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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Epic Sail in the clearest water with the largest fish yet!  |  Ep141
Sailing Fair Isle

Epic Sail in the clearest water with the largest fish yet! | Ep141

It's the last of the Cuba series, but it all happens in this episode. We sail the whole Northern coast of Cuba, hide from a storm, dock in over 30 knots of wind (without the bow thruster), run out of food and then see the other side of Cuba (it's a shock!) Then we make for the Bahamas, cat...
The worst place to run aground  |  Ep138
Sailing Fair Isle

The worst place to run aground | Ep138

The Cuban coastguard doesn't have a boat. One sailor we spoke to here was told that if he wanted his boat pulled off the rocks they would have to hire a boat from Jamaica. So, this is not the place to find yourself hard aground! Added to that, we can 't get spares here. When we ran agrou...
Sailing CUBA!  |  Ep137
Sailing Fair Isle

Sailing CUBA! | Ep137

Cuba is without doubt the friendliest and most fascinating place we've been in the Caribbean - but somewhat surprisingly, there are hardly any tourists here (and they could really use more!). Cruising here on a boat is not like other countries. Officially you can only stop and go ashore at the...
Scuppering a 2000 tonne ship then sailing to Cuba!   |   Ep136
Sailing Fair Isle

Scuppering a 2000 tonne ship then sailing to Cuba! | Ep136

We have been in the Cayman Islands longer than expected. It's a hard place to leave! But we were equally excited to be sailing to Cuba. Somewhere we have never been before. We couldn't leave without diving on the Kittiwake, an ex navy submarine rescue vessel which was scuppered by our patr...
Sailing the High Seas: Family Adventure from Isla Mujeres to Cuba!
Sailing Big Lost

Sailing the High Seas: Family Adventure from Isla Mujeres to Cuba!

Join us on our challenging sailing adventure as we set off from Isla Mujeres to Cuba! In this episode, we share the ups and downs of our journey after missing our ideal weather window. Battling rough seas and unpredictable conditions, we faced unexpected challenges that tested our family's resi...
Solo Overnight Hand steering Cuba due to Broken Autopilot
Huub Vlogs

Solo Overnight Hand steering Cuba due to Broken Autopilot

From buying a sailboat, to making it ready to sail, to sailing the Caribbean ———————————————————————————— Want to see real-life updates and chat? Would you like to support once through Paypal? Would you like to buy me a coffee? Let Amazon pay me when you shop (FREE TO YOU): —————————————————...
Cuba backpacking | Sildeshow | Cuba 🇨🇺
Bushpoint Sailing

Cuba backpacking | Sildeshow | Cuba 🇨🇺

We sailed to Cuba, put the boat in Hemingway Marina and put on our backpacks and rode all over Cuba. Do enjoy our slideshow from this beautiful Country. ⚓ Join our journey! If you enjoyed this glimpse into Cuba please Subscribe. We share stories from our sailing adventures and travels across the gl...
ESCAPING CUBA PART 2//Delivering An 82ft Boat From Cuba-Episode 29
Sailing Dauntless

ESCAPING CUBA PART 2//Delivering An 82ft Boat From Cuba-Episode 29

This week we are daring to enter Cuba to pick up an 82ft sail boat and deliver it back to the US. Come along with us as we sail the Caribbean, through the Florida Keys and back home to Dauntless. Check Out Mike's Channel Sailing Vessel Luxor: Want to go on a sailing adventure? Contact Geoff ...
ESCAPING CUBA//Delivering An 82ft Boat From Cuba To The US-Episode 28
Sailing Dauntless

ESCAPING CUBA//Delivering An 82ft Boat From Cuba To The US-Episode 28

This week we are daring to enter Cuba to pick up an 82ft sail boat and deliver it back to the US. Come along with us as we fly to 2 different countries, almost get deported and witness an amazing sunset in the middle of nowhere. Check Out Mike's Channel Sailing Vessel Luxor: Want to support ...
Changing of the Guards | Santa Ifigenia Cemetery | Cuba 🇨🇺
Bushpoint Sailing

Changing of the Guards | Santa Ifigenia Cemetery | Cuba 🇨🇺

Experience a moment of powerful Cuban history. This footage captures the ceremonial changing of the guard at the magnificent mausoleum of national hero José Martí in Santiago de Cuba. The Santa Ifigenia Cemetery is a place of immense significance, serving as the final resting place for icons like Fi...
Sailing from Florida to Cuba in a Scary Lightning Storm! | Episode 31
WE|Sail

Sailing from Florida to Cuba in a Scary Lightning Storm! | Episode 31

We return back to the states and work on the boat in Fort Lauderdale. After all, we were in the heart of the boat capital. Marine stores on every corner, shopping, dinning, and air conditioning! It was a nice change to be back in the land of plentiful things, but we were anxiously awaiting our next ...
10000 miles in 10 minutes – Ep 90 Sailing Luckyfish
Sailing Luckyfish

10000 miles in 10 minutes – Ep 90 Sailing Luckyfish

10000 miles in 10 minutes. If you have only heard of Luckyfish this is the video to see what we are all about. Sailing Cape Town, Namibia, St Helena Island, Ascension, trans-Atlantic to Barbados, the Windward Islands, Bahamas, Florida, Cuba and Guatemala. We look back over the last 4 years and ask &...
Is Sailing Communist Cuba Worth the Trouble? | S03E49
Sailing Project Atticus

