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 1-15 of 15 results
Ep. 101, Shell Key Beach 🏖 Sandbar!
Part 29 of a series: Sailing Tampa Bay to Key West. Anchored at the North end of Shell Key at the Pass A Grille Channel sandbar, we are recognized by YouTube subscribers! After a walk on the beach, we move to the Tiera Verde Marina and then on to Bunces Pass to catch some fish! MORE videos on Patreo...
Ep. 100, The Joy Of Sailing ⛵
Part 28 of a series: Sailing Tampa Bay to Key West. Leaving Archie's Island and traveling through John's Pass, we set sail on the Gulf of Mexico! The weather is perfect for rookie sailors like ourselves and we truely experience the joy of sailing. After flying our spinnaker we switch to...
Ep. 95, Caladesi Island 🏝 The Best Beach in Florida?
Part 23 of a series: Sailing Tampa Bay to Key West. Caladesi Island (State Park) near Clearwater Beach Florida is the best tropical island beach we've found in Florida (in our opinion, so far). The water is filled with Snook. Ashley and Mike string up a hammock and a Park Ranger explains that ...
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: (open with browser, not Vimeo app) MORE VIDEOS! Get behind th...
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 West! MORE VIDEOS! Get behind the scenes! Pri...
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 make our way to Sarasota Bay and meet with Bil...![Ep. 52, Sail Boat Launch and FIRST SAIL! [Tampa Bay] ⛵](https://i.ytimg.com/vi_webp/aIxMSA5r7PE/mqdefault.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 uncensored content: Check out this Bill Gil...![Ep. 43, Cruising [Elliott Key] 🎶 Clear Green Water](https://i.ytimg.com/vi_webp/23kCmbDV354/mqdefault.webp)
Ep. 43, Cruising [Elliott Key] 🎶 Clear Green Water
Part 20 of a Series: Sailing Miami to Key West. We capture a drone crash after fighting a large fish! Ashley and I show the beauty of Elliott Key on land, in the air and on the crystal clear green water. For uncensored content: Check out this Bill Gillenwater song on Amazon Continue to shop on A...![Ep. 40, Sailing [Red, Right, Returning?]](https://i.ytimg.com/vi_webp/iCVfGTRyuFA/mqdefault.webp)
Ep. 40, Sailing [Red, Right, Returning?]
Part 17 of a series: Sailing Miami to Key West. Navigating into the Hawk Channel outside Boca Chita Key and Elliot Key, Ashley and I discuss navigational buoys while she soaks up the sun. Nudity on our sail boat is common as we are naturists and this is a lifestyle documentary. Thank you for you...
Ep. 38, Day Sail 2 – Biscayne Bay = Premier Sailing ⛵
Part 15 of a series: Sailing Miami to Key West. We sail through Stiltsville using our spinnaker. Anticipation builds as we continue to fish while we sail. The wind begins to build, so I take down the spinnaker single handed. Ashley unfurls the head sail (genoa) and the boat heals as we pick up s...
Ep. 35, Sailing to Key Biscayne (No-Name Harbor)
Part 12 of a series: Sailing Miami to Key West. We Sail in open water for the FIRST time! The wind is strong enough on Biscayne Bay to reef the main sail. Ashley and I reflect on our decision to reef and footage from that epic sail is fast forwarded. We arrive at No Name Harbor and are disappoint...
Ep. 34, Best Sailing of our Lives! (So Far)
Part 11 of a series: Sailing Miami to Key West. We sail past Tequesta Point Miami and sail under the William Powell bridge! Overcome with joy and excitement, I realize this is the best sailing day of our lives! Previously unreleased drone footage and a future plan is revealed at the end of the vi...![Ep. 30 [Actually] Sailing the ICW (Miami)](https://i.ytimg.com/vi_webp/etVJ0C-ktCk/mqdefault.webp)
Ep. 30 [Actually] Sailing the ICW (Miami)
Part 7 of a series: Sailing Miami to Key West. We pull anchor and set sail! Light winds make it a challenge, but we sail under a bridge with little room for error! The Intracoastal Waterway in Miami is busy with huge yachts. We discover a convenient way for boats cruising through Miami to get gr...
Ep. 23, Outdoor Shower on a Sailboat!
Sailing on a gusty day. We reef the sails and still enjoy good boat speed. The weather is hot, so Ashley decides to use our new outdoor shower to cool off. We now have a drone and show some footage over Lake Wylie. Looking forward to the beautiful footage it will provide in Florida! Help support ...