Passages
Find Your Next big adventure
2026-2027 Passage ScheDule
Join Outer Passage aboard one of our vessels for a season of ocean adventures, from cruising the Mediterranean coast and island-hopping through the Caribbean to crossing the Atlantic Ocean. With multiple boats offering different routes throughout the year, it’s a great time to build experience and explore by sea. We’ll be announcing our 2027 passage schedule soon, so stay tuned!
If our passages dates don't align with your schedule, please contact us.
Newport to Annapolis (7 Days)
WAITLIST
Loki / Darren & Amanda
Sail the East Coast’s most iconic waterways, from Long Island Sound and New York City to the C&D Canal and Chesapeake Bay, with hands-on coastal training and classic harbors along the way…
TRANS-ATLANTIC! Canaries to Caribbean (21 Days)
WAITLIST
Bucket List Experience! Set sail on a long, trade winds passage across the Atlantic Ocean with many days of spinnaker sailing, surfing down waves and plenty of time at the helm.…
Caribbean New Year’s Sailing Adventure (8 Days)
$25,500 - Total Boat Booking (4 Guests) / AVAILABLE
Pressure Drop
Ring in the new year sailing and cruising in paradise as we island hop the Caribbean, chasing steady trade winds, exploring remote beaches, and swimming in crystal-clear waters…
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!