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.

Showing 1-24 of 194 results
Ep. 241, ⛵️ Going in Deep!
Barefoot Sailing Adventures

Ep. 241, ⛵️ Going in Deep!

Part 169 of a series: Sailing Tampa Bay to Key West. Canal crusing in Port Charlotte, Florida. Heading to a secret location, we reflect on how much we love our shallow draft, trailer sailer. Although every boat is a compromise, this Odin 820 is extremely versitile.
Ep. 240, ⛵️ Hidden Secret Destination!
Barefoot Sailing Adventures

Ep. 240, ⛵️ Hidden Secret Destination!

Part 168 of a series: Sailing Tampa Bay to Key West. A perfect day for a canal cruise in Port Charlotte, Florida, on our trailer sailer. Cruising to a secret location, we tour a waterfront, sailboat access home for sale.
Ep. 239, Secret Destination! ⛵️ Sailboat Cruising
Barefoot Sailing Adventures

Ep. 239, Secret Destination! ⛵️ Sailboat Cruising

Part 167 of a series: Sailing Tampa Bay to Key West. After Ashley does some fishing, a canal cruise on our shallow draft, trailer sailer, brings us closer to a secret destination.
Ep. 238 ⛵️ Sail Boat Fixing 🛠
Barefoot Sailing Adventures

Ep. 238 ⛵️ Sail Boat Fixing 🛠

Part 166 of a series: Sailing Tampa Bay to Key West. After bending the stainless steel pulpit on the bow of our trailer sailer, Mike and Ashley attempt to fix it. Ashley begins to do some fishing.
Ep. 237, ⛵️ Problems Continue
Barefoot Sailing Adventures

Ep. 237, ⛵️ Problems Continue

Part 165 of a series: Sailing Tampa Bay to Key West. Problems continue as we prepare to repair the bent and broken anchor pulpit. Ashley assists as water in the ballast tank needs to be emptied by powering up this extremely fast sailboat.
20 Feet of Awesome! | Nordica 20 Micro Cruiser | Full Tour
BoatFools Sailing

20 Feet of Awesome! | Nordica 20 Micro Cruiser | Full Tour

#nordica20 #pocketcruiser #microcruiser #trailersailer #boatfoolssailing #sailing 20 Feet of Awesome! | Nordica 20 Micro Cruiser | Full Tour The Nordica 20 is one of the most capable micro cruisers (or "pocket cruisers") ever built—and Canadian Ken and I loved it! Designed by Malta-Mull...
Ep. 236, ⛵️ Trouble in Paradise
Barefoot Sailing Adventures

Ep. 236, ⛵️ Trouble in Paradise

Part 164 of a series: Sailing Tampa Bay to Key West. While attempting to retrieve the anchor, a major problem occurs. The bow pulpit on our sail boat completely bends and is destroyed.
Ep. 235, ⛵️ Living on a Sail Boat is FUN!
Barefoot Sailing Adventures

Ep. 235, ⛵️ Living on a Sail Boat is FUN!

Part 163 of a series: Sailing Tampa Bay to Key West. We are having fun living on our sail boat, even if we have to take cold showers. Anchored at Port Charlotte Beach Park, Ashley prepares to sail to the next location.
Ep. 234, ⛵️ Developing Our Skills
Barefoot Sailing Adventures

Ep. 234, ⛵️ Developing Our Skills

Part 162 of a series: Sailing Tampa Bay to Key West. Ashley explores Port Charlotte Beach Park. Hurricane destruction and reconstruction is highlighted.
Should We Rescue This Free Sailboat??
Practical Sailor

Should We Rescue This Free Sailboat??

Should We Rescue This Free Sailboat? A friend is giving away an old sailboat for free, and now we have to answer the dangerous question every sailor secretly loves: is this a cheap sailing adventure waiting to happen, or is a “free boat” just the most expensive kind of boat? In this Practical Sailo...
Ep. 233, ⛵️ The Power of a Hurricane
Barefoot Sailing Adventures

Ep. 233, ⛵️ The Power of a Hurricane

Part 161 of a series: Sailing Tampa Bay to Key West. Ashley explores Port Charlotte Beach Park. Hurricanes Helene and Milton devastated this beautiful place, but is currently rebuilding. Before and after the destruction is highlighted.
26 Feet, 2 Cabins & Only $5,400! | 1977 Parker Dawson 26 Pocket Cruiser | Full Tour
BoatFools Sailing

26 Feet, 2 Cabins & Only $5,400! | 1977 Parker Dawson 26 Pocket Cruiser | Full Tour

#boatfoolssailing #pocketcruiser #Budgetboat #sailboat #trailerablesailboat #boattour 26 Feet, 2 Cabins & Only $5,400?! | 1977 Parker Dawson 26 Pocket Cruiser | Full Tour As of 05/15/2026: SOLD ***Quick note: technically this boat has a swing keel, which is 1,100 lbs, and locks in the down ...
Ep.  232, ⛵️ Hurricane Season Ahead!
Barefoot Sailing Adventures

Ep. 232, ⛵️ Hurricane Season Ahead!

