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May 30, 2025
Barefoot Sailing Adventures – Page 3
Ep. 46, Sailors are VIP @ Gilbert’s (Key Largo)
Part 23 of a series: Sailing Miami to Key West. Ashley and I meet the coolest people on the docks of Gilbert's Resort! There's a lot of laughing as everyone gets to know one another. Dinner at the tiki bar is filled with conversation and more laughter. ...
Ep. 48, Catching Fish 🎣 Snook’s Tiki Bar Key Largo
Part 25 of a series: Sailing Miami to Key West. Ashley and I sail to Snook's Tiki Bar, catch fish, meet a fellow Odin owner, fly the drone and party on the docks. Live music fills the air as underwater lights set the stage for laughing and fun. The se...
Ep. 26, World Famous Naturist Beach!
Part 3 of a series: Sailing Miami to Key West. Haulover Naturist Beach in North Miami Beach is known as one of the best nudist beaches in the world! Ashley and I walk from Haulover public boat launch to see it for ourselves and participate. For uncensore...
Ep. 49, Bucket List Sailing Journey Begins!
Part 1 of a series: Sailing Tampa Bay to Key West. A bucket list sailing journey begins by hauling the sailboat to Tampa Bay Florida. Ashley and I recount our successful fishing and bad weather anchoring on our trip back from Key Largo. For uncensored ...
Ep. 50, Little Harbor Resort
Part 2 of a series: Sailing Tampa Bay to Key West. The Resort at Little Harbor in Ruskin, Florida is an ideal place to unwind after a long drive. The multiple restaurant/bars within walking distance provide a festive atmosphere. Sunset at the beach is st...![Ep. 51, Trouble: Raising the Mast ⛵ [Mistakes to Avoid]](https://i.ytimg.com/vi_webp/G34rTLv5rwc/maxresdefault.webp)
Ep. 51, Trouble: Raising the Mast ⛵ [Mistakes to Avoid]
Part 3 of a series: Sailing Tampa Bay to Key West. Ashley and I struggle to raise the mast on our water ballast, trailer sail boat. Several mistakes are highlighted at Simmons public boat launch in Ruskin Florida. For uncensored content:https://vimeo.com...![Ep. 52, Sail Boat Launch and FIRST SAIL! [Tampa Bay] ⛵](https://i.ytimg.com/vi_webp/aIxMSA5r7PE/maxresdefault.webp)
Ep. 52, Sail Boat Launch and FIRST SAIL! [Tampa Bay] ⛵
Part 4 of a series: Sailing Tampa Bay to Key West. Ashley and I launch our trailer sailer at E.G. Simmons State Park public boat launch in Ruskin, Florida USA. After a fuel stop at Little Harbor Marina, we motor out, then set sail for Beer Can Island. For ...
Ep. 53, Sailing to Beer Can Island (Tampa Bay)
Part 5 of a series: Sailing Tampa Bay to Key West. A relaxing sail to BCI Tampa reveals a stunning island oasis with beautiful white sand beaches, towering pine trees and a bar! Actually called Pine Island, Ashley and I learn that it was recently purchas...
Ep. 55, Bikinis and Beer 🌴 BCI Tampa
Part 7 of a series: Sailing Tampa Bay to Key West. Beer Can Island Tampa is a world class party island. The tiki bar is filled with women in thong bikinis celebrating. BCI features it's own beer brewed by Rock Brothers Brewery in Tampa Florida USA. Whi...
Ep. 57, Naturist Island 🏖 (Tampa Bay)
Part 9 of a series: Sailing Tampa Bay to Key West. Passage Key is the most naked island in SW Florida! Ashley participates immediately. Relaxing in the water and exploring the beach, wildlife is everywhere. The song "Naturist Island" by Harper and Foote...
Ep. 58, Clothing Optional Island (FISHING!!!) 🎣
Part 10 of a series: Sailing Tampa Bay to Key West. Our second day at Passage Key, (a famous naturist island) Mike and Ashley catch a Snook! After snorkeling nude, we put clothes on and find that most people were clothed on this particular day. If you li...
