne toast. Captain Kevin and other crew members share local stories, but rough seas and spray are part of the deal.

“Informative tour. Beautiful views of the coast. Varied by day, based on weather, but the crew works hard to give you the best experience. Food was excellent & drinks plentiful!”

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Oahu: Waikiki Sunset Catamaran Sail and Swim - The swim stop before sunset
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Oahu: Waikiki Sunset Catamaran Sail and Swim

15.Waikiki Sunset Catamaran Sail and Swim

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

Spend two hours on Pink Sails Waikiki’s catamaran, leaving Waikiki for a sunset cruise with views of Diamond Head and the shoreline lights. You can jump into the ocean before sunset or stay aboard. English-speaking crew members such as Jamie, Alexio, Peter, and Morgan have earned praise for friendly service, music, photos, and good humor.

“AWESOME! best thing i did in waikiki!!!!! the crew (alex, nici and mo) was amazing and the vibes were GREAT!”

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Newest in Sunset Sailing Cruises in the USA

★ 5.0Coast of Ka’anapali Beach Sunset Dinner SailFrom $158121 reviews
★ 4.5Key West Dolphin Watch and Sunset Sail on CatamaranFrom $11733 reviews
★ 5.0Sunset Sail + Reef Snorkel & SandbarFrom $14329 reviews
★ 5.02-Hour Sunset Sailing With Wine In Stock IslandFrom $12594 reviews
★ 5.0Key West Historic Schooner When And If Sunset Cruise114 reviews
★ 5.0Private 2-Hour Wind and Wine Sunset Sail in Key WestFrom $4,00087 reviews
★ 4.5Private Key West Sunset Sail49 reviews
★ 5.0Bimini Charters – Private Luxury Catamaran 3-hr Sunset SailsFrom $1373 reviews
★ 5.0Golden Hour Escape: Private Sunset Sail in Coastal MaineFrom $849 whole boat, up to 620 reviews
★ 5.0Private Sunset Sail of NYC Skyline and Statue of LibertyFrom $725 whole boat, up to 62 reviews
★ 5.0Rosé Golden Hour Sunset Sail12 reviews
★ 4.5Sunset Sail and Dolphin/Manatee watch in Daytona BeachFrom $7916 reviews
★ 5.0Serene Private Sunset Sail on Lake Michigan – Navy Pier, ChicagoFrom $508 whole boat, up to 627 reviews
★ 5.0Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOBFrom $760 whole boat, up to 655 reviews
★ 5.0Private Sunset Sail BYOB Dolphin/History Tours on 43ft MystiqueFrom $599 whole boat, up to 642 reviews

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