Land first.
You arrive, check in, have dinner with everyone, and get to know the people you’ll be spending the week with.
Small-group sailing journeys
A trip that happens to move by boat.
Sailing journeys for gay men who want to experience the parts of a place you can’t reach by road. Small groups, private catamarans, great food, and a week built around good places and good people.
Where this started
I had to convince people to trust me with their vacation.
I had an idea for a travel company. That was the easy part.
The hard part was asking people to hand over a week of their vacation to someone doing this for the first time — and to a company making its first trip.
They said yes anyway.
In July 2026, we sailed from Athens to Mykonos via Paros, Milos, and a few smaller places along the way. We came back with a full week of photos, stories, and people already asking when we were doing it again.
Greece, July 2026.
Not a schedule — a rhythm
A week has a shape.
By the end of the first day, it already feels a little unreal: you wake up somewhere new, get in the water, find something good to eat, go explore, and watch the sun go down.
There’s a rhythm to the days, but no pressure to stick to a rigid schedule.
Then the sea.
You wake up somewhere new. Each day brings a different island, cove, beach, or stretch of coastline to explore.
Eat together.
Some meals are quick and easy between activities. Others turn into long dinners that stretch well into the evening.
Shared platters, fresh fruit, pita sandwiches, local food, good wine — whatever fits the day.
Go explore.
An island to explore, a beach to find, a village to wander through, a trail to hike where the itinerary allows. Sometimes there’s a road. Sometimes there isn’t.
A night out.
Depending on the destination, we’ll have opportunities to go out, grab a drink, find some music, and have some fun together. What you join is up to you.
Greece, July 2026.
What the days are made of
Explore. Swim. Eat. Connect. Go out. Sail. Stargaze.
A good day might mean swimming off the boat, snorkeling over coral reefs, spotting sea turtles or dolphins, exploring an island, finding a great meal, watching the sunset, and looking up at a sky full of stars.
And when the sun goes down, the day doesn’t necessarily end. Depending on the destination, we might head out for dinner and drinks, find some music, or stay on board with a drink and keep the evening going.
Explore
Go beyond the obvious.
We see the famous places. Then we keep going — to the beach nobody else walked to, the little village with one good restaurant, the cove you can only reach from the water.
“We spent the week exploring hidden coves, jumping off cliffs, swimming in crystal-clear water…” Eric Liu · Greece, July 2026
Eat
Long dinners, shared.
Meals are part of the experience, not something squeezed between activities.
Sometimes it’s a quick lunch on deck before the next adventure. Sometimes dinner stretches for hours.
Good food, good wine, and nowhere else you need to be.
“Every meal was somewhere I would never have found on my own.” Garret, New York · Greece, July 2026
Connect
The group is part of the journey.
You’re not just sharing a boat. You’re sharing meals, swims, adventures, inside jokes, and a week of your life.
A catamaran gives each journey a natural size — small enough that you actually get to know the people you’re traveling with. A lot of guests come alone, but you won’t spend the week feeling like you’ve joined a tour group. You eat together, swim together, explore together, and somewhere along the way, the people you arrived not knowing become the people you’re sharing the week with.
“I felt so comfortable being myself while also making meaningful connections.” Denis Grela · Greece, July 2026
Sail
Wake up somewhere different.
You don’t need to know how to sail. The crew handles the boat while you swim, eat breakfast, read, or relax on deck. And if you want to take a turn at the helm, you can.
The boat gets us from one place to the next while you enjoy the ride.
“I had wondered whether a private catamaran would really deliver something different. … Traveling by boat is different.” Garret, New York · Greece, July 2026
Why a boat
Places you can’t reach any other way.
This is the whole point of doing it by sea.
The catamaran is your base, your ride, and part of the experience. You unpack once, wake up somewhere new, swim straight from the boat, and reach beaches, coves, and islands that have no hotel at all.
No long sea days waiting for the next port, no hotel changes, no transfers, no driving from one beach to the next. Just more time experiencing the places you came to see.
It’s comfortable, but it’s still a boat — and that’s part of the adventure.
The journey starts on land
Before the boat.
Every journey begins with a night in the city, not at the dock.
