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The US and Spanish Virgin Islands · Booking now

The Glow Up.

The Caribbean with the gays — nine days of summer in the middle of February, a small group who all wanted the same week, and a bay that lights up when the sun goes down.

February 5–13, 2027 $4,190 per person, excluding flights 9 days · 8 guests
Duration
9 days
Group size
8 guests
The route
Charlotte Amalie→Culebra→Culebrita→Vieques→Charlotte Amalie

What the journey feels like

Somewhere it’s still summer.

Between St. Thomas and Puerto Rico are a handful of islands you can only really experience by boat. For one week in February, that’s where you go — with a small group of men who picked the same week for the same reason you did.

There are white-sand beaches you’ll have almost to yourselves. An old lighthouse above the water. Wild horses wandering onto the shore at sunset. A tiny Caribbean town where the golf carts outnumber the cars — and WWII tanks sit on the beach.

And then there’s the bay that lights up when you touch the water. Paddle through the darkness and every movement sends blue light flickering around your hands, your paddle, the hull. We go on the darkest nights of the month, when there’s no moonlight to wash it out.

This is a small-group gay journey. Eight of you, one catamaran, and nowhere else to be. Small enough that everyone eats at the same table. Long enough that the days stop having names.

It’s February. The water is 79°F. And you are not at home.

SailSwimSnorkelExploreEatStay out late
The group round a table together on the first night

Who you go with

Eight men, one boat, a week of summer. And the right people to share it with.
Swimming and paddleboarding off the back of the catamaran

Why February

February is the problem. This is the answer.

Nobody’s summer is in February. It’s the long grey part of the year — cold, dark, and far too long.

So take a week out of the middle of it. In the Virgin Islands, February brings days around 81°F, nights around 75°F, and sea temperatures around 79°F. It’s the driest stretch of the year.

79°F

Sea temperature across the week — warm enough to swim before breakfast.

81°F

Typical daytime high in February.

New moon

Around February 6th, the darkest skies of the month make the bioluminescent bay and the stars overhead even more spectacular.

The coast of Culebra from the air

The coast of Culebra.

The route

Four islands. One group. A lot to remember.

It starts and ends in Charlotte Amalie, a colorful old harbor town on St. Thomas. In between, you’ll swim off deserted white-sand beaches, wander a tiny island town, watch wild horses come down to the shore, snorkel over reefs, and paddle through water that glows blue in the dark.

We’ll spend our days exploring islands, swimming and snorkeling, finding great beaches, and watching the sun go down. Evenings are for good food, drinks, and having fun together on board or ashore.

Four islands, one loop. No two days alike.

Lying out on the trampoline of the catamaran over turquoise water

The boat

It takes you where the roads don’t.

The best parts of these islands have no road to them. The beaches on the far side of Vieques, the uninhabited island with the lighthouse, the reefs just offshore — places you can only really reach from the water.

And the boat is part of the fun. There’s room for everyone to hang out together, a spacious cockpit for meals, a foredeck for lounging, a flybridge for sunset, and a swim platform for jumping straight into the Caribbean.

With eight guests and three crew, it’s small enough to feel personal. We eat together, explore together, and spend the week sharing the same floating home.

Denys leads the trip — @denys.journeys — alongside a professional skipper and private chef.

  • The boatPrivate catamaran, built for island hopping
  • CrewGroup leader, a professional skipper, and a private chef
  • CabinsTwo guests per cabin
  • Shared spacesCockpit, saloon, foredeck lounge, flybridge, swim platform
  • On boardWater sports equipment, including stand-up paddleboards

Our first journey

What a week with us actually looks like.

The group in a rooftop hot tub at night, drinks in hand
Climbing back aboard after a swim
A round of drinks going round the table
The group heading down the dock to the boat, bags in hand
The group out at a bar in the evening
A table spread of grilled food, potatoes, and olives
Riding out along an island road behind the rest of the group
The group at a long table on a rooftop at golden hour

Our inaugural journey. Greece, July 2026.

The price

$4,190 per person.

Nine days, four islands, and a private catamaran, excluding flights.

