Thank you for finding your way to our channel! We are Jillian and Brian from Stillwater, Oklahoma. We are a blue collar couple who enjoy traveling as much as our bank account and busy lives will allow. We love turquoise water, rum, and every place in the Caribbean that we have dipped our toes into. We have a passion for sailing and in our downtime you will find us on a charter somewhere with our friends and family.

We started our channel to document our travels and share our love of sailing and travel. We are working hard on our retirement plan to purchase our own catamaran and set sail for the Caribbean! Start our own charter business and supplement our retirement by providing people the opportunity to relax or to live like a modern day pirate on board our boat, while we show them around the paradise we have came to love.

I hope we can enjoy an umbrella drink with you sometime in the future. Cheers!

youtube.com/channel/UCBusRK4UPRVsEOzvz3Zpvpw?sub_c…


Sail Stillwater

Of all the stickers out there, we put ours right below The Wandering Hillbilly’s at the Puerto Real Marina in Puerto Rico. We mentioned him in our last video! Go give it a watch and a thumbs up!

8 months ago | [YT] | 3

Sail Stillwater

We are here at Puerto Real awaiting a weather window to cross to the Dominican Republic. Found this crazy looking boat here at the marina. Who knows what it is? Maybe a autonomous weather boat?

9 months ago | [YT] | 4

Sail Stillwater

There are good ships, and wood ships, and ships that sail the sea. But the best ships are friendships, may they always be!

9 months ago | [YT] | 7

Sail Stillwater

It is a great day. For a rum drink!

9 months ago | [YT] | 4

Sail Stillwater

This week Brian leaves for a mile building trip from Fajardo Puerto Rico to Punta Cana Dominican Republic on board a 34' monohull. The last trip like this he went on was was in 2022 on board a 65' monohull from Cartagena Columbia to Panama, via the remote San Blas islands. Great experience visiting some remote places and freshening up the sailing skills!

9 months ago | [YT] | 4

Sail Stillwater

Which charter boat do you prefer? We have been on 3 of the 4, and will be on a Bali 4.8 in June. What is your preference? Comment and let us know what boats you and chartered.

9 months ago | [YT] | 1

Sail Stillwater

We're gearing up for our next video at Sail Stillwater and we want to hear from YOU! Drop your questions in the comments below — anything you want to know about sailing, booking a sailing charter, or where to charter, we’re here to answer them!



Don’t miss out — your question could be featured in the video!



#SailStillwater #AskUsAnything #SailingAdventures #SailingLife #GetReadyForAdventure

9 months ago | [YT] | 3

Sail Stillwater

We hit the goal of all small YouTube channels! Finally hit 1,000 subscribers (with a day left to spare in 2024). Thanks to everybody who watches and supports our channel! Here’s to 2025! 🍻

1 year ago | [YT] | 5

Sail Stillwater

If you had to get rid of 1 Christmas movie… Which would you choose?

1 year ago | [YT] | 1

Sail Stillwater

“It's remarkable how quickly a good and favorable wind can sweep away the maddening frustrations of shore living".

-Ernest Gann

1 year ago | [YT] | 4