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.
Antigua to Bermuda (9 Days)
$10,800 Per Cabin / Waitlist
The escape to the Caribbean on the classic 'I-65' route where we set our heading North to Bermuda. This is a great adventure for those looking to gain some offshore miles, learn more about weather routing and seriously disconnect from cell phone range….
Bermuda to Newport (7 Days)
$9,500 Per Cabin / Waitlist
Offshore sailing at its finest. This is a 650NM passage from the island group of Bermuda in the Atlantic, to the heart of New England sailing in Newport, RI. After clearing customs, we will point almost due North as we navigate the Gulf Stream and various weather systems…
Newport Coastal Adventure (7 Days)
$10,500 Per Cabin / Waitlist
Lets go for a week-long sailing sabbatical around the heart of New England sailing. Newport, RI is an ideal location to begin exploring sites such as Block Island, Cuttyhunk, Martha’s Vineyard and Nantucket…
Newport Coastal Adventure (5 Days)
$7,500 Per Cabin / Waitlist
Lets go for a 5 day sailing sabbatical around the heart of New England sailing. Newport, RI is an ideal location to begin exploring sites such as Block Island, Cuttyhunk, Martha’s Vineyard and Nantucket…
Cruise The Grenadines (7 Days)
$11,900 Per Cabin / 2 Cabins Available
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 (5 Days)
$8,500 Per Cabin / 2 Available
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…
Guadeloupe Getaway (5 Days)
$8,500 Per Cabin / 2 Available
Join us for five days of relaxed island-hopping and hands-on sailing with good company as we explore the stunning waters of Guadeloupe and Les Saintes. It’s the perfect mix of learning, exploring, and just kicking back on the water…
USVI Cruising Week (7 Days)
$11,900 Per Cabin / 2 Available
Join us for seven days of hands-on sailing and easygoing island-hopping through the U.S. Virgin Islands. Whether you're here to build confidence at the helm or just enjoy the rhythm of life on the water, this trip blends skill-building, exploration, and total relaxation in one of the Caribbean’s most accessible and stunning cruising grounds…