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.
USVI Adventure (5 Days)
$7,050 Per Cabin / WAITLIST
Tiger Lily / Phoebe & Xander
Sail away in the U.S. Virgin Islands, where warm tropical breezes and laid-back island vibes meet effortless cruising. Swim, snorkel, hike and unwind as you discover the natural beauty of the Virgin Islands National Park and enjoy life aboard…
Exumas Adventure (8 Days)
$7,050 Per Cabin / Waitlist
Tiger Lily / Phoebe & Xander
Launching from George Town, this five-day sailing adventure takes you through the Exumas’ best spots. Learn the ropes, explore the turquoise waters and quiet beaches…
Exumas Holiday Week (7 Days)
$9,900 Per Cabin / WAITLIST
Tiger Lily / Phoebe & Xander
Leaving out of Nassau, quickly settle into island time on a weeklong sailing journey through the Exumas. Swim in crystal-clear waters, wander on the white-sand beaches, and relax onboard…
Abacos Holiday Week (7 Days)
$9,900 Per Cabin / 2 Available
Tiger Lily / Phoebe & Xander
Step aboard for a week of sailing through the turquoise waters and island chain of the Abacos in The Bahamas for the perfect blend of relaxed cruising and hands-on sailing…
Block Island Weekend Escape (3 Days)
$4,200 Per Cabin / 2 Available
Tiger Lily / Phoebe & Xander
Experience three days of beautiful New England summer on this weekend trip to Block Island. We’ll enjoy three great days of sailing with exploring in between.
New England Adventure (5 Days)
$7,050 Per Cabin / 2 Available
Tiger Lily / Phoebe & Xander
Cruise from Newport to Martha’s Vineyard and Cuttyhunk aboard a Balance 502. Short sails, classic harbors, swims off the stern, and long, easy evenings at anchor.
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!