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.

Sort by:

4.55

Key West Private Tiki Boat Cruise

From $565

1 provider live

Experience the cool waters of the Florida Keys

A US Coast Guard certified captain

4.55

Key West Private Sunset Charter with Music

From $899

1 provider live

Sail into the sunset

Music and drinks for all visitors

4.54

Key West Harbor Sailing Charter

From $395

1 provider live

Sail the scenic Key West harbor

Bottled water

4.54

Key West Catamaran Champagne Sunset Sail 1.5 hr

From $80

1 provider live

Sail into a stunning Key West sunset

Two marine heads

4.53

Key West Sunset Dinner Cruise with Live Music

From $120

1 provider live

Savor a tropical buffet

2 modern restrooms

4.53

Key West Hobie Wave Cat Rental

From $105

1 provider live

Sail across the serene Wai Kai Lagoon

1-hour Hobie Wave Cat rental

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

4.52

Key West Sandbar Boat Tour and Swim

$600-$661

2 providers combined

Cruise through scenic mangrove trails

Guide

4.52

Marathon Sandbar Cruise & Sightseeing Adventure

From $114

1 provider live

Explore the scenic waters of Marathon

Soda/Pop

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

4.48

Key West Schooner Sail with Full Bar 2 hr

From $49

1 provider live

Sail on a majestic 2-masted schooner

Soda/Pop

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