Come sail with us on the beautiful, clear waters of the Florida Keys. Take one of our gorgeous sunset cruises, set sail for fun day on the water or let us help you plan a custom sailing vacation in The Keys. Our Florida Keys charters are fully crewed and private - with the exception of our our Just-For-Fun-Sail package, your party will have the whole boat to themselves. Cool island drinks and gourmet meals complete the fantasy of a lifetime. Help raise the sails or just sit back and enjoy the warm winds and clear waters. Either way we guarantee one of the best sailing experiences you've every had.
We depart from Marathon on Boot Key. We sail the clear warm waters from Key West to Biscayne Bay and have enjoyed many seasons of great cruises in this beautiful area. We offer private, fully crewed charters on our 43 foot sailing ketch for a great personalized experience - you won't be fighting 50 other guests for that watered-down rum punch.
"Fantastic blue waters with dolphins swimming about. Topped off with a great dinner and sunset view. Can't wait to do it again!" - G. I.., Hopewell Jct, NY
Select from one of our special packages below or call us to customize your charter. Additional information on each charter, along with more pictures, can be found by clicking on the link below or selecting the specific charter type from the menu on the left.
Sunset Dinner Cruise - Our most popular charter! Come join us for an awesome sail along The Keys enjoying the clear water and great views. We'll anchor in our special place and serve you a gourmet dinner while you watch your private "Keys" sunset to end another beautiful day.
Just-For-Fun Sail Sail the beautiful Florida Keys for over two hours and enjoy your own romantic "Keys" sunset from the water.
Keys Luncheon Sail Cruise along The Keys for over 4 hours and enjoy the clear waters, great boat and lively conversation. We'll serve you a gourmet lunch of your choice while underway.
Florida Keys Vacations Experience a truely unique vacation of a lifetime on Second Wind. We'll wine-n-dine you on a private sailing charter that is customized especially for you. Take advantage of our sailing and cruising experience in the beautiful Florida Keys to visit isolated anchorages and island getaways. Help raise and trim the sails or just sit back and enjoy the ride - either way you'll leave us with memories to last a lifetime. These are all-inclusive, private sailing charters. You will be the only guests on our boat and we'll do everything possible to make sure it is the best vacation you've ever had.
Come sail with us on the beautiful, clear waters of the Florida Keys. Take one of our gorgeous sunset cruises, set sail for fun day on the water or let us help you plan a custom sailing vacation in The Keys. Our Florida Keys charters are fully crewed and private - with the exception of our our Just-For-Fun-Sail package, your party will have the whole boat to themselves. Cool island drinks and gourmet meals complete the fantasy of a lifetime. Help raise the sails or just sit back and enjoy the warm winds and clear waters. Either way we guarantee one of the best sailing experiences you've every had. 
Select from one of our special packages below or call us to customize your charter. Additional information on each charter, along with more pictures, can be found by clicking on the link below or selecting the specific charter type from the menu on the left.