Watch Sailing & Boating Adventures Around the World tagged “Sailing to cuba” – Page 8 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.

Showing 169-190 of 190 results
Ep. 278 Margarida living it up in Havana! – Worlds apart – Sailing and adventure in Cuba
SAILING into FREEDOM

Ep. 278 Margarida living it up in Havana! – Worlds apart – Sailing and adventure in Cuba

We are still on opposite sides of Cuba. Margarida is still with her parents enjoying the sites while I have an easy run back to Cayo Largo in order to be ready to pick Margarida from the Airport. Give it a thumbs up if you liked this episode! Get your Sa...
Ep.277 Margarida leaves for Havana, Cuba and I sail away  – Sailing and adventure in Cuba
SAILING into FREEDOM

Ep.277 Margarida leaves for Havana, Cuba and I sail away – Sailing and adventure in Cuba

What can I say? Margarida leaves and I am alone....oh well it's a sad time but I find a wise moray eel and she becomes my teacher - my moray eel teacher, and it teaches me not to dangle my fingers too close to its mouth....I am not sure what that is suppos...
Ep. 276 Margarida’s parents come to visit us in Cayo Largo – Love, Sailing and Adventure in Cuba
SAILING into FREEDOM

Ep. 276 Margarida’s parents come to visit us in Cayo Largo – Love, Sailing and Adventure in Cuba

Margarida's parents come to visit us and we do a tour of Cayo Rico and Hijo Reef. Southern Cuba is a sailor's dream with crystal clear water, the whitest sandy beaches and stunning coral reefs. We show them all to Teresa and Pedro and we have a ball. Giv...
Harold the Amazing Guy – YOUTUBE star viewer – Anything goes Tuesdays
SAILING into FREEDOM

Harold the Amazing Guy – YOUTUBE star viewer – Anything goes Tuesdays

Harold is really supporting both my channels by watching 1000's of times. I didn't know how he did it so I rang up YOUTUBE and got the inside scoop. The latest on Spearfishing Nomad is up ready to watch https://youtu.be/uVQMa7ujYc4 Give it a thumbs up if...
Ep.275 Who needs clothes at Iguana Beach – Sailing and Adventure in Cuba
SAILING into FREEDOM

Ep.275 Who needs clothes at Iguana Beach – Sailing and Adventure in Cuba

We leave beautiful Cayo Rico and finally get in to Cayo Largo, Cuba. We check in and have a problem with all the fresh groceries that we have brought in. The Agriculture Department want us to throw them out or can we bribe them to allow us to keep them? Ou...
Furling an unfurlable sail before the next storm comes in – sailing an adventure in Panama
SAILING into FREEDOM

Furling an unfurlable sail before the next storm comes in – sailing an adventure in Panama

Just before arriving to see Margarida I was hit by several squalls and the furler got jammed in both directions - I could not furl or unfurl the genoa. This video is about what I did to recover the sail. It is not the best solution. Squalls were coming thr...
Ep.274 Exploring southern Cuba by yacht – Sailing adventure in the Caribbean – off grid living
SAILING into FREEDOM

Ep.274 Exploring southern Cuba by yacht – Sailing adventure in the Caribbean – off grid living

Check out the new channel Spearfishing Nomad https://youtu.be/Bu4boWa_H0g The champion Margarida gets us conch and hogfish for dinner. I give a lesson on how to sail southern Cuba. We don't make our destination of Cayo Largo but end up at Cayo Rico with a...
Back to Margarida – the good, the bad and the ugly
SAILING into FREEDOM

Back to Margarida – the good, the bad and the ugly

We are finally back together and talk about what is happening between us. Give it a thumbs up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: https://teespring.com/stores/sailing-into-freedom Want more? Became our patron and get a...
Ep. 273  Fishing and the boat hits a rock . Damage report is *&%^@# – Sailing in Cuba
SAILING into FREEDOM

Ep. 273 Fishing and the boat hits a rock . Damage report is *&%^@# – Sailing in Cuba

