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Sailing Tipitina
Private charters aboard Tipitina-a 55-foot classic yacht in St John, USVI.
Your day, your boat, your pace.Sail, swim, sip and celebrate in barefoot luxury.
Crystal waters. Hidden Coves.
Gourmet lunch. Zero crowds.
Booking=Zero Hassles
Direct: No fees, No deposit. No cancellation fees.
Cash, Venmo, Paypal, Zelle at end of sail (10% cash discount).
Call/Text Bonnie 340-201-4657
call or text
The Boat:
Tipitina
Fast. Luxe. Legendary.
55-foot high performance monohull.
$1.2 mil. refit. Aft cockpit for sunset chills.
Built for speed. Designed for comfort.
America's Cup Heritage.
Your Crew:
Captains Matt and Bonnie
Aussie Sailor + Southern Nurse.
USCG Masters + Rescue Diver.
Liveaboard with two salty boat dogs.
The Dogs:
Oyster and Ruby
Passport-stamped pups.
Will steal your heart and maybe your lunch.
Come as guests, leave as friends.
Book a Trip with Tipitina
Elegant and Effortless
Ditch the floating sardine cans and skip the battered relics with cluttered decks.
Step aboard pure elegance where you will be welcomed like family and not herded like sheep.
Tipitina stands alone as the only true luxury monohull day-sail charter based in St. John—and at 55 feet, the largest you’ll find.
She is a custom-built thoroughbred that fuses timeless style, blistering speed, and every modern comfort.
Revitalized in 2016 with a $1.2 million re fit, her sleek aft cockpit and sugar-scoop stern deliver effortless water access for snorkeling and serene, private lounging.
So let’s set sail for the ultimate Caribbean escape: glide across crystal-clear waters, uncover hidden coves and vibrant reefs untouched from the masses.
This isn’t just a sail—it’s your once-in-a-lifetime journey.
Meet Oyster and Ruby
Ahoy, These two floppy-eared buccaneers have called Tipitina home since their wide-eyed puppy days, racking up passport stamps like buried treasure—from the Bahamas to Grenada.
Oyster, our salt-crusted first mate, serves up a grin that melts hearts faster than island ice in a dark ’n’ stormy.
Ruby, our spirited Vizsla and newest crew member, is already stealing the spotlight.
Though we hold the memory of our beloved Pearl close to our hearts, Ruby’s boundless energy, sea-and legendary coconut-retrieving skills have every guest completely enchanted.
Together, they’ll greet you with kisses, victory laps around the cockpit, and a tail-wagging invitation to the wildest, friendliest sailing adventure in the Caribbean.
Your Captains
Bonnie and Matt
Saltwater Souls
Born and raised in Fremantle, a rugged port city on Western Australia’s untamed coast—Matt grew up with salt in his veins. Boating, fishing, and diving were his first language. Boats carried him across the globe, from crafting superyachts to restoring wooden classics as a shipwright.That life led him to Seattle’s rain-slicked docks, where he met his beautiful wife, Bonnie. A travel nurse from Jackson, Mississippi, she’d wandered the Deep South before anchoring in the Pacific Northwest. Their first shared voyage? Sailing the cold, gray waters of the Puget Sound—where overcast skies only deepened their craving for the return of sunshine.They found it in San Diego. Amid fleet races and sunset beers, the dream took shape: Buy a boat. Sail the Caribbean.Now, as USCG-licensed Master Captains, they call St. John, USVI home. From Fremantle boatyards to turquoise anchorages, their story is woven in wind, waves, and the quiet courage to chase a horizon—just the two of them, their pups, and the boat that carries their dreams.
Contact Us
St. John is a playground for sailing and island hopping.
Come as strangers, leave as friends.
For "NO FEE BOOKING" call or text
Bonnie 340-201-4657
We settle up at the end of the charter and accept
CASH, VENMO and PAYPAL
10% Cash Discount
No deposit, No cancellation fees
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