Watch Sailing & Boating Adventures Around the World – Page 24 of 29

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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Underwater Huntress Sailing GBU
Sailing Good, Bad, and Ugly

Underwater Huntress Sailing GBU

This week on sailing GBU I go spearfishing for the first time to show you how we live off the land. I had more success than I thought and caught a couple fish. Most of the time we catch our dinner. I proved that I am an underwater huntress and now have a new hobby! Matt might want to buy an apron! I...
BOAT LIFE: From living aboard our multihull to crewing on a monohull. EP36
Sailing Starship Friendship

BOAT LIFE: From living aboard our multihull to crewing on a monohull. EP36

Doesn’t look like Starship does it? That’s because it is not. While David returns to his office to work, Kellie has set off on a special sailing adventure. For the next few weeks Kellie and a wonderful group of humans are sailing from Antigua to Newport RI on a 65’ Oyster named Hurrah. If you'...
CRAZY Outboard Motor DISASTER!
Sailing Good, Bad, and Ugly

CRAZY Outboard Motor DISASTER!

Our Mercury outboard motor almost broke off the transom and flew to space! Luckily Matt used his strong grip to hold it or else this would have been more of a disaster for us. We came up with a plan and bolted it to the transom. Now it will be hard to take it on and off but we have no choice at this...
Sailing to surf in another country!
Sailing Good, Bad, and Ugly

Sailing to surf in another country!

Matt finally got to surf in another country. We checked that of our bucket list! We go back to the chat n chill and play corn hole. George town bahamas is the best play for cruisers! --------------------------------------------------------------------- If you enjoyed our video and want to get to kno...
WORK LIFE and our new SAILBOAT | Sailing on a Whim Ep.6
Sailing on a Whim

WORK LIFE and our new SAILBOAT | Sailing on a Whim Ep.6

On this episode of Sailing on a Whim, learn more about our work life as we take you along to see our biggest event of the year, the Crystal Ball New Year’s Eve in Minneapolis. In the midst of planning and running this HUGE event, we finalize the purchase on our new sailboat and move Whim to her new ...
George Town Bahamas shenanigans!
Sailing Good, Bad, and Ugly

George Town Bahamas shenanigans!

George Town Bahamas is full of opportunity for shenanigans! We are currently located at Great Exuma the same island of the Fyre Festival! Hope you enjoy our day in the life episode of us exploring and relaxing. --------------------------------------------------------------------- We upload a new vid...
Ep. 211 A simple Life
SAILING into FREEDOM

Ep. 211 A simple Life

Our water pump died so we find a well on one of the islands to wash up and clean ourselves. The water has a bit of a taste to it but we dont care so I grab a 100 litres so we can live another week or so on the boat. Margarida is spearing more fish and catches us all dinner as well as getting us som...
Sailing to an anchorage of our own
Sailing Good, Bad, and Ugly

Sailing to an anchorage of our own

We start to sail south to Lil Farmers Cay. The sailing was a breeze hahaha. Winds were a little against us so we used the opportunity to sharpen our sailing skills. As a liveaboard couple its good for both of us to be comfortable on all points of sail. Our sailboat did good. Also for a good read che...
Ep.209 The islands of Panama simply magical
SAILING into FREEDOM

Ep.209 The islands of Panama simply magical

Margarida is back and we go sailing to explore some of the most beautiful places that the southwestern Caribbean has to offer. Margarida gets seasick on the journey but she soldiers on because she is a tough old trooper. We show off our new Tohatsu 9.8 that was generously bought for us by our wonde...
Ep. 208 Fixing it all up in Panama
SAILING into FREEDOM

Ep. 208 Fixing it all up in Panama

More boat fixes. Likely to be the most boring video we have ever done so save this for when you need some zzzzzzzzzzzzz in a difficult situation, like if you need to get to sleep before an exam and you are too worried. Just turn on this video and you will be out within 2 minutes. Insomniacs, I have ...
Pablo Escobars underwater plane!
Sailing Good, Bad, and Ugly

Pablo Escobars underwater plane!

