Fun on Holiday Sailing

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Fun on Holiday Sailing Zach and Lindy retired at 38, sold most of their stuff, and moved onto their Tartan 37 sailboat

New episode!
30/11/2025

New episode!

In our first days back in the BVI after our sail from St Maarten, we hike to the highest peak on Virgin Gorda from the North Sound, go to the pirate show at ...

New episode! Lots of sailing!
23/11/2025

New episode! Lots of sailing!

We leave from Simpson Bay lagoon on St Maarten aboard our Tartan 37, SV Holiday, for a 16 hour overnight sail to Virgin Gorda in the BVI.

New episode!
16/11/2025

New episode!

We rent a car for a few days to get off the sailboat and explore around the 2 countries of the island. We go to quite a few beautiful beaches and also use th...

New episode!
09/11/2025

New episode!

We set sail from St Barts and head to St Maarten aboard our Tartan 37, SV Holiday. We arrive during the Heineken Regatta so our transit through the Simpson B...

New episode is live!
02/11/2025

New episode is live!

Aboard our Tartan 37, SV Holiday, we hit up the Jimmy Buffett hangouts of Le Select and Autour du Rocher in St Barts. We also anchor in Gustavia and Anse du ...

New episode!
05/10/2025

New episode!

We sail from Nevis to St Kitts on our Tartan 37, explore the island, then set off on a long sail to St Barts.

New episode on a new island!
28/09/2025

New episode on a new island!

Aboard our Tartan 37, SV Holiday, we explore the tiny island of Nevis in the northeast Caribbean for a couple of days.

New episode!
21/09/2025

New episode!

We check out of Antigua and sail 42 miles on a beautiful down wind run to Nevis on our Tartan 37, SV Holiday.

New episode!
14/09/2025

New episode!

We enjoy the beach and boat life in Jolly Harbour, Antigua before moving the boat around to anchor at Falmouth Harbour. Falmouth is full of crazy huge mega y...

New episode!
07/09/2025

New episode!

We work through some boat projects on our Tartan 37 while chilling out in Jolly Harbour and enjoying life back afloat with Lindy cooking yummy meals.

Season 9 first episode is up, and Holiday goes back in the water in Antigua!
31/08/2025

Season 9 first episode is up, and Holiday goes back in the water in Antigua!

We return to Antigua after 6 months away from our Tartan 37 sailboat, Holiday, and start getting her ready for another year of cruising.

Last road trip episode! Sailing episodes and Season 9 will start next weekend. Thanks for following along on our land ad...
24/08/2025

Last road trip episode! Sailing episodes and Season 9 will start next weekend. Thanks for following along on our land adventure!

As our 7,000 plus mile road trip in our 2004 Toyota Tundra comes to a close, we tour downtown Houston then do a marathon drive all the way back to Cortez, FL.

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