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.
New Year’s Antigua & Barbuda (9 Days)
$30,000 - Total Boat Booking (4 Guests) / Available
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…
Antigua Adventure (5 Days)
$8,500 Per Cabin / 2 Available
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…
Guadeloupe Cruising Week (7 Days)
$11,900 Per Cabin / 2 Available
Spend seven days sailing through the French-Caribbean gems of Guadeloupe and Les Saintes. With perfect trade winds, vibrant anchorages, and a mix of sailing, watersports, and culture—this is Caribbean cruising at its finest…
Antigua & Barbuda Adventure Week (7 Days)
$11,900 Per Cabin / 2 Available
Sail the trade winds through Antigua and Barbuda on a week-long journey of turquoise waters, pink sand beaches, and unforgettable anchorages. Perfect for adventurers, sailors, and wind-lovers alike—this trip blends hands-on exploration with laid-back island living…
St Barths Sailing Escape (5 Days)
$8,500 Per Cabin / 2 Available
Sail in style through the turquoise waters of St. Barths and its surrounding isles. This five-day adventure blends luxury, vibrant island charm, and wind-filled exploration—perfect for sailors, riders, and anyone ready for a refined Caribbean getaway…
BVI Ultimate Holiday (9 Days)
$30,000 - Total Boat Booking (4 Guests) / Available
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…