About Us

The "CREW" in Osterville, MA


I have spent the last 18 years in the field of Human Resources and Technology.  In my career, I have worked for Oracle, been CEO of Xcelicor and most recently a partner at Deloitte Consulting, LLP.  I have alway said when 'work' is no longer 'fun' it is time for a change...and I hit that wall recently - deciding to take a Sabbatical from the rat race and spend quality time with my family.  When will I go back?  I have no idea, but it probably won't be anytime too soon...

As a kid going to Florida for family vacations, we would sail small boats, and owned a Sunfish that I sailed with my father.  To this day it is a great memory and we had fun learning how to sail, and eventually taking the boat out myself with no adult supervision.  From the Sunfish we moved up to sailing a 16ft Hobie..and with the jib, brought a new dynamic (not to mention speed) to the experience.  It was great.

I have been blessed with a great family.  The top priority for me is to spent quality time with my family and have fun.  When the 'net fun' experience no longer outweighs all the 'challenges', it will be time to cash in the chips and get back on land, starting another company.  Until this happens...and 'if' it happens, we will be working hard as a family to figure out all the details about sailing and discover the world via water.  It won't be easy, nothing ever is that is worth having...so here we go...writing another chapter in the Silverstein Family memoirs...


How did I get signed up for this?  One of the things I have loved most about Mark is his sense of adventure.  He gets me out of my comfort zone and has shown me a world where fear and worry take a back seat to creating memories and new experiences.  From our honeymoon in Costa Rica to the motorcycle trek from Nashville to Yellowstone, I knew I better just hang on for the ride!

Honestly, my two personas have dueled from the time this sailing venture was a blip on the screen.  One side of me can't wait for the simplicity, down time, exploration, and family experience.  But the other, can't even fathom why in the world we'd want to do this... the immunizations, the lack of babysitters, the tight quarters, the homeschooling, not to mention the sailing experience - which I don't have lots of!  Throughout the planning and process, I've had to remind myself that God will be everywhere we are, and that His purposes and plans for us are so much greater than my worries.

I am a certified teacher with a masters degree in Elementary Education.  Although, I haven't taught since our first child, Elizabeth, came along, I have kept my foot in the teaching realm.  I have been involved in Teen MOPS (supporting young moms) and volunteer in the classroom from time to time.  It will be a sweet challenge to homeschool my own kiddos.  My friends and family are very important to me, and I am making sure they are all signed up for Skype, so that we can stay connected.


I'm Elizabeth, the big sister.  I'm 8 years old and am in the third grade.  I like to swim and play in the sand.  

I'm Michael, the little brother.  I'm 6 years old and am in first grade.  I like to play on the iPad and catch fish.  We have lived on our boat for 2 years so far.  Some of our favorite places were Hog Island in Grenada, Patagonia, Boston, Bahamas, and Bonaire. 

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