A long weekend in Key West, FL

Oh, the Keys.

Growing up in south Florida, my family made a number of trips down to the Keys - but last weekend we went back for the first time in at least 15 years - one last family adventure before Kay and I relocate to New York. We all piled into a rented van and drove down together and while everything seemed a little familiar, it was like a whole new experience to explore the islands as an adult.

Part touristy-wonderland, part tropical paradise, and part history-rich destination, The Florida Keys are so much more than Duval Street (picture Bourbon St, but with more flip flops).

Never been or looking to go again? Here’s a quick rundown of some of the best spots in Key West.

On The Way Down

Getting there is half the fun

Given that flying directly into Key West is so pricey, it’s safe to assume you’ll be driving down from say Miami, or Fort Lauderdale.

First stop, Key Largo.

If you need a bite to eat, I highly recommend Snappers. It’s the kind of place you’re not likely to find without someone suggesting it - and it’s simple waterfront seafood at it’s finest. Plus, The Blonde Giraffe is just down the road and offers up some of the tastiest Key Lime Pie on the islands.

John Pennekamp Coral Reef State Park is just off Key Largo and offers some of the best diving and snorkeling in the Keys. Be sure to set aside some time for a day trip out on the reef amongst the coral, fish and sea turtles. You won’t regret it.

Looking for some only-to-be-found-in-the-keys Florida Kitsch? Drop into the Rain Barrel on Islamorada. You can’t miss the enormous lobster outfront.

If you’re breaking up your trip down the keys into more than a day’s drive - book a room at the new Post Card Inn on Islamorada. A modern take on the island get away and perfect place to unwind after a day on the road or the reef.

Bloodline fan? Visit - or stay at the Moorings Village aka - The Rayburn House. We’re all big fans of the show, so we made it a point to drop in and check out the infamous Rayburn House. It’s a sprawling property and they don’t exactly welcome non-guest visitors, but it was fun to walk around the beautiful lush grounds.

Islamorada is also home to another can-only-be-found-in-the-keys attraction - Robbies Tarpon. Walk out onto their docks with some bait fish in hand and watch the water roil with these prehistoric leviathans.

As you make your way south, you’ll come across Bahia Honda - a beautiful state park that straddles both the Gulf and the Atlantic. Stretch your legs on their beautiful grounds, take a dip in the crystal clear water, snorkel nearby Looe Key, take some instagram-worthy shots of the old bridge - just enjoy. My dad has stories of camping on top of and jumping off of the old bridge, which sounds like an amazing experience that is thoroughly discouraged these days.

Fair warning though - look out for iguanas. This invasive species is taking over the upper keys.

Key West

Home to more than Jimmy Buffett

What to Do while you’re here...

Start off by just walking around! Key West is so lush and tropical, it’s hard to not enjoy a stroll through the neighborhood.

OK, this sounds (and maybe even looks) touristy - but hop on to the Conch Train tour. It’s a great way to get an entertaining overview of the city and get a crash course in the island’s  prominent and lesser known, but highly entertaining history.

Hemingway's writing studio and infamous swimming pool.

Hemingway's writing studio and infamous swimming pool.

Speaking of history, make some time to visit the Hemingway House (just get there early to avoid the line) and join one of the guided tours. The tours offer a plethora of anecdotes and background - as well as the science behind the generations of six-toed cats that reside over the property. There was so much more to Hemingway than i thought i knew, and it’s great to see the studio where he wrote the bulk of his works.

Exploring the Key West Garden club.

Exploring the Key West Garden club.

This trip we discovered what is likely Key West’s best kept secret - The Key West Garden Club. The Garden Club is a Civil War era fort right on the Atlantic that in 1955 was converted into a tropical garden. It’s free to the public, but judging by how few people were there when we visited, it’s relatively undiscovered. It’s only a few acres, but beautiful, shady and offers great views of the ocean.

Higgs Beach

Higgs Beach

The Garden Club is adjacent to Higgs beach, one of the few sandy beaches on Key West. It’s another excellent spot to relax, swim in the clear blue waters or stroll out on the pier.

Can’t decide between exploring island history or a day out on the water? Do both! Book a seat on a charter out to The Dry Tortugas and explore the island fortress on Fort Jefferson and dive the beautiful waters surrounding it. It’s the largest brick masonry structure in the states and the southernmost national park.

Lastly, every night Mallory square is host to an enormous celebration at sunset. As the sun sinks down into the gulf, performers, vendors and bars entertain thousands of visitors.


The Blue Macaw - home to what may be Florida's best cubano (sorry Miami!)

The Blue Macaw - home to what may be Florida's best cubano (sorry Miami!)

Where to Eat...

The Blue Macaw is a great spot which from the outside seems like your standard florida meets Caribbean restaurant, but all their dishes are uniquely elevated and outstanding. Home to possibly the best Cubano I’ve ever eaten

Tropical atmosphere and local lobster eggs Benedict - what's not to love at Blue Heaven!?

Tropical atmosphere and local lobster eggs Benedict - what's not to love at Blue Heaven!?

Blue Heaven. Blue Heaven is the kind of spot where you have to wait an hour or so to get a table, but you’ll hardly notice since there’s ping pong, great drinks and an amazing atmosphere under the shady canopy. Oh - and the food is totally worth the wait

Garbo’s Grill is tucked away behind a small bar - but make sure you stop by this airstream diner for some out of this world asian-fusion. I recommend the Korean BBQ (in either taco or burrito form)!

Kay agrees, Key Lime Pie on a stick is amazing!

Kay agrees, Key Lime Pie on a stick is amazing!

Top it all off with a visit to Kermits for some dark-chocolate-dipped Key Lime Pie on a stick. Is it gimmicky? Yes. Is it delicious? Hell yes.


Other Odds and Ends...

Wear comfortable shoes - it’s a small island, but you’ll do enough walking to regret only packing flip flops. That, and flip flop tans are the worst.

Yeah, there are roosters and chickens everywhere. After cockfighting was banned, all they just sort of took over.

If it's in season - get some hogfish. They're hard to come by north of the Keys, and its a very good fish. Just don't get it fried - you can do better.

Speaking of fish - there are a ton of restaurants that will cook your catch. 

It’s Florida - the southernmost part of Florida at that, so it can get pretty hot. While the weather is great in the winter, that’s when you’ll find the biggest crowds so book your trip in the shoulder seasons.

Don’t forget your sunscreen!