Showing results for Sailing View All
Experiences just outside of Monroe County
From $123
4.9
870 Ratings
Sunset Sailing: Key West Schooner America 2.0 Tour
Key West
From $95
4.9
276 Ratings
Key West Sunset Sail: Traditional Pirate Experience
Key West
From $156
5.0
185 Ratings
Eco Tour: Key West Wildlife Exploration
Key West
From $35
4.5
92 Ratings
Key West Catamaran: Snorkel and Mimosa Cruise
Key West
From $169
4.2
15 Ratings
Sebago Catamaran: Key West Sailing Adventure
Key West
From $102
5.0
9 Ratings
Florida Keys Sunset Cruise: Scenic Catamaran Tour
Marathon
From $130
4.0
4 Ratings
Florida Keys Sandbar: Relax on a 53’ Catamaran
Marathon
From $700
5.0
3 Ratings
Key West Snorkeling: Crystal Waters Adventure
Key West
From $100
5.0
1 Rating
Smathers Beach Day: Paddleboard, Kayak, Sail
Key West
From $65
1.0
1 Rating
Sunset Cruise: Florida Keys Golden Hour Views
Marathon
From $79
1.0
1 Rating
Key West Dolphin Watch: Snorkel & Dine
Key West
From $350
Dock Side Adventure: Kayak, Paddle Boarding, Sunfish Sailboats
Naval Air Station Key West
From $230
Key West: Smathers Beach Sunset Catamaran Experience
Key West
From $135
Key West Adventure: Sandbar, Snorkel, Sunset
Key West