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 / Waitlist
Darren & Amanda
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...
TRANS-ATLANTIC! Bermuda to Azores (15 Days)
$17,100 Per Cabin / WAITLIST
Pressure Drop / Elliot, Anais & North
Check off that bucket list item and experience crossing an ocean with Outer Passage! This is an ocean crossing in all it’s glory, the most authentic and rewarding offshore adventure.…
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!