Passages
Find Your Next big adventure
2025-2026 Passage ScheDule
|||
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
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…
Antigua to BVi (5 Days)
$7,500 Per Cabin / 2 Available
Loki / Darren & Amanda
Join us for a five-day Caribbean sailing adventure from Antigua to the British Virgin Islands. This passage is designed as an approachable introduction to offshore sailing, combining relaxed island cruising with a short, downwind overnight sail through classic trade-wind conditions…
Ladies Only Sailing Week (5 Days)
$3,825 Per Person / 1 Spot Available
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 / 1 Available
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…
Newport to Boston (7 Days)
$10,500 Per Cabin / 2 Available
Loki / Darren & Amanda
Experience the best of New England sailing with coastal exploration, real passage training, nighttime navigation, and an unforgettable sail into Boston Harbor.
Boston to Lunenberg (9 Days)
$13,500 Per Cabin / 1 Available
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…
Newport to Annapolis (7 Days)
$10,500 Per Cabin / 2 Available
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…
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!