62 experiences to discover
Explore the best cruises & sailing tours tours and activities in Key West. Our unbiased ratings help you find the perfect experiences for your trip.
From $4000
Sail into the sunset on a 65-foot schooner
Bottled water
From $695
Sail into the sunset on a private charter
Light refreshments
From $109
Sail into a stunning Key West sunset
Soda/Pop
From $49
Sail on a majestic 2-masted schooner
$79-$80
Savor unlimited drinks and appetizers
Sunset sailing trip
From $90
Sail into a stunning sunset
Two marine heads
Sail with a warm tropical breeze
Signature Bloody Mary or Dark & Stormy cocktails
From $65
Savor unlimited craft cocktails
Unlimited drinks (open bar)
$134-$135
Sail into the Floribbean sunset
From $81
Toast the sunset with your favorite drink
Life vests
$127-$137
Savor unlimited drinks at the sandbar
Unlimited draft beer, mimosas, wine, and champagne
From $565
Explore turquoise waters on a tiki bar boat