Watch Sailing & Boating Adventures Around the World

Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.

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Did Our Charter Gambit Work? | Mid Season Update
BoatFools Sailing

Did Our Charter Gambit Work? | Mid Season Update

@boatfools #sailboatcharter #bareboatcharter #morgan382 #morgan384 #sailingmaine Did Our Charter Gambit Work? | Mid Season Update Was putting our own sailboats into charter a brilliant idea—or a terrible mistake? We're halfway through our first charter season, and it's time for an hone...
Would You Save This Beautiful Swedish Hallberg Mistral 33 Sailboat? | $12k | Tour
BoatFools Sailing

Would You Save This Beautiful Swedish Hallberg Mistral 33 Sailboat? | $12k | Tour

#hallbergrassy #hallbergMistral33 #sailboat #Sailing #boattour #boatfools Would You Save This Beautiful Swedish Hallberg Mistral 33 Sailboat? | $12k | Tour Would you save this beautiful Swedish yacht? In this episode of BoatFools Sailing, Canadian Ken and I tour a classic 1970 Hallberg Mistral 33...
BEST ANCHORAGES IN PENOBSCOT BAY:  Rockland, Hurricane, Vinalhaven, Pulpit, The Barreds
Sailing PILAR - Blue Dot Voyages

BEST ANCHORAGES IN PENOBSCOT BAY: Rockland, Hurricane, Vinalhaven, Pulpit, The Barreds

Penobscot Bay Maine best sailing anchorages exceeded our expectations! Maine boasts more than 4,600 islands, each with its own mystery, its own story. The question was which ones we’d have time to explore. With the help of the Cruising Club of America website and the Waterway Guide, we set our cours...
SAILING JEWELL ISLAND MAINE | EXPLORING WORLD WAR BUNKERS & TOWERS | CARETAKER’S CABIN LOBSTERS
Sailing PILAR - Blue Dot Voyages

SAILING JEWELL ISLAND MAINE | EXPLORING WORLD WAR BUNKERS & TOWERS | CARETAKER’S CABIN LOBSTERS

Jewell Island Maine was exactly that - a jewel of a sailing anchorage. We explored World War bunkers and towers, spent an evening cooking lobsters with the Jewell Island caretaker, hiked the Maine Island trails, found Buoy Beach, Smugglers Cove and Pass, learned how to land your dinghy for 10 ft ti...
Sailing Maine’s Stunning Coast & Islands!
BoatFools Sailing

Sailing Maine’s Stunning Coast & Islands!

#boatfoolssailing #SailingMaine #Gunkholing #sailinglife #Morgan382 #CruisingSailboat #coastalcruising 5 Days Gunkholing The Maine Coast! 5 Sailboats, 85 NM, and the Sturgeon Moon! Join Green Mountain Josh and me as we take our Morgan 382 on an unforgettable 4-night, 5-day gunkholing cruise from...
SEGUIN ISLAND MAINE LOBSTER BOAT WEDDING IN THE FOG
Sailing PILAR - Blue Dot Voyages

SEGUIN ISLAND MAINE LOBSTER BOAT WEDDING IN THE FOG

Seguin Island Maine was our next stop, where we took photos of a sunrise wedding on a lobster boat, hiked the trails and toured the lighthouse with a rare fresnel lens still in operation. Our journey to Seguin Island from Jewell Island was just a short hop - 15 miles - on a reasonable weather da...
HOW TO SAFELY REMOVE A SNAGGED LOBSTER POT FROM YOUR RUDDER SAILING TO MAINE
Sailing PILAR - Blue Dot Voyages

HOW TO SAFELY REMOVE A SNAGGED LOBSTER POT FROM YOUR RUDDER SAILING TO MAINE

Sail with us from Nantucket to Richmond Island - near Cape Elizabeth, Maine. Learn how to safely release a lobster pot from your rudder. And we reveal a top hike - the Richmond Island perimeter trail. When we left Nantucket, we kept saying we were going to stop here, then there, then we just ke...
HOW TO SAFELY REMOVE A SNAGGED LOBSTER POT FROM YOUR RUDDER (SAILING – NANTUCKET TO PORTLAND MAINE)
Sailing PILAR - Blue Dot Voyages

