by Jamie Rich | March 4, 2024

Editor’s Note: Great Expectations

Set sail with Flamingo on the Spring 2024 Travel Issue to navigate Florida's coast and discover the enchanting stories that unfold on the open water.

Editor in Chief Jamie Rich recounts some of her favorite stories inside Flamingo’s Spring 2024 Travel Issue. Photography by Kristen Penoyer.

It was June 2005 when I stepped on to a sailboat for the first time. My husband Brian and I were in the British Virgin Islands on our honeymoon, and the 36-foot monohull, Great Expectations, would be our home for the next two weeks. No captain, no crew, just the two of us. It might sound romantic, and it was, but at 27 years old I knew nothing about tying knots, hoisting sails, pulling sheets, dropping anchor, hooking up to a mooring ball or even operating the rubber dinghy tethered to the back of the boat. Thankfully Brian grew up sailing, and he taught me the basics during those first 14 days of our marriage as we island-hopped from Tortola to Jost Van Dyke through the Bitter End Yacht Club at Virgin Gorda and on to remote Anegada.

I still remember the first time a gust of wind filled the mainsail. All the dishes below deck crashed across the galley as the boat heeled over to one side. Brian was elated. “Now we’re cooking,” he shouted, trimming the sheets. I gripped the white fiberglass hull, alarmed at our angle over the water and wondered how the boat was going to stay upright as we sailed along at 6 knots. “Are you sure we’re not going to tip over?” I asked. Brian assured me that the vessel was designed to do this and explained about the massive keel underneath that kept the boat from capsizing. Many sailing trips later, I’ve learned to embrace that heeling feeling.

Miracles and magic, after all, are what Florida is all about.
– Jamie Rich

My maiden voyage aboard Great Expectations held so many experiences that made it magical: exploring new places by water, waking up and going whichever way the wind blew, changing our scenery every day and making friends with fellow sailors we’d meet at our mooring each night. The moments I loved most, however, were the hours long crossings between islands sitting at the helm next to Brian, wind in our faces, Caribbean sun on our skin and water lapping against the boat’s hull as the world rolled slowly by. It’s a rare atmosphere of calm and connection that can only be created on a sailboat.

Over the last 18 years, we’ve sailed routes through the Bahamas, Caribbean and Windward Islands, dropping anchor at spots like Mustique, Saint Lucia and the Grenadines. Eventually, the student became the teacher when we began taking our daughters sailing, and I found myself explaining to them the physics of it all and assuring them that the boat wasn’t going to tip over. Our nautical adventures are some of my most treasured memories, and now they’re a source of inspiration for Flamingo. People often ask how we come up with story ideas, and one way is through personal experiences.

Rich now teaches her two daughters how to sail and to embrace the “heeling feeling” on sailing trips through the Caribbean. Photography courtesy of Jamie Rich.

It’s no secret that Florida is a boater’s paradise but figuring out the best way to navigate and enjoy it can be overwhelming. In this Travel Issue of Flamingo, writer Kim Kavin shows us a range of charter styles, from sailing in the Keys to cruising on the Gulf Coast and yachting in luxury through the Bahamas in our guide to some of the region’s best on-water experiences. Then, back on dry land, writer Nila Do Simon checks into the ultra-exclusive Flagler Club, perched at the top of The Breakers in Palm Beach, for an inside look at its recent refresh and the storied property’s rich history. Not all travel experiences are measured by their level of luxe, and our next feature takes us to a city rich with heart. Writer Carrie Honaker challenges readers to forget what they think they know about her hometown of Panama City, which was torn apart by Hurricane Michael five years ago and is now back and better than ever. And finally, Eric Barton goes off grid in Central Florida to meet some of our state’s most awe-inspiring residents in a feature about a great ape sanctuary and a little-known miracle that took place there.

Miracles and magic, after all, are what Florida is all about. But the stories that most define the Sunshine State don’t often come packaged the way readers expect. Flamingo’s mission is to showcase those unexpected and over-the-top tales. From sushi-making musicians to psychic encounters to an Old Florida art revival, the pages of this issue are packed with surprises from every corner of the state. So sail away with us this spring and see where the wind takes you. Your next great adventure may await just beyond the horizon.