Still Cruising the Caribbean After 25 Years

View of the Caribbean
View of the Caribbean

Each winter, in the depths of February, the Annual Friends & Family Winter Caribbean Cruise is called to order. Note the capital letters. Surely we’ve earned official status, as this February, aboard Emerald Princess, we’ll celebrate the 25th gathering of our ever-expanding group.

To think it all started with a randomly assigned table of eight aboard the cruise ship, Fair Princess. As we had before, I was taking a winter getaway cruise to the Caribbean with my parents, who were avid cruisers, and my sister, Gail, when we won the lottery on great tablemates. Those four strangers were to become as close as family and form the nucleus of our successful travel group.  

There were Eileen and Nadine, who knew each other from high school and were escaping the Boston cold, and Sonny and Andy, two IT guys from Michigan, on a similar mission to get out of town. On paper, we didn’t have much in common. I was a college student, Gail was still in high school and my dad was a general contractor in Connecticut. But we clicked, to the point where our lively conversations and frequent bursts of raucous laughter caused the people sitting around us to say they wished they could sit at our table, too.

The next year, we asked Eileen, Nadine, Sonny and Andy to join us as we took another winter cruise to the Caribbean sun, and the rest is history.

And as the years unfolded, so did our lives. In time, my sister, Eileen and Nadine married and their husbands became part of the group. On my partner Stephen’s first cruise vacation with us 17 years ago, he fit in beautifully with the rest of the gang.

Our one table has now grown to a cluster of three or four, and we still attract the attention of other passengers. “Next year, we want to come with you,” we’ll hear. And some have and are now members of the group. Some years we number 40-plus.

Not everyone can come each year, but we always attract a nice crowd. Each year, well in advance, I put out an email suggesting some dates for the winter cruise. Whether it’s an eastern or western Caribbean cruise is not the point, we are looking for sunny skies, warm air and balmy waters.

Typically, our group breaks off into smaller pieces for shore excursions or pool-sitting during the day. But each night at 7 p.m., without fail, all of us meet for cocktails before heading off for our second-seating dinner. From night to night, we change seats so that everyone gets to see everyone.  

Dinner conversations always flow easily, focusing on life updates for the first day or two then segueing into making plans for smaller summer travels or penciling in the dates of upcoming milestone events among our families.

Over the years, we have become a family ourselves. We’ve attended each other’s weddings, graduations, first communions and bar mitzvahs. We are there for each other when times are tough, seeing our group members through the pain of divorce, death of spouse and other trials of life.

Five years ago, when my parents, the founding members, died within weeks of each other, the consolations flowed in. On each cruise, we always take a moment to raise our glasses and toast them, imagining they are dancing up there in the big cruise ship in the sky.

It’s rare enough in these times, when life seems to roar by so quickly, to maintain friendships with neighbors from across the street. So it has been an incredible joy to maintain close ties with Eileen, Nadine, Sonny and Andy, randomly assigned tablemates from Fair Princess 25 years ago, and all the others who have joined us on the Annual Friends & Family Winter Caribbean Cruise.

So far, 34 are booked for the 2014 Annual Friends & Family Winter Caribbean Cruise, and may grow even more. In addition to the winter sailing, Mark and Stephen try to take one to two additional cruises each year, venturing to Europe, Hawaii, Alaska and beyond.