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.
Guadeloupe Cruising Week (7 Days)
$11,900 Per Cabin / 2 Available
Pressure Drop / Elliot, Anais & North
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 / 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) / Available
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…
Guadeloupe Getaway (5 Days)
$8,500 Per Cabin / 2 Available
Darren & Amanda
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…
Women’s Retreat (5 Days)
$2,950 Per Person / 4 Spots Available
Tiger Lily / Phoebe & Arisa
Join us for the maiden voyage of our first ever women’s retreat! Spend five days onboard sailing, and exploring the beautiful Bahamas amongst a crew of amazing women…
BVI Balance Rally (5 Days)
$8,500 Per Cabin / 2 Available
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…
Ladies Only Sailing Week (5 Days)
$3,825 Per Person / 4 Spots 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…
BVI to Bermuda (9 Days)
$11,700 Per Cabin / 2 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…
UsVI to Bermuda (9 Days)
$11,700 Per Cabin / 1 Available
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…
Abacos Holiday Week (7 Days)
$9,900 Per Cabin / 2 Available
Tiger Lily / Phoebe & Xander
Step aboard for a week of sailing through the turquoise waters and island chain of the Abacos in The Bahamas for the perfect blend of relaxed cruising and hands-on sailing…
Block Island Weekend Escape (3 Days)
$4,200 Per Cabin / 2 Available
Tiger Lily / Phoebe & Xander
Experience three days of beautiful New England summer on this weekend trip to Block Island. We’ll enjoy three great days of sailing with exploring in between.
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.
New England Adventure (5 Days)
$7,050 Per Cabin / 2 Available
Tiger Lily / Phoebe & Xander
Cruise from Newport to Martha’s Vineyard and Cuttyhunk aboard a Balance 502. Short sails, classic harbors, swims off the stern, and long, easy evenings at anchor.
Boston to Lunenberg (9 Days)
$13,500 Per Cabin / 2 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…
Ibiza/Formentera Adventure (5 Days)
$8,500 Per Cabin / 2 Available
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’.
Ibiza To Mallorca (7 Days)
$10,500 Per Cabin / 2 Available
Join us for a week of Mediterranean adventure as we sail from Ibiza to Mallorca, blending island cruising with a short open-water passage across the Balearic Sea.
Mallorca To Cannes (7 Days)
$10,500 Per Cabin / 2 Available
Join us for a true Mediterranean cruising adventure with a seven-day passage from Mallorca to Cannes, combining open-water sailing with coastal exploration.
Annapolis Boat Show Balance Demo Days
Fully Booked - WAITLIST
Join us at Outer Passage for a sail around the bay! If you are considering us for a passage, this is a great time to meet the crew and the Balance 526 Catamaran, Pressure Drop…
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!