Gulfport is one of our favorite stops along Florida’s southwest coast. Who wouldn’t love a place whose official town motto is “Proudly Weird”? There is a large, protected anchorage just off town center, a dedicated dinghy dock to welcome transient boaters (more on that later), colorful open-air bars lining the waterfront, and loads of interesting shops and art galleries. It reminds us of Key West, but less touristy (‘touristy’ may not be a real word, but ya’ll know what I mean). Gulfport is an authentically southern small town with a cool Key West vibe, filled with genuinely friendly folks. And it is home to one of our favorite Italian restaurants, Pia’s Trattoria (right up there with our absolute favorite, Ferruci Ristorante in Panama City). Pia’s is so popular that the only dinner reservation we could secure was for a table at 5:30. Oh well, since we are generally in bed by 9pm (so called “Looper’s Midnight”), making the transition to “old folks” dinner hour (5pm or so) wasn’t exactly a hardship.

As we approached the town dinghy dock, we realized we had failed to do our research (rookie mistake, not seeking current information about an old favorite). The dinghy dock was a wreck, the victim of back-to-back hurricanes that had sideswiped Gulfport in late 2024 (Helene and Milton). Now the quandary: How to get the Admiral ashore (now claiming the title “Princess”) without getting her only pair of tennis shoes wet. My knight in shining armor waded through the water dragging the princess and the dinghy behind and found a low concrete wall where she could step delicately from the dinghy onto dry land (happy to report that chivalry is still alive and well after thirty-eight years :-).

We chatted with some locals fishing from the shore and learned about the devastation wrought by the two storms from which Gulfport was valiantly still recovering, the first bringing a high water surge that had flooded much of downtown and even took out the main street along the waterfront (it had reopened only earlier this week), and the second storm a high wind event that damaged much of what had survived the first storm. The locals were philosophical, and (like our experience following Hurricane Michael) reported that in many ways the storm brought out the best in people with neighbors helping neighbors and the community pulling together.

We strolled the waterfront and then the commercial blocks in the Historic Waterfront Arts District. A luminous oil painting of a conch shell drew me into the August Veron Galleries, and I would have bought it if I could have possibly found a place for it on Assisted Living. I have saved the gallery business card to explore the possibilities when we have returned from our trip. Further down the way, a lively outdoor bar, Stella’s, was advertising a Peppermint White Russian as its drink of the day. We couldn’t resist (I can picture Catharina Whitehead rolling her eyes as she reads this, as I absolutely swore off White Russians after a long and pleasant afternoon at the St. Andrews Bay Yacht Club sipping White Russians while we waited for our sons to come in from a regatta. This time, older and wiser, I knew to stop at just one.)

The food, wine and service at Pia’s Trattoria was as good as we remembered. The eggplant parmesan served in its own individual sizzling cast iron skillet is to die for. The tomato sauce ladled over the top was as fresh and bright as the sauce we ate in Italy. George always enjoys their seafood, and this time ordered the clams. Loopers, if you stop by Gulfport and are lucky enough to eat at Pia’s, make sure to order a full loaf of homemade Ciabatta Bread – you can take the leftovers to your boat, and I promise you will thank me for it.

After dinner we donned our high-powered headlamps (a good look – but oh so essential for finding your boat in a dark anchorage at night) and slowly motored our way back to Assisted Living.