We complete our loop; Antigua, Sint Maarten, British Virgin Islands, USVI, St Croix, and Guadeloupe. This trip is always bittersweet, given that it marks our ...

We complete the final portion of our 200nm offshore passage from St Croix to Iles des Saintes, Guadeloupe, and find things exactly as we left them last year. ...

Sail with us from through New England as we leave Martha’s Vineyard behind and head for the fog-shrouded shores of Nantucket aboard our rugged aluminum ...

In certain months of the Caribbean sailing season you can almost be assured of getting hit by squalls. As I mention in this episode, when doing short ...

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 ...

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 ...

Get a signed copy while they last → http://bethecaptain.com In this video, I’m sharing the story behind Be The Captain—why I wrote it, what I’ve learned from ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 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 ...

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 ...

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AHOY - We're Ben, Tambi, & Molly - a trio of sailors who are creating a sailing vlog series! Our mission is to show the world that you can do VERY BIG ...

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) ...

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, ...

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 ...

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 ...

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 ...

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 ...

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 ...