CREWED CATAMARAN CHARTERS · USVI & BVI

Sail Pretty Lucky

Your private floating villa across the Virgin Islands — crewed, curated, unforgettable.

Check Availability View Rates

The Vessel

A Lagoon luxury catamaran with generous deck spaces, a bright open saloon, and three queen guest cabins. Crewed by Captain Shaun and a dedicated mate, Pretty Lucky is run as a full-service charter business — every detail handled so you only unpack once.

~56'Length
3Queen Cabins
6Guests
2Crew
USVI+BVICruising

Gallery

Aboard Pretty Lucky — from the wide exterior sightlines to the salon, galley, and the life that happens on the water.

Exterior

Pretty Lucky — white hull and flybridge on turquoise coastal water
EXTERIOR · HULL & FLYBRIDGE
Pretty Lucky — aft exterior deck at the marina
EXTERIOR · AFT DECK
Pretty Lucky forward deck
FORWARD DECK
Pretty Lucky cockpit lounge
COCKPIT
Pretty Lucky — aft deck seating and swim platform
AFT DECK
Pretty Lucky — exterior detail
EXTERIOR
Pretty Lucky — on the water
ON THE WATER
Pretty Lucky
EXTERIOR
Pretty Lucky
EXTERIOR
Pretty Lucky
EXTERIOR
Pretty Lucky
EXTERIOR
Pretty Lucky — aerial view at anchor
EXTERIOR · AERIAL
Pretty Lucky under full sail
EXTERIOR · UNDER SAIL
Pretty Lucky — hull and deck detail
EXTERIOR · HULL
Pretty Lucky — foredeck
EXTERIOR · DECK
Pretty Lucky — stern and swim platform
EXTERIOR · STERN
Pretty Lucky under sail in the Virgin Islands
EXTERIOR · UNDER SAIL
Pretty Lucky — hull and deck detail
EXTERIOR · HULL
Pretty Lucky — forward deck and trampoline
FORWARD DECK

Interior

Pretty Lucky salon
SALON
Pretty Lucky galley
GALLEY
Pretty Lucky — galley prep and counter
GALLEY
Aboard breakfast — eggs, bacon, and fresh fruit on the table
ABOARD DINING

Life on the Water

Guests embrace on a palm-fringed tropical beach
BEACH
Guest relaxing in a rope hammock under palm trees
HAMMOCK
Friends wading in clear turquoise shallows
SHALLOWS
Guests toasting aboard a small boat in turquoise water
SUNSET TOAST
Friends laughing on a floating wooden deck
DECK
Guests at Foxy's Tamarind Bar
FOXY'S
Guests at a beach-bar wooden dock
DOCK BAR
Iced coffees at a beach club
BEACH CLUB
Guest in a Pretty Lucky tee on the beach
PRETTY LUCKY
Pretty Lucky — life on the water
ONBOARD
Pretty Lucky — charter memories
CHARTER
Pretty Lucky — tropical anchorage
ANCHORAGE
Pretty Lucky
ONBOARD
Pretty Lucky
ONBOARD
Guests on a Caribbean beach
BEACH
Couple embracing on the beach at sunset
SUNSET
Sunset over the anchorage
SUNSET
Guests with cocktails aboard
COCKTAILS
Snorkeling in clear turquoise water
SNORKEL
Aboard drinks and toasts
ABOARD
Captain Shaun in Pretty Lucky gear on the beach
CREW · SHAUN

Video

Aboard Pretty Lucky — life on the water.

Charter Rates

Fully crewed, all-inclusive charter (crew, fuel for the itinerary, standard provisioning, and water toys).

Standard Week

$29,000/ week

  • 7 nights · up to 6 guests
  • Captain + mate
  • Standard provisioning & bar
  • USVI + BVI itinerary (BVI leg included)

Peak / Holiday

$36,000/ week

  • High-season & holiday weeks
  • Premium provisioning options
  • Custom routing on request
  • Priority calendar booking

Plus applicable BVI & USVI fees/permits where required. Sleep-aboard and shortened stays quoted on request.

Sample 7-Day Itinerary

A classic USVI → BVI loop. Every crewed charter includes a BVI leg (required for our operating structure).

  1. Day 1Red Hook, St Thomas → Cruz Bay, St John. Board, brief, and a calm first-night anchorage at Maho Bay.
  2. Day 2St John → Jost Van Dyke, BVI. Clear into the BVI, beach bar at White Bay, anchor at Great Harbour.
  3. Day 3Virgin Gorda. The Baths, Devils Bay, and dinner at Leverick Bay.
  4. Day 4North Sound → Anegada. Snorkel the reefs; anchor off Loblolly Bay.
  5. Day 5Anegada → Norman Island. The Indians & the Caves; famous Willy T. stop.
  6. Day 6Norman → St John. Salt Pond Bay, snorkel, final beach day.
  7. Day 7Cruz Bay → Red Hook. Disembark, already planning the next trip.

What's Included

A crewed charter means you unpack once and we handle the rest. Your rate covers the boat, the crew, and a full provisioning plan.

2Crew Onboard
3Cooked Meals / Day
BarOpen Provisions
ToysSnorkel · SUP · Tenders
USVI + BVIFuel for Itinerary

Standard provisioning, housekeeping, and linens are included. Premium provisions, special dietary requests, and dockage/specific mooring fees can be arranged in advance.

Meet the Crew

Pretty Lucky runs as a full-service charter — captained, hosted, and cared for by a dedicated two-person crew.

Captain

Shaun

USCG Master 100-Ton (Near Coastal) with sail endorsement. Years on the water across the Virgin Islands — easy, safety-first, and happy to tailor the trip to your crew.

Mate & Host

Wendy

Runs the galley, the provisioning, and the day-to-day comfort of the boat — the reason guests say they only unpack once. Your first point of contact for planning.

Planning a trip? Send an inquiry and Wendy will reply within 24 hours.

Availability & Reservation

Live availability is managed by the owner. Click a date to mark it booked/available (saved on this device), then send an inquiry for the week you want.

Month
Available Booked Past

Owner tool: toggling updates this browser only. For guests, the public calendar reflects confirmed bookings. Inquiries route to the owner below.

Inquire / Book

Tell us your dates and group. We reply within 24 hours to confirm availability and provisioning.