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.
Antigua Adventure (5 Days)
$8,500 Per Cabin / 2 Available
Pressure Drop / Elliot, Anais & North
Join us for an unforgettable five days of exploring Antigua and Barbuda’s turquoise waters, pristine beaches, and ideal wind conditions. Perfect for gaining hands-on experience with the cruising lifestyle…
Antigua & Barbuda Adventure Week (9 Days)
$11,900 Per Cabin / 1 Available
Pressure Drop / Elliot, Anais & North
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 / 1 Available
Pressure Drop / Elliot, Anais & North
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 (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…
BVI Balance Rally (5 Days)
$8,500 Per Cabin / WAITLIST
Pressure Drop / Elliot, Anais & North
Join Pressure Drop for a 5-day Outer Passage adventure during the Balance Rally with group sails, beach gatherings, iconic BVI anchorages, and the rare chance to experience the Balance fleet cruising together…
BVI to Bermuda (9 Days)
$11,700 Per Cabin / 1 Available
Pressure Drop / Elliot, Anais & North
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…
TRANS-ATLANTIC! Bermuda to Azores (15 Days)
$15,750 Per Cabin / 1 Available
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.…
Ibiza/Formentera Adventure (5 Days)
$8,500 Per Cabin / 2 Available
Pressure Drop / Elliot, Anais & North
Pack your bag and join us for a Balearic sailing adventure like no other! These Mediterranean isles host idyllic summer sailing conditions, perfect for gaining hands-on experience while enjoying restful evenings on the hook in a picturesque ‘cala’.
Balearics Adventure (5 Days)
$8,500 Per Cabin / 2 Available
Pressure Drop / Elliot, Anais & North
Pack your bag and join us for a Balearic sailing adventure like no other! These Mediterranean isles host idyllic summer sailing conditions, perfect for gaining hands-on experience while enjoying restful evenings on the hook in a picturesque ‘cala’.
Mallorca Adventure (5 Days)
$8,500 Per Cabin / 2 Available
Pressure Drop / Elliot, Anais & North
Pack your bag and join us for a Balearic sailing adventure like no other! These Mediterranean isles host idyllic summer sailing conditions, perfect for gaining hands-on experience while enjoying restful evenings on the hook in a picturesque ‘cala’.
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!