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Sunset Cruises in Key West

Sunset is the thing Key West is organised around, and the town celebrates it on land for free: the Sunset Celebration at Mallory Square runs every evening of the year, starting about two hours before the sun goes down. So the honest question about a sunset sail is not whether the sunset is worth it – it is whether being out on the water, away from several hundred people, an open bar in hand, is worth the ticket.

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Top rated · Season 2026

The tours travellers book most

Ranked by the number of verified reviews – the closest thing there is to a count of people who actually went.

23 tours available · Sorted by number of verified reviews. Prices and availability come live from GetYourGuide.

Key West: Reef Snorkeling with Drinks and Sunset Option

Key West: Reef Snorkeling with Drinks and Sunset Option

⏱ 3 hours · 4.5 (600)

Set sail on a catamaran for an unforgettable Key West snorkeling adventure. Choose from morning, afternoon, or sunset tour times and enjoy delicious alcoholic drinks after snork…

from €43 per person

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Key West: Dolphin Watching and Snorkeling Sunset Cruise

Key West: Dolphin Watching and Snorkeling Sunset Cruise

⏱ 3 hours · 4.4 (571)

Watch dolphins playing in their natural habitat. Snorkel in the Key West National Wildlife Refuge and enjoy an ice cold beer on the way back with the sunset in front of you.

from €70 per person

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Key West Signature Sunset Cruise with Open Bar, Food & Music

Key West Signature Sunset Cruise with Open Bar, Food & Music

⏱ 2 hours · 4.6 (509)

Board one of Key West's most popular sunset sailing trips. Enjoy an open bar, a great selection of appetizers, and live music.

from €70 per person

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Key West: Schooner Sunset Sail with Food & Drinks

Key West: Schooner Sunset Sail with Food & Drinks

⏱ 2 hours · 4.9 (335)

Watch the sunset over Key West from the deck of the elegant 105-foot schooner America 2.0 and sit back, relax, and see some of the top sights of the area.

from €108 per person

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Key West: Sunset Dinner Cruise with Open Bar & Live Music

Key West: Sunset Dinner Cruise with Open Bar & Live Music

⏱ 2 hours · 4.5 (288)

Watch the famous Key West sunset on-board a boat with live music, an open bar and buffet dinner.

from €82 per person

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Key West: Sunset Sail with Live Band, Drinks, and Appetizers

Key West: Sunset Sail with Live Band, Drinks, and Appetizers

⏱ 2 hours · 4.8 (199)

Climb aboard a spacious catamaran and be entertained by some of the best musicians from Key West. Party the night away and watch a magical sunset on a cruise out at sea.

from €64 per person

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Key West: 2-Hour Sunset Sail with Live Music

Key West: 2-Hour Sunset Sail with Live Music

⏱ 2 hours · 4.7 (144)

Experience the magnificent Key West sunset from the water on this all-inclusive sailing trip. Indulge in spectacular views, unlimited drinks and appetizers, and live music. Enjo…

from €70 per person

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Key West: Glass Bottom Boat Reef Tour with Sunset Option

Key West: Glass Bottom Boat Reef Tour with Sunset Option

⏱ 1h 45m · 4.2 (120)

Stay cool and dry as you view a stunning array of tropical marine life in air-conditioned comfort aboard a glass-bottom boat. Witness the wonder of North America’s only living c…

from €56 per person

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Key West: Dolphin & Reef Snorkel Trip with Sunset Option

Key West: Dolphin & Reef Snorkel Trip with Sunset Option

⏱ 3 hours · 4.4 (90)

Cruise to Key West’s Dolphin Playground, snorkel among vibrant reefs, and enjoy unlimited drinks. Choose a daytime trip or upgrade to include a stunning sunset cruise!

from €67 per person

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Key West: 2 Reef Snorkel With Sunset Cruise, Includes Drinks

Key West: 2 Reef Snorkel With Sunset Cruise, Includes Drinks

⏱ 3 hours · 4.4 (84)

Snorkel two stunning reef spots, then relax with unlimited drinks as you sail into a Key West sunset aboard our newest catamaran—perfect for beginners and seasoned snorkelers al…

from €61 per person

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Captain's Choice: Dolphin Watch Sunset Sail

Captain's Choice: Dolphin Watch Sunset Sail

⏱ 2h 30m · 4.6 (54)

This sunset sail is the ultimate VIP sunset sailing experience! Expect an intimate, three hour sail that is one of the top things to do in Key West!

from €79 per person

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Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion

Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion

⏱ 4.5 hours · 4.8 (24)

Embark on a 4.5-hour Afternoon Excursion: snorkel, kayak, and sail on our shallow draft schooners, ensuring an adventure-filled day on the Florida Keys waters!

from €118 per person

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Key West Wind and Wine Sunset Sail aboard a classic Schooner

Key West Wind and Wine Sunset Sail aboard a classic Schooner

⏱ 2 hours · 5.0 (22)

Savor an enchanting Key West sunset sail with fine wines, upscale beers, and delectable hors-d'oeuvres aboard a classic Key West Schooner! This is a truly unforgettable expe…

from €118 per person

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Key West: Windjammer Champagne Sunset Sail

Key West: Windjammer Champagne Sunset Sail

⏱ 2 hours · 5.0 (19)

