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.
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Hey, You Can’t Park There! Anchoring Our Sailboat in Annapolis, Maryland |Episode 16
No mooring balls. Tight quarters. And a captain determined to make it fit. 😅 Welcome to Annapolis! After our first three-day crossing from Charleston to Virginia, we’re making our way up the Chesapeake Bay—with plenty of chaos along the way. We explore Fort Monroe, attempt a peaceful sunset dinner ...
We Left Idaho… To Come Home to This
The crew of Big Lost returns to their Vision 444 catamaran in Tahiti, navigating from Phaeton Bay past Marina Taina to Airport Anchorage.
A Perfect Sail to St. Lucia… Until We Reached the Island! E404
After stocking up provisions in Le Marin, Martinique, Alex and Cory sail SV Wildly Intrepid across the Saint Lucia Channel through steep swells to anchor in Rodney Bay and clear customs.
It was a tough passage…but we made it!
Kieran and Leeann Raftery navigate a 100-mile coastal run from the Gold Coast to Yamba aboard SV Awry, managing rolling beam seas, nighttime sail changes, and a falling-tide bar crossing.
We Tore Apart Our Floating Home!
Finding Our Isla tackles an extensive list of catamaran repairs in Grenada, tearing out worn cabin floors, servicing engines, wiring underwater lights, and sewing custom cushions.
Did We Make the Right Choice for Our Kids?
After two years and five months cruising aboard Big Lost, the family returns to Idaho to visit friends, inspect property pheasant pens, and reflect on raising teenagers at sea before returning to French Polynesia.
This simple failure could sink your boat!
Kieran and Leeann depart Brisbane aboard Awry, confronting an emergency bilge leak underway before outrunning an unforecast 30-knot midnight thunderstorm toward Gold Coast.
Exploring Charleston, South Carolina While Living On A Sailboat
Join Sailing Banana Pancakes in Charleston, South Carolina as they anchor in the harbor, visit the aquarium, walk 10 miles through the historic walled city, and tackle boat projects.
The Hardest Part of Living in Paradise
Living in paradise sounds like a dream… until it's time to get your boat ready to actually enjoy it! 😂⛵ After spending the summer back in Idaho, our family is finally back in Grenada and ready to kick off Season 2 aboard our Lagoon 450 catamaran, Isla! But before we can return to the beautifu...
We Visited a ZOO Built Around VOLCANO RUINS! Martinique E402
A ZOO built among the ruins of a devastating volcanic eruption?! Welcome to one of the most unique family adventures we've experienced while sailing the Caribbean! This week, we explore Zoo de Martinique – Habitation Latouche, near Saint-Pierre, a beautiful tropical zoo and botanical garden bu...
Exploring a WW2 Aircraft Carrier | USS Yorktown in Charleston, South Carolina
On our last episode, we left Brunswick, Georgia, with no real plan for where we’d stop. This time, we kept heading north toward Charleston—and boat life had a few surprises waiting for us. A loose water maker hose emptied our tanks into the bilge, leaving us with a lot of water to make and a long o...
Earthquake In Paradise?! | Real Life Aboard Motherload Sailing | EP149 HD 1080P
Aboard Lagoon 410 Motherload in Bocas del Toro, Amy and MJ experience a major island earthquake, assist with boatyard fiberglass repairs, and celebrate Nautis' 7th birthday.
Trapped on our boat for 7 days!
We're leaving the beautiful Whitsunday Islands behind and beginning the long sail south towards Hervey Bay, Queensland! ⛵️ With plenty of miles to cover, overnight sailing with two little kids, and stops at some of our favourite places along the Queensland coast, this leg of our family sailing...
The Simple Life | Living On a Sailboat
We left Cumberland Island for what should have been a quick sail to Brunswick. Instead, our watermaker started acting up, a huge storm rolled in, and the lightning got close enough to make everyone rethink being outside. Once we made it safely to the dock, we reunited with our friends from Waves of...
Are we making a MISTAKE?
After spending our first season sailing the Caribbean as a family, we returned home to Idaho... and suddenly, going back to boat life didn't feel quite as simple as we thought it would. Being home meant family, friends, mountains, camping, birthdays, Yellowstone, and everything we had left beh...
We Swam With Humpback Whales… Then Left Our Boat Behind
The Sailing Big Lost crew goes swimming with humpback whales offshore in Moorea before motoring 46 miles to Phaeton Bay, Tahiti to secure their catamaran for a trip home.
Episode 320 – The Sailing Master Potter!
While recovering from a spinal injury, Bear of the Sailing Pickle Family tackles wheel pottery and cathedral heights as the crew readies SV Pickle for Queensland.
Shipwrecks, Volcano Ruins & a HUGE Family Surprise! | Martinique E401
We’re exploring St. Pierre, Martinique, a Caribbean town with an incredible—and tragic—history. Once known as the “Paris of the Caribbean,” St. Pierre was devastated by the eruption of Mount Pelée in 1902. We wander through the ruins left behind, explore the remains of the old theatre, and visit t...
Storms at Sea | Will We Make it? Episode 11
After making it to St. Augustine, we thought we were ready to move on—but then a sailing family with four boys reached out, and we decided to stay a little longer. The boys hit it off right away, and we got to enjoy a beach day, swimming, football, and an unforgettable night of ’90s music aboard the...
We Didn’t Know If We’d Ever Sail Again
After our first year of sailing the Caribbean as a family, we sailed our Lagoon 450 south to Grenada to haul her out for hurricane season. But as we prepared to leave our floating home behind, we honestly didn’t know if we’d ever come back. Our final sail takes us from Martinique past the incredibl...
Episode 319 – 13 New Things for the Birthday Sailor!
Aboard SV Pickle, Nikki and Chris manage pediatric orthopedic recovery for Bear while refitting systems along Queensland's coast before resuming offshore voyaging.
Dominica Didn’t Let Us Leave Easily… E400
Our time in Dominica comes to a pretty rough ending! We grab a mooring in Roseau and head ashore to explore downtown, only to realize we’ve LOST our cellphone as we head back home. 😩 Not exactly how we planned to spend our last days on one of our favorite Caribbean islands! Back at the boat, thing...
We Found the WILDEST Island in the Caribbean
We thought we knew what Caribbean adventure looked like… then we got to Dominica. This island completely blew us away. We chased waterfalls through the rainforest, swam beneath one of them, explored the famous Indian River, stepped into a filming location from Pirates of the Caribbean, and somehow ...