Watch Sailing & Boating Adventures Around the World
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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Victory 21 Regatta Nationals | Sailing Avocet
On the heels of the High Sierra Regatta, Chris and I geared up to race Geronimo two more times in our fleets national championship regatta on Huntington Lake. This regatta brought Victory 21's from San Diego's Mission Bay Yacht Club to our local Fresno Yacht Club - even Chris's big br...
Fresno Yacht Club’s High Sierra Regatta | Sailing Avocet
From Puerto Peñasco to our stomping grounds at 7000 feet, we didn't skip a beat with sailing and were stoked to get back and sail our Victory 21 in the 70th Annual High Sierra Regatta at Huntington Lake! This two-day regatta was packed with wind, competition, and fun with our Fresno Yacht Club ...
Is This the Ultimate Pocket Trimaran? | Dragonfly 25-2
Practical Sailor Article on high tech line clutches: Looking for speed, style, and serious fun on the water? In this video, we dive into the Dragonfly 25-2 sailboat—a trailerable trimaran that blends cutting-edge design, exhilarating performance, and surprising comfort in one sleek, foldable packa...
Ep. 173, ⛵️Our First Sail!
Part 101 of a series: Sailing Tampa Bay to Key West. We cast off to set our sails after final preparations at Lashley Public Boat Launch in Punta Gorda Florida. This is our first sail since putting our shallow draft trailer sailer back in the water. Ashley and Mike cross under the highway 41 brid...
Ep. 147, ⛵️Welcome to Stump Pass 🏝
Part 75 of a series: Sailing Tampa Bay to Key West. Stump Pass near Englewood Florida is a beautiful place to spend time on our trailer sailer. Ashley catches a fish, and we travel to Stump Pass Beach Park on Manasota Key. MORE VIDEOS on Patreon! UNCENSORED Content: (open with browser to see full ...
Ep 3 Sailing Through Sharky Storms pt 1
Hey all, here is the story of how the sailing journey began - with the sailboat Sharky. We sail it around the bay area and talk about some of the obstacles we had to overcome to make it all happen. Stay tuned for part 2 very soon!
Fixing our Race Boat for the High Sierra Regatta
Boat projects and sailing in the SAME video? Wild. We know! Join us as we head back to the Ventura Harbor Boatyard for another round of projects, this time on our race boat, a Victory 21' previously known as "Christopher." Eight days and a lot of sanding later we had a stronger and fr...
Salt & Tar: Ep.127- New Captain on the Block
Allegra 24 named Freyja. Our buddy's first sailboat. She needs some love and has two major problems; the motor and her companionway leaks. We help Hoffa with one of the two issues. First, though, we had to get all the previous owners' old stuff out and clean. Then, we install an outboard m...
Ep. 94, Sailing to a Tropical Island 🏝 Beach! (Caladesi Island)
Part 22 of a series: Sailing Tampa Bay to Key West. After sailing in the Gulf of Mexico, we drop anchor at a tropical island beach! Caladesi Island State Park is large, secluded and beautiful with white sand, Palm trees and clear water. MORE videos on Patreon! UNCENSORED Content: (open with browse...
Ep. 86, Trailer Sailer=The Easiest Way to Go Sailing? ⛵
Part 14 of a series: Sailing Tampa Bay to Key West. Anclote River Park is where we decide to raise the mast on our trailer sailer. After rigging and launching our sailboat , we are recognized by YouTube subscribers! UNCENSORED Content: (open with browser, not Vimeo app) MORE VIDEOS! Get behind th...
Ep. 85, Goodbye (Fantasy Fest) Key West
Part 49 of a series: Sailing Miami to Key West. Ashley and Mike are parrot heads at Margaritaville on Duval Street Key West. After a relaxing time in the pool at The Perry Hotel, we take the mast down and load our sailboat on it's trailer at Boyd's Campground on Stock Island. This marks th...
Ep. 78, Arriving (Key West) on a Sailboat! ⛵
Part 42 of a series: Sailing Miami to Key West. As we approach Key West, emotions are high! Excitement, joy and the feeling of accomplishment are overwelming. Stock Island Marina is the arrival location. MORE VIDEOS! Get behind the scenes! Private message us! UNCENSORED Content: Check out this Bil...
Ep. 77, Sailing to Key West ⛵ the Final Passage!
Part 41 of a series: Sailing Miami to Key West. The final passage to Key West on our water ballast, swing keel, trailer sailboat was a bit rough. After the tiki bar on Ramrod Key and wishing Captain Jack farewell the following day, we make our way to Key West! MORE VIDEOS! Get behind the scenes! Pri...
Ep. 74, Picnic Island 🏝 (Florida Keys)
Part 38 of a series: Sailing Miami to Key West. Ashley and Mike drop anchor at Picnic Island in the Florida Keys. We catch small sting rays, swim and explore the surroundings. Mike sits on shore feeling accomplished then a storm rolls in. The dive mask with ear protection Continue shopping on Am...
Ep. 73, Shark Catch! 🦈 Fishing on a Sailboat ⛵ (Florida Keys)
Part 37 of a series: Sailing Miami to Key West. We catch our first shark! Anchored at Molasses Key, morning brings an issue with the outboard motor. We continue south. Fishing while we travel on the Atlantic Ocean and catch two large barracuda! MORE VIDEOS! Get behind the scenes! Private message ...
Ep. 69, ⛵ Sailing Marathon (Florida Keys) A Warm Welcome 🐬
Part 33 of a series: Sailing Miami to Key West. Ashley and I hoist the sails and enjoy a spirited sail to Marathon in the Florida Keys. A large pod of friendly dolphins greet us as we arrive. MORE VIDEOS! Get behind the scenes! Private message us! Barefoot UNCENSORED: Get the song "Winter D...
Ep. 62, ⛵Trailer Sailer=BIG Adventures!!!
Part 26 of a series: Sailing Miami to Key West. Dolphins play near our trailer sailer (Tampa Bay) as we power up and go home to the Carolinas to do lawn care. Next, Ashley and I trailer the boat to Key Largo to continue our sailing journey to Key West! Get behind the scenes on Patreon! UNCENSORED...![Ep. 51, Trouble: Raising the Mast ⛵ [Mistakes to Avoid]](https://i.ytimg.com/vi_webp/G34rTLv5rwc/mqdefault.webp)
Ep. 51, Trouble: Raising the Mast ⛵ [Mistakes to Avoid]
Part 3 of a series: Sailing Tampa Bay to Key West. Ashley and I struggle to raise the mast on our water ballast, trailer sail boat. Several mistakes are highlighted at Simmons public boat launch in Ruskin Florida. For uncensored content: Check out this Bill Gillenwater song on Amazon Continue to...![Ep. 30 [Actually] Sailing the ICW (Miami)](https://i.ytimg.com/vi_webp/etVJ0C-ktCk/mqdefault.webp)
Ep. 30 [Actually] Sailing the ICW (Miami)
Part 7 of a series: Sailing Miami to Key West. We pull anchor and set sail! Light winds make it a challenge, but we sail under a bridge with little room for error! The Intracoastal Waterway in Miami is busy with huge yachts. We discover a convenient way for boats cruising through Miami to get gr...
Ep. 27, Sailboat Launch and 1st SAIL!!! (Miami)
Part 4 of a series: Sailing Miami to Key West. We launch the Sail Boat at Haulover Beach Florida. After pulling away from the dock, we set the sails and head south. Ashley and I reflect on what a productive year 2018 was. After our shake down sail, we drop anchor at a beautiful island beach (Me...