Thursday, December 9, 2021

Island Gypsy Restaurant Fulfills Your Wandering Needs on Isles of Capri

Rumination from the Rock and Beyond

Photos by Jory Westberry
| Part of the original Island Gypsy yacht.


It’s a balmy Saturday afternoon and the urge hits us to go to the Island Gypsy Café & Marina Bar for lunch. Since most of the time we prepare our own meals, this is a welcome reprieve on a beautiful day on the Isles of Capri. Plus, we have a new rescue dog that needs to have more experiences other than her past life. So, we took her with us for the first time, fingers crossed.


The Island Gypsy was packed with locals and visitors and we had to wait for seats to vacate at the bar or wait longer for a table. Luckily, two lovely, seated citizens were leaving and bequeathed their stools to us and we happily settled in and ordered beverages before menu items.

Formally from Boston, owner Jerry Alajajian, was the first general manager of Tommy Bahama Restaurant and Bar off Third Street in Naples and later launched Handsome Harry’s Third Street Bistro on the same street! Alajajian and his long-time woman-friend bought the site of the Island Gypsy in 2011 and have developed it into “a great place to be.” The Key West ambiance, the marina, with on-the-water adventure rentals adds more fun to the unique delectable menu items and signature cocktails, a big incentive for diners from miles around.

We engaged in conversation with adjacent diners and found rave reviews from those who were repeat customers. They had high praises for the food and ambiance at the Island Gypsy. One woman raved over her bowl of clam chowder and said it was the best she had ever had. Ironically, this menu item is listed as “The Best” Cape Cod Clam Chowda! She joined the “Clean Bowl Club”. We had some humorous interactions. There was a woman shrieking at a table nearby and the man next to me turned my way and said, “relative of yours?” 

Insight Alert: I’ve noticed that those who frequent “happy places” such as this are in a congenial state of mind and have more of laissez-faire attitude about the service and time for meals to be delivered. The reality is that anything ordered this time of year is going to take more time than usual because of the demand, so appreciating the weather, location and the great outdoors adds to the ambiance. This is also a place that naturally generates goodwill conversations with other, like-minded folks, enjoying each other and their experience at The Island Gypsy.



The servers, bartenders, receptionist, and staff all wear masks and only took them off when asked for a photo for The Coastal Breeze News. Safe distance, of course, was maintained. Outside seating has been expanded along with a plethora of blue- and yellow-colored umbrellas to fend off the UV rays or the occasional shower.

Lisa, Drew, and Ashley – pros at congeniality and mixology.

Known locally as “The Gypsy,” there are pontoon boats and kayaks for rent. Just think, after a day on the water fishing, exploring, swimming, or shelling on one of the local beaches, you can return for one of the many scrumptious fish dishes on the menu or choose from many sandwiches, such as burgers and grouper, served with fries and coleslaw. There’s something for everyone. The menu is impressive, and the carrot cake dessert is so huge it can be shared with several diners. The joke at The Gypsy is that the huge dimension of the carrot cake slice takes center stage in more photos than the eclectic restaurant. There are also daily dinner specials that your server can tell you about and get your mouth watering.

So where did the Island Gypsy get its name? You’ll have to read about The Legend of the Island Gypsy on the menu – it’s quite an interesting tale of the sea. If you know any of the original men and women on its early voyages, please let me know their names; it would be fun to follow up with any of them. As you walk up to the receptionist’s desk, you can’t help but wonder how the stern of the boat ended up at the front of the restaurant – it’s quite a conversation piece.

There are some artsy fish painted on the sidewalk that, if you follow them, will lead you to the restrooms or to a well-stocked gift shop on the premises. There are lots of T-shirts, hats with the Island Gypsy logo and motto, “Locally World Famous”, along with jewelry, clocks, stickers for your car, ukuleles, and more great stuff you just “have to have” to remind you of your great times at The Island Gypsy and Marina on Isles of Capri.



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