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.
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...
Sometimes the best cruising stops are the ones you never planned! ⛵🌴
We sail out of Portsmouth, Dominica, hoping to make a quick hop around the coast and drop anchor just around the corner. But our anchoring plans don’t exactly go as expected…
That little failure leads us to Coulibistrie, an unexp...
We set out to explore Dominica’s famous Indian River… but somehow managed to lose the trail!
What followed turned into one of those adventures that makes Dominica so incredible. We wandered through thick jungle, crossed the river and found ourselves surrounded by huge twisted roots that looked str...
We say goodbye to Guadeloupe and set sail for Dominica, but it definitely isn't the smooth Caribbean sail we were hoping for!
The day starts with a bad feeling in my gut before we head out into a rough, lumpy sea for the crossing to Dominica. 🌧️⛵ It isn't our most comfortable passage, but...
Sailing Guadeloupe with the family ⛵ Another beautiful stretch of Caribbean cruising!
We start out anchored in Malendure, where it’s time to tackle one of the less glamorous parts of boat life — the grocery run! With the boat stocked up, we jump into the clear Caribbean water for another incredible...
Our 4-year-old Coral is taking her underwater adventures to a whole new level! 🤿🌊
We explore the incredible Réserve Cousteau in Guadeloupe, where the water is crystal clear, the reef is full of life, and Coral starts diving below the surface all on her own. Watching her confidence grow underwater a...
One last adventure at Grande Anse, one of the most beautiful beaches we’ve found in Guadeloupe before making the short hop to Deshaies. There we enjoy some delicious local treats and cool off with a swim in the river. Then it’s time to keep sailing south along the coast of Guadeloupe. The condition...
Anse Leroux, Guadeloupe is perfect, with crystal-clear water, a close by beach and fantastic snorkeling just a short ride from the boat.
From there, we take a long dinghy ride to the colorful village of Deshaies, where we wander the charming streets and discover an amazing local bakery serving deli...
Leaving Saba was one of the hardest departures yet. It quickly became one of our favorite islands in the Caribbean, but the weather had other plans. With stronger winds on the way, it was time to keep heading south.
Our original plan was to spend a few days exploring St. Kitts and Nevis, but the an...
Saba completely stole our hearts, and saying goodbye wasn't easy. 🌋❤️ Before setting sail, we squeezed every last adventure out of what has become our favorite island in the Caribbean.
Our final day starts with one last spectacular hike from The Bottom to Windwardside via the beautiful Crispee...
Saba completely blew us away. 🤯
After waiting for the perfect weather window, we finally sailed to one of the least-visited islands in the Caribbean—and it instantly became one of our favorites.
Towering straight out of the sea, Saba looks more like something from Jurassic World than the Caribbean...
After finally finding the perfect weather window, we arrive in spectacular Saba and check in by sailboat to one of the most unique islands in the Caribbean.
Our adventure begins with a ride along the legendary "Road That Couldn't Be Built"—an engineering marvel carved into impossibly...
After a much longer stay in Saint Martin than we ever planned, the day has finally arrived—we're setting sail for Saba! 🌊⛵️
Known as the Island in the Clouds, Saba rises dramatically from the sea as a towering volcanic peak, creating one of the most breathtaking landscapes in the Caribbean. We...
Life in Saint Martin is looking much brighter this week! 🌴⛵ After a rough stretch of boat problems and setbacks, we're finally enjoying island life again.
Coral is having the time of her life jumping off the sailboat into the crystal-clear Caribbean waters, and we experience the vibrant atmosp...
People often see the beautiful beaches, sunsets, and tropical anchorages... but this is the side of cruising life nobody talks about.
What started as a simple solar panel upgrade quickly turned into the worst week we've had in a long time.
⚠️ Kai falls and splits his forehead open
⚠️ Everyone...
If you're visiting Saint Martin / Sint Maarten, these are experiences you won't want to miss!
We hop on a local bus to the Dutch side and head to the world-famous Maho Beach, where massive jets fly just overhead before landing at Princess Juliana Airport. Seeing these giant planes pass on...
After exploring beautiful St. John in the US Virgin Islands, it's time to check out of Cruz Bay and set sail for a long overnight passage to the island of Saint Martin!
The crossing keeps us busy as the fishing lines come alive and we land multiple tuna along the way. After arriving in Marigot...
This week aboard SV Wildly Intrepid we continue exploring the stunning island of Saint John!
We sail from beautiful Waterlemon Bay to the world famous Trunk Bay with its crystal clear turquoise water and perfect white sand beach. A tropical rain shower clears the crowds and leaves us almost alone i...
This week aboard SV Wildly Intrepid we explore what might be the most beautiful island we’ve visited all season… 🌴🇻🇮
Sailing the US Virgin Islands with our buddy boat, we explore St John Island and hike the incredible trail from Francis Bay while discovering the crystal clear waters of Francis Bay ...
🌴 Island hopping through the USVI brought us from the busy streets of Charlotte Amalie on St. Thomas to the wild beauty of St. John… and what an adventure it turned into.
We wandered the steep chaotic roads of Charlotte Amalie (definitely not the most pedestrian-friendly place 😅), got rescued with ...
Our sail from Puerto Rico to the US Virgin Islands started off absolutely perfect… warm winds, beautiful seas, and another unforgettable Caribbean passage aboard SV Wildly Intrepid. But once we arrived in St. Thomas, things got interesting fast.
We explored the abandoned tunnels of Fort Segarra on ...
What started as a simple sail turned into a full-on emergency…
As we left Vieques, a hose clamp suddenly snapped—dumping all our engine coolant in seconds. With no engine and two little ones onboard, we had no choice but to drop anchor fast and figure things out.
From there, we sail on to Culebra—...
Not every stop is planned… and sometimes those are the best ones.
We dropped anchor in Puerto Patillas, Puerto Rico and were blown away. A peaceful anchorage, a waterfront park with a playground (perfect for homeschooling days), live music, and even iguanas roaming around—it quickly became one of t...
Not every sailing day goes to plan… and this one REALLY didn’t 😅
We kick things off with a beautiful, calm sail past Cabo Rojo Lighthouse—one of the most stunning coastlines in Puerto Rico. But from there… things start to unravel.
We anchor in La Parguera hoping to experience the famous biolumines...
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