We continue to prepare our monohull sailboat for our sail east across the North Atlantic Ocean from St. Martin in the French Caribbean and are working on boat ...

We're pulling the anchor up and headed for the Hudson River! It's finally time to repair the damage from our hit and run boater, in the meantime we'll do some ...

We're going sailing and Tara, our new crew member, is hoisting the sails! We'll sail towards New York where we'll anchor off of a famously haunted island where ...

This week we sail from St. Martin/Sint Maarten to the British Virgin Islands in big seas and big waves! We anchor in the deepest water to date and show you how ...

I take Tara to a pub where she decides to take one for the team...She's slurping it down so we can enjoy a cold one! Then we're sailing to a favorite local ...

After sitting tight in an anchorage waiting out high winds, we finally move our sailing monohull over to another bay in St Martin, on the French side of The ...

We're in Montauk, New York waiting out a big blow. We'll go exploring which turns into day drinking in one of America's most lovely towns! Come see all the ...

We're on Block Island in the Northeast U.S., we meet some amazing new friends who offer us their sweet classic Jeep for a day of exploring! Come experience ...

This episode, we share an update what we've been up to, the sale of our monohull sailboat, our sailing plans, what's next for us and what to expect for Jibsea ...

We've pulled the anchor up and departed for an offshore sail to Block Island! Tara immediately learns what it means to have a sailboat moving under you, come ...

Thanks to Skillshare for sponsoring this episode. The first 1,000 people to use the link or our code sailingjibsea will get a 1 month free trial of Skillshare: ...

Tara, the new nanny, is onboard! We get her settled in, fix some boat issues, and visit a local historic destination before setting sail for Martha's Vineyard! ...

After our weekend in Provincetown we sail 20 miles south to the Cape Cod Canal where we deal with high currents and bridges. Then we're off to get our ...

Join us as we sail our monohull sailboat 80 nautical miles from Barbuda to Saint Martin, a french Caribbean Island. Fishing, big waves, ocean to table, conch ...

We're sailing to an historic town in America! We'll grab some fuel, deal with another crazy boater, get the most expensive mooring ball ever and explore a ...

We sail our monohull from Antigua to Barbuda and enjoy endless miles of amazing beachfront. It's a few windy days here but an amazing time nonetheless ...

We're moving on...From a month of bad events, we've set sail and are headed east. Come hang out in a couple of Long Island Sound anchorages with us as we catch ...

We're relaxing in a new anchorage when a seemingly intoxicated boater comes and slams into Calypso right before a storm hits. There's a struggle to get them ...

Thanks to Skillshare for sponsoring this episode. The first 1,000 people to use this link will get a 1 month free trial of Skillshare: ...

It's catch and cook on our monohull sailboat this week! You'll never guess what we found in the belly of our snapper that we caught while trolling on our sail ...

We JUST got hit by a Hurricane, come see the aftermath. We notice we have some damage, then we try to get off the dock when we get some terrible news..all ...

This week we sail our monohull to the east coast of Antigua and explore a the private and uninhabited Green Island, and go on a dinghy adventure to Devil's ...

This week we sail from Guadeloupe to the yachting hub of the caribbean where there's no shortage of luxurious mega yachts and super yachts. We explore Antigua ...

It's a snoozy morning that gets destroyed by a Hurricane! We're hunkered down for what turns out to be way worse of a storm than anyone could have guessed. ...