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.
Cruise The Grenadines (7 Days)
$11,900 Per Cabin / 2 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...
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…
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…
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!