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.
Annapolis Boat Show Balance Demo Days
Only 6 spots available per trip
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…
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 / 2 Available
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…
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 (5 Days)
$8,500 Per Cabin / 2 Available
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 / 2 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…
Island Hopping in the BVIs (5 Days)
$8,500 Per Cabin / 2 Available
Pressure Drop / Elliot, Anais & North
Escape to the iconic British Virgin Islands for sailing, sun, and sea. From stunning anchorages to wind-filled afternoons and laid-back beach stops, this adventure packs big experiences into a short, unforgettable getaway…
USVI Cruising Week (7 Days)
$11,900 Per Cabin / 2 Available
Darren & Amanda
Join us for seven days of hands-on sailing and easygoing island-hopping through the U.S. Virgin Islands. Whether you're here to build confidence at the helm or just enjoy the rhythm of life on the water, this trip blends skill-building, exploration, and total relaxation in one of the Caribbean’s most accessible and stunning cruising grounds…
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…
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.…
BVI Coastal Adventure (5 Days)
$10,500 Per Cabin / 2 Available
Lets go for a week-long sailing sabbatical around the heart of New England sailing. Newport, RI is an ideal location to begin exploring sites such as Block Island, Cuttyhunk, Martha’s Vineyard and Nantucket…
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…
Balearics Coastal Adventure (5 Days)
$7,500 Per Cabin / Waitlist
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 Coastal Adventure (5 Days)
$7,500 Per Cabin / Waitlist
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 Coastal Adventure (5 Days)
$7,500 Per Cabin / 1 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’.
St. Augustine to Key West (7 Days)
Guest Suite - $5,950 SOLD / Master Suite - $6,650 SOLD
Join us for the Key Lime Run as we seek lower latitudes for warmer weather, clear turquoise water and pie! A sailing experience between two of our favorite, iconic and historic places in Florida….
Downeast Maine - 4 Days
Starting at $1,700 per person
This adventure showcases the exceptional sailing of Penobscot Bay, starting and ending in Rockland, ME. This area, known as Down-East Maine, is full of wonderful sights, challenging navigation, amazing hiking, and gorgeous anchorages…
Downeast Maine - 7 Days
Guest Suite - $5,600 SOLD / Master Suite - $6,300
Enjoy our extended week-long sailing extravaganza through the July 4th weekend! This adventure showcases the exceptional sailing of Penobscot Bay, starting and ending in Rockland, ME. This area, known as Down-East Maine, is full of wonderful sights, challenging navigation, amazing hiking, and gorgeous anchorages…
Downeast Maine - 4 Days
Starting at $1,700 per person (One Cabin Left!)
This adventure showcases the exceptional sailing of Penobscot Bay, starting and ending in Rockland, ME. This area, known as Down-East Maine, is full of wonderful sights, challenging navigation, amazing hiking, and gorgeous anchorages…
Newport to Portland - 4 Days
Guest Suite - $3,200 / Master Suite - $3,600
Get your sea legs as we set sail out of Newport Harbor and navigate through the scenic Cape Cod Canal before crossing the great Cape Cod Bay heading north on a long ocean stretch to the heart of Downeast Maine…
The Ocean Race - Start!
May 21st, 2023
Day Sail - $150 per person (SOLD OUT)
Ever wanted to see the fastest offshore racing sailboats take to a start line? This is an incredible chance to follow the fleet of 5 IMOCA 60ft foiling racing boats sail out of Newport Harbor…
Passage Around Long Island - 5 Days
Guest Suite - $4,250 / Master Suite - $4,750
Join us in Newport, RI where we will set sail for a circumnavigation around Long Island. Learn how to navigate through busy marine traffic and anchor at night with one of the most iconic backdrops in NYC…
Newport Spring Fling - 3 Days
Guest Suite and Master Suite (Total Boat Booking) - $4,800
Let’s go for a Spring Fling long weekend sail! Newport, RI is an ideal location to begin exploring sites such as Block Island, Cuttyhunk, Martha’s Vineyard and Nantucket…
Bermuda to Newport - 7 Days
Guest Suite- $3,955 / Master Suite- $4,550
Offshore sailing at its finest. This is a 650NM passage from the island group of Bermuda in the Atlantic, to the heart of New England sailing in Newport, RI. After clearing customs, we will point Panda ROSSO…
USVI to Bermuda - 9 Days
Guest Suite - $5,085 / Master Suite - $5,850 SOLD
Caribbean escape! This is the classic 'I-65' route from the Caribbean where we set our heading North to the beautiful island sanctuary of Bermuda. This offshore passage will begin…
Caribbean Multihull Challenge Event
Guest Suite - $4,000 SOLD / Master Suite - $4,500
5 Days - Ever wanted to be part of a multihull regatta? Fancy a little friendly competition? Join us as we embark on Panda ROSSO’s first ever sailing event, where we take part in the ‘Pirate Class’…
St. Croix Dash - 4 DayS
Guest Suite - $3,200 SOLD / Master Suite - $3,600
Let’s go Sailing! That’s the theme for this 4 day adventure aboard Panda ROSSO. We will begin in St. Thomas, and depart for a fun and fast sail to St. Croix, some 40 miles due south…
USVI Inter-Island - 5 DayS
Guest Suite - $4,000 / Master Suite - $4,500 Sold Out
Need that quick sailing getaway? This is a great week-long sailing adventure where we depart St. Thomas and sail to St. Johns for amazing scenery and clear Caribbean water…
USVI Inter-Island - 5 Day
Guest Suite - $4,000 / Master Suite - $4,500
Want to experience the bliss of inter-island sailing and beautiful anchorages? In this inshore sailing adventure, we will explore the US virgin island…
USVI Inter-Island - 3 Day
Guest Suite - $2,400 / Master Suite - $2,700
Need that quick sailing getaway? This is a great long-weekend sailing adventure where we depart St. Thomas and sail to St. Johns for amazing scenery and clear Caribbean water…
USVI Inter-Island - 3 Day
Guest Suite - $2,400 / Master Suite - $2,700
Need that quick sailing getaway? This is a great long-weekend sailing adventure where we depart St. Thomas and sail to St. Johns for amazing scenery and clear Caribbean water…
Bermuda to USVI - 9 Days
Guest Suite - $5,085
This is the classic 'I-65' route to the Caribbean where we sail south on the 65 deg West longitude line right to to St. Thomas, USVI. This offshore passage…
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!
Downeast Maine Inshore - 2
Full
An inshore exploration of Penobscot Bay, starting and ending in Rockland, ME. Full of wonderful sights, challenging sailing and gorgeous anchorages. These four days of sailing will make you fall in love, just as we have, for Maine’s rugged coast.
Downeast Maine Inshore - 1
Available
An inshore exploration of Penobscot Bay, starting and ending in Rockland, ME. Full of wonderful sights, challenging sailing and gorgeous anchorages. These four days of sailing will make you fall in love, just as we have, for Maine’s rugged coast.
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!