Watch Sailing & Boating Adventures Around the World – Page 3 of 9

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 49-72 of 194 results
Ep. 196, Dreaming BIG!
Barefoot Sailing Adventures

Ep. 196, Dreaming BIG!

Part 124 of a series: Sailing Tampa Bay to Key West. We tour a 68 foot Lazzara motor Yacht in Boca Grande on Gasparilla Island, Florida.
Ep. 195, ⛵️ What the Doctor Ordered 🏝
Barefoot Sailing Adventures

Ep. 195, ⛵️ What the Doctor Ordered 🏝

Part 123 of a series: Sailing Tampa Bay to Key West. Boca Grande on Gasparilla Island has exceptionally beautiful beaches and clear blue and green water. Swimming and relaxing at the pristine, uncrowded beach, is just what the doctor ordered.
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 cart.
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 open waters.
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 aboard their sailboat.
Ep. 184, Hurricane Destruction🌀Matlacha, Florida (Before and After)
Barefoot Sailing Adventures

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 delicious culinary offerings. Witness the har...
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 expert sailor's tips and tricks to keep your...
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 food and cold drinks. The "shipwreck ...
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 on Patreon! UNCENSORED Content: (open wit...
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! UNCENSORED Content: (open with browser to see full library) Check out the rest of ...
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 sunset. MORE VIDEOS on Patreon! UNCENS...
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 in Punta Gorda, Florida. MORE VIDEOS on ...
Ep. 174, ⛵️ Sailing Topless 🫣
Barefoot Sailing Adventures

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. MORE VIDEOS on Patreon! UNCENSORED Content:...
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, FL has the same owners and is also highlig...
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! UNCENSORED Content: (open with browser to see full library) Chec...
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