Sailing trips · SUNSET SAILING CRUISES IN THE USA

Top 15 Sunset Sailing Cruises in the USA

43 trips  ·  from $40 a head

This is the shortlist you would send a friend: 15 sunset sailing cruises in the USA worth the money, each with its price, its traveller verdict and the one thing to know before the lines come off.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - The Key West sights from the water
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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 sunset views, live local music, an open bar, shrimp, antipasti, mini tarts, and soft drinks. Arrive 30 minutes early, claim a good bow seat, and bring a sweater for breezy 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 - A two-hour route along Waikiki and Diamond Head
Bay, Harbour & Coastal Sailing, Evening Experiences, Oahu Sailing Trips, Sailing Trips, Sailing Trips with an Open Bar in Oahu, Sailing Trips with Open Bar & Drinks, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

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

2.Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89Top rated

Set sail from Kewalo Basin Harbor for two hours along Waikiki and past Diamond Head. The Moana Catamaran offers a barefoot cruise, a premium full bar with your first drink included, and a chance to spot dolphins or humpback whales. Crew members such as Vivian help keep the mood warm and relaxed.

“The crew were very attentive and made the trip enjoyable despite the rough seas and some people suffering from sea sickness. Drinks were plentiful with a good variety.”

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Sunset & Dolphin Catamaran Cruise with Island Time - Key points at a glance
Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, Island Hopping Sailing Trips, Panama City Beach Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips, Whale & Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Sunset & Dolphin Catamaran Cruise with Island Time

3.Sunset & Dolphin Catamaran Cruise with Island Time

★★★★★★★★★★5.0 · 1,867 reviews · 2 hours (approx.) · from $57

Spend about two hours aboard Island Time Sailing’s catamaran from Panama City Beach. Cruise Grand Lagoon, watch for dolphins near St. Andrews State Park, enjoy sunset views, music, and drinks from the onboard bar. The crew, including Captain Clay and Cristo, may also invite you to dance and play games at the dock.

“This is an incredible experience! Crew was excellent and friendly! Dolphins and sunset was amazing. Highly recommend!”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Checking in at 255 Front Street
Evening Experiences, Key West Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips, Wine Tours

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

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

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125

Board Danger Charters at 255 Front Street for a two-hour sunset sail limited to 26 people. Crew members such as Mary, Connor, Lexi, Tony, and Molly have served wines, beer, small bites, stories, and blankets while the boat heads offshore for sunset.

“The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!”

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San Francisco Bay Sunset Catamaran Cruise - Alcatraz at twilight and the changing San Francisco skyline
Bay, Harbour & Coastal Sailing, Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, San Francisco Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

San Francisco Bay Sunset Catamaran Cruise

5.San Francisco Bay Sunset Catamaran Cruise

★★★★★★★★★★5.0 · 1,342 reviews · 1 hour 35 minutes (approx.) · from $88

Board Adventure Cat at Pier 39 for a 1-hour-35-minute sunset sail past Alcatraz and beneath the Golden Gate Bridge. Choose a sheltered seat or the open trampoline, enjoy one beer, wine, or soft drink, and bring a jacket for the chilly bay air.

“It was freezing and so windy I thought I would go overboard. The opportunities for photos were not many so it felt like a bit of a waste of $$$. I would check the weather before hand the fog rolled in and the bridge was barely visible. They did have jackets but like if you can’t even walk up outside onto the deck cause it’s so windy what’s the point. Also too many people.”

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San Francisco Bay Sunset Cruise by Luxury Catamaran - A 90-minute route through the heart of the bay
Bay, Harbour & Coastal Sailing, Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, San Francisco Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips, VIP

San Francisco Bay Sunset Cruise by Luxury Catamaran

6.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, open-air trampoline nets, sheltered seating, and audio commentary in several languages. Bring warm layers for the cool, sometimes wet bay air.