HOW TO SAFELY REMOVE A SNAGGED LOBSTER POT FROM YOUR RUDDER (SAILING – NANTUCKET TO PORTLAND MAINE)

Sail with us from Nantucket to Richmond Island - near Cape Elizabeth, Maine. Learn how to safely release a lobster pot from your rudder. And we reveal a top hike - the Richmond Island perimeter trail. When we left Nantucket, we kept saying we were going to stop here, then there, then we just ke...
We Fell Hard for This 47-Foot Classic Sailboat! Eldredge-McInnis Cutter at $60k | TOUR
BoatFools Sailing

We Fell Hard for This 47-Foot Classic Sailboat! Eldredge-McInnis Cutter at $60k | TOUR

#boatfoolssailing #classicyacht #CutterSailboat #sailboatforsale #WoodenBoatLove We Fell Hard for This 47-Foot Classic Sailboat! Eldredge-McInnis Cutter at $60k! [PRICE REDUCED AS OF 08/30/2025] Chapters: 00:00 Where is Canadian Ken? 00:50 Intro to this Beauty and to Jordi St. John and MITA 03...
The MATRIARCH of MAINE Coast Cruising! Meet Jan Taft, the co-author of the Maine’s Sailing “Bible.”
BoatFools Sailing

The MATRIARCH of MAINE Coast Cruising! Meet Jan Taft, the co-author of the Maine’s Sailing “Bible.”

@boatfools  #sailingmaine #sailinglife #sailingcommunity #mainesailing The Matriarch of The Maine Coast was a special video for us to make. Jan and Hank Taft set out in the early 1980s to create one of the most beloved cruising guides ever published. In its seventh edition with more than 50,000 cop...
Sailing Solo: My Perfect October Sail & Last of 2023. Played hooky & had the perfect day on the bay!
BoatFools Sailing

Sailing Solo: My Perfect October Sail & Last of 2023. Played hooky & had the perfect day on the bay!

@boatfools  #sailingme #sailingmaine #camdensail #solosailing #penobscot #sailingadventures #sailingday #autumnsail Sailing Solo is the best but sailing into Autumn can be hit or miss - especially this year when we've had such wacky weather. So when opportunity knocked - I kicked open the doo...
Shakedown Cruise! Storms, Oysters, and Sunsets. First sail of the 2023 Maine summer season!
BoatFools Sailing

Shakedown Cruise! Storms, Oysters, and Sunsets. First sail of the 2023 Maine summer season!

@boatfools  #sailing #mainecoast #mainesailing #schooner Our shakedown cruise of the 2023 season on the old Morgan 382 was a ball and had a bit of everything. We finally get our mast stepped, the boat provisioned, and off the mooring for our shakedown cruise and overnight. We venture to Pulpit Har...
#206 Maine MADNESS: Sailing, Seafood & UNEXPECTED MISHAPS | Sailing Sisu Leopard 45 Catamaran
Sailing Sisu

#206 Maine MADNESS: Sailing, Seafood & UNEXPECTED MISHAPS | Sailing Sisu Leopard 45 Catamaran

Welcome to another exciting episode of our sailing adventures. In this video, we take you on a journey through some more of Maine's most charming towns, where we experience the thrill of sailing in different conditions and encounter a few unexpected challenges. We de-sleeve two of our lines und...
Sailing Downeast Maine, 2021 part 2
The Meri Crew

Sailing Downeast Maine, 2021 part 2

Here is the second half of our summer in Maine. We travel Downeast to Roque Island to our favorite northern beach, have some family aboard, do a lot of hiking and enjoy the beautiful Maine coast from the water and ashore.
Epic Spinnaker Sailing to Maine on our Seawind 1600 Catamaran | Harbors Unknown Ep. 40
Harbors Unknown

Epic Spinnaker Sailing to Maine on our Seawind 1600 Catamaran | Harbors Unknown Ep. 40

Epic Spinnaker Sailing to Maine on our Seawind 1600 Catamaran | Harbors Unknown Ep. 40 We’ll be at the Annapolis boat show in October so if you’re planning to attend please let us know in the comment section. We’d love to connect! Be sure to use promo code harborunknown2021 for $5 off admission. W...
The beautiful islands of the Maine coast, 2021
The Meri Crew

