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.
New Year’s Antigua & Barbuda (7 Days)
$24,000 - Total Boat Booking (4 Guests) / Available
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…
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…
USVI Adventure (5 Days)
$7,050 Per Cabin / WAITLIST
Tiger Lily / Phoebe & Xander
Sail away in the U.S. Virgin Islands, where warm tropical breezes and laid-back island vibes meet effortless cruising. Swim, snorkel, hike and unwind as you discover the natural beauty of the Virgin Islands National Park and enjoy life aboard…
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…
Cruise The Grenadines (7 Days)
$11,900 Per Cabin / Waitlist
Darren & Amanda
Join us for a week sailing adventure through the Grenadines designed to grow your confidence, sharpen your skills, and immerse you in the cruising lifestyle. With steady trade winds, hands-on learning, and unforgettable island anchorages, it’s the perfect next step for any aspiring sailor...
Antigua & Barbuda Adventure Week (7 Days)
$11,900 Per Cabin / 2 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…
Grenadines Getaway (7 Days)
$24,000 Total Boat Booking / Waitlist
Darren & Amanda
Join us for five unforgettable days exploring the Grenadines—hands-on sailing, easygoing island hops, and time to relax in some of the Caribbean’s most beautiful anchorages. No stress, just wind, water, and good company…
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…
Exumas Adventure (8 Days)
$7,050 Per Cabin / Waitlist
Tiger Lily / Phoebe & Xander
Launching from George Town, this five-day sailing adventure takes you through the Exumas’ best spots. Learn the ropes, explore the turquoise waters and quiet beaches…
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…
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 / 5 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…
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 / 2 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…
TRANS-ATLANTIC! Bermuda to Azores (15 Days)
$17,100 Per Cabin / WAITLIST
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.…
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…
Cannes Yachting Festival - Balance Sailing Days
BALANCE SAILING DAYS
Join us at the Cannes Yachting Festival for a sail around the bay! If you are considering us for a passage or want to experience a Balance Catamaran on the water, this is a great time to meet us and the Balance 526, Pippilotta…
Open House Sailing Experience
SOLD OUT
Take a tour and hoist the sails of our Neel 45 performance trimaran Panda ROSSO. This is your opportunity to meet the boat and crew of Outer Passage during the Annapolis International Sailboat Show.
Annapolis Sunset Sail
SOLD OUT
Take a tour and hoist the sails of our Neel 45 performance trimaran Panda ROSSO. This is your opportunity to meet the boat and crew of Outer Passage during the Annapolis International Sailboat Show and enjoy a sunset sail.
Open House Sailing Experience
SOLD OUT
Would you like to tour our Neel 45 performance trimaran? Even better, want to hoist the sails and take Panda ROSSO for a spin? This is your opportunity to meet the boat and crew of Outer Passage!
Open House Sailing Experience
SOLD OUT
Would you like to tour our Neel 45 performance trimaran? Even better, want to hoist the sails and take Panda ROSSO for a spin? This is your opportunity to meet the boat and crew of Outer Passage!
Open House Sailing Experience
Available
Would you like to tour our Neel 45 performance trimaran? Even better, want to hoist the sails and take Panda ROSSO for a spin? This is your opportunity to meet the boat and crew of Outer Passage!
Open House Sailing Experience
1 Spot Available
Would you like to tour our Neel 45 performance trimaran? Even better, want to hoist the sails and take Panda ROSSO for a spin? This is your opportunity to meet the boat and crew of Outer Passage!
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!