Schooner Windfall II Charters and Sailing School

08/12/2026

TBH, Sundae still doesn’t know how to sail!

07/06/2026

Love the pics from the Jolly! (And the puppers are pretty cute, too!)

06/09/2026

Many of our passengers have met Yazzi — she wears many hats on Ocracoke including being great crew!
She’s also a baker at Ocracoke Coffee Company and here she is demonstrating her skills!

Since Ocracoke is known for their great figs, Yasmine Colebank joined us in the HRS kitchen and made Gail’s Fig Bars.

05/26/2026

Thanks to Jen for including footage taken on the Windfall II!

05/20/2026

Beautiful!

In case you had any doubts, here’s proof positive you should be here right now. We truly are simply beautiful this spring—come and see for yourself. 📸: Mav at NCCAT last night, no filter needed.

05/15/2026

Great pic of the ol’ skipper!

05/08/2026

Some of you may remember Captain Rob’s son, Emmet, who first took the wheel when he was three days old! (31 years ago!)
He’ll be on the island for June and July to help out the old man!
Meanwhile, we appreciate this photo from Jeanne Brook from a sail when Emmet was visiting this spring!

05/08/2026

Capt. Rob loves passing on the love of sailing!

11/29/2025

The Windfall II was in the Holiday Boat Parade again this year! What a fun way to kick off the holiday season!

08/23/2025

Captain Rob got to do something he almost *never* gets to do: drink a beer and let another captain take over the boat!
We went out sailing tonight with Captain Emmet (our firstborn and a lifelong Windfall crew member) and Yasmine (she’s been working on the boat since last summer.) It was a nice family cruise, and something we don’t get to do during the peak season except when there’s an evacuation. What a gorgeous night! And it’s actually a little chilly!
Family sailing is fun, but Rob would sure like to take some paying passengers tomorrow night!
Please give him a call at 252-928-7245!