After they were married, the Caldwells enjoyed their
34-foot Downeast lobsterboat so much that they found
themselves spending half the week living aboard with
their two Labradors. Sea Bound was a tight fit for all four
of them, so in 1995 they sold the house and bought their
current boat, Sandy Hook.
At that point Chris and Alyse were living aboard
full time, cruising for long weekends and extended
vacations, and for the next five years they continued
their careers in New Orleans (Chris in engineering
sales and Alyse as a hospital nursing director). Planning
a one-year sabbatical to cruise in 2000, they sold the
cars, got rid of the business suits, and set out to do the
Great Loop. After that year went by, they decided that
life was too short and they couldn’t go back to New
Chris and Alyse thought their services would do
just that. Training aboard Sandy Hook was a natural
progression for their business for those who wanted to
learn about life aboard, but didn’t yet own a trawler.
TIME FOR TRAINING
So here we were—one couple ready to teach aboard
their boat, another couple eager to learn firsthand about
the cruising lifestyle, and me, ready to observe it all and
still find the answer to the million-dollar question: How
do the Caldwells get along so well?
I slept well in the V-berth and awoke to finally meet
Claudia and Kenny. Alyse’s multicourse breakfast filled
the boat with a glorious aroma. My first lesson: Just
because we were on a boat, didn’t mean the galley
Left: Alyse and Claudia learning how to properly tie a line for storage. Who said learning can’t be fun? Right: Chris and Alyse
teach Kenny and Claudia the right way to use a chart and how to plot a course to our final destination.
Orleans. They observed other people living the dream
and thought, “Maybe it’s our time.”
Alyse acquired her captain’s license in 2001 and
both found seasonal jobs in the Chesapeake driving
water taxis. The couple lived as snowbirds for a few
more years, and as funds dwindled, they picked up odd
jobs helping other boaters with maintenance and boat
delivery. Just when they thought their fun was over and
it was time to get back to the real world, fate stepped in.
In August 2005 the Caldwells bought plane tickets
to New Orleans to scope out jobs, housing, and a place
to dock Sandy Hook. Scheduled to land a few days after
Hurricane Katrina hit, the airport was closed and the
couple had to reconsider their plans. Cruising for a
few months in the Bahamas helped them think things
through and before they knew it, they came up with a
business plan to start Captain Chris Yacht Services.
While observing other cruisers, they saw that some
owners weren’t comfortable handling their new boats
and often paid high labor fees for basic maintenance
because they had never been taught to do it themselves.
was limiting. This meal was hardly the cereal and milk
I had expected. Alyse taught us that advance meal
preparation was a must on board so that the cook and
the crew could share their meals together. We enjoyed
“Sausage Pinwheels” (sausage wrapped in crescent rolls,
sliced, and baked) and “Breakfast in a Bucket” (ham as a
liner in a muffin pan, baked with an egg in the center).
As we talked during breakfast, I knew immediately
that Claudia and Kenny were going to be ideal cruising
companions. Newlyweds for a little over four months,
the couple lived in Arizona and were very much in love.
I couldn’t help but let their positive energy and warmth
rub off on me. They were anxious to get things started,
and so was I.
Kenny owned a collection of diners across the
United States and also had his private pilot’s license.
Claudia was a Southwest Airlines flight attendant.
Kenny was no stranger to boats and knew that his
future plans included living aboard and eventually
cruising full time. Claudia loved the idea of being on
the water but didn’t have much experience with boats.