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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I Finally Sailed to Maui — Where It All Began
Sailing With Phoenix | Oliver

I Finally Sailed to Maui — Where It All Began

We set sail from Hilo to Maui with light winds 90% of the way, finally catching a chill downwind run. I reflect a little bit on why I love sailing so much and how the hard work does eventually pay off. After arriving in Lāhainā we battle surf breaks to get the dinghy ashore and then hike a wild loca...
Sailing the Wrong Way across the Alenuihaha Channel from Maui to the Big Island on a 30ft Sloop
Sailing Triteia

Sailing the Wrong Way across the Alenuihaha Channel from Maui to the Big Island on a 30ft Sloop

Episode #252 : Season 8 : The Hawaiian Adventures Hello Friends, On this episode @kimberlywood-saltybutterfl262 and myself make passage across the dreaded Alenuihaha Channel between Maui and the Big Island of Hawaii. After an easy but very wet passage we arrive at Nishimura Anchorage and enjoy s...
WE Sail from Maui to Molokai | Episode 124
WE|Sail

WE Sail from Maui to Molokai | Episode 124

This episode we get some spectacular final underwater exploring around the beautiful beaches of Maui before setting sail and sailing around the beautiful but secluded island of Molokai. We have enjoyed our short time visiting Maui and as our time comes to an end we spend it mostly underwater, snork...
WE Were Maui Wowied on the Road to Hana | Episode 123
WE|Sail

WE Were Maui Wowied on the Road to Hana | Episode 123

Another land adventure on another Hawaiian Island. After finding an anchorage that allowed us to comfortably leave the Wolfhound for a couple days, we rented a car and drove the infamous Road to Hana around Maui. Don't go chasing waterfalls, they said...but honestly that's exactly what w...
HAND-STEERING to HONOLULU [Adventure #133]
Adventure Adrift

HAND-STEERING to HONOLULU [Adventure #133]

Because when you have a non-working autopilot, a windvane that needs repairs, and basically no marine supplies available, that’s what you got to do! Come along with us for a beautiful sail from Maui, along the incredible cliffs of the North shore of Molokai, all the way to the crazy developed Waiki...
Conquering THE LIST [Adventure #132]
Adventure Adrift

Conquering THE LIST [Adventure #132]

In Maui, we get serious about tackling and checking off all the boat projects we need to finish before setting sail to Oahu. Repairing out torn genoa, picking up supplies and spare parts, finding leaks in the boat, and replacing soft shackles with jib snaps. ________________ We hope you enjoy our...
Sailing a Homemade Outrigger Canoe in Hawaii (Ep.11 Sailing w/the Litzenbergers)
Sailing with the Litzenbergers

Sailing a Homemade Outrigger Canoe in Hawaii (Ep.11 Sailing w/the Litzenbergers)

We're still in Maui! A friend of ours takes us sailing on his homemade outrigger canoe. The whole experience gets us super excited for our upcoming trip! #SailingHawaii #MoanaSailing #SailingCanoe
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