Is Sailing Communist Cuba Worth the Trouble? | S03E49

We arrive in Cayo Largo and discover that finding convenient and affordable drinking water, groceries, and internet access isn’t going to be as easy as we thought. So, we set sail south to Grand Cayman and the first world and say goodbye to the hardships of Communist Cuba. Did you like this video?...
Sailing on a Budget | The Reef is Our Grocery Store | S03E48
Sailing Project Atticus

Sailing on a Budget | The Reef is Our Grocery Store | S03E48

While sailing Cuba’s Southern coast, we haven’t been able to provision for over a month! Our fridge is almost empty, so we decide to take the difficult route to Cayo Largo (our final destination) to attempt to spearfish a remote reef. On the way we struggle to anchor overnight in a bug infested mang...
Sailboat Life | Living off the Sea | Sailing Cuba | S03E47
Sailing Project Atticus

Sailboat Life | Living off the Sea | Sailing Cuba | S03E47

After sailing east for 2 weeks along the Southern Coast of Cuba, we finally arrive at Cayo Campos, the coolest freaking island in Southern Cuba. Jordan explores the mangrove cuts on Little Shit, we stumble upon a HUGE pack of monkeys, we explore a secluded beach trail, and we barter for and catch en...
Sailing in Light Winds & Sketchy Waters | Cuba, South Coast | S03E46
Sailing Project Atticus

Sailing in Light Winds & Sketchy Waters | Cuba, South Coast | S03E46

After sailing east along the South Coast of Cuba for 2 long and difficult weeks, we are finally two days and 1 sketchy pass away from arriving in the most beautiful island in Cuba, but light winds and shallow waters are going to put our sailing skills to the test! Did you like this video? Please do...
Sailing 50 miles Out of Our Way For Fresh Water | Sailing Cuba | S03E45
Sailing Project Atticus

Sailing 50 miles Out of Our Way For Fresh Water | Sailing Cuba | S03E45

After sailing a week along the Southern Coast of Cuba, we start to run low on water. Because Cuban maritime law prohibits sailors from entering most coastal towns, we are forced to sail 50 miles out of our way to fill up our water tanks at a small government run marina way out it the middle of nowhe...
Buddy Boating: Sailing with Friends in Remote Cuba | S03E44
Sailing Project Atticus

Buddy Boating: Sailing with Friends in Remote Cuba | S03E44

After spending a couple pleasant days anchored at a remote lagoon in the south coast of Cuba we get a weather report and discover that a cold front is on it’s way. The next day after tackling a few small projects we set sail for a much more protected anchorage. Along the way run into our friends on ...
Day in the Life: Anchored in Paradise || Sailing Cuba | S03E43
Sailing Project Atticus

Day in the Life: Anchored in Paradise || Sailing Cuba | S03E43

While Sailing in Cuba we spend several lazy days in a remote anchorage, trading rum for lobster with the local fishermen, walking on pristine beaches and living off the sea. The anchorage is located in a lagoon near Cayo Siju in the Cayos de San Felipe and was one of our favorite spots on the sout...
Hit by a DANGEROUS Squall || Sailing Cuba || S03E42
Sailing Project Atticus

Hit by a DANGEROUS Squall || Sailing Cuba || S03E42

We get nailed by a squall and pinned to a concrete dock AGAIN! After collecting ourselves, we finally prep Atticus and round the Western tip of Cuba, hoping that our weather routing will help us avoid the dangerous seas that the cape is known for. Did you like this video? Please don’t forget to g...
I messed Up…| Sailing Cuba | S03E41
Sailing Project Atticus

I messed Up…| Sailing Cuba | S03E41

Before sailing to the south coast of Cuba, we go on a side excursion 40 miles to the North West to snorkel, lobster, and explore. Although we anticipate an easy sail, we get beaten up by hard winds on the nose and can’t find a good snorkel spot. Jordan realizes he made a mistake and apologizes to De...
Island Sailing Isn’t Easy | S03E40
Sailing Project Atticus

Island Sailing Isn’t Easy | S03E40

While waiting for a weather window before sailing around the western tip of cuba, we take a short trip North East to explore what we’ve heard to be an untouched reef system. Along the way we are caught off guard by several unexpected challenges caused by the microclimate of Cuba. Did you like this...
We Ran Aground! Sailing Cuba | S02E10
Sailing Project Atticus

We Ran Aground! Sailing Cuba | S02E10

Our cruising experience in Cuba, after leaving Havana, got progressively more desolate as we headed farther and farther away from a big city. We rarely saw other vessels out on the water, and were the only boat in both of the anchorages where we dropped the hook for a night of sleep in Cayo Ines de ...
Snorkeling hidden reefs in Cuba | S02E08
Sailing Project Atticus

Snorkeling hidden reefs in Cuba | S02E08

When checking into Marina Hemingway, the port captain told us that we could not go ashore anywhere along the N.W Cuban Coast except Cayo Levisa between Havana and Cabo de San Antonio because there weren't any facilities to officially check into on any other coastal towns. We had read in Cheryl ...
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