Outings & Adventures – Inaugural Voyage Windjammer Cruise

Join us on our Inaugural Voyage on a Windjammer Cruise of the leeward Caribbean Islands! Lots of great surprises in store as we take to the crystal blue waters. Space is extremely limited with a maximum capacity of 24 guests  and a crew of 10.

Windjammer ships are known by a variety of names – sailing ship, tall ship, schooner, clipper, barque… No matter what you call her, a tall ship is graceful, romantic, sexy, and fun! There’s no better way to island hop.

The minute you step aboard, the island rhythm takes over. Days are marked by sunrises and sunsets; how much or how little happens in between is completely up to you. That’s part of the charm of an Outings & Adventures Windjammer sailing vacation.

Outings & Adventures has exclusively chartered the entire vessel be surrounded by likeminded gay men on our inaugural tall ship Caribbean sailing adventure.


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