Watch Sailing & Boating Adventures Around the World – Page 2 of 7
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.
Kevin & Wendy Rough Sail to St Croix
In this episode we make the hop from St Thomas, USVI to St Croix, a passage of about 34nm due south. As has happened previously, the wind speeds turn to sustained 30 knots. We end up with at least two failures, which seems par for the course.
But overall, a...
We’re finally back at sea! After months on land, we’re setting sail from Georgia and making our way to the Bahamas — this time as a family of four. With our 7-month-old baby and dog onboard, we navigate a mix of the Intracoastal Waterway and offshore passages, adapting our route with the weather as ...
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In this video, I’m sharing the story behind Be The Captain—why I wrote it, what I’ve learned from thousands of readers like you, and a preview of what’s inside.
Thank you for all the support, encouragement, and energy you've sent my way. I can't wait ...
More Sailing Adventures in the BVIs:
Please forgive us if the dates are a bit disjointed. We were using 3x Apple iPhone 14 Pro phones and 5x GoPro action cameras (luckily no drone footage added to the mix), and this meant that this episode is the cleanup of our BVI stint.
But to be honest, althoug...
The BVIs Never Disappoint Cooper, Norman, Jost Van Dyke
In this episode we’re still kicking around the British Virgin Island chain. Not much to say other than what's in the title; Cooper Island, Norman Island, Jost Van Dyke. Tons of fun as always.
sailing yacht tal...
Is This the Most Popular Cruising Ground in the World?:
I did some internet searching and the results were inconclusive. Google’s AI reported Croatia as being the most popular, but the source was a single Croatian charter company. And while we sailed the Mediterranean (Adriatic Sea included) for th...
Midnight Express:
I actually hate night passages, especially when there’s no moon. This is because in the Caribbean at night, and the warm-water Atlantic Ocean south of Bermuda, squalls tend to form with a particular regularity. Absent moonlight and modern doppler radar, these often-violent squalls...
This is the Cruising Life!
In Episode 168, We finally get prepared enough to begin our cruising season. The shakedown portion was a simple motor-sail from Jolly Harbour to Falmouth harbour, both in Antigua, followed by a couple of weeks at anchor and quick stop at the Catamaran Marina (also in Falm...
March 30, 2025 Q & A Live
Join us LIVE as we answer all your burning questions about our next big adventure! We’re sharing our plans for finding a new boat—Leopard 46 or Leopard 50? Plus, when we plan to leave, where we’re headed next, and reflecting on our past episodes from Season 1. We’ll al...
Boat Projects in Paradise Part II:
In Episode 167, we continue to crank through the various boat projects. We’re in the water now, but that just means a different sort of prep.
Projects highlighted in this episode:
Bad battery
Getting hoisted to the masthead
New Elvstrom sails
Upper mainsail in-ma...
2025 Season Opener:
In Episode 166, our 2025 season opener, we cover just a small sample of the various projects required to get the boat on the water. This follows from breaking a lot of stuff the previous season, and needing parts and research to get them sorted.
Projects highlighted in this epi...
Antigua by Drone:
In Episode 165, our season finale, we go for something completely new. It’s a whirlwind of nothing but aerial footage (with all new music) of Falmouth Harbour and English Harbour, two of the preeminent cruiser-friendly anchorages in the Caribbean. Superyachts and high-end recreati...
Kevin and Wendy Sailing:
It seems like there's always drama in Simpson Bay Lagoon. Between the high (often katabatic) winds, generally poor anchor holding, crazy boaters, and hurricane debris under the water, there's always something interesting to going on. You hope that it won't inv...
Following our leaving for the USVI’s after being disappointed by the BVI’s ridiculous 30-day tourist visa rules, we return knowing that the officious behavior is simply the gatekeeping, and we know from long experience that these challenges are rarely, if ever, representative of the greater populati...
I feel a bit bad about calling this episode “Exploring”. It’s really more about showing viewers what the anchorages are like and letting them know that these are areas to stop at. But I couldn’t come up with a better word, or one I liked better that didn’t introduce complexity. Anyway, we have more ...
We just can’t get past the problems with our upper swivel on the mainsail furler and the problems created by “sail repairs”.
But that being the case we still try to enjoy the beauty of the British Virgin Islands, which are probably the preeminent sailing, cruising, and charter grounds in the world...
In this episode we make the hop from Sint Maarten to the British Virgin Islands without fully completing the projects we were working on. And, of course more crop up.
And things go from mere nuisance to much bigger problems when our mainsail starts jamming so brutally that it actually breaks the a...
The cruising life is full of challenges, and truth be told, it would lessen the enjoyment were it not for both the failures and the successes.
And there are times when you almost want to give up, but you can’t. These are necessary and important tasks that must be seen through to completion. Should...
This episode isn't too complicated. We prep the boat for launch with a long list of projects to complete. We ride out a Cat 1 hurricane (Tammy), then it's back to work. Our new drone gives us some impressive footage as I learn to fly it. It's a new DJI Mini 3, and it's smaller an...
For this episode we present a somewhat simple docking challenge, but one that is seen frequently and has been know to put skippers on edge. After all, you never want to scuff up another boat.
sailing yacht talisman, sailing, sailing youtube, boating, top sailing, oyster yac...
For the upcoming PatronsOnly update:
What an inspiring group of people and place we've been fortunate to be a part of! La Cruz is unique. I really hope you enjoy the glimpse into life here and the sailing community.
Thanks for watching!
p.s. I try and reply to as many comments as I can but...
This is a bit of a mashup of footage we took while at our home base of Antigua, W.I. Starting with a rather pedestrian 2 mile motor-sail from Falmouth Harbour over to Nelson’s Dockyard, we find ourselves entering the land of clustered superyachts that almost defines the location. Falmouth and Nelson...
EXPENSIVE MISCALCULATION
As longtime viewers will know, the point of this channel has never been to shine a favorable light on ourselves. Instead, we're brutally honest when it comes to admitting our fails. And despite all efforts to be the “no drama” channel, things rarely go perfectly for ver...
Sailing back to the magical island of Rapa Nui (Easter Island), we take locals sailing, harvest honey, and have the privilege of recording a local artist. This is the highlight of a beautiful 10 days in an unimaginably beautiful place.
❤️ Support this channel:
Come sailing with us!
Patreon:
T-s...
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