Watch Sailing & Boating Adventures Around the World – Page 10 of 138
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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Episode 4: After Hitting the Reef, I’m Alone and Trying to Bring Calico Skies Back
This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue with the journey of Calico Skies! Ov...
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...
Sail Plans REVEALED 😱 (Custom Aluminum Catamaran Build Pt. 43)
After soooo much research and planning, we're super excited to reveal our sail plan for Delos 2.0 🥳. We've been working closely with Quantum Sails to really hone in on our needs and preferences to come up with something that will give us performance, versatility, and durability to tackle ...
BUILD ➜ SAIL: Installing the Sailing Hardware ⛵️
We're building a custom aluminum expeditionary catamaran from scratch, and in our latest episode we're taking you on a deep dive into the sailing hardware install! Watch the full episode here:
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...
Episode 3: Haul Out After Hitting the Reef – How Bad Is the Damage? Rudder Trouble Again?!
This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue with the journey of Calico Skies! Ov...
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...
BUILD ➜ SAIL: Installing the Sailing Hardware ⛵️ (Aluminum Catamaran Build Pt. 42)
Get behind the scenes with exclusive bonus content, early & ad free videos, meet up invites, and more! We're back at it with the sailing hardware! You might recall that this was one of the last projects that we had been really focused on before leaving to French Polynesia, and it fe...
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 ...
What Happened to Our Boat?! (Back At The Build!) 🛠️ Aluminum Catamaran Build Pt. 41
Going to therapy is a sign of strength, not weakness. My paid partner BetterHelp makes therapy simple, with 10% off your first month to help you get started: The moment is finally here that I know so many of you have been super excited for, we're back at the build! It was such a happy reunion...
Episode 2: Heavy Seas & Healing a Heavy Heart & Answering the Question Everyone keeps Asking 🧐
This is my new channel where I will continue the story aboard Calico Skies, but with a fresh perspective, new adventures, and the same passion for sailing, discovery, and storytelling that has always been at the heart of my journey. Please Subscribe and continue with the journey of Calico Skies! In...
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...
Day ONE of our TWO Week Sail from TAHITI to HAWAII | Episode 316
Welcome back to another episode of WE|Sail! We had done about a week of good hard work to prep the boat for this long sail north to Hawai'i and now it was go time!! It had been a good week and we had been able to tackle just about every known issue with this well used, 13 year old boat, as ...
THIS IS THE END 🥹
After 14 years & 55,000 nautical miles, Kazza has accomplished something that feels crazy to even say out loud...Join us for the final miles of her complete circumnavigation of planet earth and relive all the magic with us. Watch the full episode here:
THIS IS THE END 🥹…Sailing Vessel Delos Ep. 527
Use code SVDELOS at the link below to get an exclusive 60% off an annual Incogni plan: Can't believe this episode is finally here 🥹 It’s the end of a circle that’s been 14 years in the making. After 54,508 nautical miles, countless laughs, storms, sunrises, and everything in between — Kazza h...
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 ...
The Ghost Crew: Sailing With Faces I Couldn’t Show
We set sail from Port Washington to Huntington Bay, Long Island — a beautiful day on the water with two amazing crew members. But after the trip, they asked not to appear in the video… so I had to blur them out. It turned into one of the most challenging edits I’ve ever done — and a strangely fittin...
Our LAST EVER Passage on Delos 🥹 (Pt. 2 of 3)
After 15 years and 80,000 miles, it's finally time to close this chapter. Join us for our last ever passage on Delos. Part 2 is live now, check it out here:
Reality of Sailing (When It’s Not Fun) Pt. 2 of 3 ⛵️ Sailing Vessel Delos Ep. 526
Snag some of our sweet Delos Tumblers & Waterbottles at We're comin' at ya with part 2 of our LAST EVER passage on Delos 🤯 And apart from the weight of it all and bittersweet feelings of this chapter closing... Let's just say it's not all sunshine and rainbows. The conditi...
Giving Away My Sailboat to One of You!
🎉 BIG ANNOUNCEMENT – I’m giving away my sailboat, and YOU could be the new owner! ⚓️ This is your chance to win "SV Nauti Dogs" a 1989 Ta Chiao CT-56 bluewater cruiser, the yacht that has taken me on so many incredible adventures. Instead of selling it the traditional way, I wanted to giv...
Sailing Fiji to French Polynesia; Hired for My FIRST Boat Delivery | Episode 315
Welcome back to another episode of WE|Sail! Warren barely has time to unpack his bags in Fiji before he's off on his next adventure – his very first boat delivery! This week, he's heading to French Polynesia to take on a delivery of a used Catana 55 from Tahiti to Hawaii. Boat deliverie...
Sailing NYC with Emma from Flying Doodles! | East River to Long Island Sound
We set sail right through the heart of New York City! Emma, the host of Flying Doodles, and her boyfriend join me on Nauti Dogs as we cruise past Manhattan, up the East River, and into the Long Island Sound. We make it to Port Washington, where Emma and her boyfriend wrap up their quick visit before...
The Beginning (of the END) Our Last Ever Passage On Delos Pt. 1
After 15 years and 80,000 miles, it's finally time to close this chapter. Join us for our last ever passage on Delos. Part 1 is live now, check it out here: