Watch Sailing & Boating Adventures Around the World – Page 3 of 5

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 49-72 of 116 results
#78: How To Budget (and Brace) for BIG Boat Repairs
HaveWindWillTravel.com

#78: How To Budget (and Brace) for BIG Boat Repairs

Unexpected mast pulls can happen to you! While we've dealt with our fair share of boat projects at it's good to be reminded there will always be more and you need to know "How To" be ready -- both mentally and financially. Have fun watching Annie go up the mast (I lost count h...
Boat #10: 1985 Alberg 37 (Rigged Up for Cruising with Kids!)
HaveWindWillTravel.com

Boat #10: 1985 Alberg 37 (Rigged Up for Cruising with Kids!)

You may know these two sexy sailors: Jeremiah and Brittany from Lazy Gecko Sailing ( Now you're going to get to know their "sexy boat," a beautiful, solid, well-built bluewater boat, a 1985 Alberg 37. Watch as Jeremiah gives you a detailed tour and shows off Brittany's ingeniou...
#77: How to Make Money Remotely (and Keep Your Daydream)
HaveWindWillTravel.com

#77: How to Make Money Remotely (and Keep Your Daydream)

If you feel money is your biggest roadblock to living a life of travel and adventure NOW, this video is for you. I have shared the numerous, creative ways I have found to make money so Phillip and I can cruise (as well as the many mistakes and failures I experienced along the way) and have also col...
OFFICIAL TRAILER: “Trans-At on a Fast Cat”
HaveWindWillTravel.com

OFFICIAL TRAILER: “Trans-At on a Fast Cat”

At that's exactly what we do: Ride the wind and travel! This time, to France! Phillip and I recently completed our first trans-Atlantic passage crewing aboard a 46' catamaran and sailing 4,600 nautical miles across the Atlantic Ocean from Florida to France. It was an incredible adventu...
#76: How to Cross Oceans (My Trans-At Movie Trailer)
HaveWindWillTravel.com

#76: How to Cross Oceans (My Trans-At Movie Trailer)

What do you need to cross an ocean? A level-head, an adventurous spirit and a sense of humor! Exciting news guys! I have completed the complete, 90+ minute movie from mine and Phillip's first trans-Atlantic this past June when we crewed aboard a 46' catamaran from Florida to France. It...
#75: How to Get Your Wife to Go Cruising
HaveWindWillTravel.com

#75: How to Get Your Wife to Go Cruising

"She is NOT a passenger, she is crew!" is one of our main tips at There's no magic secret to getting your wife (husband, boyfriend, girlfriend, significant other) on board with cruising. She just needs to know the realities and infinite rewards of the lifestyle and want those. Sha...
Boat #9: 1985 Niagara 35
HaveWindWillTravel.com

Boat #9: 1985 Niagara 35

That's right. It's s/v Plaintiff's Rest from post re-rig, re-fit and repairs. I will also show you each of the features on our boat that Phillip and I believe make it a great cruising vessel from engine access to battery maintenance to the sump box and more. If any of you out ther...
Countdown to Cuba!  (Announcing Season 4)
HaveWindWillTravel.com

Countdown to Cuba! (Announcing Season 4)

Quick video sharing some of our fun ideas for Season 4 on the Tube! Feel free to chime in. While we prepare to go cruising this winter, we're going to share it all in a series of "How To's" as steps towards cruising. What topics would you like us to cover? And, are you ready ...
2nd Gift of Cruising Winners: Hallie & Joe!
HaveWindWillTravel.com

2nd Gift of Cruising Winners: Hallie & Joe!

We're giving it away at Our second Gift of Cruising, a 6-day bareboat charter course through Lanier Sailing Academy in Pensacola, Florida goes to lucky Patron Hallie Heuser (pronounced "High-zer," as in Anheuser Busch she told me!) and her awesome boyfriend Joe. We've got a ...
#74: Splash Day!  (Say “Bye, Bye Shipyard!”)
HaveWindWillTravel.com

#74: Splash Day! (Say “Bye, Bye Shipyard!”)

We completed our three-month stint at the yard, documented in complete detail at Phillip says "Take that 'Hard Times on the Hard!'" We are out of the yard! Looking back, though, it almost seemed easy. Almost. But it was definitely worth it. After three months in the yard, ...
Get Inspired. Get on Board!
HaveWindWillTravel.com

Get Inspired. Get on Board!

Curious about cruising? Come aboard. At we're creating cruisers, one dreamer at a time by sharing our story through books, blogs and videos, touring boats and giving away "Gifts of Cruising" (currently a 6-day bareboat charter course) to help people just like you who have the dream...
#73: Raising the New Rig — Part 2
HaveWindWillTravel.com

#73: Raising the New Rig — Part 2

Here comes the Hotstepper! And here comes the hi-mods. Watch as we step the mast and install mechanical fittings (hi-mods) on each of the stays and shrouds to complete the final phase of replacing our original 1985 rod rigging with uniform 5/16 stainless steel wire. Now that the stick is back up,...
#72: Raising the New Rig — Part 1
HaveWindWillTravel.com

#72: Raising the New Rig — Part 1

Three months in the yard and we are finally ready to raise the new rig. Watch as we assemble the shrouds and stays, put our first hi-mod mechanical fitting on the forestay and complete all of the leg-work in order to (finally!) step the mast and raise the new wire rig. Curious about cruising? Com...
Gift #2: 6-Day Bareboat Charter Course!
HaveWindWillTravel.com

Gift #2: 6-Day Bareboat Charter Course!