We decided to sail across to Normans Cay. It was a nice sail and beautiful water. The next day we snorkeled the sunken plane and saw what the island had to offer. -------------------------------------------------------------------------------------------------------- We upload a new video every week...
Ep.207 Sailing with The Boys Part 2
SAILING into FREEDOM

Ep.207 Sailing with The Boys Part 2

We continue the saga of Plukky, Dougy and Adam, our dynamic intrepid trio, sailing to Panama. We have a flooded front cabin, an engine that keeps overheating and very flat batteries forcing us to steer whenever possible. Will they be able to sail in through the channels in the reef without their p...
Sailing in Isolation and Running out of Provisions (E.72 Sailing w/the Litzenbergers)
Sailing with the Litzenbergers

Sailing in Isolation and Running out of Provisions (E.72 Sailing w/the Litzenbergers)

The game continues... ****Here are links to our Social Media Pages Facebook! Instagram! Our Website! Our Podcast! on iTunes (or it's available where ever you get your podcasts) Song Credits: *Digital Voyage by Twin Musicom is licensed under a Creative Commons Attribution license ( Art...
Ep.206 Sailing with the boys Part 1
SAILING into FREEDOM

Ep.206 Sailing with the boys Part 1

Sorry for losing a week, as you may know San Blas its not know for having much phone service aka internet. We hope this video makes it for the lost week. The trip to Panama was expected to be all plain sailing. Does that sound right? OF course not. We broke and fixed the autopilot, the motor could...
Using a Dinghy to Tow a Sailboat and Spearfishing Giants (E.71 Sailing w/the Litzenbergers)
Sailing with the Litzenbergers

Using a Dinghy to Tow a Sailboat and Spearfishing Giants (E.71 Sailing w/the Litzenbergers)

Helping friends, foraging for food and sailing to far off places, it's all apart of the sailing game! Follow Tipsy Gypsy on instagram: ****Here are links to our Social Media Pages Facebook! Instagram! Our Website! Our Podcast! on iTunes (or it's available where ever you get your ...
She’s Back!  Sailing a Monohull!
Sailing Doodles

She’s Back! Sailing a Monohull!

Laura returns as we set sail in Thailand on a brand new monohull Bavaria C45 and have an Island Spirit 410 Catamaran join us! This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron Donate Via Paypal to help us get a new drone: ...
Ep.205 Sailing to Roatan
SAILING into FREEDOM

Ep.205 Sailing to Roatan

Plukky, Dougy and Adam strike east in light conditions and get to Roatan (Bay Islands, Honduras), a magical diver's paradise. With water visibility in the hundreds of feet, plentiful fishes because of the marine park and the beautiful coral, they enjoy a short stay in this tropical paradise. G...
Sailing the most DANGEROUS route from Key West to the Bahamas
Sailing Good, Bad, and Ugly

Sailing the most DANGEROUS route from Key West to the Bahamas

We did it! We didn't give up and hard work pays off. About 400 miles of hard sailing though the gulf stream, by Cay Sal, and tongue of the ocean. Going south of Andros was a decision we made to get to an island that was less populated and not very common for cruisers. We made it and probably w...
Ep.204 Leaving Rio Dulce – Guatemala
SAILING into FREEDOM

Ep.204 Leaving Rio Dulce – Guatemala

Sorry for losing a week, as you may know San Blas its not know for having much phone service aka internet. We hope this video makes it for the lost week. Margarida has gone for family reasons and I find 2 patreons to come and help me sail to Panama. Dougy is a Canadian who has raced very small boa...
What it’s Like to Remodel a Cruise Ship (E.68 Sailing w/the Litzenbergers)
Sailing with the Litzenbergers

What it’s Like to Remodel a Cruise Ship (E.68 Sailing w/the Litzenbergers)

People always ask how we afford to sail full time, for the past year and a half. Well, here's a little work vlog. Hope you enjoy! ****Here are links to our Social Media Pages Facebook! Instagram! Our Website! Our Podcast! on iTunes (or it's available where ever you get your podcas...
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 subscribe to watch our next attempt at sai...
Retiring Early on a Sailboat in the Bahamas (E.67 Sailing w/the Litzenbergers)
Sailing with the Litzenbergers

Retiring Early on a Sailboat in the Bahamas (E.67 Sailing w/the Litzenbergers)

We get a mooring ball in Elbow Cay, Bahamas and really dig into the retiree lifestyle! Follow MV/Radiowaves on Instagram: ****Here are links to our Social Media Pages Facebook! Instagram! Our Website! Our Podcast! on iTunes (or it's available where ever you get your podcasts) #Saili...
Our first crossing didn’t go as planned: Sailing the Gulf Stream
Sailing Good, Bad, and Ugly

Our first crossing didn’t go as planned: Sailing the Gulf Stream

For months we have been planning this trip, saving money working in Key West while working on our Hunter 37. When we felt we were finally ready, we got impatient and didn't wait for the ideal weather window. That started out the many mistakes to come during our attempt to sail from Key West t...
Ep.203 She Left Me
SAILING into FREEDOM

Ep.203 She Left Me

On this episode we enjoy the local gastronomy and get our hands to work on the last preparations before our departure to Panama. And Margarida leaves for Portugal. Give it thumbs a up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: Want more? Became our patron and get acce...
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