Watch Sailing & Boating Adventures Around the World – Page 5 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. 139, ⛵️Gulf of Mexico-Day Sail to Snake Island 🏝
Part 67 of a series: Sailing Tampa Bay to Key West. Venice Inlet is a perfect place to access the Gulf of Mexico for a day sail with our shallow draft trailer sailer. We raise our main and headsail but as the wind diminished. Later we use our colorful spinnaker to move our 2005 Odin 820 gracefully ...
Ep. 138, Sailing to Hidden Places ⛵️ Making New Friends!
Part 66 of a series: Sailing Tampa Bay to Key West. Arrival in Venice Florida with our trailer sailer begins with mooring at Pop's Sunset Grill and Tiki Bar. Exploring further south we have to navigate dangerous waters with cautionary signs that read "local knowledge only". We ignore...
Ep. 137, Actually Sailing the ICW ⛵️
Part 65 of a series: Sailing Tampa Bay to Key West. Sailing in the narrow ICW of southwest Florida can be challenging. Before we set sail, Ashley rides our electric scooter. MORE VIDEOS on Patreon! UNCENSORED Content: (open with browser to see full library) Check out the rest of our apparel option...
Ep. 136,🍍Provision a Sail Boat⛵️
Part 64 of a series: Sailing Tampa Bay to Key West. Provisioning our trailer sailer is made easier and more fun by using a foldable electric scooter. Blackburn Point Park public boat launch in Sarasota County Florida allows boaters to dock for free. This allows Ashley and Mike to Provision at nearby...
Ep. 135, ⛈️ Storms Rage On 😳
Part 63 of a series: Sailing Tampa Bay to Key West. Storms with high winds rain and lightning are always scary on our sailboat. Anchored in Midnight Pass near Sarasota Florida, the storms rage on as we run from midnight pass beach to take shelter on our small sail boat. MORE VIDEOS on Patreon! UNCE...
Ep. 133, STUCK in Midnight Pass 😳
Part 61 of a series: Sailing Tampa Bay to Key West. After a stop at Spanish Point where we see Guy Fieri, a short boat ride to Midnight Pass provides protection from an upcoming storm. Anchored very close to shore, we witness a nearby boater get stuck and remain hard aground. MORE VIDEOS on Patreon...
Ep. 132, “I’m sorry for what I said when we were docking”
Part 60 of a series: Sailing Tampa Bay to Key West. We explore beautiful Midnight Pass Beach. A windy day makes it difficult to dock at near-by Spanish Point Tiki Bar and Grill. After musical entertainment and a great meal, famous TV personality Guy Fieri arrives in a very large fishing vessel and w...
Ep. 131, 🤫 Secret (Hidden) Midnight Pass 🏖
Part 59 of a series: Sailing Tampa Bay to Key West. Fishing from our shallow draft sailboat, we catch a stingray and a catfish. Navigating the very shallow Midnight Pass and anchoring close to shore reveals a beautiful park setting with grassy trails, palm trees and mangrove canopy. A gopher tortois...
Ep. 130 🏖 Welcome to Turtle Beach!
Part 58 of a series: Sailing Tampa Bay to Key West. Ride with us on our trailer sailer as we access Turtle Beach near Sarasota Florida. We dock at the public boat launch and walk to the beach. After seeing the gorgous sights, we anchor nearby and begin to fish. MORE VIDEOS on Patreon! UNCENSORED ...
Ep. 129, ⛵️Secret Spots (Shallow Draft Sailboat ONLY)
Part 57 of a series: Sailing Tampa Bay to Key West! Our shallow draft trailer sailer is perfect for getting into the areas that other sailboats can not go. Cruising the ICW south of Sarasota we visit The Boatyard Seafood Restaurant and Turtles Restaurant. MORE VIDEOS on Patreon! UNCENSORED Conten...
Ep. 127, 🏖 Another Naturist Island 🏝
Part 55 of a series: Sailing Tampa Bay to Key West. Naturism is healthy and freeing lifestyle. We enjoy the physical and mental health benefits and practice naturalism whenever possible. Edwards Island is a perfect place to relax and enjoy. Next we move to a nearby island to explore. MORE VIDEOS o...
