“I'd never sailed before and was nervous joining solo. By Day 2 it felt like I'd known the crew for years. The islands, the snorkelling stops, the dinners in Gustavia, it's the trip I keep telling people about.”
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4.9Adventure on Yachts
Sailing the Leeward Islands:Carnival Edition
7 days · 7 guestsA week of sailing, island-hopping and Carnival in St. Martin
5 of 7 spots leftApply
As featured inAuthority Magazine
What guests say
“The food on board from the private chef was AMAZING. We wanted to bring the chef home with us.”
“I'd sailed a bit before and the captain let me take the helm on the crossings, which was huge. Every evening there was something different going on, beach bars in St. Barts, paddleboarding, night swims, never a dull moment.”
“It was the perfect mix of luxury and genuine connection. If you want a trip that's a little extra and a lot of fun, you have to check them out.”
“I've done two Hidden Jam trips now, a surf one and this Caribbean one. Both unforgettable. The only problem is you can't get enough.”
“As a solo female traveller I was nervous booking. Ended up one of my favourite trips ever.”
What's included
Everything's taken care of. You just show up.
From €4,990 all-in
Carnival Experience
Four days inside St. Martin Carnival: costumes, music, street parties and dancing.
Skippered sailing
7 days island-hopping from St. Martin to Antigua with an experienced skipper. No sailing experience needed.
Trip photos
Professional shots from the week: the sailing, the islands, the in-between moments.
Private chef
A high-level dinner by a private chef with wine and local ingredients.
Swimming & snorkelling stops
Crystal-clear Caribbean water, reefs and coves you can't reach by land.
Farewell dinner
The last night, done properly.
We're picky about who joins. We hope you are too.
This isn't for everyone.
For you if…
You've never sailed and that's exactly why you want to try. The boat is skippered, you can do as much or as little as you like.
You're ready for the unexpected. Sailing is about spontaneity. We stick to our route, but sometimes a toilet breaks, the weather turns, plans shift. If you can roll with that and laugh about it, you'll love this.
You're coming alone. 80% of our guests do. The group is up to 14 people, and by Day 2 no one feels alone.
You care who's at the dinner table. We don't take everyone. Every guest goes through a 15-minute call before confirming a spot.
You want to meet people you'd actually stay in touch with. Founders, creatives, and people running their own things, mostly from New York, London, Paris, Berlin, Tel Aviv. We truly welcome everyone, regardless of age or background.
Not for you if…
You're looking for a party-week-on-water. This is more swimming, sunsets and conversation than beach clubs and 4 a.m.
You want every hour scheduled. There's structure: sailing legs, free time on the islands, slow mornings at anchor.
You'd rather skip the intro call and just book. We don't book without one. It's how we keep the group right.
Apply
If you're nodding through the left column, apply.
Schedule*
Seven days, day by day.
Day 1Sunday · St. Martin
We meet at the marina in St. Martin in the morning, settle into our cabins and get to know the crew and the group over a welcome drink.
There’s time to unpack, grab lunch, take a swim and get comfortable on the yacht before our first dinner together. We spend the night in the marina, ready to set sail in the morning.
Day 2Monday · Anguilla
We wake up to coffee and breakfast on board, then leave the marina and set sail for Anguilla.
It’s our first proper sailing day, with warm Caribbean water, music on deck and plenty of time to swim along the way. We anchor in Anguilla and spend the afternoon exploring the island, walking along the beach and finding somewhere for a drink before sunset.
Dinner is back on the yacht, with the lights of Anguilla in the distance.
Day 3Tuesday · St. Martin · Carnival
We wake up slowly in Anguilla, have breakfast on board and take one last swim before pulling up the anchor and sailing back towards St. Martin.
Once we’re back, we head straight into the Carnival atmosphere. We explore the island, grab lunch and spend the afternoon getting into the spirit of the celebrations before heading ashore for music, drinks and the first taste of St. Martin Carnival.
The yacht is waiting for us when we’re ready to call it a night.
Day 4Wednesday · St. Martin · Carnival
Today is the big one.
We start with breakfast on the yacht before heading ashore for a full day of St. Martin Carnival. Expect colourful costumes, music, dancing, street parties and the kind of energy that makes it very difficult to stand still.
We spend the day moving between the Carnival celebrations, drinks and the island before heading back to the yacht later in the evening.
Yacht by day. Carnival by night.
Day 5Thursday · St. Barts
After Carnival, we take the morning slowly with coffee and breakfast on board.
Once everyone’s recovered, we set sail for St. Barts. It’s a short crossing, giving us plenty of time to swim, relax on deck and enjoy lunch on the water.
