Showing results for Sailing View All
From $69
4.5
45 Ratings
Nights of Lights Cruise: Historic St. Augustine Views
St. Augustine
From $89
5.0
22 Ratings
Schooner Adventure: Sail Key West in Style
Key West
From $116
4.9
597 Ratings
Sunset Sailing: Key West Schooner America 2.0 Tour
Key West
From $85
4.9
201 Ratings
Schooner Clearwater: True Sailing Experience
Clearwater
From $64
4.6
129 Ratings
Daytona Beach Catamaran: Small-Group Sailing Tour
Daytona Beach
From $91
4.9
199 Ratings
Key West Sunset Sail: Traditional Pirate Experience
Key West
From $120
5.0
343 Ratings
Private Sailboat Charter: Fort Lauderdale Adventure
Fort Lauderdale
From $130
5.0
41 Ratings
Orion's Child Sailboat Tour: Experience Gulf Wildlife
Fort Myers Beach
From $80
5.0
39 Ratings
Orlando Sailing Tour: Private Day Experience
Orlando
From $120
4.9
273 Ratings
Fort Lauderdale Sailing Charter: Customizable Private Cruises
Fort Lauderdale
From $64
4.9
74 Ratings
St. Augustine Sunset Sail: All-Inclusive Catamaran Cruise
St. Augustine
From $175
4.9
70 Ratings
Private Sailing on the Miami Bay
Miami
From $440
4.9
134 Ratings
Private Sailing Tour: Stiletto Catamaran Experience
Goodland
From $80
4.7
18 Ratings
Crab Island Charter, Family Friendly 4 Hour Experience
Fort Walton Beach
From $2,400
5.0
1 Rating
Key West Snorkel Adventure: Reefs, Drinks, and Snacks
Key West
From $1,300
Luxurious Experience on a 75’ Ferretti Yacht
Miami
From $1,200
Luxurious Experience on a 60’ Sea Ray Yacht
Miami
From $225
5.0
3 Ratings
Fort Lauderdale Sailing Charter: Customizable 8-Hour Experience
Fort Lauderdale
From $999
Florida Keys Sunset Cruise: Romantic 2-Hour Sail
From $2,100
Florida Keys Day Sail: Historic Schooner Experience
Key West