“Liked being with a small group as opposed to a large group on a bigger boat, getting up in the captain’s chair was really cool!”

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Key West Sunset Sail with Live Music, Drinks and Appetizers - Getting to Fury’s Greene Street dock
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Key West Sunset Sail with Live Music, Drinks and Appetizers

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

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

Board Fury’s 65-foot catamaran at Greene and Elizabeth Streets for two hours of live cover music, unlimited margaritas, beer, wine, Champagne, and seasonal appetizers. Sail past Mallory Square and possibly Fort Zachary Taylor while the crew picks the best route for sunset. Arrive early for seating.

“Not your usual review as our sunset cruise was cancelled by a freak raging windstorm. Just wanted to thank the team there at the pier that handled everything so professionally and quick. Rescheduling was offered but we had opt for cancellation as it was our last night in town.”

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Sunset Sail in Key West with Beverages Included - Sailing through Key West Harbor
Evening Experiences, Key West Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

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

Board Floridays at Hyatt Centric Key West for a relaxed 90-minute sail with up to 24 people. Eric, Carlo, Hunter, Janet, Chuck, Lori, and other crew members may handle the evening. Enjoy champagne, wine, margaritas, beer, and soft drinks while watching the sunset and Sunset Celebration from the water.

“There are bigger boats and longer trips and options out there for dinner cruises, etc. But we just wanted a nice 90 minute trek around the port with a small number of people on a sailboat. The bar service was a bonus to me. Captain Chuck and Lori were great hosts and were glad to let people drive the boat, take pictures of us and play tunes. We had very good weather and wind so we sailed most of the trip which is much better that motoring around IMO.”

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Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB - Sailing toward Diamond Head
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Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

9.Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

★★★★★★★★★★5.0 · 836 reviews · 2 hours (approx.) · from $44Best value

Join Oahu Catamarans for a relaxed two-hour sunset sail from Honolulu. Captains such as Krash and Carlos guide the 40-foot catamaran toward Diamond Head, while the crew serves pupus and helps with photos. Bring your own alcoholic drinks if you are 21 or older, and watch Waikiki light up after dark.

“Very relaxed experience and we were out for a long enough time. Refreshments included which was nice. Would definitely recommend!”

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Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - What the sunset portion is really like
Drinking Tours, Evening Experiences, Key West Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

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

Spend two hours sailing Key West aboard the replica schooner America 2.0. Captain Janet, Captain Rae, or Captain Dan may lead the trip, with crew serving plated hors d’oeuvres, beer, wine, Champagne, and soda while you pass Fort Zachary, Sunset Pier, and Sand Key Lighthouse.

“Fun and good information! Fun to learn how the boat worked! The the Keys are beautiful and the water was great.”

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Sunset Dolphin Sail Aboard the Privateer Catamaran - A relaxed two-hour route across the Gulf
Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, Panama City Beach Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips, Whale & Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Sunset Dolphin Sail Aboard the Privateer Catamaran

11.Sunset Dolphin Sail Aboard the Privateer Catamaran

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

Sail from 4114 Jan Cooley Drive on the 52-foot Privateer catamaran for two hours along the Gulf of Mexico. Expect sunset views, possible dolphin sightings, one included drink, tropical music, and an onboard bar. Captain Mike, Lamar, Teagan, and other crew members are known for keeping the ride friendly and lively.

“It’s a fun time you enjoy the ocean life the crew is very nice you have a good experience with everybody my family really enjoyed the time on the ocean”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Dolphin watching without false promises
Evening Experiences, Key West Sailing Trips, Sailing Trips, Sailing Trips with Lunch & BBQ, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips, Whale & Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA, Wine Tours

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

12.Dolphin Watching, Wine, and Tapas

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

Set out from Key West Historic Seaport for a 2.5-hour catamaran cruise with dolphin watching, wine, beer, champagne, and chef-selected tapas. Expect views of Mallory Square, Fort Zachary Taylor, and Sunset Key. Crew members such as Captain Daniel, John, Gracie, Jordan, and Brandon have been praised for friendly service, though dolphin sightings depend on nature.