Arrive, check into the hotel, and meet the group over dinner. We’ll also spend some time getting to know the place we’re sailing from — whether that’s exploring Athens before heading into the Cyclades or discovering Charlotte Amalie before setting out into the Caribbean islands.
By the time we board, you’ve already had a drink, shared a meal, and met the people you’ll be spending the week with.
Athens · Greece, July 2026.
Who’s coming
A small-group trip for gay men.
A lot of people come alone. Some come as a couple. Some bring a friend.
Everyone arrives for the same thing: a beautiful week, good people, great experiences, and a little adventure built in.
We keep the group intentionally small, so it’s easy to meet people and spend time together without ever feeling like a crowd.
Who’s coming
A mix.
Different ages, cities, backgrounds, and personalities — but everyone chose to spend a week experiencing amazing places with other gay men.
That’s the mix that makes a small group work: you arrive for the same kind of experience, then get to know the people who came along for it.
Your days, your pace
Be as active as you want.
Swim, snorkel, explore island towns and villages, hike where the itinerary allows — or stay on the boat and enjoy the view.
Join whatever sounds good. Skip whatever doesn’t. The trip has a shape, but your day is still yours.
The nights
Good nights, wherever we are.
Dinner somewhere great. Drinks by the water. Live music. A late night out if the night takes you there.
Some nights end early. Some absolutely don’t.
Greece, July 2026.
What you’re actually booking
You’re not just booking a cabin. You’re joining a small group for a week built around good places and good people.
Our inaugural journey
Greece, July 2026.
Athens, then the Cyclades. Our first trip, with the people who came with us.
Our inaugural journey. Greece, July 2026.
Guest stories
From the people who went first.
It was the perfect mix of making new friends and spending more quality time with old ones. We spent the week exploring hidden coves, jumping off cliffs, swimming in crystal-clear water, and, of course, doing some gay shit together. … It was wholesome! Definitely a trip to remember.
Eric LiuInaugural Greece journey · July 2026
I truly loved the group of people I had the privilege to meet and spend time with. The atmosphere felt private, exclusive, and completely relaxed — I felt so comfortable being myself while also making meaningful connections. The organization, excursions, and activities were top-notch. … I would definitely go again!
Denis GrelaInaugural Greece journey · July 2026
Whatever anxiety I had about traveling with strangers evaporated over wine and stories. … I’d been to that cliff before and chickened out. This time I had people I’d known for two days telling me I had it, and I jumped.
Garret, New YorkInaugural Greece journey · July 2026
Overall an incredible trip with incredible people. Loved the small LGBTQ+ group format. The sites we visited were beautiful, and there were a lot of laughs and adventures the whole time.
Solomon KimInaugural Greece journey · July 2026
Greece was unforgettable. From the insane beaches and crystal-clear water to the amazing people I met, every moment felt special. … Beautiful places, unforgettable moments, and friendships I’m so grateful for. Already wishing I could go back.
Camilo FernandezInaugural Greece journey · July 2026
One of my favorite parts was getting to explore the different Greek islands, experience the unique culture and scenery of each place, and fully embrace everything Greece had to offer. … The trip gave me memories and friendships that I’ll always cherish.
Alex HunterInaugural Greece journey · July 2026
One of the coolest parts was jumping off the boat and swimming to different shores and hidden spots. … Overall, it was an awesome mix of adventure, nightlife, and exploring somewhere new.
Damiano LodatoInaugural Greece journey · July 2026
Great foods, great people, awesome captains!
Kimbo GohInaugural Greece journey · July 2026
I liked the whole journey and people I shared this experience with.
Chris HeychenkoInaugural Greece journey · July 2026
The next journey · Booking now
The Glow Up.
The Caribbean · February 5–13, 2027
Nobody’s summer is in February. Take a week out of the middle of it.
Nine days through the U.S. and Spanish Virgin Islands on a private catamaran — white-sand beaches, coral reefs, sea turtles, wild coastline, and a night kayaking through glowing water.
Same small group. Long dinners. Plenty of swimming. A few nights out. No need to rush.
- WhenFebruary 5–13, 2027
- Group size8 guests
- Price$4,190 per person, excluding flights
- To reserve$1,000 deposit, refundable for 48 hours
More journeys are coming.
Every journey starts with the people who want to come. Join the list to hear about new destinations before we announce them publicly — and help shape where we go next.