Watch Sailing & Boating Adventures Around the World tagged “Trailer sailer” – Page 3 of 8
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.
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...
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.
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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.
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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.
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Part 94 of a series: Sailing Tampa Bay to Key West. Living in our truck camper in Florida, Ashley and Mike make preparations for the sailing journey to Key West. Explore fun and historic places around Punta Gorda.
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Part 91 of a series: sailing Tampa Bay to Key West. Living in our slide-in truck camper while traveling to our trailerable sailboat, off grid techniques allow freedom of movement. Camping in a parking lot in beautiful Venice Florida, we travel to Punta G...
Part 90 of a series: Sailing Tampa Bay to Key West. Tour our Lance truck camper at beautiful North Jetty Beach near Venice, Florida. We are traveling toward our trailerable sail boat in Punta Gorda so we can continue the sailing journey to Key West! These...
Part 89 of a series: Sailing Tampa Bay to Key West. Traveling on our sailboat, Punta Gorda FL is a lovely place to explore. As the weather continued to be gloomy, we decided to take a break from living on the boat. Welcome, the newest member of the family!...
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...
Part 87 of a series: Sailing Tampa Bay to Key West. A severe puncture by a salt water catfish is a very painful experience. The venom in the barbed and spiked pectoral fin enters Mike's hand and Ashley helps to remove it after much difficulty and discomfor...
Part 86 of a series: Sailing Tampa Bay to Key West. The Gasparilla Sound is an ideal place to go boating! Gasparilla Marina and Smokin' Jerry's Tiki Bar and Grill is perfect for quality food, fuel, supplies, and bait. We make our way to Dog Island Campgrou...
Part 85 of a series: Sailing Tampa Bay to Key West. Anchored in the Gasparilla Sound, we move our shallow draft, trailer sailer to Dog Island near Boca Grande and drop anchor again. Ashley and I discuss topics regarding anchor types and techniques.
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Part 84 of a series: Sailing Tampa Bay to Key West. After deploying a second anchor, we stopped dragging in high winds. Between storms, Ashley gets a chance to shower. Lightning storms rage on throughout the night with high winds and waves.
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Part 83 of a series: Sailing Tampa Bay to Key West. After making it through the Boca Grande Causeway Bridge, we are met with a blustery storm. We drag anchor across the Gasparilla Sound and lose control of our sailboat and have to deploy a secondary anchor...
Part 82 of a series: Sailing Tampa Bay to Key West. Leaving the narrow and shallow entrance of Don Pedro Island State Park, we end up on the docks at Palm Island Resort and Rum Bay Restaurant. After a satisfying meal and refreshing atmosphere, we travel so...
Part 81 of a series: Sailing Tampa Bay to Key West. Don Pedro Island State Park is a very secluded tropical beach setting. Only accessible by boat, there are few beachgoers on this weekday. Our shallow draft trailer sailer is versatile enough to take us to...
Part 80 of a series: Sailing Tampa Bay to Key West. Leaving Stump Pass, Don Pedro Island State Park has a scary, narrow entrance. Navigating with our shallow draft, trailerable sail boat was a challenge, but we made it to the public docks.
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Part 79 of a series: Sailing Tampa Bay to Key West. Anchored at Stump Pass Beach State Park on our trailer sailer, Ashley explores the beach. A short boat ride brings us to Stump Pass Marina and Lighthouse Grill, where we meet our friend and songwriter, B...
Part 78 of a series: Sailing Tampa Bay to Key West. Traveling on our shallow draft trailer sailer, we encounter playful dolphins as we approach The White Elephant Bar and Grill. After an outdoor shower and a restful night sleeping on the boat, Ashley and M...
Part 77 of a series, Sailing Tampa Bay to Key West. The Stump Pass Day Drinkers gave us a very warm welcome! Meeting friendly people on this tropical beach was a pleasure. Lots of smiles, laughing, music, and great times.
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Part 76 of a series: Sailing Tampa Bay to Key West. Stump Pass Beach on Manasota Key is a perfect place to anchor our shallow draft sailboat. Ashley explores the beautiful surroundings, and we begin to meet local boaters. We all reminisce about our time at...
Part 74 of a series: Sailing Tampa Bay to Key West. Leaving the Venice Florida area and heading south towards Stump Pass on our trailer sailer, we encounter several bridges. Challenges occur, but we successfully traverse the narrows of the Intracostal Wat...
Part 73 of a series: Sailing Tampa Bay to Key West. Beautiful Venice Florida is a perfect place to explore by sail boat. Our shallow draft trailer sailer can get close to the gorgeous islands to more easily access them.
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Part 72 of a series: Sailing Tampa Bay to Key West. We are in Love with Venice Florida! After visiting the Nokomis Drum Circle, we travel to our favorite waterfront tiki bar, Nokomos Sunset Hut. A beautiful morning sail boat ride to a tight spot at an isl...
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