Gift of Cruising Campaign #2 ... LAUNCHED! I'm giving away a 6-day live-aboard Coastal Cruising and Bareboat Charter course through Lanier Sailing Academy ( in Pensacola, FL this October which will (of course!) include a tour of our Niagara 35 post-shipyard and a day sail with Phillip and I ab...
#71: The 847 Other Boat Projects We Did at the Yard
HaveWindWillTravel.com

#71: The 847 Other Boat Projects We Did at the Yard

Three months at the yard documented in detail at They say: "If you're going to haul out, be sure to do this and that and this while you're out of the water." Well, trust me. We did. I have spared you for quite some time but I now think you're ready. I give you .... jus...
Boat #8: 1988 (Slow Boat to the Bahamas!) Island Packet 31
HaveWindWillTravel.com

Boat #8: 1988 (Slow Boat to the Bahamas!) Island Packet 31

Celebrity boat tour here! Our very own fellow sailing author, blogger and podcaster, Linus Wilson's, 1988 Island Packet 31 -- THE slow boat to the Bahamas ( Not only do you get a glimpse of my SlowBoatSailing video podcast interview, but also an in-depth insightful tour of Linus's boat -...
Boat #7: 1997 Norseman 43
HaveWindWillTravel.com

Boat #7: 1997 Norseman 43

Wow. This is an exquisite Catamaran. A comfortable, durable coastal cruiser that looks like and feels like a five-star condo on the water. Thank you Tom and Karen for Sunday Funday drinks and the hospitality. Enjoy the tour! And, if you want to tour another Catamaran, jump on Patreon to check o...
#68: How NOT to Run Steering Cable
HaveWindWillTravel.com

#68: How NOT to Run Steering Cable

Plenty of how NOT-to videos at Another valuable lesson here from Video Annie: "Don't Shoot the Messenger!" I keep telling myself I'm learning how to fix things at sea if they break in the most inopportune way (like back up in the steering column). Great tutorial here on how t...
Boat #6: 1985 Nonsuch (Like It!) 30
HaveWindWillTravel.com

Boat #6: 1985 Nonsuch (Like It!) 30

In honor of my book release THIS WEEK, this is it -- the s/v Tanglefoot from my None Such Like It. The book is out now on and on discount this week only. Go get it for an even more intimate, first-hand feel for this comfortable, trusted coastal cruiser. Thank Mr. While You're Down There for...
#67: How NOT to Re-Bed a Bow Pulpit
HaveWindWillTravel.com

#67: How NOT to Re-Bed a Bow Pulpit

Boat projects galore at I've shared a few "hows" from our stint at the yard, now it's time for a few "how nots." Watch as we re-bed the bow pulpit not once, but twice (because it was so much fun the first time) for your viewing pleasure. Hint, watch the feed of wire...
#66: Re-bed Windows with Butyl and Magic Bolts
HaveWindWillTravel.com

#66: Re-bed Windows with Butyl and Magic Bolts

Plenty of boat magic tricks at Ooooh, says Video Annie. Magic bolts! Watch as we get our window frames blasted and painted and get "real creative" (Brandon term) making custom bolts to fit the stupid binding posts for re-mounting the windows on our 1985 Niagara 35. Thanks, as always, ...
OFFICIAL TRAILER: None Such Like It (Coming out this May!)
HaveWindWillTravel.com

OFFICIAL TRAILER: None Such Like It (Coming out this May!)

First he was in shock, then he was angry. Other times he denied it ever happened. But it was one hell of an entertaining journey helping deliver this Nonsuch and watch as the old gal gave our buddy Mitch (Mr. "While You're Down There" from Salt of a Sailor) plenty of grief. New boo...
Boat #5: 1981 Tartan 37
HaveWindWillTravel.com

Boat #5: 1981 Tartan 37

This is a real treat for you here guys. This is our buddy, Mike (the beekeeper's) boat who was our neighbor at the shipyard, so you get to see some before and after footage from his ongoing restoration of this beautiful Tartan that unfortunately sank at the dock, as well as a mast climb and a ...
#65: Worst Project of the Re-Fit
HaveWindWillTravel.com

#65: Worst Project of the Re-Fit

See all projects of the re-fit at You might have thought it was the new wire rigging, or the bottom job, or the (oh yeah) falling-off keel but you'd be wrong. It was the horrendous job of popping our our windows, scraping away the mess, replacing the crackled lexan, then painting and putting...
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