Antigua · St. Martin — two home ports across the Leeward Islands
Crewed voyages aboard Cap II and Flying Wing — a 77 ft CNB flagship and a 75 ft classic, home-ported in Antigua, each offering its own character, scale, and rhythm at sea.
Private proposals within 48 hours · No published rates
Introductions via
Jumby Bay Island · Hermitage Bay · Hodges Bay Resort · Eden Rock St Barths · Virtuoso · MYBA
Historic spirit. Refined Caribbean sailing.
RexSailing offers a more distinguished way to charter — through privately crewed sailing yachts, thoughtful service, and a deep respect for seamanship.
Private Charters
Crewed and all-inclusive
Antigua and St. Martin
Two home ports
Day & Multi-Day Voyages
Custom itineraries
Classic Sailing Experience
Authentic and refined
75 ft|Flagship yacht
A distinguished sailing yacht with commanding presence, elegant lines, and the comfort expected of a refined private charter.
Length
75 ft
Charter Type
Day & Multi-Day
Best For
Families & groups
Region
Antigua · St. Martin · Leeward Islands
77 ft|Intimate charter yacht
A more intimate yacht designed for guests who value simplicity, beauty, and the quiet pleasure of traditional sailing.
Length
77 ft
Charter Type
Day Charters
Best For
Couples & small groups
Region
Antigua · St. Martin · Leeward Islands
37 ft|Entry-level sailing yacht
A spirited 37-footer for guests who want real sailing without the price of a flagship — the most accessible crewed sail in the Leeward Islands.
Length
37 ft
Charter Type
Day Charters
Best For
Couples & small parties
Region
Antigua · St. Martin · Leeward Islands
From a flagship yacht to an entry-level sailing day, each boat is delivered with the same care, hospitality, and seamanship.
Flying Wing - Flagship yacht
Best for:
✦Full-day private charters
✦Sunset sails
✦Multi-day island itineraries
✦Families and larger groups
Cap II - Intimate charter yacht
Best for:
✦Couples
✦Smaller private groups
✦Elegant day sails
✦More personal pace
SISU - Entry-level sailing yacht
Best for:
✦First-time charterers
✦Couples on a budget
✦Half-day and full-day sails
✦A taste of the Leeward Islands
Every charter is all-inclusive
Private crewed yacht
Chef-prepared meals
Premium bar
Fuel & moorings
Snorkel kit · paddleboards
Private transfer to the marina
Rates are all-inclusive — specialty wines, shoreside dining, and off-region port fees are billed at cost.
Four of our most-requested day charters — each with a full hour-by-hour itinerary on the Day Charter page.
From $1450
Pink Sand Beach · Frigate Bird Sanctuary · 9 hrs
A passage north to Barbuda's pink sand beaches, a quiet lunch at anchor, and a downwind return by late afternoon.
View itinerary →
From $1650
Reef swim · West Coast · 10 hrs
The iconic day — snorkel the protected reefs along Antigua's leeward coast, beach lunch in a quiet cove, sunset return.
View itinerary →
From $750
Falmouth Harbour · 6 hrs
A relaxed introduction to the Leeward coast — Antigua's south shore, Pigeon Beach, lunch on board.
View itinerary →
From $1950
Gustavia · Shell Beach · 10 hrs
A long downwind run to Gustavia's harbour, lunch ashore, and a starlit return — a true Leeward Islands day.
View itinerary →
Yachts with soul, style, and a sense of history - never mass-produced in feel.
No crowds. No fixed schedules. Just your guests, your crew, and the open sea.
Led by experienced professionals who know these waters and sail them well.
RexSailing is not an open charter. Voyages aboard the fleet are arranged discreetly, with a small circle of returning guests, luxury hoteliers, and trusted travel advisors.
Two classic sailing yachts — Cap II and Flying Wing — privately operated by their captains. A small number of guests each season.
Charters are arranged by private introduction: luxury travel advisors, hotel concierges, and returning guests.
Itineraries are planned in confidence. Named guests, private anchorages, and bespoke routes are never published.
Additional concierge and editorial introductions on request.
A small window into life aboard Cap II and Flying Wing — follow @rex_sailing for the current season.
A quiet word on how charters are arranged, what is included on board, and the rhythm of a season aboard the RexSailing fleet.
Enquiries are handled privately. Write to us directly, or be introduced through a luxury travel advisor or one of our hotel partners. We reply within one working day with a personalised proposal.
Within one working day. A full written proposal — confirmed dates, yacht, itinerary, and rate — follows within 48 hours. Every enquiry is read and answered personally; we do not use automated replies.
For peak-season weeks (December through February) we recommend enquiring 3 to 12 months ahead. Shorter windows are often possible for day charters, for the shoulder months of the season, and for specific yachts — please ask.
The fleet is home-ported in Antigua. Typical departures are from Jolly Harbour or Falmouth Harbour. Pick-up from Barbuda, St. Kitts, or any nearby Leeward island can be arranged by private transfer.
Private crew, fuel and dockage, provisioning of fresh food and fine wines, snorkelling equipment, paddleboards, and local excursions. Menus and beverage service are tailored in advance of your voyage.
Both yachts comfortably host small private groups — exact configuration depends on your party size and whether you're day sailing or cruising overnight. We confirm cabins and layout with you when planning the charter.
Rates are not published. A confidential proposal is prepared for each enquiry, based on your preferred dates, itinerary, and party.
The fleet sails the Leeward Islands from late November through May, when the Caribbean trade winds are at their finest. A small number of bespoke weeks are also offered outside the main season.
Yes. Both Cap II and Flying Wing are commercially surveyed, fully insured for charter, and operate with all required certifications. Safety protocols are reviewed each season.
Tell us your dates, group size, and preferred experience - we will match you with the ideal yacht.
Private proposals within 48 hours · Enquiries handled discreetly
RexSailing · Antigua · St. Martin
