Passages
Find Your Next big adventure
2025-2026 Passage ScheDule
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Join Outer Passage aboard one of our boats as we sail the New England coast, island-hop through the Caribbean, cross the Atlantic, and cruise the Mediterranean. With multiple vessels and a full season of ocean adventures, it’s a great time to build experience and explore by sea.
New Year’s Antigua & Barbuda (9 Days)
$30,000 - Total Boat Booking (4 Guests) / Available
Ring in the new year sailing and cruising in paradise as we island hop from Antigua to Barbuda, chasing steady trade winds, exploring remote beaches, and launching into crystal-clear waters for epic kite and wing sessions…
Antigua Adventure (5 Days)
$8,500 Per Cabin / 2 Available
Join us for five unforgettable days exploring Antigua and Barbuda’s turquoise waters, pristine beaches, and ideal wind conditions. Perfect for gaining hands-on experience with the cruising lifestyle…
Guadeloupe Cruising Week (7 Days)
$11,900 Per Cabin / 2 Available
Spend seven days sailing through the French-Caribbean gems of Guadeloupe and Les Saintes. With perfect trade winds, vibrant anchorages, and a mix of sailing, watersports, and culture—this is Caribbean cruising at its finest…
Cruise The Grenadines (7 Days)
$11,900 Per Cabin / 2 Cabins Available
Join us for a week sailing adventure through the Grenadines designed to grow your confidence, sharpen your skills, and immerse you in the cruising lifestyle. With steady trade winds, hands-on learning, and unforgettable island anchorages, it’s the perfect next step for any aspiring sailor...
Antigua & Barbuda Adventure Week (7 Days)
$11,900 Per Cabin / 2 Available
Sail the trade winds through Antigua and Barbuda on a week-long journey of turquoise waters, pink sand beaches, and unforgettable anchorages. Perfect for adventurers, sailors, and wind-lovers alike—this trip blends hands-on exploration with laid-back island living…
Grenadines Getaway (5 Days)
$8,500 Per Cabin / 2 Available
Join us for five unforgettable days exploring the Grenadines—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…
St Barths Sailing Escape (5 Days)
$8,500 Per Cabin / 2 Available
Sail in style through the turquoise waters of St. Barths and its surrounding isles. This five-day adventure blends luxury, vibrant island charm, and wind-filled exploration—perfect for sailors, riders, and anyone ready for a refined Caribbean getaway…
BVI Ultimate Holiday (9 Days)
$30,000 - Total Boat Booking (4 Guests) / Available
Spend your days sailing turquoise waters, exploring the BVI’s iconic anchorages, and soaking in island vibes. From epic sailing and vibrant marine life to kite sessions and laid-back beach time, this Easter escape is your ideal tropical adventure…
Guadeloupe Getaway (5 Days)
$8,500 Per Cabin / 2 Available
Join us for five days of relaxed island-hopping and hands-on sailing with good company as we explore the stunning waters of Guadeloupe and Les Saintes. It’s the perfect mix of learning, exploring, and just kicking back on the water…
USVI Cruising Week (7 Days)
$11,900 Per Cabin / 2 Available
Join us for seven days of hands-on sailing and easygoing island-hopping through the U.S. Virgin Islands. Whether you're here to build confidence at the helm or just enjoy the rhythm of life on the water, this trip blends skill-building, exploration, and total relaxation in one of the Caribbean’s most accessible and stunning cruising grounds…