Trailer sailer YouTube Videos
Showing 16-30 of 151 results

Ep. 188, Sailing Adventure Begins! ⛵️
Part 116 of a series: Sailing Tampa Bay to Key West. Living on our sailboat in Matlacha, Florida, Ashley unties the lines and a sailing adventure begins. The trailerable, shallow draft motor sailer is able to achieve twenty miles per hour on the way to o...
Ep. 187, Old Florida at it’s BEST!
Join us for an incredible journey to Matlacha Island as we explore its breathtaking landscapes, hidden gems, and local culture. Experience the thrill of boating adventures like never before!
Ep. 186, ⛵️ Sailboat Life is Working Out!
Join us on this captivating adventure where Ashley showcases her remarkable physical prowess, highlighting the strong connection between sailing and fitness. Experience the invigorating blend of exercise and exploration that fuels their love for life aboar...
Ep. 184, Hurricane Destruction🌀Matlacha, Florida (Before and After)
In this episode of Barefoot Sailing Adventures, we journey through the picturesque fishing village of Matlacha, Florida before the onslaught of Hurricane Ian. Experience the quaint town's charm as we explore its artsy streets, lively atmosphere, and delici...
Ep. 183, ⛵️ Sailing Into the Path of a HURRICANE 🌀 (Part 2 of 3)
Embark on an adrenaline-pumping journey as the crew from Barefoot Sailing Adventures finds themselves sailing in the path of a sudden storm and navigating through treacherous waters.
Ep. 182, ⛵️ Sailing Into the Path of a HURRICANE🌀Matlacha Florida
Experience an adrenaline-fueled sailing voyage in Episode 182, where Barefoot Sailing Adventures heads straight towards Hurricane Sam along the beautiful coastline of Matlacha, Florida. Explore the stunning marine town while weathering the storm with exper...
Ep. 181, ⛵️ Sailing to Burnt Store Marina (Punta Gorda, FL)
Embark on a captivating sailing journey with Barefoot Sailing Adventures as they explore the beautiful Burnt Store Marina in Punta Gorda, Florida. Experience the thrill of navigating through Charlotte Harbor aboard their versatile Odin 820.
Ep. 180, Ashley Explores: Boat Grave Yard (Part 2)
Join Ashley as they explore a fascinating boat graveyard filled with potential finds. Experience their thrilling journey to find the perfect boat while overcoming natural disasters in this captivating episode.
Ep. 179, ⛵️ Sailing to Shipwreck Marina!
Part 107 of a series: Sailing Tampa Bay to Key West. Sailing to Riviera Bar and Grill in Punta Gorda, Florida, reveals a derelict marina that resembles a boat grave yard. The Riviera Bar and Grill was a welcoming oasis with a comfortable atmosphere, great...
Ep. 178, Naked ⛵️ Sail Boat Race 🫣
Part 106 of a series: Sailing Tampa Bay to Key West. Charlotte Harbor near Punta Gorda, Florida, is a premier bay for sailing. Practicing naturism, Ashley removes her bikini. Another sailboat approaches from behind, passes us then turns around. MORE VIDEOS...
Ep. 177, Setting Sail ⛵️ Southbound!
Part 105 of a series: Sailing Tampa Bay to Key West. Fishermen's Village Marina in Punta Gorda, Florida, is a perfect place to ready the sailboat before setting sail in Charlotte Harbor. MORE VIDEOS on Patreon! https://www.patreon.com/Barefootsailingadvent...
Ep. 176, Ashley Explores-Fisherman’s Village!
Part 104 of a series Sailing Tampa Bay to Key West. Docking in front of a large crowd at Harpoon Harry's in Punta Gorda Florida is very exciting! After a meal, Ashley continues to explore the rest of Fisherman's Village, a perfect place to watch the sunse...
Ep. 175, ⛵️ Sailing + Naturism = FUN!
Part 103 of a series: Sailing Tampa Bay to Key West. Sailing using a spinnaker sail is very exciting and fun! The fun increases when clothing is removed, and naturism is practiced. After sailing on the Charlotte Harbor, we arrive at Fisherman's Village i...
Ep. 174, ⛵️ Sailing Topless 🫣
Part 102 of a series: Sailing Tampa Bay to Key West. We raise the spinnaker sail on our shallow draft, trailer sailer. Traveling on the Charlotte Harbor near Punta Gorda, Florida with light wind and beautiful weather, naturist sailing is what we prefer. ...