Watch Sailing & Boating Adventures Around the World – Page 5 of 9

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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114. What’s Inside this IMMACULATE World Cruiser? [Full Tour] Learning the Lines
Learning the Lines

114. What’s Inside this IMMACULATE World Cruiser? [Full Tour] Learning the Lines

The Ta Shing Baba 30, designed by Bob Perry, is a renowned go-anywhere bluewater cruiser. Her classic lines and functional design can get you across an ocean in comfort. This particular boat is in immaculate condition. It's obvious in the video we just couldn't get over how well she'...
Great start to a new decade! [S1:E02]
Sailing The Far Side

Great start to a new decade! [S1:E02]

Still hanging out in Key West working on some final touches before we officially start our trip. Had some friends over for a New Years brunch, and were spoiled with some chefs aboard. Learned some massage techniques to soothe our sore muscles after the long sailing days to come. Took a family trip o...
Savor the Last Sail | Sailing Soulianis – Ep. 52
Sailing Soulianis

Savor the Last Sail | Sailing Soulianis – Ep. 52

With just a few days left before we haul the boat out for hurricane season, we sail as much as we can — even when the wind is so light we’re hardly moving at all — to savor our last moments on the water. Join us for our last sail of the season, and our haulout into a landlocked boatyard on the west...
Sailing Backwards | Sailing Soulianis – Ep. 51
Sailing Soulianis

Sailing Backwards | Sailing Soulianis – Ep. 51

Buy a sailboat, then sail over the horizon, right? Oh if it was that simple! Often you zigzag, and sometimes you backtrack. In our last episode, we made it to the Florida Keys. But before pressing on any further, we had some big projects to take care of — including applying new antifouling paint to...
Fast Sailing Overnight to Key West | Sailing Soulianis – Ep. 50
Sailing Soulianis

Fast Sailing Overnight to Key West | Sailing Soulianis – Ep. 50

The seemingly smallest thing can drastically change the experience of a journey on the sea. Like forgetting to take seasickness meds. Then what a difference a few hours makes — from night to day, from dark ominous waves to calm electric blue sea. Sail with us to Key West! Hope you enjoy! Lauren &am...
110. SPEARFISHING the Florida Keys! | Learning the Lines
Learning the Lines

110. SPEARFISHING the Florida Keys! | Learning the Lines

This one's a little different! We took a 2020 Key West 219 FS out to the reef in Islamorada, Florida to do a little spearfishing last weekend. We're still novices at freediving and spearfishing, but we hope to practice much more in the coming year so that we can be good at obtaining our ow...
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. ...
Sailing Miami Style – S4:E07
Sailing Doodles

Sailing Miami Style – S4:E07

We sail from key west past Miami to Fort Lauderdale on an Alpha 42 Catamaran. We fight strong headwinds ands big seas in the Gulfstream. Buy this boat: email [email protected] charter this boat: This channel is funded by viewers like you. Please help us keep this channel creating great conten...
Drifting Helpless Out To Sea – S4:E06
Sailing Doodles

Drifting Helpless Out To Sea – S4:E06

Our Dinghy motor quit and left us drifting out to sea in a very strong current. 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:
DANGEROUS Shark Fishing! Sailing GBU
Sailing Good, Bad, and Ugly

DANGEROUS Shark Fishing! Sailing GBU

Dangerous shark fishing! catch and release We did a lot of fishing in the Bahamas! --------------------------------------------------------------------- We upload a new video every week! Dont forget to subscribe and share the video --------------------------------------------------------------------...
Sailing & Exploring Key West – S4:E04
Sailing Doodles

Sailing & Exploring Key West – S4:E04

We take a day sail from Key West to nearby reef and the we explore Key West and Duval Street. Buy this boat: email [email protected] charter this boat: This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron Donate Via Paypal ...
Her First Look at the New Catamaran S4:E03
Sailing Doodles

Her First Look at the New Catamaran S4:E03

We sail from Key Largo to Key West and Laura get her first look at the new catamaran we are sailing. 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:
Hit by a Squall! – S4:E02
Sailing Doodles

Hit by a Squall! – S4:E02

We sail to the Florida keys from fort Lauderdale and Miami and get hit by a pretty strong Squall! 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: Check out Guns and Hoses an...
My First Offshore Sailing Passage on Icebear with @59NorthSailing @SailingAWEN
Sailing AWEN

My First Offshore Sailing Passage on Icebear with @59NorthSailing @SailingAWEN

My First Offshore Sailing Passage with 59 North. We sailed 1,300 nautical miles from Key West to Bermuda over eight days. This video summarizes the trip. Photo credits to 59-North for some pictures taken in this video.
SailAway 61 | The Key West LIE No One Wants You to Know! | Sailboat Living Sailing Vlog
SailAway World Sailing

SailAway 61 | The Key West LIE No One Wants You to Know! | Sailboat Living Sailing Vlog

SOUTHERNMOST POINT!? The KEY WEST LIE NO ONE WANTS YOU TO KNOW! ;-) And MORE Key West Hijinks. This week we conclude our little land voyage to beautiful Key West with more beautiful sunsets, even tastier drinks, and TONS of live music. We also expose the COVER UP and CONSPIRACY that has perpetuat...
Dry Tortugas & Key West to New Orleans 🐊, Refit UPDATE!
Jessica and Ryan Adventures

Dry Tortugas & Key West to New Orleans 🐊, Refit UPDATE!

It's been a busy busy few weeks! Let's get you caught up a bit. There's a lot so let's stick to the highlights. :) We started in Key West and did a quick trip to and from the Dry Tortugas which were way cooler than we thought they'd be. People talk them up. Now we know why,...
For Whom the Ship’s Bell Tolls
How to Sail Oceans

For Whom the Ship’s Bell Tolls

So of course a visit to Key West must include a visit to the home of Ernest Hemingway. I also have to check out the famous (or infamous) nightlife on Duval street and I am pleased to find a vibrant live music scene. I purchase a second hand Phantom 3 drone but find out that I cannot fly it in Key...
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...
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...
Diving for treasure in a BUSY marina!
Sailing Good, Bad, and Ugly

Diving for treasure in a BUSY marina!

So much fun making this video. Shout out to jigging with Jordan check out his channel! ---------------------------------------------------------------------------------------------- If you want to show us some love ----------------------------------------------------------------------------------...
A Brief Morning in Key West | Learning the Lines [Casual Friday]
Learning the Lines

A Brief Morning in Key West | Learning the Lines [Casual Friday]

For today's Casual Friday video we're taking you along with us on a quick little trip to Key West. ----------------------------------------------------------------------------------------------------------------------------------------------- Not-A-Broker Consulting: Facebook: Instag...
Shark Fishing BATTLE!
Sailing Good, Bad, and Ugly

Shark Fishing BATTLE!

We did it! We had a lot of fun taking time off from our projects to SHARK FISH! Catch and release he was on his way! ------------------------------------------------------------------------------- We upload a new video every week! ---------------------------------------------------------------------...
Best place to anchor in Key West Fl
Sailing Good, Bad, and Ugly

Best place to anchor in Key West Fl

All you need to know about the Key West anchorage. From experience we let you know what will be right for you from marinas to the mooring field. ---------------------------------------------------------------------------------------------------------- We upload a new video every week! ------------...
VOODOO in KEY WEST!!
Sailing Good, Bad, and Ugly

VOODOO in KEY WEST!!

Key West Florida seems to have a lot of haunting stories surrounding it. We decided to take a deeper look in to the story of Robert the doll. It is said that Robert the doll is the inspiration for the infamous "Chucky" character in Childs Play. --------------------------------------------...
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