Key West Cruises & Sailing Tours - Page 3

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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4.52

Key West Tiki Boat Party & Mini Sandbar 2 hr

From $403

1 provider live

Set sail for a unique tiki adventure

Licensed Captain

4.5

Key West Wind and Wine Sunset Sail

From $4000

1 provider live

Sail into the sunset on a 65-foot schooner

Bottled water

4.5

Marathon Sandbar Cruise & Sightseeing Adventure

From $114

1 provider live

Explore the scenic waters of Marathon

Soda/Pop

4.49

Key West Catamaran Champagne Sunset Sail 1.5 hr

From $80

1 provider live

Sail into a stunning Key West sunset

Two marine heads

4.49

Key West Sandbar Cruise with Lunch

$140-$151

2 providers combined

Cruise through mangrove channels

Soda/Pop

4.48

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

4.47

Key West Sunset Sail Cruise

From $95

1 provider live

Sail on Key West's iconic tall ship

Coolers of ice with cups and bottled water

4.47

Key West Schooner Sunset Sail

From $123

2 providers combined

Feel the wind as you sail into the sunset

2-hour sailing experience aboard America 2.0

4.46

Key West Schooner Appledore Star Sunset Sail

From $110

1 provider live

Savor a Key West sunset on a classic schooner

Homemade sangria, wine, beer, liquor, soft drinks, and filtered water

4.46

Key West Sandbar Boat Tour and Swim

$600-$661

2 providers combined

Cruise through scenic mangrove trails

Guide

4.46

Key West Windjammer Champagne Sunset Sail

From $90

1 provider live

Experience an iconic Key West sunset

Sunset cruise

4.42

Key West Schooner Sail with Full Bar 2 hr

From $49

1 provider live

Sail on a majestic 2-masted schooner

Soda/Pop