by Jamie Rich | October 14, 2020

Seeking Safe Harbor

How sailing the open waters on a beat-up boat reconnected Editor in Chief Jamie Rich with the nostalgia of Old Florida.

Audrey pictured here at the 120-year-old Collier Inn on Useppa Island.

“Are we there yet?” 

Our 9-year-old daughter Audrey belted out the phrase for the hundredth time as we pulled into the parking lot of a high-rise marina complex in Cape Coral, a small Gulf Coast harbor town tucked between Fort Myers and Sarasota in the state’s southwest corner and a not-so-quick five-hour drive from our home in Ponte Vedra. 

It was late August, and we wanted to go somewhere—anywhere—and explore before the girls returned to in-person school this fall. A friend had recommended a bareboat charter company down south, and an island hopping adventure sounded like the perfect pandemic-friendly remedy to our cabin fever. One week before the trip, we booked the last yacht available in the company’s rental fleet.

When the girls heard the word “yacht,” they had envisioned something a bit more… er … luxurious than the 1995 navy-blue-hulled, 45-foot trawler (or “Oldsmobile on the water” as my husband, Brian, described it) that awaited us at the marina. But I came to think of her as our own slice of Old Florida: wood paneling lining the walls, nautical-motif, navy-and-teal pillows accenting the cabins and newly purchased sheets (thankfully) awaiting in each berth. Despite her age and well-worn condition (broken AC and deflated dinghy), a timeless beauty still shone through.

Comic Relief, as she was named, would serve as both our hotel and mode of transportation over four days of cruising from Cape Coral, north 25 miles to Gasparilla Island and back again. The next morning we shoved off, motoring full speed ahead at 12 knots toward the port of Boca Grande, known for its world-class tarpon fishing and quaint main street village. Suitably, Radio Margaritaville provided the soundtrack to our journey, but it wasn’t long before grey thunderheads crowded the blue sky and sheets of rain started pelting our family of four. Brian steadied the boat while I scurried to secure the clear plastic glazing surrounding the helm. Jimmy Buffett crooned in the background as a Coast Guard officer implored us through the radio to, “Seek safe harbor.” 

Audrey’s little voice chimed in again, “Are we almost there yet?”

Rich and her family explored Southwest Florida aboard Comic Relief, a 1995, 45-foot trawler.

Things were off to a slightly bumpy start, but we trudged ahead, our destination just within reach. Two wet hours later, we arrived at Boca Grande, where we watched the worst of the storm roll out from the safety of our slip at the marina. 

Over the past few months, I’ve learned that sometimes hunkering down isn’t an option, and you have to take action and adapt to unexpected conditions. We saw examples of that enduring seafaring spirit at every stop along our trip, whether it was the small, family-owned shops in Boca Grande welcoming masked visitors, the historic Collier Inn that has stood atop Useppa Island for more than 120 years or the prehistoric turtles roaming among cheeseburger-eating tourists on Cabbage Key. Perseverance, patience and ingenuity have kept these iconic places and their people going in the face of adversity for more than a century.

Flamingo had its own storm to weather this summer as a result of coronavirus. We quickly activated our Flamingo Friends campaign to help us keep sailing. Our readers, friends and family responded generously. And because of that, we’re able to bring you our fall 2020 edition and a heaping taste of Old Florida with inspiring stories of endurance and survival at every turn. 

In this issue, writer Craig Pittman explores the reinvention of Derby Lane, the 95-year-old greyhound racing track now on its final lap before the sport discontinues at the end of the year. Moni Basu takes a soul-searching trip to Cassadaga, known more for fortune tellers and psychics than the spiritualist community conjuring hope and meaning among its members. Eric Barton unpacks the stories of Florida’s first black collegiate football players and what it was like for those trailblazers to take the field with their white teammates and fans in the 1960s. Flamingo assistant editor Jessica Giles dives deep into the heart of our state’s small towns to find out why some of them struggle to find relevance when others thrive. And columnist Diane Roberts dissects our state’s checkered past with federal elections. As always, we have chefs, musicians, artists, authors and entrepreneurs from around the state to introduce and celebrate. 

With the turn of 2020 on the horizon, we haven’t let a little rain send us off course. And for those who can’t quite break away to cruise new waters in a beat-up boat, we hope to spark inspiration and adventure with our collection of stories on this Old Florida voyage. 

Despite her well-worn nature, Comic Relief provided a much-needed escape from daily life.

Click here to read more from Flamingo Editor in Chief Jamie Rich