Historic Schooner Daysails and Key West Sunsets

From morning sails on the bright blue water, through sun-soaked afternoon sailing to our famous Key West Sunset Sail, our historic schooner is ready to take you sailing!

When and If

Morning trips

Up to 32 guests
Start your day right with a refreshing sail on an ocean breeze before the heat of the day sets in. Our historic schooner Morning Sail brings you out to enjoy the gorgeous aqua waters and cerulean skies of Key West as you spot for turtles, dolphins and the proliferation of bird life that surrounds us here in the Florida Keys. Help raise sail, take a turn at the helm or simply relax and enjoy this unique and timeless experience.
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When and If

Afternoon excursions

Up to 32 guests
Come enjoy a sun-soaked Florida Keys afternoon sail aboard historic schooner When And If. Complimentary boutique wine and select beers on ice will keep you cool as you watch for the dolphins, turtles and abundant bird life that surround our island paradise. With all that the bright light and aqua waters have to offer, Key West afternoon sailing is truly a warm, breezy delight that returns you to the dock just in time for Happy Hour.
Book My Key West Sunset Sail
When and If

Sunset sails

Up to 32 guests
Join us on a perfect Schooner Sunset Sail, enjoying the unspoiled view and blue water sailing off the Keys' Atlantic coast from our gorgeous classic schooner yacht When And If.  With complimentary boutique wine and select beers on board this gorgeous 1939 historic schooner we invite you to sail with us for an unparalleled Key West Sunset Sail experience.
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