Watch Sailing & Boating Adventures Around the World – Page 2 of 3

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 25-48 of 69 results
#46: Can You Dig It?
HaveWindWillTravel.com

#46: Can You Dig It?

Mmm-hmmm, we make "hazmat" look good. First real dig into our rotten stringers. You'll be shocked to see how low we can go! Then we suit up solid to start buzzing into the fiberglass. Here we go! And, only $106 to go on our Give the Gift of Cruising campaign. Get on board!
#45: The Tunnel of Doom
HaveWindWillTravel.com

#45: The Tunnel of Doom

Prepping our boat for the fiberglass job took a lot of cleaning, a lot of a plastic and a lot of tape, cut mostly by my teeth! Pretty cool to see her all ready for surgery, though. Lookout rot! Here we come!
#44: Gift #1 – Pam Wall Cruising Consultant Package
HaveWindWillTravel.com

#44: Gift #1 – Pam Wall Cruising Consultant Package

Big news kids! I'm going to give an invaluable gift of cruising to one of my Patrons. If you all help just a little, I can give something very BIG to one of YOU. I believe this is the best way to use my Patreon funds to give back with an exclusive Pam Wall Cruising and Sailing Consultant, &q...
#43: Removing the Shrouds: How Many Lawyers Does it Take?
HaveWindWillTravel.com

#43: Removing the Shrouds: How Many Lawyers Does it Take?

Two apparently! Removing these shrouds required some hefty plumbing wrenches and a few bad lawyers jokes but we finally got them off! Enjoy!
#42: Taking Some Hits at the Yard
HaveWindWillTravel.com

#42: Taking Some Hits at the Yard

It seems the boys at the shipyard like to pick on the DIY'ers. But, we can take a few light hits. We'll probably need their help along the way when it comes time to disassemble and fix all this stuff, so bring it on boys! Many thanks to the www.perdidosailor.com guys for giving us hell.
#41: The Cause of our Rotten Stringers
HaveWindWillTravel.com

#41: The Cause of our Rotten Stringers

Complete rotten stringer repair documented in vlogs at Here, we found out why our stringers rotted. You want to know? Mud clogging the weep hole in our mast step which allowed water to sit constantly in the step and eventually seep down into the stringers because they were not glassed on top. V...
#40: Missing the Mast Already
HaveWindWillTravel.com

#40: Missing the Mast Already

It's sad to see our mast lying lonely on her side at the shipyard. She loves to be standing tall, with lots of folks "hanging around." But I sleep soundly knowing she's got sunny, silky dreams to keep her warm. More sailboat silking at
#39: Pulling the Mast
HaveWindWillTravel.com

#39: Pulling the Mast

Watch us run around like chipmunks in time-lapse mode as we pull the mast. Pretty interesting to see her become completely detached and lifted away. Also, enjoy the Video Breakdown by Yours Truly!
#38: Here Comes the Crane!
HaveWindWillTravel.com

#38: Here Comes the Crane!

Just a few last detachments (just a few, I swear!). This mast pull prep is no effin joke. But all that's left now are the rods holding her up. Here comes the crane!
#37: Here Comes the Boom!
HaveWindWillTravel.com

#37: Here Comes the Boom!

You guys watch closely, because we're counting on you to help us put all of this crap back together. Preparing the boat to pull the mast turned into one heap of a mess, but don't let it get you down! Getting that stringer fixed will get us one step closer to sailing south! Follow along ...
#36: Happy New Years-in-Review!
HaveWindWillTravel.com

#36: Happy New Years-in-Review!

Happy New Years kids! I thought it would be fun to give you guys a photo history montage of our sailing days, back before everything became YouTube history. Enjoy!
#35: Time to Replace the Old (B)rods
HaveWindWillTravel.com

#35: Time to Replace the Old (B)rods

The only really bad thing about rod rigging is that she doesn't show her age, but we knew, at 30+ years, our original rods were getting up there. If we wanted to sail south next season, a re-rig was in high order. Let the debate begin ... rod versus wire.
#34: A Christmas Gift for You!
HaveWindWillTravel.com

#34: A Christmas Gift for You!

Merry Christmas kids! As thanks for your support and encouragement this year ... a FREE eCopy of (the still #1 bestseller) Keys to the Kingdom. Shoot me an email between now an NYE and she's yours! -- [email protected] -- And enjoy this fun outtakes reel over the holiday. Roll that Video...
#33: Havana Daydreaming
HaveWindWillTravel.com

#33: Havana Daydreaming

We've got a TON of projects coming up kids, so I wanted to give you a little glimpse of what it is that motivates us when we're doing all of this scraping, cleaning, sanding and prepping. Plenty of cruising vids at
#32: When Rigging Fails
HaveWindWillTravel.com

#32: When Rigging Fails

Because sometimes it just does, although our takeaway here was: check your chafe points. But, we were surprised to see our mast (even with a rotten base) stood up to some of the heaviest forces she has ever seen. This was, easily, our worst sail ever on the boat.
#31: The Blues Bring Bad News
HaveWindWillTravel.com

#31: The Blues Bring Bad News

A rotten discovery in the bilge brings us the blues during Blue Angles weekend. Find out what tragedy just made our project list a helluva lot longer!
#30: My Last Legal Battle
HaveWindWillTravel.com

#30: My Last Legal Battle

In honor of the Keys to the Kingdom release, I thought I'd share some footage with you of my last legal battle. Clearly, I had a hunger to win. Scarf it up -- then go get my new book! Hard copy: Kindle:
#29: We Got Screwed
HaveWindWillTravel.com

#29: We Got Screwed

We did! This handrail rebed is for the birds! Never again. But it sure is fun to watch us occasionally FAIL. Thank goodness Bottom-Job Brandon (www.perdidosailor.com) was there to rescue (and make fun of) us. Handrail rebed ... take two!
#28: You’re Doing WHAT with the Handrails?
HaveWindWillTravel.com

#28: You’re Doing WHAT with the Handrails?

If we want to get that boat moving south next year, it's time to get to work. It's stupid what one "little leak" can do to your boat. Rebed Take One (because, yes, this is worthy of a three-part saga). Enjoy! Thanks to my Patrons who make it all possible. Get inspired. Get ...
#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 who inspire us: Dani &a...
#26: Where Have You Been?
HaveWindWillTravel.com

#26: Where Have You Been?

Before we tell you where we're going, I thought it might help to know where we've been. In fact, I wrote it all down for you in my first sailing book -- SALT OF A SAILOR (FREE TODAY on Kindle): Happy Thanksgiving followers!
#25: What is Your Story, Annie?
HaveWindWillTravel.com

#25: What is Your Story, Annie?

Time to get real people. I've had a great time making entertaining videos but it seems folks want to know the REAL STORY. Well, this is it. The story of me. Stay tuned for the Keys to the Kingdom book launch at
#24: White Girls Can’t (Yet) Jump
HaveWindWillTravel.com

#24: White Girls Can’t (Yet) Jump

Ever wondered what it feels like to kite-surf? Well, I'll take you along with me, show you a few things I can do and one thing I certainly can't. You ready? Come aboard!
#23: Racing on Hula Girl
HaveWindWillTravel.com

#23: Racing on Hula Girl

Lost Bay Regatta 2015 and we get heeled over with quite a few "puffs" crewing aboard s/v Hula Girl and get challenged to a true hula hoop throw-down. Enjoy!
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