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.
Newport to Boston (7 Days)
$10,500 Per Cabin / 2 Available
Loki / Darren & Amanda
Sail with us from Newport to Boston Harbor on a coastal cruising adventure through some of New England’s most iconic summer sailing grounds. We’ll make our way north one anchorage at a time, balancing hands-on sailing with relaxed evenings on the hook, charming harbor stops, and the simple pleasure of life aboard…
Ibiza/Formentera Adventure (5 Days)
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)
1 Cabin 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…
TRANS-ATLANTIC! Canaries to Caribbean (21 Days)
1 Cabin Available
Bucket List Experience! Set sail on a long, trade winds passage across the Atlantic Ocean with many days of spinnaker sailing, surfing down waves and plenty of time at the helm.…
Caribbean New Year’s Sailing Adventure (8 Days)
$25,500 - Total Boat Booking (4 Guests) / AVAILABLE
Pressure Drop
Ring in the new year sailing and cruising in paradise as we island hop the Caribbean, chasing steady trade winds, exploring remote beaches, and swimming in crystal-clear waters…
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!