Passages
Find Your Next big adventure
2026-2027 Passage ScheDule
Join Outer Passage aboard one of our Balance Catamarans for a season of ocean adventures, from cruising the Mediterranean coast and island-hopping through the Caribbean to crossing the Atlantic Ocean. With multiple boats offering different routes throughout the year, it’s a great time to build experience and explore by sea. We’ll be announcing our full 2027 passage schedule soon, so stay tuned or contact us for more information.
Guadeloupe Sailing Adventure (7 Days)
WAITLIST
Tiger Lily / Phoebe & Braden
Pack your bag and join us for a Caribbean sailing adventure like no other! Guadeloupe and Les Saints host idyllic tradewind sailing conditions and tropical islands to explore. Perfect for gaining hands-on experience with the cruising lifestyle…
Women’s RETREAT (6 Days)
$3540 PER PERSON (shared cabin) / 6 SPOTS AVAILABLE
Tiger Lily / Phoebe & Arisa
THE INTENTION: A Creative Reset at Sea
We spend so much of our lives building businesses, making work, and keeping up that it's easy to lose sight of what made us curious in the first place. Sway at Sea trades the noise for the quiet, and the pressure to produce for the freedom to explore. We'll move our bodies, share stories under the stars, and make things simply because we can.
Martinique to Bequia (8 Days)
WAITLIST
Tiger Lily / Phoebe & Braden
Sail south through the Windward Islands on a one-way journey to Bequia, hopping between islands like St. Lucia along the way. Expect a mix of hands-on sailing, beautiful anchorages, swimming, exploring ashore and plenty of Caribbean variety from one stop to the next.
Grenadines Getaway (7 Days)
WAITLIST
Tiger Lily / Phoebe & Braden
Join us for five unforgettable days exploring the Grenadines with hands-on sailing, easygoing island hops, and time to relax in some of the Caribbean’s most beautiful anchorages. No stress, just wind, water, and good company…
Bequia to Dominica (8 Days)
$11,900 Per Cabin / 2 Available
Tiger Lily / Phoebe & Braden
Work your way north through the Windward Islands on a sailing-focused passage through St. Vincent, St. Lucia, Martinique and beyond. A great trip for building experience on longer inter-island legs while still enjoying time exploring the islands.
Women’s Only Caribbean Sailing Week (7 Days)
$4,900 per person / 3 Spots Available
Tiger Lily / Phoebe & Perrine
Join our next women-only sail training passage, seven days of confidence building and true hands-on sailing in the French Caribbean, plus snorkels, hikes, and sunset toasts together…
Guadeloupe to St Martin (7 Days)
$10,900 Per Cabin / 2 Available
Tiger Lily / Phoebe & Braden
Sail north through the Leeward Islands on a one-way adventure that blends real sailing with unforgettable island stops. Every day brings a new horizon, a new anchorage and a new stretch of Caribbean to explore.
St Martin to USVI (5 Days)
$7,900 Per Cabin / 1 Available
Tiger Lily / Phoebe & Braden
Cruise, explore and then wait for the right window to make the downwind run from St. Martin to the U.S. Virgin Islands. It’s a short, exciting trip that blends relaxed Caribbean cruising with the thrill of a proper passage.
USVI to Bahamas (8 Days)
WAITLIST
Tiger Lily / Phoebe & Braden
Trade island hopping for open water on this roughly 700 NM offshore adventure to Georgetown, Bahamas. Build real miles, stand watches day and night, and experience the decisions and routines that make offshore sailing so rewarding.
Nassau to Newport (10 Days)
$11,500 per cabin / 2 Available
Tiger Lily / Phoebe & Braden
Take on approximately 1,000 NM of offshore sailing from the Bahamas to Newport, Rhode Island. Ride the Gulf Stream north, round Cape Hatteras, and experience the kind of passagemaking that sailors remember for years.
Don't see dates that match your schedule?
We understand travel arrangements can be complicated, and we're often able to offer some flexibility. If our passages dates don't align with your schedule, please contact us. We'd love to discuss creating a customized sailing experience for you!