The beautiful islands of the Maine coast, 2021

We arrive in Penobscot bay and begin exploring the wonderful towns and islands in the area. We visit Rockland, Camden, Belfast and Castine as well as the islands of Vinalhaven, Isleboro, Deer, Swan's, Isle Au Haut, North Haven, Hurricane and a few others.
Sailing… A Different Kind of Fun | S06E16
Sailing Project Atticus

Sailing… A Different Kind of Fun | S06E16

When we first started sailing we had a REALLY hard time dialing in our sailboat, learning to communicate effectively, and figuring out how to rely on ourselves, and not feel like complete idiots with each new challenge. We wondered when we were going to get to the FUN of it all. We’ve since learned ...
Sailing Through a MINEFIELD  | S06E15
Sailing Project Atticus

Sailing Through a MINEFIELD | S06E15

This week we sail to Vinalhaven for an impromptu Pacific Seacraft Owner’s meetup and live concert performed by singer songwriters Bennett and Perkins aboard their sailboat. On our passage North, we sail through a sea of lobster buoys which tests our patience and resolve. Bennett and Perkins St...
Injury at Sea (Calico Skies Sailing, Ep. 79)
Calico Skies Sailing

Injury at Sea (Calico Skies Sailing, Ep. 79)

When it rains, it pours! This episode opens with us disconnecting our tow from S/V Delos and getting Calico Skies anchored under power from our dinghy. We being the process of flushing the transmission fluid several times after getting the dipstick caught in the gears. With the transmission issue r...
Delos & Calico Livin’ large off the Sea on our Private Island (Calico Skies Sailing, Ep 73)
Calico Skies Sailing

Delos & Calico Livin’ large off the Sea on our Private Island (Calico Skies Sailing, Ep 73)

If you had to spend 14 days "self isolating" upon entering the state of Maine, can you picture a better way to spend it than on a private island?!?! We got really lucky this past August as our friends on S/V Delos were offered the use of an island off the coast of Port Clyde, Maine. This i...
Maine Part Two (remastered)
The Meri Crew

Maine Part Two (remastered)

Sorry about the poor video and audio quality the first time around - we've got this video fixed up now for you. The second half of our time in Maine, Summer 2019. We visit Frenchboro and Belfast, go hiking in Acadia National Park, look for whales off Mt. Desert Rock, go kayaking in Seal Bay a...
The Meri Crew sails to Maine, Part 1
The Meri Crew

The Meri Crew sails to Maine, Part 1

We make a passage from Norfolk, VA to Dutch Harbor, RI and then on to Rockland Maine! We spend time cruising the Penobscot Bay archipelago enjoying the rustic beauty. During summer it is a sailing and cruising paradise here. The water is a little cold, but the lobster is great!
ep34 – Sailing Maine – Camden, Boothbay Harbor, Portland – Hallberg-Rassy 54 Cloudy Bay – Jul 2018
Sail Cloudy Bay

ep34 – Sailing Maine – Camden, Boothbay Harbor, Portland – Hallberg-Rassy 54 Cloudy Bay – Jul 2018

From Camden, s/v Cloudy Bay (Hallberg-Rassy 54) motored in thick fog to Boothbay Harbor, where the boat was moored for 3 weeks while we took a trip to Europe. We returned from our vacation to lots of deliveries and had a few days of boat maintenance, before sailing to Portland, our last port in Main...
ep33 – Sailing Maine – Mount Desert Island to Camden – Hallberg-Rassy R54 Cloudy Bay – July 2018
Sail Cloudy Bay

ep33 – Sailing Maine – Mount Desert Island to Camden – Hallberg-Rassy R54 Cloudy Bay – July 2018

Sailing Maine back south: From our most northern Maine destination, Mount Desert Island, s/v Cloudy Bay (Hallberg-Rassy 54) starts the gentle cruise back south. In this sailing adventure we visit Winter Harbor where we buy some lobsters, then the quaint fishing village of Stonington, where we cook t...
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