Caribbean Winter Escape
One week in the Caribbean's most famous sailing ground. Leave your routine behind and come home a little changed.
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The concept
Two things make this week different.
Where it is:
The water every sailor eventually wants to have sailed — trade winds, real ocean. Short passages between islands, and something at every stop you can only reach from the water.
What it does to you:
A week long enough to think about something important. People go home with new ideas, sometimes real changes — 700+ guests say it themselves.
One week, in the middle of a grey January. You leave the routine in Europe and come home with something better.
Where it is:
The water every sailor eventually wants to have sailed — trade winds, real ocean. Short passages between islands, and something at every stop you can only reach from the water.
What it does to you:
A week long enough to think about something important. People go home with new ideas, sometimes real changes — 700+ guests say it themselves.
One week, in the middle of a grey January. You leave the routine in Europe and come home with something better.
How does this trip work
You will live and travel on a catamaran between the British Virgin Islands, anchoring in bays and coves that can only be reached from the water.
Mostly solo travellers from across Europe. Everyone is vetted through a call with the captain before booking, so the group works.
You don't need any experience. Sailing tuition with the captain runs all week and it's entirely optional — take the helm or don't.
January in the Caribbean is dry, steady trade-wind season. Swim and snorkel daily — caves, reefs, The Baths — unreachable by land.
Why you will enjoy traveling with us
-
8 years of group sailing tripsWe've been organizing yacht adventures worldwide since 2018, so we know how to create the perfect sailing week. -
Small groupsExpect up to 8-9 like-minded vetted people on one yacht for your comfort and quality networking. -
A call with the captainGet to know who will take care of your vacation and ask questions directly before a trip -
New clean yachtsFor you, we choose a modern, fully equipped fleet that typically 3-7 years old. No smelly and crumbling yachts.
Sailing route
Tortola
Your Caribbean adventure begins here, the heart of the British Virgin Islands. Bustling yet beautiful, Tortola welcomes you with palm-lined beaches, reggae rhythms, and crystal-clear anchorages.
Norman Island
Legends say it inspired Treasure Island, and when you sail into its secret coves, you’ll see why. Swim into caves with shimmering light, snorkel with tropical fish, and toast the sunset on the deck. This island whispers mystery and feels like stepping into a storybook.
You don`t need any previous experience to join the team for this trip. The route is flexible and can be changed due to the weather
Start and finish: near Road Town, Tortola. 30 minutes away from the nearest airport: Beef Island (EIS)
Start and finish: near Road Town, Tortola. 30 minutes away from the nearest airport: Beef Island (EIS)
Cooper Island
Home of slow mornings and starlit evenings. We anchor close to Cooper Island Beach Club, craft cocktails, good vibes, and reef snorkeling just a dinghy ride away. If you like your sailing days with a side of comfort, this stop is for you.
Virgin Gorda — The Baths
If you’ve ever seen those dreamy boulders on Instagram, this is the place. Climb, crawl, and swim your way through ancient granite caves and hidden pools. Virgin Gorda feels like nature’s playground and yes, it’s even better in person.
Jost Van Dyke
The Soggy Dollar Bar on White Bay has no dock. You anchor off, swim in, and pay with wet money — which is exactly where the name comes from, and where the Painkiller was invented in the 1970s. On the wild north coast, the Bubbly Pool: a rock channel where the Atlantic swell breaks through and turns a natural pool into a jacuzzi.
Wow-Places to Explore on Land
Coming early or staying longer? These are the places you don’t want to miss:
Turn this video into your reality
Common zones in the cockpit, on the deck, upper level, and inside
Salon with equipped kitchen: fridge, freezer, cooker, oven
Cold and hot water, generator, air conditioning, water maker (desalinator)
Cabins: 4
Outer zones: 3
Outer zones: 3
Our home for
7 days of adventures
7 days of adventures
Sail and motor catamaran, fully equipped for autonomy in the seas and oceans
Your captain
Hello!
I am Sergey – Skipper, with 8 years of experience. I got a license in Ireland after passing the Royal Yacht Association (RYA) program and I'm ISSA licensed too. Navigated 25 000+ nautical miles on yachts in the seas and Atlantic, Indian and Pacific oceans.
I live my life like you and organize soulful trips on seas and oceans in Europe, Asia, and America.
My goal is to open a world of a completely different and unique type of adventure as sailing is to as many people as possible. It happened to me 8 years ago, and now I want to show you how majestic the world can be from a yacht view.
I live my life like you and organize soulful trips on seas and oceans in Europe, Asia, and America.
My goal is to open a world of a completely different and unique type of adventure as sailing is to as many people as possible. It happened to me 8 years ago, and now I want to show you how majestic the world can be from a yacht view.
If you want to become my colleague and become a skipper, I have an official permit to educate you and issue a license.
Look how it was with us last time
guests on one yacht in average
8-9
years of experience
in sailing with teams
in sailing with teams
8+
people felt in love with a yachting with us
700+
€2070
Included:
€1670
Invest in your impressions
Additional budget:
Yacht charter (+ motor boat)
Yacht insurance
Licensed captain
Learning to steer the yacht and the art of sailing
Freediving masterclass
Final cleaning
Bed linen and towels
Yacht insurance
Licensed captain
Learning to steer the yacht and the art of sailing
Freediving masterclass
Final cleaning
Bed linen and towels
Food, drinks, fuel — (shared onboard kitty) €240-300
Flight tickets
Security deposit for a yacht €250 (refundable)
Additional activities on a land (restaurants, tours etc)
Flight tickets
Security deposit for a yacht €250 (refundable)
Additional activities on a land (restaurants, tours etc)
Next price increase: 15 Oct '26
To reserve your spot you need only 200€
Cost per person
Not ready to plunge
into sailing now?
into sailing now?
Leave your details, and we`ll update
you with the dates of our next trips!
you with the dates of our next trips!
Not ready to say yes now?
Stay tuned with us!
Stay tuned with us!
Follow our captain`s blog on Instagram and Facebook to learn more about us and get a notification about the next trip!
Let our guests tell you about us!
Robert Muller, Frankfurt
Dan Drumea, London
Paula Burt. USA
Micah Neville, USA
Elena, Switzerland
Salvatore, Amsterdam
Alina, Switzerland
Victoria, Stockholm
Diana, Romania
Andi, Colombia
Robertas, Dublin
Hermian, USA
Giulio, Spain
Fernando, Spain
Trips Calendar
10-17 Oct, 2026
10-17 Oct, 2026
12-19 December
12-19 December, 2026
12-19 December, 2026
Any week 2026
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