Watch Sailing & Boating Adventures Around the World – Page 4 of 38
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Leaving Bora Bora Was Hard… But This Made It Worth It
After four unforgettable nights in Bora Bora, it was finally time to set sail. Saying goodbye to one of the most beautiful places on earth is never easy, but the adventure wasn’t over yet. We enjoyed some great sailing at first, until the wind came right on the nose and reminded us that this is stil...
Sailing Bora Bora: Sharks, Coral Reefs & a Perfect Downwind Run
We sail to the west side of Bora Bora and pick up a mooring in one of the most beautiful spots in the lagoon, surrounded by shallow coral heads and crystal-clear water. After dropping the hook, we jump in the dinghy and head out to the reef where we snorkel with dozens of blacktip reef sharks — swim...
Sailing Bora Bora + Meet Chloe | Paradise at Sea
We sail from one of the most beautiful bays we have ever spent the night in on the southeast side of Bora Bora and make our way around the island through the crystal-clear lagoon. Along the way we stop at the town dock to fill up on fresh water before grabbing a mooring right in front of the iconic ...
This Might Be the Most Beautiful Sail on Earth (Bora Bora)
We leave the Bora Bora Yacht Club and sail around the island to the far side of Bora Bora—and it turns into one of the most breathtaking sails I’ve ever experienced. Unreal turquoise water, perfect conditions, and an anchorage that honestly might be the most beautiful I’ve ever dropped the hook in. ...
Sailing to Bora Bora: Dolphins, Crystal Waters & Paradise
We set sail from Raiatea in French Polynesia and make the unforgettable journey to the legendary island of Bora Bora. With crystal-clear water, dramatic mountain peaks, and scenery that feels unreal, this is a place most people only dream of visiting. After arriving, we rent a scooter and explore th...
Life Aboard Mid-Atlantic Before the Seas Turn Rough – Day 6
Six days into our Atlantic crossing, the ocean is finally starting to show its teeth. The crew is back together—Brett, Ayanna, Jade, Dingo, and Penny—and we’re settling into the long middle stretch of life at sea. Days blur together with watches, editing, cooking, small routines, and the constant m...
Sailing French Polynesia: New Crew, New Boat, New Paradise
After a 15-hour flight halfway around the world, I finally arrive in French Polynesia — and it was worth every second. I charter a 40-foot Leopard catamaran and set off on an unforgettable 9-day sailing adventure through some of the most beautiful islands on Earth. Crystal-clear lagoons, dramatic vo...
The Last Sail: Why We Had to Leave the British Virgin Islands
Today we wrap up an incredible week of sailing in the British Virgin Islands! ⛵🌴 We lifted anchor at Jost Van Dyke one last time and set a course toward Tortola’s beautiful West End. Soper’s Hole is one of the most colorful spots in the BVI, so we stopped in for lunch at the iconic Pusser’s Rum Bar...
Perfect Day at Soggy Dollar… + Want to Join My Crew?
Today we sail into one of the most iconic places in the entire BVI — White Bay on Jost Van Dyke, home of the world-famous Soggy Dollar Bar! It was a perfect beach day with the crew (even though I didn’t film a ton… we were having too much fun 😅). After soaking up the sun in White Bay, we moved the ...
Perfect Downwind Sail to Jost Van Dyke! | Bubbly Pool Adventure & Cane Garden Bay
Today we had an absolutely perfect four-hour downwind sail from Anegada to Jost Van Dyke here in the beautiful British Virgin Islands. Conditions couldn’t have been better — blue water, steady breeze, and a happy crew enjoying every mile. Once we arrived at Jost Van Dyke, we headed straight for the...
45-Foot Catamaran to Anegada | British Virgin Islands Sailing Adventure
Today we set sail from Virgin Gorda to the unique and beautiful island of Anegada — and it ended up being one of our fastest and most fun sails of the entire BVI trip. With perfect wind, flat seas, and the crew looking amazing on the bow, we made the crossing in record time. Anegada is totally diff...
BIKINI Workout While Sailing to THE BATHS!
