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Private Sailing Charters  ·  Premier Waters Worldwide

We traded office hours
for trade winds. You're invited.

Aboard the Irish Wake — our 42-foot catamaran in the British Virgin Islands — we take small groups of fellow travellers through some of the world's most beautiful waters. No sailing experience required. Just curiosity.

Small groups — just 2–3 guest cabins per trip. A $300 deposit holds yours.

What we offer

More than a charter.

We're not a typical charter company. We're two people who love to sail — comfortably — in fantastic destinations, and we really enjoy doing so with other like-minded friends, new and old.

Expert Guides

Captain Tim holds an international sailing license and has sailed catamarans at destinations across the Caribbean, the Mediterranean, and beyond. Admiral Donna handles everything else — often better than Tim. You're in good hands.

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World-Class Destinations

The BVIs. Croatia. French Polynesia. Greece. Belize. We sail premier waters and plan every itinerary to get the most out of each destination.

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Effortless From Start to Finish

No experience, no planning, no provisioning, no stress. We handle the boat, the route, the meals, and the logistics. You just show up, settle in, and enjoy one of the best weeks you'll have in years.

Captain Tim and Admiral Donna at Foxy's Bar, Jost Van Dyke, BVI
Your Hosts

Captain Tim & Admiral Donna

We spent our careers in medicine and law. Then we bought a 42-foot sailing catamaran — the Irish Wake — and based it in the British Virgin Islands. That was one of our BEST decisions ever! And as a side benefit, it has given us access to a fleet of comparable charter vessels around the world.

We've now sailed in fantastic destinations in the Caribbean and Mediterranean and are headed to the South Pacific soon — with friends and guests who range from seasoned sailors to people who had never left the shore. We've learned a lot along the way about what makes a week at sea truly unforgettable.

We've struck out on this adventure because we want to share it — all of it. The navigating, the anchorages, the lobster dinners, the spectacular sunsets...and even the rare mainsheet override on the electric winch...'cause THAT'S fun.

Our Full Story →
42 ft Leopard Sailing Catamaran
3 En-Suite Cabins
15+ World-Class Destinations
~$2,900 Per Cabin, Per Week
Where we sail

The world's best sailing waters

Our home port is in Road Town, Tortola, in the BVIs — one of the premier sailing grounds on Earth. But we also venture much further afield.

Catamarans moored in the British Virgin Islands

British Virgin Islands

Our home waters

Saint Lucia, Eastern Caribbean

Saint Lucia

Gem of the Southern Caribbean

Sailing the Aegean Sea, Greece

Croatia & Greece

Mediterranean adventures

Bora Bora lagoon, French Polynesia

French Polynesia

Raiatea, Taha'a & Bora Bora

We also have access to vessels in the Bahamas, Belize, St. Lucia, Martinique, Antigua, Grenada, St. Martin, La Paz, Thailand, Seychelles, Sicily, Sardinia & the Bay of Naples.

Sailing catamarans moored in a BVI bay
Why charter sailing?

A week on a catamaran is unlike anything else.

A catamaran charter gives you something a resort simply can't — genuine freedom. A different anchorage every night, or the same perfect bay two nights running. The pace is yours, the agenda is negotiable every morning, and you're out on the water, not looking at it from a poolside chair.

Add good company, new friends, warm water, and a sky full of stars, and it's the kind of week people talk about for years.

And the best part? You don't have to know a thing about sailing. We take care of the boat and the route — you just bring your sense of adventure.

Read our First Timers Guide →
Sailing downwind toward Jost Van Dyke, British Virgin Islands
One day, for instance

The day everyone remembers

Ask our crew which day they'd sail again, and it's almost always this one. In the British Virgin Islands, we point the bow downwind toward Jost Van Dyke — sails full, engines off, a long easy glide with a parade of islands sliding past. If the dolphins are going to turn up, this is where they do it, surfing along the bows while everyone scrambles for a phone.

We swim off a castaway sandspit barely bigger than its palm trees, float away the afternoon at White Bay, and raise a Painkiller at the Soggy Dollar before dinner ashore at Foxy's. That's a BVI day — Croatia, Belize, Greece and the South Pacific each have one of their own. Some days at sea are merely wonderful; this is the kind people talk about back home.

See a full week aboard →
From our guests

What a week on the water does

"I'm still dreaming of our time on the Paloma (our catamaran in Croatia) and the islands. Words can't even express how amazing our trip was and how lucky I feel to have been a part of it."
Kimberly Smith— Kimberly Smith (Croatia)
"First time for us doing a sailing trip like this and it was an amazing experience. A great combination of sailing, exploring new places, and hanging out and relaxing. It was so fun learning a little about sailing, getting a little experience at the helm, and tying some knots. Would definitely do another trip."
Bill and Susan Williams— Bill Williams (USVI)
"I didn't think Tim was serious about the knots. If I had known, I would have learned them ahead of time! Tip for future crew…learning the knots (even one) before the charter really does make everything even easier!"
James Wood— James Wood (Aeolian Islands)
Melissa (see the arrow!) with the crew on a Caribbean sandbar
"Sunshine, snorkeling, lobsters, cold beer, and wonderful open-air beach dinners the nights we moored. Tim is a laid-back, seasoned captain and Donna a gracious hostess. We'll join them in Greece next summer."
— Melissa McSpedden (Saint Lucia Charter Guest)
What's coming up

2026 & 2027 Charters

We have a handful of spots remaining for 2026 and several excellent options for 2027. Cabins fill quickly — if you're interested, the time to reach out is now.

Available 💰 $1,500 Off — Just $500/cabin British Virgin Islands Just 2 guest cabins — both open · week 1 Just 2 guest cabins — both open · week 2
Jul 26 – Aug 9, 2026
Last-Minute Escape — just $500/cabin/week ($1,500 off). 42-ft, 3-cabin catamaran from Road Town, Tortola. 1- or 2-week options (swap at Tortola airport Aug 2).
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★ Featured Charter Available Belize Just 2 guest cabins — both open
Feb 6 – Feb 13, 2027
The one we picked for ourselves — flat-water sailing inside the world's second-largest barrier reef, among 450 palm-topped cays. 42-ft catamaran from Placencia (PLJ). 1-week sail.
Why Belize? →
Available British Virgin Islands Only 1 of 2 guest cabins left · week 1 Only 1 of 2 guest cabins left · week 2
Apr 22 – May 6, 2027
42-ft catamaran. 1- or 2-week options. Starting Road Town, Tortola.
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Ready to explore?

Say yes to the adventure.
We'll handle the rest.

The hardest part is just saying yes. A $300 deposit holds your cabin — we'll sort out the rest together.

Reserve Your Cabin — $300