$1,000 to reserve your spot. $3,190 due December 7th.

How booking works

Step one

A $1,000 deposit holds your cabin.

Changed your mind within 48 hours? Get your deposit back.

Step two

The remaining $3,190 is due December 7th.

Sixty days before the journey begins. Book flights and sort out travel insurance whenever you’re ready — full terms are in our terms and conditions.

Cancellation

Within 48 hours
100% refund
After 48 hours
50% of payments received, as credit

Credit is valid for 12 months from cancellation and may be transferred to another person.

What’s included

  • Hotel night in Charlotte Amalie before we board
  • Welcome dinner with the group
  • Seven nights aboard a private catamaran
  • Professional crew — a skipper and a group leader
  • Chef on board
  • Meals on board the catamaran
  • The night kayak into Mosquito Bay — the brightest bioluminescent bay in the world
  • Port fees, fuel, and marina fees
  • Water sports equipment on board, including stand-up paddleboards
  • Curated experiences and local guidance throughout

What isn’t included

  • Flights to and from St. Thomas
  • Travel insurance — not included, required
  • Some meals and drinks ashore
  • Additional tours and optional activities
  • Personal spending, tips, and souvenirs

Is this for me?

The things people actually worry about.

Comfortably. Days run to about 81°F and nights sit around 75°F, and the sea is 79°F — warm enough that nobody stands on the ladder working up to it. February is also the dry season here, and the tail end of the winter trade winds, so it is breezy rather than still.

There’s no type. The inaugural group was mostly solo travelers, gym guys and very much not, some who’d sailed before and some who’d never been on a boat. The only thing everyone had in common was wanting the same week — curious, up for the day, easy to share a small space with. That’s genuinely the whole list.

Here is what a normal day actually asks of you: getting in and out of the water from a swim platform, walking on sand and uneven ground, and a few hours of sun. The one real climb is the lighthouse hill on Culebrita, which takes about twenty minutes uphill and is optional. Nothing needs a particular fitness level, and sitting any of it out is completely normal.

No — but being comfortable in the water will make the trip much more fun. You don’t need to be a strong swimmer, but swimming and getting in the water are a big part of the experience. Flotation equipment is available, and there’s always plenty to do on land or aboard.

None. The crew sails the boat. You are welcome to help if you want to learn, and equally welcome never to touch a rope all week.

Absolutely — and many guests do. Most people come on their own, but couples and friends are very welcome too. Shared meals, swims, adventures, and a week together mean the group tends to come together quickly. And there’s always room to take an afternoon to yourself when you need it.

US citizens don’t need a passport — the US Virgin Islands and Puerto Rico are both US territory, so a REAL ID driver’s license covers it. Everyone else travels on whatever they’d need for the United States. Bring a passport if you have one either way: the USVI sits outside the US customs zone, so the boat clears customs when we cross to Culebra and again on the way back. The crew handles it and nobody gets off the boat.

Cabins are shared between two guests, four cabins for eight of us. Traveling with someone? You’ll share with them. Coming solo? We’ll pair you with another guest.

There will definitely be some late nights. The first night in town usually goes late, and there will be plenty of dinners, drinks, swims, and time together. But it’s not a nonstop party — some mornings are slow, some afternoons are for exploring, and some are for doing absolutely nothing. You set your own pace, and nobody keeps score.

Unlikely. February sits in the dry half of the year here, and what does fall tends to be a short shower rather than a day of it. If we do catch one, we’re on a boat with a saloon, and a wet afternoon with this group is not the worst thing that has ever happened to anyone.

Short. Most days are a hop between anchorages rather than a passage, with two proper sails — one out at the start of the week, one back at the end. February is trade wind season, so there is usually a decent breeze and some swell, and people generally experience less seasickness on a catamaran than on a traditional single-hull sailboat. If you think you might be prone to it, ask your doctor about a scopolamine transdermal patch before you travel.

Take it. Skip the walk, stay on the boat, wander off into a town on your own for a few hours. Sitting on deck doing nothing is a legitimate use of a day here.

Guest stories

From the people who went.

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