Start your day at Cooper Island, sail to one of the most iconic spots in the entire Caribbean, and wrap things up with a night you won’t forget. This was one of those PERFECT days in the BVI. We left Cooper Island early and made the short sail over to The Baths on Virgin Gorda, easily one of the mo...
BVI Magic: Stunning Crew Snorkels The Indians + 9-Knot Sail to Cooper Island!
Day 2 sailing through the British Virgin Islands and it was absolutely perfect. This morning we left Norman Island and sailed over to The Indians, one of the most breathtaking snorkel sites in the entire BVI. The water was crystal clear, the coral was vibrant, and the ladies looked amazing exploring...
New Crew, New Catamaran… and a Wild First Day in the BVI!
Join me as we kick off an incredible week-long sailing charter in the British Virgin Islands! We fly into the BVI to meet up with two new beautiful crew members and a returning favorite — Lauryn. After hopping aboard a brand-new Fountaine Pajot Elba 45, we set off on our first sail of the trip. Our...
The Last Sail of Nauti Dogs?
I’m sailing the boat down the East Coast for the final time before hauling her out of the water and storing her on land while the Nauti Dogs prize competition finishes up! In this episode I make the run from Atlantic City to Cape May, then across the Delaware Bay and up the Chesapeake to Annapolis,...
Living on a Boat in Manhattan for a Week!
Docked right in the heart of Manhattan at the iconic Chelsea Piers Marina, I got to experience New York City like never before — from the deck of my sailboat! I launched the dinghy and cruised down the Hudson River, exploring the skyline and even making it out to the Statue of Liberty for a once-in-...
Sailing Into New York City! Docking My Boat in the Heart of Manhattan
I sailed Nauti Dogs from Long Island Sound down the East River, under some of the most iconic bridges in the world, and right past the Manhattan skyline. From there, I rounded the southern tip of the island, cruised up the Hudson River, and docked right in the heart of New York City at Chelsea Piers...
Sailing South for the Winter: Solo Leaving Block Island
After leaving Newport, Rhode Island, I set sail solo—just me and the dogs—toward Block Island. It’s one of the most beautiful spots on the East Coast, but when the weather turned, it became a wild few days riding out a storm at anchor. Once the skies cleared, it was time to start the long journey so...
Wasn’t Supposed to Be This Rough… Solo to Newport, RI
Start speaking a new language in 3 weeks with Babbel 🎉. Get up to 55% OFF your subscription ➡️ Here: I set sail solo from Bridgeport, Connecticut, heading for Newport, Rhode Island — expecting a calm run up the coast. It turned out to be anything but calm. What was supposed to be an easy day quick...
Sailing Croatia with 4 Beautiful Crew | 1.5 Hour Adventure Film
Join me and an incredible all-female crew of four as we charter a luxury catamaran to explore the jaw-dropping Croatian coast. For seven unforgettable days, we sail from Split to the islands of Hvar, Vis, and Korčula — crystal blue water, hidden coves, epic sunsets, and more laughs than we could ha...
Organized Chaos: 100 Boats Depart the Annapolis Boat Show!
The Annapolis Boat Show is over, but the real work begins! At sunrise, I head back to the docks to help with the massive teardown — floating docks are being dismantled, crews are casting off lines, and nearly 100 boats start departing in a well-orchestrated bit of organized chaos. I’m helping move ...
Welcome back LAURA! With her two kids!
Laura — one of the original Sailing Doodles crew and a fan favorite — joins me in Annapolis for a special reunion! This time, she’s brought her two kids along for the adventure. We head to the Annapolis Boat Show, where I show her the brand-new Island Spirit 525 Catamaran — the very model I’ll be g...
My NEW Yacht Has Arrived! Delivering It to the Annapolis Boat Show
The long-awaited Island Spirit 525e hybrid-electric catamaran has finally made it to the U.S.! Hull #3 just arrived in Maryland, and since I’m getting Hull #5, I jumped aboard to help deliver her to the Annapolis Boat Show for her worldwide debut. Come along as we take this incredible new yacht on ...