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.
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…
Guadeloupe to St Martin (7 Days)
$10,500 Per Cabin / 1 Available
Loki / Darren & Amanda
Join us for a week of Caribbean sailing adventure from Guadeloupe to St. Martin. This passage is designed as an approachable introduction to offshore sailing, combining relaxed island cruising with a short overnight sail through classic trade-wind conditions…
Exumas Holiday Week (7 Days)
$9,900 Per Cabin / 1 Available
Tiger Lily / Phoebe & Xander
Leaving out of Nassau, quickly settle into island time on a weeklong sailing journey through the Exumas. Swim in crystal-clear waters, wander on the white-sand beaches, and relax onboard…
Women’s Retreat (5 Days)
WAITLIST
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…
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…
Abacos Adventure (5 Days)
$7,050 Per Cabin / 2 Available
Tiger Lily / Phoebe & Xander
Step aboard for five days 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…
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…
Abacos Holiday Week (7 Days)
$9,900 Per Cabin / 1 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…
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.
Downeast Maine (7 Days)
2 Cabins Available
Tiger Lily / Phoebe & Xander
Explore DownEast Maine by sail with cool mornings, pine-lined islands, scenic hikes, and evenings at anchor. A week of coastal cruising in a place that invites you to slow down and experience the rugged beauty that makes this coast unforgettable…
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…
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’.
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.
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’.
Maine Sailing Adventure (5 Days)
1 Cabin Available
Tiger Lily / Phoebe & Xander
Explore all that Casco Bay has to offer in a fun packed, island hopping adventure. We’ll sail to isolated coves, experience gorgeous sunsets, island hikes through pine laden trails, and sample Portland’s amazing foodie scene…
Mediterranean Cruising (7 Days)
$11,900 Per Cabin / 2 Available
Pressure Drop / Elliot, Anais & North
Sail the French Riviera from Toulon to Cannes featuring turquoise anchorages, island reserves, and classic Mediterranean cruising under summer skies…
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…
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!