How to Enjoy: The Florida Keys

I recently got back from a short but fabulous trip to the Florida Keys. I stayed on Islamorada, but was able to spend a little time exploring the islands around it. This was my third trip to the Keys; my first was when I was just one year old; my second was when I was ten. Though I have no memory of my first trip, my second trip to this beautiful string of islands stuck with me in a dramatic way. I can recall the place we stayed, that we cooked fresh fish each night, snorkeled with sea turtles, and went on the Conch Train in Key West. Ever since, I have wanted to go back.

So, this time, I want to share with you the places that enchant me each time I visit the Florida Keys.


Anne’s Beach – This was a new find on this trip to the Keys, but it’s one worth mentioning. It’s a small beach, especially at high tide, but one where you’ll find a beautiful view of turquoise water and covered picnic areas.

Anne's Beach
Anne’s Beach

Bahia Honda State Park – Bahia Honda boasts some of the most beautiful beaches in the Keys. It also offers kayak rentals and snorkeling tours to Looe Key National Marine Sanctuary. I didn’t make it there on this trip, but can’t wait to go back so I can.

John Pennenkamp Coral Reef State Park – This small but beautiful state park is always worth a visit. From here you can take snorkel trips, rent kayaks and stand-up paddle boards to explore the mangroves, and swim amongst offshore shipwrecked cannons and anchors.

Smathers Beach – We didn’t make it to Smathers Beach this trip, but I have heard that it is one of the best beaches in Key West. Looking at the photo below, I can’t disagree.

Smathers Beach, Key West

Sombrero Beach – Sombrero Beach on Marathon was another beach that was recommended to us, but that we didn’t make it to. Still, do an image search, like I did, and it will be on your list for the next time you head south!


Mallory Square – Watching the sun set at Mallory Square is a must-do if you visit the Keys. Hundreds of spectators come to watch it daily at this public square, surrounded by performers of every stripe, including musicians, jugglers, acrobats, and the “Southernmost Bagpiper”.

mallory square
Mallory Square, Key West

Ernest Hemmingway House – There is always a line to visit the home of Ernest Hemmingway. This pretty house offers a view into what life was like for the renowned author during his time on Key West. It’s just a little ways off Duval Street, Key West’s main drag.

Harry S. Truman Little White House – Another famed historical spot in Key West, the Little White House can be found in the Truman Annex neighborhood of Old Town, Key West. The house originally served as the naval station’s command headquarters during the Spanish-American War, World War I and World War II. Then, in the mid-forties, it began to serve as the “winter White House” for President Harry S. Truman.

Harry Truman Little White House

Dolphin Research Center – I still recall visiting the Dolphin Research Center as a kid. Basically, if you or anyone in your family loves dolphins, it’s worth a visit. I still may go back and swim with the dophins; you’re never too old, right?


Blue Heaven – We received rave reviews from locals about Blue Heaven. We weren’t able to make it here, but it’s at the top of my list to visit when I’m back again. There is an outstanding seafood menu, and overlooks the ocean. What more could you ask for?

Islamorada Fish Company – I first ate at the Islamorada Fish Company when I was a kid, but remembered the food and view so well I was dying to go back this trip. It’s expanded, but the food is just as incredible. Try the grilled mahi mahi or grouper while you watch the sun set. It is truly divine.

Islamorada Fish Company

Lorelei Restaurant & Cabana Bar – This restaurant was recommended to us by friends, and looks just fabulous. More fresh fish and a beautiful view? I’ll take it.

Garbo’s Grill – This small restaurant operating out of a converted Airstream trailer serves some of the most delicious and affordable fish you can find around. Try the cayo fish tacos or shrimp burrito. You won’t be disappointed.

Garbo’s Grill, Key West

I’m sure I’ve forgotten some great spots in the Florida Keys. Tell me in the comments where I’ve missed that I can’t miss next time.

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