New Friends & Sad Endings

Welcome back,” the Cruz Bay Customs Official said to me as I stepped up to clear into the United States on the island of St John. After the longest absence of our lives, we were back on U.S. soil. I have to confess that it felt good in a familiar sort of way. Like walking back into the family home after your first year of college. I don’t like everything that my country does, but I do love my country.

Back in the U.S.A.


After clearing in, we made a short sail back to Maho Bay, on St. John’s beautiful north shore. I say “back” because we have vacationed here many times with family and friends. In fact, it is the first place that I dipped my toe into the Caribbean Sea.

A homecoming.

Tree frogs calling from the twilight hillside—the white sand of Maho beach reflected in the thick moonlight—the “goat path” up to the now shuttered Maho Bay Camps—the spot where my girls would “lay out” in a fit of adolescence bliss and burn their already peeling winter skin in the Caribbean sun.

Places are like old songs, they bring memories pouring back.

And this place was making us miss our girls, and our family and friends. Sure, we had a blast snorkeling, relaxing and hiking at Maho and then again at anchorages in Leinster Bay and Salt Pond Bay. And sure the sailing is amazing and easy here with short distances between islands and waves that make you feel like you are on a Midwestern lake. But there was an underlying feeling of emptiness, as the echoes of past trips bounced around noisily in our ears.

Swimming with the Fishes–Salt Pond Bay


How We Felt After Reaching the Virgin Islands


It was the perfect time for Serendipity to join our trip again, this time in the form of “Buddy Boating.” If you’ve read this blog for some time, you may remember me talking about Scott and Brittany Meyers. The Meyers set out a few years ago from Chicago on a sailboat and haven’t looked back. I’ve followed the adventure that is their life on Brittany’s blog Windtraveler since the beginning. Three kids, two boats and thousands of sailing miles later—they are still going strong. We met Scott and Brittany in Chicago for dinner before our trip, searching for advice and maybe just a little bit of courage. A friendship was formed.

And now, serendipitously, we were getting the chance to see them again right here in the British Virgin Islands.

Shine-A-Light, Shine-A-Light, this is Asante, over.” I tell Jimmy to grab the VHF radio and answer Scott’s call to our boat, which he does. “This is Shine-A-Light, switch to channel 69, over.”  Jimmy is excited and so are Sarah and I. We’ve just grabbed a mooring ball in Great Harbour on Jost Van Dyke and the Meyers are there too on their boat Asante, along with their friends Eben and Genevieve on the sailboat Necesse. For the next four days, we get to experience what live aboard cruisers call “buddy boating.”

The Meyers’s Mini-Van Complete with Double Carseat 


Buddy boating is pretty much what you’d think. You learn that boat friends are in the area (usually this happens now via Facebook), you meet up, and you then bop around from island to island, from sundowner to sundowner, from dinner to dinner, from hike to hike, together.   It’s pretty loose and informal most times, and man is it fun.  Sarah and I wanted to get a glimpse on this trip of what it might be like to actually live on our own sailboat, and buddy boating is a big reason why we now have more “pros” than “cons” on our live-aboard sailor ledger.

Of course our favorable experience was due in large part to the awesomeness of our traveling companions. I’m not sure how Scott and Brittany pull it off, but they are raising three amazing girls on a 44 foot monohull sailboat. Oh, and did I mention that their oldest daughter just turned 3 and the two youngest are 13-month-old twins? Yep, their days are a constant sand-filled stream of crawling, feeding, napping, cleaning, crying, wiping, drooling, diapered, bucket laundry, sippy cup craziness. And they pull it off with a smile and an energy that is amazing.* Rock-Stars.

We spent time with our “buddies” on Jost Van Dyke, then moved with them to Cane Garden Bay, Tortola, to celebrate Brittany’s birthday, and finally sailed together around the north side of Tortola to Marina Cay. On our final morning together, Scott invited us over for waffles made with their new waffle iron. Scott was due in Road Town, Tortola that morning, but he rescheduled the meeting. As we lingered and talked long after the waffles were gone, it was pretty clear that we were all having trouble saying goodbye. In a few short days, a lasting friendship had been formed. The goodbyes were as hard as we expected, and we left with a strong feeling that this wouldn’t be the last time that we spent time with this amazing family.

I can’t wait to be a Dad someday,” Jimmy said to us after we untied our dingy from Asante that morning and made our way back to our own boat. I think that takeaway tells you the kind of people we had just started calling our good friends. And he wasn’t the only one that had gained a new perspective and some insights.

Spending time Buddy Boating made me think about how many of us wait for some future milestone—a job title or a 401k balance—before we “sail away.” Instead, we put in our time doing something that we don’t really love in the hopes that someday we can [fill in the blank].

Is waiting wrong? That’s a personal choice obviously, that bleeds into questions about what it means to live a full and rich life that matters to you and the people around you. These are questions I have pondered often on this trip and the crews of Asante and Necesse provided me with a different perspective. A perspective that will certainly help me as we wind up our adventure and return to our “real” lives.

Someday I’ll [fill in the blank]. It’s a question all of us should ask of ourselves. I hope you are able to design a life for yourself that makes it really hard to answer that question.

Jimmy & Isla


A Day in the Neighborhood


Waffle Party


8 thoughts on “New Friends & Sad Endings

    • Thanks Genevieve. It was so great spending time with you guys and your lovely daughters. I’m just catching up on your blog now on your Indian Rickshaw adventure. You guys are crazy-in a good way!

    • That is hilarious Heidi. Thanks for sharing. I’m following up with you now via email about getting together while you are in town. I hope that is step one to getting a smart entrepreneur like you back to the Midwest 🙂

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