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.

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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. 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 night at Old Fish House Marina. Get ready t...
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. 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. Ashley and Mike cross under the highway 41 brid...
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...
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 VIDEOS on Patreon! UNCENSORED Content: (open w...
Ep. 169, Untie the Lines! ⛵️
Barefoot Sailing Adventures

Ep. 169, Untie the Lines! ⛵️

Part 97 of a series: Sailing Tampa Bay to Key West. After launching our shallow draft, trailer sailer (using our truck camper) Ashley and Mike shake down the sail boat in the Charlotte Harbor, Punta Gorda, Florida. A sail boat with a ripped head sail on a mooring ball catches our attention, and we a...
Ep. 168, Put-it-in ⛵️
Barefoot Sailing Adventures

Ep. 168, Put-it-in ⛵️

Part 96 of a series: Sailing Tampa Bay to Key West. Put-in day is exciting! Ashley and Mike launch the trailer sailer into the Charlotte Harbor in Punta Gorda, Florida. The rooftop lounge called Perch 360 at the Wyvern Hotel is also highlighted. MORE VIDEOS on Patreon! UNCENSORED Content: (open wi...
Ep. 167, The Perfect Marriage? (Trailer Sailer and Truck Camper)
Barefoot Sailing Adventures

Ep. 167, The Perfect Marriage? (Trailer Sailer and Truck Camper)

Part 95 of a series: Sailing Tampa Bay to Key West. A trailer sailer pulled by a truck camper might be the ultimate adventure set-up! Ride with Ashley and Mike, traveling the streets of Punta Gorda to Lashley Public Boat Launch. The mast is raised in preparation for more sailing adventures. MORE VID...
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