Watch Sailing & Boating Adventures Around the World tagged “Living on a sailboat” – Page 2 of 138

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I Came Home… and He Was Gone | Sailing Avocet
Sailing Avocet

I Came Home… and He Was Gone | Sailing Avocet

Marissa left for California to get some work and snowboarding in, then returned home to a boat without Chris! @KesselUnderway sailed away to La Cruz, leaving Marissa alone aboard for a week where she quickly realized she is bad at being alone, and even wor...
Another Boat Problem, Another Lesson Learned – E.159 – Sailing SV CUBA
Sailing SV CUBA

Another Boat Problem, Another Lesson Learned – E.159 – Sailing SV CUBA

Another boat fix, another story to tell. Nothing goes to plan — but that’s sailing for you! You buy a sailboat and dream of sailing around the world, but end up fixing your sailboat all over the world. ☹️ Did I miss something?
IT’S DECISION TIME! Choosing Our Explorer Yacht
Gone with the Wynns

IT’S DECISION TIME! Choosing Our Explorer Yacht

After six months, countless miles, and what feels like a hundred boats later… 🌊 Go to https://surfshark.com/wynns or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides...
E354 Sailing to the MOST POPULAR Destination in the Bahamas GEORGETOWN
Wildly Intrepid Sailing

E354 Sailing to the MOST POPULAR Destination in the Bahamas GEORGETOWN

Every year hundreds of sailboats gather to Georgetown in the Southern Exumas. Why? Well there is everything a cruiser needs, a sheltered bay and a busy community. Our main reason to sail here was to host family because this is a great point to have guests ...
It’s Over! – Every Sailor Knows This Feeling – E.158 – Sailing SV CUBA
Sailing SV CUBA

It’s Over! – Every Sailor Knows This Feeling – E.158 – Sailing SV CUBA

That sinking feeling when your Sailboat comes out of the water. Hauling out is never easy — a mix of stress, nerves, and hope all in one moment. ⚓️ Sailboats are built to float.
Sometimes you just have to keep on Sailing [E353]
Wildly Intrepid Sailing

Sometimes you just have to keep on Sailing [E353]

Perfect conditions while we are anchored in the Berry Islands at Hoffman's and White Cay lead to spearfishing, snorkeling, paddle boarding and even a campfire. Although eventually we have to make a run South. From loosing all our water to a rough 30+ knots...
The Story Kristin Was Telling.
Harbors Unknown

The Story Kristin Was Telling.

This is the story Kristin was working on before everything changed. We fix what's broken, set sail once more, and follow the route she dreamed of sailing to Lady Musgrave and the Whitsundays.
From breakdowns to breakthroughs – Don’t Give Up Your Dream of Sailing Around the World – E156
Sailing SV CUBA

From breakdowns to breakthroughs – Don’t Give Up Your Dream of Sailing Around the World – E156

There’s an old saying that goes, “Sailing around the world is fixing your sailboat in exotic places.” It couldn’t be closer to the truth—but don’t give up your dream; things will eventually come together!
NOT Dead! NOT Divorced! | SailAway FINALE 313
SailAway World Sailing

NOT Dead! NOT Divorced! | SailAway FINALE 313

It's BEEN A WHILE! And yes, we have lots to tell you...sorry it took us this long! Enjoy!! Thanks for watching SailAway, the travel documentary of an adventurous sailing couple, kid and dog, sailing the world! [JOIN OUR CREW] Appreciate our videos? Th...
SAILING to Bahamas from Florida | Gulfstream Crossing [E352]
Wildly Intrepid Sailing

SAILING to Bahamas from Florida | Gulfstream Crossing [E352]

Crossing to the Bahamas is always an exciting moment. But it requires careful planning as we have to cross the Gulfstream which can be treacherous. A long brutal overnight pays off ass we soak in the Bahamian island life with its marvelous beaches and blue...
She’s Broken Again… Can We Bring Her Back? – E.155 – Sailing SV CUBA
Sailing SV CUBA

She’s Broken Again… Can We Bring Her Back? – E.155 – Sailing SV CUBA

We thought we fixed our sailboat… but she had other plans. 😬 Watch us dive back into another unexpected boat repair at sea! The sailing, the anchoring and living in a boat is the easy stuff, keeping your sailboat in top shape, now that's hard!
What are we building on our sailing boat home
Sailing Catalpa

