Watch Sailing & Boating Adventures Around the World – Page 2 of 3
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Showing 25-48 of 54 results
#84: How to Rig Your Boat for Heavy Weather Sailing
Even after crossing the Atlantic, I still believe some of the worst wind and sea state I have faced has been in the Gulf of Mexico. As Phillip and I prepare to sail across it to Cuba this winter, we want to be ready for whatever the Gulf may dish out. That means heavy weather sail planning in the ...
What’s Happening at HaveWind!
New to Watch this video! Phillip and I have had so much fun watching so many new subscribers and blog followers tumble in over the last few months that we thought it might be a good idea to get you newbies caught up on ALL (and there is a ton!) of fun opportunities, content and giveaways that we ...
Boat #12: 2013 Leopard 48 (Offshore Tour!)
Hey Crew! My first ever offshore boat tour! This was such a spur-of-the-moment, whirl-wind and might I say WINDY fun trip. I got invited last minute to join a yacht delivery crew taking this very nice 2013 Leopard 48 from Pensacola to Naples, FL. It was a fortuitous union of talents, good sailin...
#83: How to Get More Sailing Experience
It's simple: meet sailors, make friends, then offer to crew and bring good booze and snacks! I just returned from crewing on a pretty spur of the moment yacht delivery on a Leopard 48 and I can't wait to share the footage, lessons learned and boat tour with you, but But, the last time I w...![#82: (Halloween Special) How to Throw the Best Party at the Anchorage [PG-13]](https://i.ytimg.com/vi_webp/ZfseHFRkOoA/mqdefault.webp)
#82: (Halloween Special) How to Throw the Best Party at the Anchorage [PG-13]
If there's one thing Phillip and I learned from (surviving) our 2nd Annual Ft. McRee Boozer Cruiser, it's how to throw the best party at the anchorage. You only need four things: Costumes, Drinks, Music and Boat-to-Boat participation. Oh, and "engine wood" (new term we invented...
#81: How to Dock Single-Handed
If docking has ever been a sore spot for you and your significant other or if the inability to dock the boat alone has hindered your cruising, Phillip and I hope this video demonstration can help. Being able to bring a boat in safely single-handed is a crucial skill for any sailor both for ease of ...
Boat #11: 1969 Bill Tripp Custom 60′ Ketch
You can go offshore on this boat! Book at This stunning Bill Tripp custom-designed 60' ketch was built in 1969, originally designed for two people to handle fairly easily, it has since been re-designed, re-engineered, and completely re-fitted over the course of the last two years by Captain ...
#80: How to Find Out if Offshore Voyaging is for You
If the thought of going offshore overnight makes you a little hesitant to go cruising, that is the very reason you should do it. And, thanks to Captain Ryan with I hope I have found the perfect opportunity for you to do it on a phenomenal boat, at a discount and occasionally with Phillip and I on ...
Gift #3: Offshore with Andy Schell
Who wants to go offshore? If you said yes, then get on board with our 3rd Gift of Cruising -- an incredible offshore voyage giveaway with Andy Schell and Mia Karlsson at Here's the deal. Since this is SUCH a big gift, Phillip and I need your help. First, watch the video (particularly Andy&...
#79: How to DIY Inspect, Repair & Replace Rigging
Thank goodness we went with the hi-mods, as we were able to change these out ourselves and get our (newly-stepped) rig back up and going again on our own, without having to call in a rigger. Just some fun tips for you all that we learned while trying to drop a new main halyard, stepping the mast to...
#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!)
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)
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”
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)
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
"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
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)
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 ...
#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!
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
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
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...
#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...