Join this sunset sailing trip from Key West with drinks included. Set off from the USA's southernmost point aboard a 2-masted wooden schooner and admire the evening views.

from €79 per person

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Sandbar, Snorkel, and Sunset Sail with Drinks in Key West

Sandbar, Snorkel, and Sunset Sail with Drinks in Key West

⏱ 5 hours · 4.9 (6)

Enjoy three of the most sought-after experiences in Key West in one relaxed afternoon: extended time at a shallow-water sandbar, snorkeling in clear backcountry waters, and a su…

from €119 per person

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Key West's Schooner Appledore Star Champagne Sunset Sail

Key West's Schooner Appledore Star Champagne Sunset Sail

⏱ 2 hours · 5.0 (6)

The perfect Key West sunset sail. Picture yourself on the deck of a romantic 2-masted schooner. Wind blowing in your hair, the tall ship sails into the sunset over the southernm…

from €97 per person

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Key West: Catamaran Champagne Sunset Sail

Key West: Catamaran Champagne Sunset Sail

⏱ 1h 30m · 4.9 (4)

Sail away from Key West Historic Seaport aboard our spacious 60' sailing catamaran! Take in iconic landmarks while your captain positions the boat for the best views of the…

from €70 per person

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Key West: Happy Hour Sandbar Adventure & Sunset Cruise

Key West: Happy Hour Sandbar Adventure & Sunset Cruise

⏱ 4 hours · 4.1 (4)

Cruise through the Florida Marine Sanctuary, spotting dolphins & sea turtles on your way to a happy hour at the sandbar. Enjoy unlimited drinks, lily pads, then enjoy the legend…

from €113 per person

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Key West: Schooner Full Moon Night Sail with Drinks

Key West: Schooner Full Moon Night Sail with Drinks

⏱ 1.5 hours · 5.0 (3)

Sail in the calm waters around Key West aboard the elegant Schooner America on this nighttime boat cruise.

from €74 per person

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Dolphin Watch + Sunset Sail

Dolphin Watch + Sunset Sail

⏱ 3 hours · 4.7 (2)

Sailing in the Winter months. Join us to watch Dolphins under a setting sun and enjoy a small group catamaran sail.

from €103 per person

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Reef Snorkel + Sandbar & Sunset Sail

Reef Snorkel + Sandbar & Sunset Sail

⏱ 4h 30m · 5.0 (1)

This catamaran sunset sail, guided reef snorkel tour and sandbar visit takes full advantage of Key West’s warm, calm weather

from €126 per person

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Key West: Hula Hank's Tiki Sunset Cruise

Key West: Hula Hank's Tiki Sunset Cruise

⏱ 1.5 hours 0

Soak in the iconic Key West sunset on our one-of-a-kind Tiki boat. Cruise out of the Key West Historic Seaport and enjoy a relaxing evening with your new best friends!

from €69 per person

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Key West: Private Tiki Boat Sunset Cruise

Key West: Private Tiki Boat Sunset Cruise

⏱ 2 hours 0

Discover the sights of Key West from the water on this sunset cruise aboard a tiki bar boat. Bring your own drinks and snacks for your evening on the water.

from €401 per group up to 6

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Good to know: Check the departure time against the actual sunset for your date, not against the season. Between midwinter and midsummer the sun sets here well over an hour later, and boats shift their schedules in steps rather than daily – a two-hour trip that leaves too early spends most of it in daylight.

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Good to know

Frequently asked questions

Do I need a rental car in Key West?

Inside the island, almost never. Old Town is flat and about two kilometres across, and bicycles are what locals use. Parking is the reason: metered spaces in Old Town run around four to six dollars an hour, and the Old Town garage charges a day rate. A car earns its keep for the drive down the Overseas Highway, not once you are here.

How far is the reef, and can I snorkel from the beach?

The nearest reef sites are about ten to eleven kilometres offshore, so every reef trip means forty minutes to an hour under way each direction. The one place you can snorkel without a boat is the beach at Fort Zachary Taylor, where the shipping channel keeps the water clear. Bring footwear – it is crushed coral, not sand.

Is the Dry Tortugas trip worth a whole day?

Fort Jefferson sits about 110 kilometres west in open water and can only be reached from Key West, by ferry or seaplane. The ferry is roughly two and a half hours each way with around four hours at the island; the seaplane cuts the travel to about 45 minutes and costs several times more. If you have three days here, it takes one of them.

Do I have to pay to see the sunset?

No. The Sunset Celebration at Mallory Square is free and happens every evening of the year, starting about two hours before the sun goes down. A sunset sail buys you distance from several hundred people, a drink and a view back at the island. Check the departure time against the actual sunset for your date – it shifts by more than an hour across the year.

When is the best time to come?

December to April is dry, mild and busy – it is also when the cruise ships call and tours sell out. Hurricane season runs from June to the end of November, with September the wettest and stormiest month. Late October means Fantasy Fest and peak prices. April, May and early December are the quiet compromise.

Why do some Key West tours on other sites start in Miami?

Because Miami is a bigger market. „From Miami: Key West Day Trip" is a coach trip for people staying in Miami, three and a half hours and about 250 kilometres up the Overseas Highway. Those offers are filtered out here – everything on this site departs from Key West itself.

Key West tours from €43.39 · available today

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