Watch Sailing & Boating Adventures Around the World – Page 2 of 5
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Boat #15: 1939 John Alden Schooner
"When the war is over and if I return," said General Patton. This was his boat! An immaculately-restored 1939 John Alden Schooner, with her very own Captain Seth giving us a tour and telling us his story and plans to sail When and If around the world. They recently sailed When and If to...
#95: Historic Havana: Sail There with Me!
Mojitos at La Bodeguita del Medio, walk historic Cathedral Square, tour Hemingway's house, Finca Viega, dance at the Floradita and see inside the Casa Particular we rented for $40 CUCs/night. We take you all through Havana in this video with some very exciting news at the end. I'm going ...
Patreon Gift of Cruising Winner Updates
Hello crew! Some very exciting video updates for you all here from our previous three Gift of Cruising winners. Winner #1 has bought a boat! And you'll get to the see the make and model and learn why they chose the boat they did. Winner #2 is getting ready for another round of ASA training....
#94: Clearing Customs and Exploring Cuba
Want to know exactly what it feels like to go through the customs process after sailing to Cuba? Come along. We'll walk you through. Show you exactly who boarded and what they wanted to know. We've included a lot of great tips in here for you as well to make the check-in process easy i...
Boat #14: 2005 Hunter 36
What's the first thing we do after we dock our boat at a new location? Walk the marina or cruise around the anchorage and look at all the other boats there. We tour boats to help you all learn more about the different makes, models and features and this is one you have been asking for for a w...
#93: Cuba Voyage Finale: Gulf Stream Crossing and Landfall in CUBA!
The current of the Gulf Stream is no joke, particularly when it is pushing you into head winds. Watch as we reef up and cross a pretty kicked up sea state across the Gulf Stream, sing to our first Cuban sunrise, deal with an issue with the furling gear on our headsail, navigate the entry to Marina ...
#92: Cuba Voyage IV: Rudder on the Loose
Last time we documented power management underway, now we're dealing with a rudder post that won't stay ... put anyway. Follow along as we fix our boat in exotic places (i.e., on the way to Cuba). You'll also hear extensively from Phillip in this episode about preparing for a lightn...
#91: Cuba Voyage III: Power Management Underway
Follow along as we are mesmerized by a jumping pod of dolphins at the bow, monitor the power situation (and show you our cool below-decks inverter), and make our one BIG tack of the trip. We had some great wind that allowed us to hold a pretty steady rhumb line all the way to Cuba. Hope you guys a...
#90: Cuba Voyage II: Heavy Heeling
Get ready for it to blow! These weren't super heavy winds but they were on the nose and had Plaintiff's Rest really heeled over during the second night and day of our voyage to Cuba. Our Niagara 35 proved she was up for the task though, practically sailing herself across the Gulf. Follo...
Atlantic-Crossing Movie
Friends, followers, Merry Christmas and Happy New Year from www.HaveWindWillTravel.com! A real treat for you here, available for the first time to my entire audience: my two-hour movie from our trans-Atlantic. For those of you who are new, Phillip and I had the good fortune to be invited as part o...
#87: How to Voyage Safely Offshore (Season 4 Finale!)
PFDs, tethers, jack lines, life raft, flares, ditch bag ... oh my! We are headed out for Cuba crew, so we wanted to take a moment and share with you all of the really cool safety gear we take with us, some designed to keep us on the boat, others to get us safely off and cool electronics and gadgets...
#86: How to Provision & Prepare Your Boat for Passage
Provisioning for passage. Stowing goods on the boat (according to weight). Power conservation while underway. Watch schedules. Sleep arrangements. You name it. A ton of good, hopefully helpful info for you all while Phillip and I are preparing our boat to shove off for Cuba in just SEVEN days....
Gift #4: Sail with Us to the Miami Boat Show!
Very exciting video for you here guys. Our 4th Gift of Cruising will be a five-day offshore adventure sail from Pensacola to Miami with Phillip and I on s/v Libra to attend the Miami Boat Show, boat show tickets included. Super cool, right? We will depart February 10th and sail to the show. I wi...
Boat #13: 1979 GulfStar 44 (Motor Vessel)
My first motor vessel! I didn't even know Gulfstar made motor yachts, but this one was certainly impressive. Twin Perkins diesels, a generator, water-maker, 500 gallons of fuel, 250 gallons of water and insane amounts of storage. Thank Phil for the tour of his 1979 Gulfstar 44, m/v After Fiv...
#85: How to Take Advantage of the Wind (Go Kite-Surfing!)
Coming straight to you from Isla Mujeres, footage from our very first kite-surfing sessions of 2016! What can I say? With the shipyard work and ocean-crossing, it's been a busy year, but Phillip and I absolutely love kite-surfing and we seize any opportunity we can to get out, pump up our kit...
#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...
#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&...