Ep. 59, Day Sail ⛵ Gulf of Mexico!!!!
Part 11 of a series: Sailing Tampa Bay to Key West. After anchoring overnight in blustery conditions, Ashley and Mike sail into the Gulf of Mexico for the first time! Dolphin swim close to the boat as we sail south along the west coast of Florida. We ma...
Ep. 60, Meeting Song Writer: Bill Gillenwater!!!
Part 12 of a series: Sailing Tampa Bay to Key West. We arrive at Tarpon Bay in Sarasota Bay to meet Bill Gillenwater, a famous singer/songwriter. We discuss the meaning behind the lyrics as Mikes parents arrive. We get a private performance filled with ...
Ep.61, ⚓Droppin’ Anchors⚓
Part 13 of a series: Sailing Tampa Bay to Key West. Ashley and Mike drop anchor at Jewfish Key sandbar near Longboat Pass after discussing future plans with family. Dolphin and manatee are filmed before speaking with friendly local boaters. Mike catches ...
Ep. 62, ⛵Trailer Sailer=BIG Adventures!!!
Part 26 of a series: Sailing Miami to Key West. Dolphins play near our trailer sailer (Tampa Bay) as we power up and go home to the Carolinas to do lawn care. Next, Ashley and I trailer the boat to Key Largo to continue our sailing journey to Key West! G...
Ep. 64, Sailing YouTubers Meet ⛵(Key Largo)
Part 28 of a series: Sailing Miami to Key West. Minutes after arrival in Key Largo with our trailer sailer, a longtime subscriber, commenter and fellow YouTuber, Sailor Shawn recognized us! A discussion at Snooks Bayside on the boat transitions to Ashley...
Ep. 65, We’re Sailing! The Florida Keys ⛵ (Islamorada)
Part 29 of a series: Sailing Miami to Key West. Ashley is fishing near mangroves in Key Largo. After a bikini change, we set sail for Islamorada! Ashley handles the lines and we ejoying favorable winds and a relaxing sail just behind a storm. MORE VIDEO...
Ep.66, To Islamorada on a Sailboat! ⛵(Florida Keys)
Part 30 of a series: Sailing Miami to Key West. Ashley and I arrive at Lorelei Restaurant in Islamorada on our sailboat just before a rainstorm. The bartender shows us a video of a Crocodile swimming in the marina. We meet with a longtime friend (Josh) w...
Ep. 69, ⛵ Sailing Marathon (Florida Keys) A Warm Welcome 🐬
Part 33 of a series: Sailing Miami to Key West. Ashley and I hoist the sails and enjoy a spirited sail to Marathon in the Florida Keys. A large pod of friendly dolphins greet us as we arrive. MORE VIDEOS! Get behind the scenes! Private message us! https:...
Ep. 70,🐠Fishing Marathon (Florida Keys)🏝
Part 34 of a series: Sailing Miami to Key West. Dolphins welcome us as Ashley and Mike sail to the Keys Fisheries Bar in Marathon and enjoy a seafood lunch. Faro Blanco is the next stop. A golf cart ride to The Tackle Box bait shop Marathon for live shrimp...
Ep. 71, ⛵Sailboat Maintenance (Barefoot Style!) Marathon, Florida Keys
Part 35 of a series: Sailing Miami to Key West. We increase tension our sailboat standing rigging by increasing tension of the head stay. Getting groceries delivered to 33rd Street Public Boat Ramp in Marathon was convenient. A smiley faced sunset leads ...
Ep. 72, MOST Beautiful Island🏝 (Florida) Keys!
Part 36 of a series, Sailing Miami to Key West. Ashley drops anchor at Molasasses Key near the 7 Mile Bridge. The water is clear and sea life abundant. We catch some fish and break a fishing pole. Ashley goes swimming and sharks begin to approach our sai...
Ep. 73, Shark Catch! 🦈 Fishing on a Sailboat ⛵ (Florida Keys)
Part 37 of a series: Sailing Miami to Key West. We catch our first shark! Anchored at Molasses Key, morning brings an issue with the outboard motor. We continue south. Fishing while we travel on the Atlantic Ocean and catch two large barracuda! MORE VID...
