Sunset Sails & Cruises

KEY WEST

Best Sunset Sails & Cruises In Key West

Ranked by traveller popularity

The 10 most popular sunset sails & cruises in Key West. Here's what they actually deliver, who runs them, and what they cost.

10 Best Sunset Sails & Cruises In Key West

Concerts, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Photography & Live Music Experiences, Sunset Sails & Cruises, Tour Reviews

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

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

2.Key West Sunset Cruise: Dinner, Live Music & Drinks Included

★ 4.5

Key West sunset dinner cruise with tropical buffet, live steel drum and DJ, and unlimited drinks. 2 hours on a 65-ft yacht.

“It was a great ride out and back. Captain did an awesome job. Food was good but we didn't care for the music. Sunset was amazing”

1,707 reviews2 hours (approx.)From $92.95by Sunset Watersports

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May 24, 2026

Cruises & Boat Tours, Evening Experiences, Key West, Private & Small-Group Tours, Sunset Sails & Cruises, Tour Reviews, Wine Tours

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

Small-group Key West sunset sail with a wine tasting, unlimited beer, and hors d’oeuvres, plus crew stories and a smoother pace for two hours.

“What an amazing experience! The wine was plentiful, the snacks were delicious, and the view of the water and sunset were unbeatable. Mary, James, and Connor were professional and friendly. All around absolutely worth doing this!”

1,366 reviews2 hours (approx.)From $125.00by Danger Charters

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May 24, 2026

Concerts, Cruises & Boat Tours, Evening Experiences, Key West, Photography & Live Music Experiences, Sunset Sails & Cruises, Tour Reviews

Key West Sunset Sail with Live Music, Drinks and Appetizers

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

★ 4.5

A 2-hour Key West sunset catamaran with live music, unlimited drinks, and appetizers. Three decks for views. Check in early for seats.

“Third trip with Fury & all were an excellent experience! We can hardly wait for our next excursion with Fury.”

952 reviews2 hours (approx.)From $79.95by Fury Water Adventures

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May 24, 2026

Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Sunset Sail in Key West with Beverages Included

5.Sunset Sail in Key West with Beverages Included

★ 5.0

Small-group 90-minute sunset sail from Key West with drinks included, a great harbor view, and a water-side look at Sunset Celebration.

“Very relaxing, smaller group makes it feel much more personal.”

907 reviews1 hour 30 minutes (approx.)From $79.00by Floridays

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May 24, 2026

Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Schooner Cruises, Sunset Sails & Cruises, Tour Reviews

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

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

★ 5.0

Key West sunset on America 2.0: beer, wine, champagne, and plated hors d’oeuvres as you pass Fort Zachary and Mallory Square.

“Our captain, Janet was fantastic! She made sure our experience on her ship was perfect including the sunset. Her crew Jade, Milo & Heather were super efficient in not only tending to the ship’s duties but served their guests with a huge smile. Thanks for the great experience!🌞⛵️”

804 reviews2 hours (approx.)From $122.59by Classic Harbor Line

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May 24, 2026

Cruises & Boat Tours, Dolphin Watching, Dolphin Watching Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wine Tours

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

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

★ 4.5

Small-group Key West sunset catamaran with dolphin spotting, premium wine, and chef’s tapas. About 2.5 hours, $89.

“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!”

699 reviews2 hours 30 minutes (approx.)From $89.00by Sebago Key West

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