Key West Cruises & Sailing Tours - Page 4

62 experiences to discover

Day & Sunset Cruises Dinner Cruises Sailing Trips

Explore the best cruises & sailing tours tours and activities in Key West. Our unbiased ratings help you find the perfect experiences for your trip.

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4.44

Key West Wind and Wine Sunset Sail

From $4000

1 provider live

Sail into the sunset on a 65-foot schooner

Bottled water

4.43

Key West Sunset Sail Private Charter 2 Hr

From $695

1 provider live

Sail into the sunset on a private charter

Light refreshments

4.42

Key West Historic Schooner Sunset Cruise

From $109

1 provider live

Sail into a stunning Key West sunset

Soda/Pop

4.4

Key West Schooner Sail with Full Bar 2 hr

From $49

1 provider live

Sail on a majestic 2-masted schooner

Soda/Pop

4.4

Key West Sunset Sail with Live Music

$79-$80

2 providers combined

Savor unlimited drinks and appetizers

Sunset sailing trip

4.39

Key West Dolphin Watch Sunset Sail

From $90

1 provider live

Sail into a stunning sunset

Two marine heads

4.37

Key West Schooner Day Sail with Cocktails

From $49

1 provider live

Sail with a warm tropical breeze

Signature Bloody Mary or Dark & Stormy cocktails

4.36

Key West Cocktail Cruise at Sunset

From $65

1 provider live

Savor unlimited craft cocktails

Unlimited drinks (open bar)

4.28

Key West Sunset Sail with Wine and Hors d'oeuvres

$134-$135

2 providers combined

Sail into the Floribbean sunset

Light refreshments

4.28

Key West Tiki Bar Sunset Cruise BYOB 2 hr

From $81

1 provider live

Toast the sunset with your favorite drink

Life vests

4.25

Key West Sandbar Adventure & Sunset Cruise

$127-$137

2 providers combined

Savor unlimited drinks at the sandbar

Unlimited draft beer, mimosas, wine, and champagne

4.25

Key West Tiki Bar Boat Sandbar Tour

From $565

1 provider live

Explore turquoise waters on a tiki bar boat

Bottled water