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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This Is What Sailing Hawaii Actually Looks Like | Hilo to Honolulu
Sailing Sea Dream of Clyde

This Is What Sailing Hawaii Actually Looks Like | Hilo to Honolulu

After arriving in Hilo from Mexico just three days before, we're on the move again. Join us as we cruise the Hawaiin Islands from Hilo on the Big Island, all the way north to Honolulu aboard our old 33 ft sailboat. We learn quickly that things can get very spicy in the waters surrounding this p...
My Final Sail Aboard Phoenix (and Losing the Drone)
Sailing With Phoenix | Oliver

My Final Sail Aboard Phoenix (and Losing the Drone)

Well, my last voyage with her was bound to happen eventually. I’m glad we ended things on such a high note. The sailing conditions were perfect, magical, even (aside from losing the drone 😅). The Molokai sea cliffs at sunset were absolutely breathtaking, and she brought us home safely one last time....
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...
A Sporty 350 Mile Sail from Kona to Hilo 🌊
Sailing With Phoenix | Oliver

A Sporty 350 Mile Sail from Kona to Hilo 🌊

We battle big waves, broken gear, and beating to windward while sailing from Kona to Hilo on Hawaii's Big Island. This one was a doozy for sure. I also chat a bit about buying the new boat. More details on this very soon. And as always thank you for watching! ⛵ Join the Crew + Follow Along: 🌐...
We Broke Down in the Middle of Nowhere on Hawaii’s Big Island
Sailing With Phoenix | Oliver

We Broke Down in the Middle of Nowhere on Hawaii’s Big Island

Nothing ever goes to plan, but that's half the fun. What began as a laid-back drive to the volcano quickly turned into an off-road adventure through lava fields, green sand, and a broken-down Jeep miles from anywhere. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s P...
Sailing 220 Miles From Oahu to the Big Island
Sailing With Phoenix | Oliver

Sailing 220 Miles From Oahu to the Big Island

A 220-mile sail from Oahu to the Big Island became a lesson in patience and respect. Between calm seas and sudden squalls, we were forced to change course — the sea had other plans. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instag...
Sailing 40 Hours Back to Oahu From Kauai ⛵
Sailing With Phoenix | Oliver

Sailing 40 Hours Back to Oahu From Kauai ⛵

All good things must come to and end... After two weeks on Kauai, it’s time to sail back to Oahu. Join Phoenix, Rhoads, and me on a 40-hour passage across the Kaʻieʻie Waho Channel. ⛵ Join the Crew + Follow Along: 🌐 All My Links 📍 Live Tracker – Where’s Phoenix Now? 👕 Official Merch 📸 Instag...
I Ran Aground Sailing to Kāneʻohe Bay Sandbar – Hard Lessons Learned
Sailing With Phoenix | Oliver

I Ran Aground Sailing to Kāneʻohe Bay Sandbar – Hard Lessons Learned

Hello hello! Sailing adventures resume as my brother joins me in Hawai’i. We set sail from Waikiki Yacht Club into 30+ knot headwinds, bound for the stunning sandbar in Kāne‘ohe Bay, Oʻahu. What should have been a scenic day sail quickly turned stressful: wind advisories, towing mistakes, and hitti...
Would Your Anchor Hold Through This??
Sailing Emerald Steel

Would Your Anchor Hold Through This??

Hi guys! Being that it's still hurricane season we thought this vid might be relevant. On our maiden voyage to Hawaii we anchored in Lahaina, Maui and unfortunately were shortly thereafter hit by hurricane Iniki. Luckily we always listened to experienced old salts and it saved us and Emerald St...
#48 Installing Roller Furling At Anchor
Sailing Emerald Steel

#48 Installing Roller Furling At Anchor

Hi guys, In this video we do a recap of how we installed our Alado roller furling while at anchor...can't beat the surroundings;) Hope you enjoy the vid and please don't forget to leave a comment, thumb up👍, subscribe if your not already and click on the 🔔 to receive notifications whenever...
#47 Hideaway Anchorage Molokai
Sailing Emerald Steel

#47 Hideaway Anchorage Molokai

Hi guys, In this vid we anchor in tiny Lono harbor, Molokai....it's a cool little anchorage but we get stuck there for a few days due to high surf. Not a bad place to hang out🏝👍😀 Hope you enjoy the vid and please don't forget to leave a comment, thumb up👍, subscribe if your not already and...
#46 Anchoring In A Storm In Hawaii!!
Sailing Emerald Steel

#46 Anchoring In A Storm In Hawaii!!

Hey guys, In this vid we anchor in Kaneohe Bay, Oahu during a storm....it's pretty crazy and not too much fun but a small price to pay for our life of freedom. Remember...Hawaii is more then palm trees, beaches and clear water!🌈🏝 Hope you enjoy the vid and please don't forget to leave a co...
#45 Hawaii!!
Sailing Emerald Steel

#45 Hawaii!!

