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…
Cruise The Grenadines (7 Days)
$11,900 Per Cabin / Waitlist
Loki / 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...
Grenadines Getaway (7 Days)
$24,000 Total Boat Booking / Waitlist
Loki / Darren & Amanda
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…
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…
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…
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.…
Antigua Adventure (5 Days)
$8,500 Per Cabin / WAITLIST
Pressure Drop / Elliot, Anais & North
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…
New Year’s Antigua & Barbuda (7 Days)
$24,000 - Total Boat Booking (4 Guests) / WAITLIST
Pressure Drop / Elliot, Anais & North
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…
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!