Florida’s Best Kept Secret: Boca Grande


Rook and I recently packed up the car and headed to Boca Grande, Florida – our favorite spot to take a much-needed time-out from the real world. I used to reserve the idea of “island living” for destinations south of the continental US – places located deep in the Caribbean Sea. It turns out, there is a hidden gem buried along Florida’s western coastline. As for exotic places to travel, well.. I believe it’s Florida’s best kept secret.

Pictured above: Cooler, Luggage


Walking around the island is like stepping back in time. With strict no-franchising laws, BG is home to only locally-owned businesses, most of which have been there for 30+ years. Everyone uses golf-carts or bikes to get around, the faces you meet are friendly and welcoming, and life just seems to move a little slower here.

Pictured above: Suit (c/o BECCA Swim), Skirt, Sunnies

Pictured above: Swim Coverup, Sunnies

We spent our days alternating between the pool, the beach, and the boat. Boca Grande is known as the “Tarpon Fishing Capital of the World”, and Rook grew up fishing here. I like to think he’s taught me a thing or two in our time together, and I’ve actually caught some big fish here. Florida has strict conservation laws, so some catches we keep, some we throw back.

This was my biggest catch of 2016.

We kept Snapper and Trout to cook for dinner, as cooking is another of our favorite past times. We pour red wine, turn on Jimmy Buffet radio, and make up the recipes as we go. There’s something about the taste of a fresh catch from boat to table, and it definitely keeps us coming back to Boca for more.


On nights we didn’t cook, we ate out on the island. The restaurants you’ll find are all unique in flavor, but simultaneously fresh in taste. If you order scallops from a menu, you know they were harvested that day.

The Loose Caboose Restaurant, downtown Boca Grande

One afternoon we had lunch at The Loose Caboose, located in the old train station and with a great outdoor seating area. I ordered the grilled shrimp wrap; Rook, the crab cake sandwich. Both were delicious, and I loved watching people come and go from the restaurant’s central downtown location.

Another day, we tried Miller’s Dockside marina restaurant for lunch (I recommend the calamari salad). Our table on the outdoor patio overlooked the boats coming and going from the marina docks. It made me think about some qualities that make BG what it is.. travelers come from far and wide, lunches tend to be long and served outside, and we always end up ordering a second drink.

Pictured above: Skirt & Top (c/o MINKPINK), Sunnies

For dinner one night, we ate at South Beach Bar & Grille, both a tourist and local spot. It’s the only restaurant on the beach, so the outdoor seating is popular. The food is pretty good, and the staff is friendly.. but people really come here for the sunset view served with dinner at no additional charge.

Pictured above: Dress (c/o Copper & Ella), Sneaks, Sunnies


One night during our trip, we actually ate dinner at a restaurant on a different island called Cabbage Key. This island is home to the famous Cabbage Key Inn & Restaurant, where Jimmy Buffet is rumored to have written “Cheeseburger in Paradise”. Rook and I go ’round and ’round about whether we believe it or not, but I can definitely understand how it could be true. The open-air restaurant sits atop a small island that you can only reach by boat. The bar overlooks the open gulf waters and has been serving up drinks to local fishermen for over 60 years. They’re famous for thousands of dollar bills covering the interior walls, and of course, a damn good cheeseburger on the menu.

Boating to dinner in 2016.

Pictured above: Suit (c/o Isabella Rose), Sunnies

Leaving is always the worst part of Boca Grande. However, I’m comforted knowing that the next time we return, this sleepy island will be exactly as we left it.

Xx, Alley


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about alley

Hi there! I’m Alley, the voice behind Styled in September. I’m an ex-buyer turned lifestyle blogger, currently getting my MBA in Paris, France. With SIS, I try to share my style, beauty, and travel stories, sprinkled with a few unfiltered musings in my digital diary. Currently on tap: some behind-the-scenes takes of an American expat in Paris. Thanks for stopping by my corner of the internet!

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