We move from our friends in Cayo Campos and head East to Cayo Rosario. We sail over some shallow areas very slowly but even with Margarida keeping lookout on the bow, we hit a rock. Give it a thumbs up if you liked this episode! Get your Sailing Into Fre...
Sailing alone – The journey back to Margarida Part 2 – Sailing and adventure in Panama
SAILING into FREEDOM

Sailing alone – The journey back to Margarida Part 2 – Sailing and adventure in Panama

The final return but it isn't what you would expect. Give it a thumbs up if you liked this episode! Webb Chiles (the Legend) books on Amazon: - The Open Boat: Across the Pacific https://amzn.to/2NzMc1R - STORM PASSAGE: Alone Around Cape Horn https://a...
Ep.272 Living on a tight budget – the sea provides all – Sailing and Adventure in Cuba
SAILING into FREEDOM

Ep.272 Living on a tight budget – the sea provides all – Sailing and Adventure in Cuba

I go diving and discover lobster everywhere... so many in fact that there were not enough proper hiding spots. I even got charged by one, classic! I feed another moray eel and boy is she hungry taking 3 bloody fish. After that I shoot a trunkfish... oh no!...
Ep.271 A naughty day at the beach, Sailing and Adventure in Cuba
SAILING into FREEDOM

Ep.271 A naughty day at the beach, Sailing and Adventure in Cuba

Margarida shows us a bit of domestic life on the boat while I go out and get some dinner. I return and am greeted by a smiling darling wife ready to go to the beach but I sort of stuff it up by opening my mouth and giving some advice... nothing but qualit...
Ep.270 Tropical island paradise – Sailing and Adventure in Cuba
SAILING into FREEDOM

Ep.270 Tropical island paradise – Sailing and Adventure in Cuba

The Cuban locals love Margarida and have invited us over for dinner again. The culinary adventure continues but this time we are going to eat the hutia that we saw in the previous episode, the one in the cage... that's right people the rodent that looks li...
Ep.269 Coral reef paradise seen in the distance, Sailing to Cuba
SAILING into FREEDOM

Ep.269 Coral reef paradise seen in the distance, Sailing to Cuba

After a very easy overnight sail we are rewarded by seeing waves breaking on the outer reefs. We meander through but there is a problem... we have to stop. I recall its been more than 2 months since I have eaten fresh fish so in I go to see what there is t...
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 Charlest...
Day in the Life | Offshore Sailing to Cuba | S03E38
Sailing Project Atticus

Day in the Life | Offshore Sailing to Cuba | S03E38

We're off to Cuba on our longest passage yet! After multiple watches, the days start to blur together and we ease into the passage making groove. We encounter some issues which make for a more challenging passage than expected. Did you like this video? ...
Exhausted! Preparing for an Offshore Passage | S03E37
Sailing Project Atticus

Exhausted! Preparing for an Offshore Passage | S03E37

We've got a LONG list of to do's to get Atticus ready for our Offshore Passage to Cuba. Provisioning, cleaning the bottom, withdrawing cash, checking out of the country, filling up on gas, diesel & water, AND inspecting the rig- so much to do, and so l...
Our first crossing didn’t go as planned: Sneaking into Cuba
Sailing Good, Bad, and Ugly

Our first crossing didn’t go as planned: Sneaking into Cuba

After being exhausted and not thinking straight we sailed to Cuba. We didn't plan on going there so we did not have the proper paper work. Everything worked out and we sailed from Cuba to Key West. Thanks for watching our first big sail. Make sure to sub...
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 ...
Sailing to Cuba: We Finally Start Cruising! | S02E05
Sailing Project Atticus

Sailing to Cuba: We Finally Start Cruising! | S02E05

After sailing up to Sarasota Florida from Key West we spent the holidays with our families and got our small sailboat, Atticus, ready to leave the United States for a long time. Sailing to Cuba would be our first international landfall as well as our first...
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 ma...
#27: Where Are You Going?
HaveWindWillTravel.com

#27: Where Are You Going?

Cuba! I'm kidding (sort of). Maybe. There and 1,000 other places. I'll share our (very vague) plans but we're less than a year out and--believe me--that's not near enough time. (But it never is.) A big shout-out to just a few of the other wanderlusts...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart