Watch Sailing & Boating Adventures Around the World – Page 7 of 8

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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11 day Sail from Grand Cayman to Cuba to Charleston SC – EP27
Sailing PILAR - Blue Dot Voyages

11 day Sail from Grand Cayman to Cuba to Charleston SC – EP27

Watch the highlights of our Sailing voyage from Grand Cayman to Cuba to US. 11 days on the water with only 2 stops - Caya Largo Cuba (before the no-travel change) and Key West FL before the final leg to Bohicket Marina located in South Carolina's Charleston Sea Islands of Kiawah and Seabrook. ...
Catamaran PILAR Sails – Dry Tortugas – Cuba – Grand Cayman – EP22
Sailing PILAR - Blue Dot Voyages

Catamaran PILAR Sails – Dry Tortugas – Cuba – Grand Cayman – EP22

Catamaran Sailing Voyage from Dry Tortugas, FL - Cuba - Cayman 0:00 introduction 5:05 Blue Marlin Catch at 5:05 7:28 Dolphin Fish School 8:33 Jolly Roger Parasail flies again 16:13 New year's on our sailboat 18:41 Message in a bottle out to sea 22:05 Tarpons in Grand Cayman 22:17 Birthday sno...
Our Journey
HaveWindWillTravel.com

Our Journey

Six years now Phillip and I have been sailing and sharing here at HaveWind, and—now, especially with our first Atlantic Circle complete!—we’re often asked where all we have traveled by sailboat.  Well, this should explain it!  A six-year HaveWind animated-footage timeline as well as a graphic.  Chec...
The Windward Passage – Jamaica to Great Inagua (The Sailing Family) Ep.63
The Sailing Family

The Windward Passage – Jamaica to Great Inagua (The Sailing Family) Ep.63

- After we had visited the Blue Mountains in Jamaica where the most expensive coffee is coming from and had lunch in a Rasta community we sailed on with the positive vibes of Jamaica in the direction of Cuba and then to an island called Great Inagua. It was a nice trip with less wind. We hope by s...
Hilma Sailing, time travel to Cuba, Ep 22
Hilma Sailing

Hilma Sailing, time travel to Cuba, Ep 22

Finally, it was time to sail to Cuba. We celebrated Oskars birthday on our way there. We sailed to Santiago de Cuba and it was something totally different from the other islands in the Caribbean. We loved it. We hope you will enjoy it! If you want to support us you can become a Patreon: Or, ma...
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 ...
Sailing Cuba’s Northwest Coast as Newbie Cruisers | S02E07
Sailing Project Atticus

Sailing Cuba’s Northwest Coast as Newbie Cruisers | S02E07

Our time in Cuba was marked by extreme disbelief that we were actually cruising and using Atticus as a means to get somewhere new! In this episode, we explore a kookie artist's workshop just outside of Havana called Fusterlandia, and then leave Havana behind to explore the quieter North West Co...
Marriage Proposal in Cuba! S02E06 | Project Atticus
Sailing Project Atticus

Marriage Proposal in Cuba! S02E06 | Project Atticus

After dreaming about becoming cruisers for three years, we finally sail from Key West to Cuba and arrive at Marina Hemingway! After sleeping for 12 hours, we spend our first full day exploring Havana Vieja and are fascinated by the bustling alleyways full to the brim with locals at work or kicking b...
Interview with a happy socialist in Cuba | Sailing Zingaro
Sailing Zingaro

Interview with a happy socialist in Cuba | Sailing Zingaro

We sailed to Cuba, and rented a house from Sr. Pepe. He was nice enough to grant us an interview about his thoughts on Cuba, Socialism, History, and quality of life in this interesting country. Get a T-shirt: Please LIKE & SUBSCRIBE to see the next part of our adventure. If you liked the vi...
Epic Sailboat Adventure in Review (Bums on a Boat)
Bums on a Boat

Epic Sailboat Adventure in Review (Bums on a Boat)

There is no arguing that we 3 kids went all in on this one! Much experience was gained. There were great times and hard times. Funny how things change when you act on your deepest feelings and just go for it. Here is an honest recap. Hopefully this sheds some light and maybe even offers some perspec...
Mission Panamania 04: Longest Passage & Biggest Storm Ever (Sailing Curiosity)
Gone with the Wynns

Mission Panamania 04: Longest Passage & Biggest Storm Ever (Sailing Curiosity)

This is it! Bye Bye Bahamas, we're off to Panama! Get all the Details of our trip here: Subscribe and Keep in touch: Join our crew on Patreon and become a BIGGER part of the adventure: We're nearing the end of our Mission: Sail to Panama before the worst of the hurricane season. ...
IMPI SAILING THE WORLD (PT 1)
Catamaran Impi

IMPI SAILING THE WORLD (PT 1)

Back in South Africa visiting family and friends our You Tube followers are asking us to post more videos. I thought this would be a great opportunity to reflect on the oceans we have sailed, the places and people we have met and whilst everything cannot be shared, we hope this video will provide so...
Leaving For Good: The Plan & Our BIGGEST Passage (Sailing Curiosity)
Gone with the Wynns

Leaving For Good: The Plan & Our BIGGEST Passage (Sailing Curiosity)

We're leaving the marina in Fort Lauderdale for good and planning our BIGGEST passage yet to Panama. Here's the Links we promised: - Join our crew on Patreon: - Get all the Details here: - Our Social Channels: We want to be fully prepared for the journey ahead so we've bee...
The CUBA EXPERIENCE | Sailing Havana to Key West – Bums on a Boat Ep 13
Bums on a Boat

The CUBA EXPERIENCE | Sailing Havana to Key West – Bums on a Boat Ep 13

We spent 12 days in Cuba. Our good friend flies down from New York to visit and we meet great people from all over the world. The Bums finally got their 3rd world experience. Check out our Patreon page here
Boat #15: 1939 John Alden Schooner
HaveWindWillTravel.com

Boat #15: 1939 John Alden Schooner

"When the war is over and if I return," said General Patton. This was his boat! An immaculately-restored 1939 John Alden Schooner, with her very own Captain Seth giving us a tour and telling us his story and plans to sail When and If around the world. They recently sailed When and If to...
Solo sailing to southern Cuba | Sailing Zingaro Ep-4
Sailing Zingaro

Solo sailing to southern Cuba | Sailing Zingaro Ep-4

Sailing solo to the southern archipelagoes of Cuba. Freediving, spearfishing, sightseeing... Explore Nueva Gerona with me as I take you into a real Cuban restaurant where the food is $1 (and fantastic)! We welcome a new crew member. Welcome Mel! And get the boat off the bottom... [ SUPPORT OUR VID...
A Death-Defying Sail to CUBA – Bums on a Boat Ep 12
Bums on a Boat

A Death-Defying Sail to CUBA – Bums on a Boat Ep 12

Join along in this ride of highs and lows as we sail to Cuba. The Gulf shows its ugly teeth and the weathers proves unpredictable. A storm runs us off course and we are stuck sailing against the current and wind. The trip quickly turns into an endurance marathon with the only goal being to survive. ...
#95: Historic Havana: Sail There with Me!
HaveWindWillTravel.com

#95: Historic Havana: Sail There with Me!

Mojitos at La Bodeguita del Medio, walk historic Cathedral Square, tour Hemingway's house, Finca Viega, dance at the Floradita and see inside the Casa Particular we rented for $40 CUCs/night. We take you all through Havana in this video with some very exciting news at the end. I'm going ...
Havana locals show us the real city | Sailing Zingaro Ep-3
Sailing Zingaro

Havana locals show us the real city | Sailing Zingaro Ep-3

A look at the REAL Cuba! We sail overnight FL-Havana, go to the markets, dinner with the mayor, get a guided tour around Old Havana, Hotel Nacional and see the crew off onto their next adventure. [ SUPPORT OUR VIDEOS] Patreon: Buy us a BEER!: [FOLLOW US] Website: Facebook: Instagram: [COM...
Sailing to Cuba 101
Sailing Zingaro

Sailing to Cuba 101

Here's everything you need to know about sailing to Cuba. Well, not really sailing, more checking-in to Cuba via sailboat. It's overwhelming at first, and information was sketchy - so here's my first-person account of arriving and checking into customs in Cuba. Form 3300: USCG Do...
#94: Clearing Customs and Exploring Cuba
HaveWindWillTravel.com

#94: Clearing Customs and Exploring Cuba

Want to know exactly what it feels like to go through the customs process after sailing to Cuba? Come along. We'll walk you through. Show you exactly who boarded and what they wanted to know. We've included a lot of great tips in here for you as well to make the check-in process easy i...
#93: Cuba Voyage Finale: Gulf Stream Crossing and Landfall in CUBA!
HaveWindWillTravel.com

#93: Cuba Voyage Finale: Gulf Stream Crossing and Landfall in CUBA!

The current of the Gulf Stream is no joke, particularly when it is pushing you into head winds. Watch as we reef up and cross a pretty kicked up sea state across the Gulf Stream, sing to our first Cuban sunrise, deal with an issue with the furling gear on our headsail, navigate the entry to Marina ...
#92: Cuba Voyage IV: Rudder on the Loose
HaveWindWillTravel.com

#92: Cuba Voyage IV: Rudder on the Loose

Last time we documented power management underway, now we're dealing with a rudder post that won't stay ... put anyway. Follow along as we fix our boat in exotic places (i.e., on the way to Cuba). You'll also hear extensively from Phillip in this episode about preparing for a lightn...
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