Living on a yacht in paradise.
Partying with friends.
Island-hopping around the Caribbean.
Meeting new guys from all over.
Having adventures & shenanigans.

Never wanting to come home!

How it Works:
  • For a week, the Gay Armada boys escape winter by renting a fleet of sailing yachts in the Caribbean
  • We live on the yachts, sleeping, showering and cooking onboard.
    Every boat has a captain, and many guys have never sailed before

  • Every day, we hop around islands, doing different things on each, and creating a "Choose your own Adventure" trip.  On different islands, we might party on a beach, snorkel a reef, hike a mountain, explore culture, get pampered at a resort, wander totally empty beaches, race around on scooters, or just relax in paradise
  • At night, we rally to the same harbor, where we have theme parties in amazing local spots.  Two of the world's Top Five Beach Bars are on the trip, and every night is somewhere new and amazing
  • It's an authentic experience, and each yacht group can be itself.  Some party like rockstars, and others are quiet and chill
  • Some guys sail their own boats and cook for themselves. Others add on a Captain to sail, and a host/hostess to help cook/clean
  • The Armada is run by a volunteer team, keeping costs down, and making sure that the event is focused on fun
  • The trip is put together as a package, combining nearly everything we need (except groceries & drinks) into an easy package, and then the Armada handles all the planning and logistics.  Once you land in St. Thomas and see the greeter with our sign, you're all set.  Your taxis, ferries, yachts, events, logistics, and coordination are handled
Sound like fun?  
Here's how we sign up:

Two Ways to Register

A Full Yacht to

You pay a flat price for the yacht, and bring along anybody you want to fill it with friends.
Per person, it can end up being the cheapest option, too
You get to choose which yacht you want, and then have total flexibility of options, and more relaxed payment deadlines
Deposits are:  $1995
...and prices vary by yacht

Sailor Slots

You sign up with some friends, each pay individually, and the Armada matches you up with others to fill the yacht. If you get a big enough group, you can have your own yacht

The trip is best with friends, and this option has always been our most common
Sailors start at:  $1695
...or a deposit of only:  $440
Make sense?  The next decision is who to sail the yacht
Types of Captains


You can sail as much, or as little, as you want, because your pro skipper has it under control, and will make sure you all have an amazing time

He'll know all kinds of neat extras to do on the trip, and knows just how to handle wacky islands or tough approaches.  He also cuts your deductible down to $0

$1495 CHARGE
+Tip, Meals, and Cabin Space


The trip offers VERY discounted, subsidized rates to volunteer sailors who will take a group under his wing for the week and teach you to sail

But he's not hired staff!  He is a regular part of your yacht family, and he's paying to be there, too, so you will all have to pull your own weight, and he's there as the guru

No Charge to Group
Contingent on available volunteers, or else must hire

in Group

If your group has a qualified skipper, he can sail the boat for you for the week, giving total flexibility to your group
Self-skippered boats also have freedom to spend a night off the grid, if they want, as volunteers and staff are obligated to get to the rally points each night
No Charge
Included in Full Yacht price