Hi guys! In this episode we finally make it to Hawaii after a long passage from French Polynesia so we get to enjoy the beautiful islands! Hope you enjoy the vid and please don't forget to leave a comment, thumb up👍, subscribe if your not already and click on the 🔔 to receive notifications when...
A POD OF DOLPHINS surrounds our boat! | Makua Bay Anchorage, Oahu | Ep. 02
The Hawaii Cruisers

A POD OF DOLPHINS surrounds our boat! | Makua Bay Anchorage, Oahu | Ep. 02

Our very first anchorage⚓️ The sail was our longest one yet clocking in at about 75 nautical miles round trip. Once we arrived at our destination, we dropped anchor, swam around the boat, had some sun downers on the bow, cooked venison tacos in our galley, looked up at the millions of stars above ...
Sailing for Kailua-Kona on the Big Island of Hawaii and Farewell to Kimberly Wood
Sailing Triteia

Sailing for Kailua-Kona on the Big Island of Hawaii and Farewell to Kimberly Wood

Episode #255 : Season 8 : The Hawaiian Adventures Hello Friends, On this episode we haul up at Makalawena Beach with the help of some awesome Needle fish (AKA LONG TOMS) and head for Kailua Bay. Kimberly Wood was the skipper for the day and handled all of the driving and navigation and we arrived...
Anchoring at the Beautiful Makalawena Beach on the Big Island of Hawaii
Sailing Triteia

Anchoring at the Beautiful Makalawena Beach on the Big Island of Hawaii

Episode #254 : Season 8 : The Hawaiian Adventures Hello Friends, On this episode we anchor at the stunningly beautiful Makalawena Beach on the Big Island of Hawaii. Then @kimberlywood-saltybutterfl262 and myself head ashore to explore this remarkable landscape. If you enjoy the channel please &q...
Cruising Down The Coast of the Big Island of Hawaii by Sailboat
Sailing Triteia

Cruising Down The Coast of the Big Island of Hawaii by Sailboat

Episode #253 : Season 8 : The Hawaiian Adventures Hello Friends, On this episode @kimberlywood-saltybutterfl262 and myself keep cruising down the coast of the Big Island dropping the hook at Kawaihae where we had some disgusting overpriced burgers before we continued on with an amazing sail to Mak...
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...
The Secret Lagoons & Basalt Cliffs of La Perouse Bay! One of the Most Amazing Anchorages in Hawaii
Sailing Triteia

The Secret Lagoons & Basalt Cliffs of La Perouse Bay! One of the Most Amazing Anchorages in Hawaii

Episode #251 : Season 8 : The Hawaiian Adventures Hello Friends, On this weeks episode @kimberlywood-saltybutterfl262 and myself have some amazing adventures at the remarkable La Perouse Bay on the southern tip of Maui. From amazing basalt cliffs to lava tide pools to a hidden lagoon. This anchor...
Escaping Molokini Crater and Anchoring at La Perouse Bay on The Island of Maui in Hawaii
Sailing Triteia

Escaping Molokini Crater and Anchoring at La Perouse Bay on The Island of Maui in Hawaii

Episode #250 : Season 8 : The Hawaiian Adventures Hello Friends, On this weeks episode @kimberlywood-saltybutterfl262 and myself continue our exploration of Maui's anchorages and find ourselves in a dangerous situation at Molokini Crater with wind and seas pinning us into the small lee shore...
Visiting Lahaina and Snorkeling the Ruins of Mala Wharf on Maui with Kimberly Wood
Sailing Triteia

Visiting Lahaina and Snorkeling the Ruins of Mala Wharf on Maui with Kimberly Wood

Episode #249 : Season 8 : The Hawaiian Adventures Hello Friends, On this episode I make my way to Maui and enjoy a weeks stay at Mala Wharf Anchorage before my adventure buddy extraordinaire, Kimberly Wood ( @kimberlywood-saltybutterfl262 ) flys in to bring me some important packages that arrived...
Adventures at The Best Anchorage in Hawaii So Far: Kamala Nui Anchorage on the Island of Lanai
Sailing Triteia

Adventures at The Best Anchorage in Hawaii So Far: Kamala Nui Anchorage on the Island of Lanai

Episode #248 : Season 8 : The Hawaiian Adventures Hello Friends, I spent the morning watching the rising sun illuminate the beautiful sea stacks that give this anchorage its name and after my coffee was all consumed I hauled up and enjoyed a peaceful sail on flat seas down the coast two miles to ...
An Exciting Sail from Molokai to Nanahoa (aka 5 Needles) Anchorage on the Island of Lanai in Hawaii
Sailing Triteia

An Exciting Sail from Molokai to Nanahoa (aka 5 Needles) Anchorage on the Island of Lanai in Hawaii

Episode #247 : Season 8 : The Hawaiian Adventures Hello Friends, After two days resting at Lono Harbor it was time to haul up and make way for the Island of Lanai. I enjoyed a very SPIRITED sail across the Kalohi Channel and arrived at the famous Needles (Nanahoa) anchorage on Lanai. I dropped the...
Exploring Lono Harbor on the Island of Molokai
Sailing Triteia

Exploring Lono Harbor on the Island of Molokai

Episode #246 : Season 8 : The Hawaiian Adventures Hello Friends, After a peaceful night on the hook at Lono Harbor I made my way ashore to do some exploring. This remote, dry anchorage could easily fit in with the Channel Islands of California. I spent much of the day getting caught up on rest af...
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