Part 160 of a series: Sailing Tampa Bay to Key West. Ashley explores Port Charlotte Beach Park. Hurricane destruction of the fishing pier and surrounding area is shown.
Ep. 231, ⛵️ Peaceful Easy Feeling
Barefoot Sailing Adventures

Ep. 231, ⛵️ Peaceful Easy Feeling

Part 159 of a series: Sailing Tampa Bay to Key West. Anchored in a peaceful place, Ashley prepares to explore Port Charlotte Beach Park.
Ep. 230, ⛵️ Alligator Bay Hammock Hang
Barefoot Sailing Adventures

Ep. 230, ⛵️ Alligator Bay Hammock Hang

Part 158 of a series: Sailing Tampa Bay to Key West. Anchored at Port Charlotte Beach park, Ashley explores and we hang a hammock in palm trees at the beach.
Ep. 229, ⛵️ Beach Machine!
Barefoot Sailing Adventures

Ep. 229, ⛵️ Beach Machine!

Part 157 of a series: Sailing Tampa Bay to Key West. This unique, rare sailboat allows us to access the most beautiful beaches in our travels. A 2005 Odin 820; German design, built in Poland. Shallow draft, swing keel, water ballast, trailer sailer. A 2013 Evinrude E-Tec 115 horsepower; lightweight ...
Ep. 228, ⛵️ Safe Harbor
Barefoot Sailing Adventures

Ep. 228, ⛵️ Safe Harbor

Part 156 of a series: Sailing Tampa Bay to Key West. After running from a storm, we find a safe harbor in Alligator Bay at Port Charlotte Beach Park. Anchoring dangerously close to the beach is achieved because our trailerable motor sailer, has a very shallow draft.
Ep. 227, ⛵️  Running into a Storm
Barefoot Sailing Adventures

Ep. 227, ⛵️ Running into a Storm

Part 155 of a series: Sailing Tampa Bay to Key West. Sailing into a storm in the Charlotte Harbor, the sails are reefed. The decision is made to lower the sails completely, raise the swing keel and rudders, then motor to our intended port while allowing the ballast water to escape.
Ep. 226, ⛵️ Sailing to a Secret Location 👀
Barefoot Sailing Adventures

Ep. 226, ⛵️ Sailing to a Secret Location 👀

Part 154 of a series: Sailing Tampa Bay to Key West. Stormy weather approaches while sailing Charlotte Harbor in south west Florida. Sailing to a secret location, the wind increases and the main sail is reefed.
Ep. 225, ⛵️ (Dangerous Mistakes) Sailing: Secret Location
Barefoot Sailing Adventures

Ep. 225, ⛵️ (Dangerous Mistakes) Sailing: Secret Location

Part 153 of a series: Sailing Tampa Bay to Key West. Sailing Charlotte Harbor, toward a secret location, mistakes are made. An accidental jibe, along with not filling the ballast tank are two missteps highlighted. We reminisce about our successful sailing journey from Miami to Key West.
Ep. 224, ⛵️ Begin Sailing! (with beginners)
Barefoot Sailing Adventures

Ep. 224, ⛵️ Begin Sailing! (with beginners)

Part 152 of a series: Sailing Tampa Bay to Key West. Ride with us as we begin sailing in Charlotte Harbor near Pine Island. Watch Ashley at the helm as Mike raises the sails on route to a secret location.
Ep. 223, ⛵️ Preparing to Sail-Secret Location
Barefoot Sailing Adventures

Ep. 223, ⛵️ Preparing to Sail-Secret Location

Part 151 of a series: Sailing Tampa Bay to Key West. Anchored in Jug Creek, Pine Island, Florida, Ashley catches a spotted sea trout. We replace the furling line and prepare to sail our 2005 Odin 820: A German design, built in Poland, shallow draft, trailerable sailboat, to a secret location.
Ep. 222, ⛵️ Floating 🎣 Fishing
Barefoot Sailing Adventures

Ep. 222, ⛵️ Floating 🎣 Fishing

Part 150 of a series: Sailing Tampa Bay to Key West. Floating in Jug Creek, Pine Island, Florida, Ashley catches two catfish. We reminisce YouTube episode 159, where Mike's hand is punctured with a catfish barb.
Ep. 221, ⛵️ The Beginning
Barefoot Sailing Adventures

Ep. 221, ⛵️ The Beginning

Part 149 of a series: Sailing Tampa Bay to Key West. Anchored at Cayo Costa, Ashley walks the beach in search of wild life. After returning to the boat, Ashley pulls anchor and we cruise to Jug Creek to begin fishing.
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