About Rachel Simon (me)


I am 66 years old, single (and available)  and have lived in Honolulu for 35 years.  I’m originally from Coney Island, so I really am an “Island Girl!”  I also lived in Las Vegas for 3 years, but left because it is a Big Beach with NO OCEAN!

I have two degrees, one in Psychology and the other in Hotel Administration. (Hence Las Vegas and UNLV).   I worked in the Hotel Business for many years, until I realized that I would rather be a guest!

I am an avid sailor.  I’ve sailed all around the Islands (except the Big Island) and raced for over 25 years.  One of my huge desires was to sail across the Pacific.  So, years ago, I met two men on a Sunday, and then on Tuesday the 3 of us left on our voyage to Cabrillo Beach California.  We were on a 43 racing sailboat named Illusion, and it took us 19 days to do the delivery.   I’m glad I did it once, but don’t need to do it again.  It was a tough trip and we had to steer the boat all the way across.  We worked 3 hours on, and 6 hours off, all around the clock.

Now, I just race every Friday evening (all year round) on a friend’s boat.  It’s great fun and a great way to end the week and begin the weekend.

Below is a picture of my boat Whatevah! and me.  I love this picture.  It was taken by a photographer that was in the water.  I have had my boat for 25 years, and try to sail it every weekend.

I am also the chairperson of the Escort Vessel Boats for the Transpacific Yacht Race.  This race happens every other year, and July will be the 50th running.  This race goes from Long Beach California, and ends at Diamond Head on Oahu.  My job is to make sure that every boat that finishes the race at Diamond Head has an escort power boat to bring them into one of 3 harbors and brings them to their pre-arranged slip.  It’s a 24 hour a day job for 2 weeks, but I love it.  This summer will be my fifth time.

In 2015, I won the volunteer of the year award.  It was a great honor!