By afternoon, we’re anchored off the island. We head ashore to explore Gustavia, wander through its streets and find somewhere for drinks as the sun goes down.
Day 6Friday · ST.Barts
We stay around St. Barts today, with nowhere we need to rush to.
After breakfast, we head out to explore the island’s beaches and coves, stopping for swims whenever the water looks too good to resist. There’s time for a long lunch, a walk through Gustavia or simply staying on the boat with a book and a cold drink.
By late afternoon, everyone ends up back on deck for sunset, followed by our last proper dinner together.
Day 7Saturday · St. Martin
We wake up for one last breakfast on the yacht before checking out.
One last coffee, one last swim if there’s time, a few final photos and then it’s time to leave St. Martin.
The people who arrived as strangers leave with a week of memories, a camera roll full of evidence and, hopefully, a few new friends.
Day 8Sunday · Departure
One last breakfast on board, then we set sail back towards St. Martin.
It’s our final stretch of sailing, so we make the most of it: music on deck, a final swim in the Caribbean and lunch somewhere out on the water. By afternoon, we’re back in the marina where the trip started.
One last drink together, bags packed, and suddenly the people who arrived as strangers are saying goodbye.
* The itinerary may change at the organizers’ discretion depending on weather and sea conditions.
Our boat
A fully crewed, luxuriously spacious sailing catamaran.
Luxury Catamaran · from €4,990 · private chef on board
Private Sanctuaries
Double beds, dedicated storage, and private en-suite bathrooms in every cabin.
Shaded Living Spaces
Protected outdoor cockpit, 360° panoramic salon, and open decks for quiet mornings.
Seamless Service
Professional crew handling 100% of navigation, safety, and dining. Just step onboard and relax.
Past guests
We bring together exceptional people: founders, leaders, creatives, those with presence, big ideas, and a deep appreciation for meaningful connections.
Trip cost
Apply below to confirm your spot. We reply within 24 hours.
April 25 – May 2, 2027 · 7 days
Early Bird€ 4,990 / person
(+10.5% tax)
Available until October 30, 2026
From November 1 · € 5,990 / person (+10.5% tax)
25% deposit to secure your spot.
What's included
- 7 nights aboard a fully crewed catamaran
- A private chef: fresh breakfast every morning, lunch or dinner on the yacht
- A curated group, matched through a short call before booking
- A curated route with Hidden Jam's own spots, not just the tourist stops
- A trip organizer with you throughout the week
- Professional trip photography
- Swimming & snorkelling stops
- Farewell dinner
Not included: flights · travel insurance · marina fees, fuel & groceries (~€350pp) · meals ashore · alcohol · optional activities
FAQ
Everything you might want to know before booking.
What's included?
- 7 nights aboard a fully crewed catamaran
- A private chef: fresh breakfast every morning, lunch or dinner on the yacht
- A curated group, matched through a short call before booking
- A curated route with Hidden Jam's own spots, not just the tourist stops
- A trip organizer with you throughout the week
- Professional trip photography
- Swimming & snorkelling stops
- Farewell dinner
What's not included?
- Flights
- Travel insurance
- Marina fees, fuel, and groceries for the yacht, split among all participants (~€350 per person)
- Meals ashore
- Alcohol outside of group meals
- Optional activities
Do I need any sailing experience?
No. The boat is skippered by an experienced captain. You can help sail if you want to learn, or just relax, it's up to you.
What if I get seasick?
The Caribbean in spring is dry season, with steady trade winds and short hops between islands rather than long ocean crossings. If the forecast predicts swell, we'll share a few useful tips on how to avoid seasickness.
What are the boat options?
One: a fully crewed luxury catamaran with a private chef, from €4,990 (early bird). Double cabins with en-suite bathrooms, shaded cockpit and panoramic salon. We'll walk you through it on your intro call.
Who will be joining?
A group of up to 7 people, matched through a short call before booking. Most guests come solo.
Is this trip for solo travellers?
Yes, most guests come solo. The group is small, you eat together, and the schedule is built around shared moments. By Day 2, no one feels alone.
Where should I fly to?
Fly into Princess Juliana International Airport (SXM) in St. Martin. There are direct flights from the US, including from New York (JFK), with airlines such as JetBlue and American Airlines. Flight times are around 4–5 hours, depending on the route.
Can you accommodate dietary needs?
Yes. Yes, our private chef accommodates all diets. Just tell us when you book.
Will there be WiFi? Can I work from the trip?
There's mobile signal at most anchorages and in port. Some guests check emails in the morning. But the point is to disconnect, most people do.
Can I bring a friend or partner?
Absolutely. Mention it on the intro call and we'll book you together.