Our Crew

Laid-back attire might be common among Caribbean sailors, but a laid-back attitude towards seamanship is not! All crew members of  Random Wind are highly trained professionals and they take pride in keeping you safe while at the same time not infringing on the fun to be had.  Meet the Passionate Crew of Random Wind. We also need time off so you may have other crew at times.

Diane Morano Smith

Diane spends most of her time in Virginia with her two children, Nathan and Caroline. She worked and lived on board for years and is often there to help.

Anna Holness
1st mate, Hostess & Company Manager

From the South of England, she has traveled extensively and adores the Caribbean. She enjoys meeting new people and appreciates different cultures. She understands well the importance of customer service and it comes naturally to her. We heard her say “Making people happy is what makes me happy!” She is fully certified, experienced and open to learning new things. She loves that one of her job requirements is learning the back flip on the Tarzan Swing! Ask her if she’s gotten it yet! Anna lives on board and loves life on the sea.

Captain Details Coming Soon!

About Random Wind

Random Wind is a 52 foot luxury catamaran, originally built for chartering with 8 guests and 2 crew for a week or two at a time.

When the original Random Wind went down in Hurricane Irma, September, 2017, we were devastated. In January of 2018, we put an offer in on Camille. She was on the hard at St. Maarten Shipyard for the storm and sustained some damage to her keels, rails and stern. If you go into the photo albums and find the folder called: “Getting the New Boat Ready 2017/2018” – you will see photos of the old Random Wind after the storm as well as the new one through the refit.

Random Wind offers a lot of space, both in shade and sun. After the 2018 refit Random Wind now has tons of cushioned chill areas. Every guest has a cushioned seat.

Our new Bluetooth speakers forward and aft and can play most anything you bring. The rails run the length of the boat port and starboard and are seriously sturdy for real safety. Below are 5 cabins and 5 bathrooms. Of course one cabin is for Anna, one is for booze and sodas, etc., one is loaded with life jackets and swim vests, one has the boutique and one is for guests.

Our Mission Statement

It is the mission of Random Wind Charters, NV to bring joy to those who board our boat as well as to those we encounter on land. To attain this mission we:

  • Encourage fun and laughter in a stress-free environment
  • Treat all people equally and with respect
  • Enjoy alcohol responsibly so as to enhance the good time we are having
  • Take pleasure in the waters of Sint Maarten – Saint Martin as a green company; appreciating the beauty and leaving no footprint.


We All Rise Together ~ Diane Smith

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