Watch Sailing & Boating Adventures Around the World tagged “Shallow draft sailboat” – Page 2 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 25-48 of 119 results
Ep.194, ⛵️ Gasparilla Island 🏝 Boca Grande🌀Hurricane Destruction
Barefoot Sailing Adventures
Ep.194, ⛵️ Gasparilla Island 🏝 Boca Grande🌀Hurricane Destruction
Part 122 of a series: Sailing Tampa Bay to Key West. Gasparilla Island and Boca Grande beaches are pristine and beautiful. South Beach Bar and Grill is highlighted before and after Hurricane Ian, Helene, and Milton. Ashley explores Boca Grande on a golf ca...
Ep. 193, ⛵️ Boat Life: On Shore
Barefoot Sailing Adventures
Ep. 193, ⛵️ Boat Life: On Shore
Part 121 of a series: Sailing Tampa Bay to Key West. Docked at Whiddens Marina, Boca Grande FL, Ashley explores the historic, interesting and charming establishment. Walking the beautiful streets of Boca Grande historical district, we rent a golf cart.
Ep. 192, ⛵️ Daily Routine on a Small Sail Boat
Barefoot Sailing Adventures
Ep. 192, ⛵️ Daily Routine on a Small Sail Boat
Part 120 of a series: Sailing Tampa Bay to Key West. Anchored in Boca Grande on Gasparilla Island, Ashley gets ready for the day. Docking at Widdens Marina, we begin to explore Boca Grande.
Ep. 191, ⛵️ Perfect Sailing
Barefoot Sailing Adventures
Ep. 191, ⛵️ Perfect Sailing
Part 119 of a series: Sailing Tampa Bay to Key West. Naturism is an enjoyable, exciting and healthy lifestyle. Combined with sailing, fun is the result. Traveling on our sail boat, we arrive in Boca Grande.
Ep. 190, ⛵️ Naturist Sailing!
Barefoot Sailing Adventures
Ep. 190, ⛵️ Naturist Sailing!
Part 118 of a series: Sailing Tampa Bay to Key West. Sailing in the Charlotte Harbor toward Boca Grande, Ashley removes her clothes to enjoy the naturist lifestyle. Sailing in the nude is an incredible experience!
Ep. 189, ⛵️ Setting Sail!
Barefoot Sailing Adventures
Ep. 189, ⛵️ Setting Sail!
Part 117 of a series: Sailing Tampa Bay to Key West. Leaving Matlacha Florida, Ashley gets topless immediately. Setting sail in the Charlotte Harbor, the wind blows us toward Boca Grande.
Ep. 188, Sailing Adventure Begins! ⛵️
Barefoot Sailing Adventures
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!
Barefoot Sailing Adventures
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!
Barefoot Sailing Adventures
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. 185, Ashley Explores ⛵️ Matlacha, Florida 🏝 Day Trippin’ 🎶
Barefoot Sailing Adventures
Ep. 185, Ashley Explores ⛵️ Matlacha, Florida 🏝 Day Trippin’ 🎶
Join Barefoot Sailing Adventures as they explore the quaint fishing village of Matlacha, Florida, visiting the popular Blue Dog restaurant and discovering hidden gems like the colorful art show of world-renowned artist Love Gro and experiencing a memorable...
Ep. 183, ⛵️ Sailing Into the Path of a HURRICANE  🌀 (Part 2 of 3)
Barefoot Sailing Adventures
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
Barefoot Sailing Adventures
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)
Barefoot Sailing Adventures
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)
Barefoot Sailing Adventures
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!
Barefoot Sailing Adventures
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 🫣
Barefoot Sailing Adventures
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!
Barefoot Sailing Adventures
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!
Barefoot Sailing Adventures
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!
Barefoot Sailing Adventures
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. 173, ⛵️Our First Sail!
Barefoot Sailing Adventures
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. Ash...
Ep. 172, The Nav-A-Gator!
Barefoot Sailing Adventures
Ep. 172, The Nav-A-Gator!
Part 100 of a series: Sailing Tampa Bay to Key West. After visiting the Nav-A-Gator Bar and Grill near Punta Gorda, FL, we return to show you the changes and updates after the historic and devastating flood from Hurricane Ian. The Rum Bucket in Buckingham...
Ep. 171, STUCK ⛵️ Hard Aground 😳
Barefoot Sailing Adventures
Ep. 171, STUCK ⛵️ Hard Aground 😳
Part 99 of a series: Sailing Tampa Bay to Key West. Cruising the Peace River near Punta Gorda FL, our shallow draft, trailer sailer runs aground in alligator infested waters near the Nav-a-gator Bar and Grill. MORE VIDEOS on Patreon! https://www.patreon.co...
Ep. 170, ⛵️The Peace River ✌️
Barefoot Sailing Adventures
Ep. 170, ⛵️The Peace River ✌️
Part 98 of a series: Sailing Tampa Bay to Key West. Traveling from Punta Gorda, FL, the Charlotte Harbor, and up the Peace River, adventure awaits with a beautiful beach. Anchoring close to shore is possible thanks to our shallow draft sail boat. MORE VIDE...
Ep. 160, ⛵️Change of Plans
Barefoot Sailing Adventures
Ep. 160, ⛵️Change of Plans
Part 88 of a series: Sailing Tampa Bay to Key West. Venom from a saltwater catfish barb causes incredible pain. The risk of infection forces a change of plans. We travel to Punta Gorda Florida on our shallow draft trailer sailer in order to be close to med...
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