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.
Downeast Maine (7 Days)
WAITLIST
Tiger Lily / Phoebe & Perrine
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 Lunenburg (9 Days)
WAITLIST
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)
WAITLIST
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)
WAITLIST
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 Cruising Week (5 Days)
WAITLIST
Tiger Lily / Phoebe & Perrine
Learn to sail a Balance 502 while exploring Maine’s idyllic Casco Bay. We’ll teach you the ropes on everything you need to know about cruising…
Maine Sailing Adventure (5 Days)
WAITLIST
Tiger Lily / Phoebe & Perrine
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…
Mallorca to Cannes (7 Days)
WAITLIST
Pressure Drop / Elliot, Anais & North
Join us for a true Mediterranean adventure with this seven-day passage from Mallorca to Cannes, combining the best of both worlds, open-water sailing with coastal exploration.
Newport to Annapolis (7 Days)
WAITLIST
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…
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!