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Ballards on Dock by S-Y STARFISH with Captain Sam and FirstMate and Chef Jen

First Time’s a Charm: Notes from a First Yacht Charter Adventure

“Day 3: Kids are exhausted from water-sports, we are headed to Cooper Island for the day and will have dinner there. Best trip ever.”

Recently, a dear friend of mine took his family on their first yacht charter vacation – destination the Virgin Islands. He’d read many of my posts about yachting and travel and periodically messaged me asking where I thought he should go, what would the best yacht be for his family, etc.

Understanding Charter Vacations

When Michael and I got down to the really planning his vacation, I knew it was (understandably) hard for him to wrap his head around the whole thing that is a yacht charter.  It is a big expense and many charterers save a long time to take such a trip, so I did not take this task lightly.  I knew if a friend had the faith in me to move forward and book a boat for him and his family, that I better make sure they’re on the right one, going to the right destination with the right crew.

First Yacht Charter Ever

Since it was Michael’s first private yacht charter, I was looking to match him with a team that was good with kids, offered great service, and also fell within the value category: those boats book up very quickly.  Many family friendly boat charters offer discounts ($250.-$500 Per Child) to children under the ages of 10 or 12 years old.

We started the search early and were lucky to land the S/Y STARFISH, a 46’ Leopard Catamaran run by the fabulous duo of Jen & Sam Augspurger.

Beautiful STARFISH is the winner of the 2018 Best in Show in the Under 52’ category at the USVI Charter Yacht Show.

Captain Only or Crewed Charter

Michael was hesitant to eat all the meals on board; he thought he would feel trapped. This is a common worry for first-timers.  I suggested a Captain Only where all expenses are additional. I wasn’t going to force him into something he wasn’t comfortable with.

We talked about the captain-only option and he seemed to like that initially, so we booked S/Y STARFISH with just Captain Sam.  As the process of going over all the details began and we reviewed how to order food & drink – how much they would need, the cost, where to eat out, etc. – Michael started to realize that handling all that and making those decisions can be time-consuming and tiresome.

Yachts of Options

I suggested that we revisit a fully-crewed charter with a few meals off.  STARFISH offers all these great options so I said, “Trust me, this is the way to go. You know I won’t steer you wrong.”  So he listened and things became quite simple after that.

Once Michael’s wife, Anne, was “on board”, it was smooth sailing!


Our job as charter brokers is to lead the client to the boat and crew that best matches their needs based on what we learn at yearly boat shows.  We can suggest locations, itineraries and activities based on our experiences but after that, the crew step in and guide the client through the rest.

Jen and Sam on S/Y STARFISH are exceptional at this!  I can say, hands-down, they may be one of the best crews I’ve ever worked with.  Their communication, suggestions and basic handholding skills are to be admired.  I suggested hotels but Jen organized all the transportation for Michael and his family – something that I might do but she was kind enough to handle.

Expectations Exceeded

I was copied in on every email so I knew exactly what was happening with my friend and client; this step is so important to a broker that has the client’s best interest at heart.

Michael messaged daily from his vacation.  He absolutely could not believe what was happening.  I don’t think he fully understood what a charter was all about until he got on and experienced each activity, meal and just the general pleasure of being with people who look after you the entire time.

No decisions needed to be made except, “Would you and the kids like to snorkel, waterski, wakeboard, tube, kayak or SUP today?”

And, ”What type of cocktail/mocktail might you want to try at happy hour?”

For people who work very hard in their jobs and day-to-day life, this is hard to put a price tag on.  I’ve actually seen people’s whole body language change by about Day 3 when they really get into the groove.  The kids are off devices and in the water all day and playing games as a family at night.  When’s the last time you’ve done that?

Michael’s first message said: “No words after the first day, seriously zero.  The kids are already asking to make this an annual trip.  Jen and Sam are amazing.  What a crazy experience”.

Charter. Rinse. Repeat.

On the last day she sent me a group photo and thanked me for the charter and for entrusting them to take good care of my friends and clients.

Then on Day 3 he sent: “Kids are exhausted from water-sports, we are headed to Cooper Island for the day and will have dinner there. Best trip ever.”

And finally, on Day 7: “Sue, in 2021 I want to do Starfish again over Father’s Day Week”.

Jen and Sam wrote to me on Day 1 letting me know that Michael and his family were on board safely and about to look for turtles in Maho Bay, St. John.

Chef Jen mentioned how happy they were to have such nice guests for their last trip of the season.

Breaking News: Kids Try New Foods!

They also sent me a daily rundown of what the Ballards did and even ate.  Captain Sam taught the kids games at night, sometimes giving Michael and Anne a little well-deserved alone time.

Jen’s impressive menu is always a crowd pleaser and Michael credits her for getting his kids off their pizza and ice cream diet.  (A common occurrence on charters is kids trying lots of new foods.)

This diary made me feel like I was there with them!

It was so cool to read what my friends were experiencing; it even brought a tear to my eye knowing that this was the best yacht, crew and destination match I could have made for them.

My work was done here…on to the next!

Sharing is Caring

Many people wonder why I post so much on social media – especially about yachting and travel.  I’m sure my posts get annoying (and may even seem like bragging) but I really love what I do for work – and for fun and sharing it with the large audience that technology allows.

I want as many people to experience what I have been lucky enough to.  I could not sell something I do not believe in; it’s just not who I am.  I truly feel that chartering a boat is one of the best vacations you can ever take with your spouse, family & friends.


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