Ep. 125, Sailing to the Perfect Island 🏝
Part 53 of a series: Sailing Tampa Bay to Key West. After viewing the mansion homes on Lido Key, we motor our sailboat to South Lido Beach where we raise the sails. A short sail brings us to Siesta Key bridge and on to Edward's Island. MORE VIDEOS on Patreon! UNCENSORED Content: (open with br...
Ep. 124, ⛵ Morning Routine on a Small Sailboat
Part 52 of a series: Sailing Tampa Bay to Key West. The Anchorage between Otter Key and Lido Key is a very peaceful and beautiful place to prepare to set sail! After enjoying the sunshine and inspecting our shallow draft trailer sailer, we learn about Osprey's from a passing kayak tour. MORE V...
Ep. 123, 🏖 The Backside: Lido Key Beach
Part 51 of a series: Sailing Tampa Bay to Key West. The Tiki Bar at Lido Key Beach is a fun spot to eat and grab a drink. We walk the beautiful back side of the beach and when we return, we find that our trailer sailer is still anchored exactly where we left it. After a swim, we find a quiet anch...
Ep. 121, 😱 Problems Arise ⛵ Sailboat Fail
Part 49 of a series: Sailing Tampa Bay to Key West. Problems arise as we attempt to dock our sailboat at O'leary's In Sarasota. The line attached to the swim ladder gets caught in the propeller which bends the ladder and causes other problems. We remove the line from the prop and are able...
Ep. 118, Exciting Sailing!⛵Sarasota Bay
Part 46 of a series: Sailing Tampa Bay to Key West. After leaving Beer Can Island, we travel south to the Sarasota Bay where we unfurl the head sail. The wind picks up and we have an exciting sail all the way to the city of Sarasota! MORE VIDEOS on Patreon! UNCENSORED Content: (open with browser ...
Ep. 117, Extreme Beauty 🏝 Beer Can Island!
Part 45 of a series: Sailing Tampa Bay to Key West. We arrive at Beer Can Island (Greer Island) Longboat Key to find beautiful white sand beaches, a towering pine forest and a gorgeous sunset. With our shallow draft trailer sailer anchored just off the beach, we are the only people there so we take ...
Ep. 116, Cruising to Beer Can Island! (Longboat Pass)
Part 44 of a series: Sailing Tampa Bay to Key West. After lunch at Tidetables Restaurant in Cortez, Ashley catches a fish and we continue cruising our trailer sailer south. We drop anchor at the north end of Longboat Key which the locals call Beer Can Island. MORE VIDEOS on Patreon! UNCENSORED Con...
Ep. 115, Getting Lucky🍀The Fishing Village of Cortez
Part 43 of a series: Sailing Tampa Bay to Key West. We are feeling lucky as we enjoy a beautiful day together catching fish near the quaint fishing village of Cortez. MORE VIDEOS on Patreon! UNCENSORED Content: (open with browser to see full library) Check out the rest of our apparel options here...
Ep. 110, 🏝 Gilligan’s Island! (Tampa Bay)
Part 38 of a series: Sailing Tampa Bay to Key West. Leaving Naturist Island, we anchor at Gilligan's Island (Tampa Bay) and find dolphins jumping out of the water. After Ashley completes her work out on the front of our shallow draft, trailerable sailboat, we motor to nearby Safe Harbor Marina ...
Ep. 109, Naturist Island Return!
Part 37 of a series: Sailing Tampa Bay to Key West. We sail to Naturist Island (Passage Key) and find many people on the Island! MORE VIDEOS on Patreon! UNCENSORED Content: (open with browser to see full library) Check out the rest of our apparel options here: MUSIC
Ep. 108, Sailing to Naturist Island 🏝 (Passage Key)
Part 36 of a series: Sailing Tampa Bay to Key West. We sail to Naturist Island (Passage Key). Anna Maria Island has a more protected harbor, so after a comfortable night there we set sail for Naturist Island again the following day! MORE VIDEOS on Patreon! UNCENSORED Content: (open with browser to...
Ep. 107, Setting Sail ⛵ Naturist Island!
Part 35 of a series: Sailing Tampa Bay to Key West. We finally set sail for Naturist Island after a beach walk on Shell Key Island Preserve! MORE videos on Patreon! UNCENSORED Content: (open with browser to see full library) Check out the rest of our apparel options here: Music by Harper and Foo...