THE USA

The 15 Best Sunset Sailing Cruises in the USA

55 sailing trips  ·  from $40 a head

Key West built an economy on this hour and Waikiki is not far behind. The 15 below compare boat size, what is poured and how long you are out, with prices per person.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - What the route shows you in two hours
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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

Key West sunset sail review with open bar, live music, shrimp, spacious catamaran decks, practical tips, value, weather advice, and FAQs.

“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 - Sunset views, city lights, and changing weather
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - A wine tasting that fits a moving boat
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Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

Key West Sunset Sail with Live Music, Drinks and Appetizers - Boarding the 65-foot Fury catamaran
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Key West Sunset Sail with Live Music, Drinks and Appetizers

Sunset Sail in Key West with Beverages Included - Sailing through Key West Harbor
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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 Key West Harbor aboard a small boat, sip included drinks, and watch the famous sunset with attentive crew and room to relax.

“Very relaxing, smaller group makes it feel much more personal. The captain and his first mate were great. My husband & I very much enjoyed it.”

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Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - The early route: Fort Zachary and the Key West shore
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Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

Sunset Dolphin Sail Aboard the Privateer Catamaran - Meeting at Paradise Adventures on Jan Cooley Drive
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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

Review of Panama City Beach’s Privateer sunset dolphin sail, with pricing, views, drinks, music, logistics, drawbacks, and booking advice.

“Mike, Lamar, Jess and Jeff (singer/guitarist) were the best at Sunset Paradise Adventure!!! Even though it was raining the best experience ever, my family loved it and we saw SO MANY GROUPS OF DOLPHINS!!! This has to be the best experience we ever had. Thank you for making this the most memorable experience!”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Looking for dolphins along Key West’s water
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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

Key West sunset sail review with dolphin watching, wine, champagne, tapas, landmark views, practical tips, pricing, and honest drawbacks.

“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 - What Sailing on Cool Beans Feels Like
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Sightseeing and Sunset Catamaran Sailing Excursion

Sunset Sail Along the San Diego Skyline - Settling into the bean bag seats
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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

Review of San Diego’s small-group sunset sail, with skyline views, sea lions, practical tips, pricing, comfort, and honest drawbacks.

“Captain was totally disengaged. Experience did not match description. Skyline of San Diego was never even acknowledged. Engine was on the entire trip with unpleasant diesel odor on deck.”

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Evening Colors Sunset Sail Tour in Seattle - Seattle’s skyline from the sound
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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

Sail Seattle’s Puget Sound at sunset aboard a tall ship, with skyline, Mount Rainier, Olympic Mountain views, drinks, and a possible cannon salute.

“Fun hosts, beautiful views. Romantic sunset with my husband! Beverage service available on the boat. Best part of my trip to Seattle.”

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Small-Group San Diego Sunset Sailing Excursion - Settling Into The Catalina-Style Sailboat
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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 at sunset aboard a six-person Catalina-style boat with skyline views, drinks, snacks, music, and a relaxed bay cruise.

“Beautiful experience sailing on this state of the Art sailboat. The captain is the best and we highly recommend this Sunset small group Sailing on the San Diego Bay.”

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Waikiki Sunset Cocktail Sail with Open Bar - The open bar and the value of the price
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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

Review of Waikiki’s 1.5-hour sunset catamaran sail, with an open bar, Diamond Head views, barefoot boarding, pricing, tips, and drawbacks.

“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 - The four-hour Na Pali sightseeing run
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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

Review of Kauai’s Leila Na Pali sunset dinner sail, with boat details, food, weather advice, price value, and tips for a smoother outing.

“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 swimming 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

Review of Oahu's $44 Waikiki sunset catamaran sail, with ocean swimming, Diamond Head views, crew tips, value, and practical advice.

“Captain Jaime, Big Mike, and Alex did a great job on the cruise. They were fun and interactive with the group. Made it a great experience”

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