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.
Exumas Adventure (8 Days)
$11,314 Per Cabin / Waitlist
Tiger Lily / Phoebe & Xander
Launching from George Town, this eight-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…
BVI Ultimate Holiday (7 Days)
$24,000 - Total Boat Booking (4 Guests) / Waitlist
Pressure Drop / Elliot, Anais & North
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…
Ladies Only Sailing Week (5 Days)
$3,825 Per Person / WAITLIST
Loki / Amanda & Anais
Join our first women-only sail training passage, five days of confidence building and true hands-on sailing in the USVI, plus snorkels, short hikes, and sunset toasts together…
USVI to Bermuda (9 Days)
$11,700 Per Cabin / WAITLIST
Loki / Darren & Amanda
Set your heading north and join us for a true bluewater passage from the Caribbean to Bermuda. This is an unforgettable opportunity to gain offshore miles, disconnect from land life, and experience real-world seamanship aboard a performance cruising catamaran…
TRANS-ATLANTIC! Bermuda to Azores (15 Days)
$15,750 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.…
Boston to Lunenburg (9 Days)
$13,500 Per Cabin / WAITLIST
Loki / Darren & Amanda
Sail from the heart of Boston to the UNESCO harbor of Lunenburg. This passage contains coastal cruising, a 400 nm offshore passage, and a stunning North Atlantic landfall…
Maine Cruising Week (5 Days)
WAITLIST
Tiger Lily / Phoebe & Xander
Learn to sail a Balance 502 while exploring Maine’s idyllic Casco Bay. We’ll teach you the ropes on everything you need to know about cruising…
Maine Sailing Adventure (5 Days)
WAITLIST
Tiger Lily / Phoebe & Xander
Explore all that Casco Bay has to offer in a fun packed, island hopping adventure. We’ll sail to isolated coves, experience gorgeous sunsets, island hikes through pine laden trails, and sample Portland’s amazing foodie scene…
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!