What are we building on our sailing boat home

To get 20% off Florence Marine https://www.florencemarinex.com/pages/sailing-catalpa use the code 20CATALPA0724 Cheers everyone for watching!! Subscribe @SailingCatalpa Become a Patron https://www.patreon.com/sailingcatalpa To DONATE just because you...
The Challenge Is OVER!!!!  (Days 102-115/100 Day Water World Challenge)
Adventureman Dan

The Challenge Is OVER!!!! (Days 102-115/100 Day Water World Challenge)

It has been one HELL of a ride for the past 115 days! What was suppose to be a challenge lasting only 100 days was just too much fun to stop. So I kept it going a bit longer. Also, check out these adventures on Nicole's channel: www.youtube.com/@NicoleDem...
The Ultimate Explorer Yacht Test
Gone with the Wynns
SAILING the Florida ICW after 4 months of hard work [E351]
Wildly Intrepid Sailing

SAILING the Florida ICW after 4 months of hard work [E351]

The craziest overhaul of our boat. After 4 months time to set sail down the ICW to make our way over to the Bahamas. Filmed winter 2025. If you like what you see don't forget to give us the thumbs up! #sailing #sailingfamily #cclandfallsailboat *******...
End of the Line: Surrounded by Ice and Nowhere to Go – Ep 254
Sailing Jibsea

End of the Line: Surrounded by Ice and Nowhere to Go – Ep 254

Bluetti Elite 200 V2 Amazon Page: http://amzn.to/4mFmPGA Discount Code: FALLPDOFF (5% OFF) Sailing through Greenland’s stunning Prince Christian Sound, we navigate between massive icebergs, scattered ice, glaciers, and towering mountains. We encounter s...
Life between islands: 40 nautical miles of full sails and smooth seas
WhiteSpotPirates

Life between islands: 40 nautical miles of full sails and smooth seas

Become part of the crew http://www.patreon.com/WhiteSpotPirates A new sailing day begins in the Canary Islands as we lift anchor in Gran Canaria and set our course for Tenerife. It’s a 40-nautical-mile passage of smooth seas, steady winds, and that spec...
Mistakes, money saving and lessons we learned buying an old sailing boat
Sailing Catalpa

Mistakes, money saving and lessons we learned buying an old sailing boat

We talk about some of the mistakes we made and some of the ways we saved money refitting our old sailing boat. Cheers everyone for watching!! Subscribe @SailingCatalpa Become a Patron https://www.patreon.com/sailingcatalpa To DONATE just because you...
How our kids were schooled living on a boat travelling
Sailing Catalpa

How our kids were schooled living on a boat travelling

The honest truth about raising our kids on the ocean. We openly talk about our homeschooling experience and the path we chose on schooling our 2 kids while sailing the world. Cheers everyone for watching!! Subscribe @SailingCatalpa Become a Patron ht...
What It’s ACTUALLY Like, at Sea, on an Explorer Yacht
Gone with the Wynns

What It’s ACTUALLY Like, at Sea, on an Explorer Yacht

Life Aboard a Trawler. Want better sleep? Try our favorite sleep aid, Dream! Click https://shopbeam.com/WYNNS and use code WYNNS for up to 35% off. Limited time only! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Pho...
The Whole FAMILY is hard at keeping water out [E350]
Wildly Intrepid Sailing

The Whole FAMILY is hard at keeping water out [E350]

Water needs to stay out of a sailboat at all cost. This is why we are doing so much work below the waterline. Fiberglass, sanding, thru-hulls, cracks, shaft, propeller, rudder. Nothing gets left alone. And we also seal a window which was the cause of so mu...
Sailing Lifestyle & Local Spirit: Fishermen Festival in the Canaries
WhiteSpotPirates

Sailing Lifestyle & Local Spirit: Fishermen Festival in the Canaries

Join the Crew on Patreon http://www.patreon.com/WhiteSpotPirates Sailing life in Gran Canaria brings us not only beautiful anchorages but also a chance to dive into local culture. While anchored in the south of the island, we joined the Santa Águeda fest...
Our Best Sailing DIY Yet? You Decide! Ep.154
Sailing SV CUBA

Our Best Sailing DIY Yet? You Decide! Ep.154

Learn a Language by Watching TV with Lingopie! Start your free trial today: https://learn.lingopie.com/sv_cuba #sailing
A typical day  in the WORK YARD in Green Cove Springs [E349]
Wildly Intrepid Sailing

A typical day in the WORK YARD in Green Cove Springs [E349]

In order to enjoy paradise we have to put in a lot of work to get our sailboat ready. Join us as we share with you what it looks like working on your boat while living at the marina on land. Plus taking care of a baby and toddler makes everything more inte...
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