“Captain Daniel and John were outstanding and very accommodating. The tapas were exceptional, much more than we anticipated and would give the chef 5 stars!”

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Sunset Catamaran Cruise in Ft. Lauderdale - Leaving Spirit of Lauderdale and finding your boat
Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, Fort Lauderdale Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

Sunset Catamaran Cruise in Ft. Lauderdale

13.Sunset Catamaran Cruise in Ft. Lauderdale

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

Cruise from Spirit of Lauderdale past waterfront mansions and Port Everglades before raising the sails offshore for sunset. You get one complimentary glass of champagne, shaded seating, music, a restroom, and a cash bar. Guides such as Justin, Maria, and Captain Jim help set the tone.

“It was actually better than anticipated! Beautiful views, sailing out in open waters, the sights and and watching the sails go up was fantastic. The Captain and his mate were very friendly and assisting!”

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Sightseeing and Sunset Catamaran Sailing Excursion - The Sunset Cruise: Champagne and Changing Color
Catamaran Cruises, Catamaran Cruises in the USA, Evening Experiences, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, Tours, USA Sailing Trips

Sightseeing and Sunset Catamaran Sailing Excursion

14.Sightseeing and Sunset Catamaran Sailing Excursion

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

Board the 20-passenger catamaran Cool Beans at Capri Boulevard for a 2 to 2.5-hour sail near Naples. Captain Dan, Patrick, Dave, and crew members such as Kyle and Jack may take you past dolphins, birds, mangroves, and waterfront homes, with swimming and shelling on day sails and a champagne toast at sunset.

“Great trip! Captain Dan was a lot of FUN. Got to see Dolphins, enjoyed unlimited drinks, and the Sunset was gorgeous. Would definitely do again!”

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Sunset Sail Along the San Diego Skyline - Passing the USS Midway and Maritime Museum
Evening Experiences, Sailing Trips, San Diego Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in San Diego, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Trips

Sunset Sail Along the San Diego Skyline

15.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 sets. Captains such as Aaron, Patrick, Adam, and Derek keep the outing friendly and informative. Bean bags, blankets, cushions, and an onboard bathroom add comfort.

“Fun and scenic activity. Good value. About an hour and a half. Parking at marina $20-$30 in addition.”

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New in Sunset Sailing Cruises in the USA

★ 5.0Deluxe Sunset & Day Sail Small GroupFrom $119245 reviews
★ 5.02.5-Hour Small-Group Catamaran Sunset Sail with DrinksFrom $119223 reviews
★ 5.0New York City Sunset Cruise on a YachtFrom $113331 reviews
★ 4.9Sunset Sail Aboard Schooner AdirondackFrom $90283 reviews
★ 4.9Sunset Sail Aboard a SchoonerFrom $101344 reviews
★ 4.5Sunset Sail from Ma’alaea HarborFrom $151207 reviews
★ 4.8Ka’anapali Luxury Sunset Dinner SailFrom $169123 reviews
★ 4.7Ka’anapali Luxury Sunset Cocktail Sail with Open BarFrom $134150 reviews
★ 5.0Seattle Sunset Sail BYOBFrom $71187 reviews
★ 4.8Tall Sailboat Sunset Harbor CruiseFrom $79223 reviews
★ 4.7Waikiki Sunset Catamaran Cocktail CruiseFrom $99348 reviews
★ 4.5Reef Snorkel Adventure and Sunset SailFrom $59370 reviews
★ 5.0Newport Sunset Sail on Schooner AdirondackFrom $7480 reviews
★ 4.6Charleston Harbor Sunset Cruise with Music & Onboard BarFrom $6566 reviews
★ 4.8‘Alihilani Sunset Sail Catamaran TourFrom $114348 reviews

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