Ep. 74, Picnic Island 🏝 (Florida Keys)
Part 38 of a series: Sailing Miami to Key West. Ashley and Mike drop anchor at Picnic Island in the Florida Keys. We catch small sting rays, swim and explore the surroundings. Mike sits on shore feeling accomplished then a storm rolls in. The dive mask ...
Ep. 76, Hidden Spot! Deep in the Florida Keys 🏝 Ramrod Key
Part 40 of a series: Sailing Miami to Key West. After meeting Captain Jack and other locals, we travel the canals of Ramrod Key to the Shell gas station and nearby Tiki Bar. The narrow canals make maneuvering our sailboat challenging. MORE VIDEOS! Get be...
Ep. 77, Sailing to Key West ⛵ the Final Passage!
Part 41 of a series: Sailing Miami to Key West. The final passage to Key West on our water ballast, swing keel, trailer sailboat was a bit rough. After the tiki bar on Ramrod Key and wishing Captain Jack farewell the following day, we make our way to Key W...
Ep. 78, Arriving (Key West) on a Sailboat! ⛵
Part 42 of a series: Sailing Miami to Key West. As we approach Key West, emotions are high! Excitement, joy and the feeling of accomplishment are overwelming. Stock Island Marina is the arrival location. MORE VIDEOS! Get behind the scenes! Private message ...
Ep. 79, Stock Island Marina! (a Warm Welcome)
Part 43 of a series: Sailing Miami to Key West. Stock Island Marina provides a warm welcome to transient boaters. Ashley reflects on the successful journey and Mike begins to cry from joy. We explore the Perry Hotel pool and bar. Get the song! Livin' on ...
Ep. 80, Wet and WILD (Stock Island) Pool Party for Fantasy Fest!
Part 44 of a series: Sailing Miami to Key West. Stock Island Marina is a great place to meet nice people, rent a scooter and have an epic pool party! We visit 3 boat ramps on Stock Island: Key Haven Boat Ramp, Murray Marine and Boyd's Key West Campground....
Ep. 81, Explore Key West! (Fantasy Fest)
Part 45 of a series: Sailing Miami to Key West. After the Hurricane Hole, we visit 11th Street Public Boat Launch, Smathers Beach, City Marina, and the Key West Express. Dante's Pool Bar is filled with naturism and fun. We finally make it to Duval Street w...
Ep. 82, Duval Street (Fantasy Fest) Key West FUN!!!
Part 46 of a series: Sailing Miami to Key West. Ashley arrives on Duval Street and gets body painted! We park at the Hog's Breath Saloon, walk to the Smallest Bar, Capt.Tony's Saloon and Rick's Bar. Irish Kevin performs an Irish song, then we visit Sloppy ...
Ep. 84, Feelin’ Frisky in Key West (Fantasy Fest)
Part 48 of a series: Sailing Miami to Key West. Live music at Schooner Wharf Bar is a tranquil experience during Fantasy Fest. The Green Parrot is fun and everyone was feeling frisky at Willy T's on Duval Street. After some ice cream from Kilwins, Ashley ...
Ep. 85, Goodbye (Fantasy Fest) Key West
Part 49 of a series: Sailing Miami to Key West. Ashley and Mike are parrot heads at Margaritaville on Duval Street Key West. After a relaxing time in the pool at The Perry Hotel, we take the mast down and load our sailboat on it's trailer at Boyd's Campgro...
Ep. 86, Trailer Sailer=The Easiest Way to Go Sailing? ⛵
Part 14 of a series: Sailing Tampa Bay to Key West. Anclote River Park is where we decide to raise the mast on our trailer sailer. After rigging and launching our sailboat , we are recognized by YouTube subscribers! UNCENSORED Content: https://vimeo.com/...
Ep. 87, A Sailing Journey Begins!
Part 15 of a series: Sailing Tampa Bay to Key West. Ashley and Mike untie the lines and enjoy the freedom of the sea! North Anclote Key and sandbar is filled with boaters. UNCENSORED Content: https://vimeo.com/ondemand/barefootuncensored (open with browse...