Key West Sailing Trips

12 experiences to discover

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

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4.69

Key West Schooner Race on America 2.0

From $116

2 providers combined

Sail aboard the iconic Schooner America 2.0

A boxed lunch

4.64

Stock Island Sunset Wine and Sail 2 hr

$134-$135

2 providers combined

Sail into the Floribbean sunset

Premium wine and cold beer

4.59

Marathon Sailing Adventure in Florida Keys

From $120

1 provider live

Sail through the Florida Keys Marine Sanctuary

Soda/Pop

4.57

Bimini Catamaran Sail and Snorkel 6 hr

From $1400

1 provider live

Sail the pristine waters of Bimini

English Guide

4.56

Key West Windjammer Day Sail

From $50

1 provider live

Sail past Key West's iconic landmarks

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

4.52

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

4.52

Key West Harbor Sailing Charter

From $395

1 provider live

Sail the scenic Key West harbor

Bottled water

4.46

Key West National Wildlife Refuge Full Day Tour

From $120

1 provider live

Sail a tall ship to Key West's backcountry

Sail on a tall ship

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

4.36

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

4.2

Key West Schooner Day Sail with Drinks 1.5 hr

From $79

2 providers combined

Sail the elegant Schooner America 2.0

1.5-hour coastal sailing tour

3.69

Key West Dolphin Catamaran Sail

$59-$60

2 providers combined

Sail on a 60' catamaran

Roundtrip catamaran ride