2 Things You Should Never Do in Key West and 10 You Should

By Cacinda Maloney / Points and Travel

Key West is laid-back and beautiful, but also touristy — so it helps to know which attractions to hit, and which to avoid. I recently went back after not having visited for years during my college days. I had fond memories of riding bikes along the historic seaport area, sipping drinks in a Hemingway bar, and visiting the famous writer’s home and six-toed cats, but that was about it. How refreshing it was to revisit my old haunts, and to see what’s still worth a visit and what’s not worth the touristy trouble. 

What to do in Key West

Key West is laid-back and beautiful, but also touristy. It helps to know which attractions to hit, and which to avoid.  (Photo: Cacinda Maloney / Points and Travel)

1. Take the Conch Tour Train

This or one of the other tours (like the Old Town Trolly) is something I always recommend to anyone new to an area. Do this on your first or second day so you can get the lay of the land. This gives you an overview of what there is to see and do, and then you can go back to the places that interest you.

(Photo: Cacinda Maloney / Points and Travel)

2. Go to Fort Jefferson in the Dry Tortuga Islands

You can take a seaplane to Fort Jefferson (which I wholeheartedly recommend) or you can hop the ferry that goes out there every day. The seaplane, by far, was the highlight of the trip, as was the time spent on Dry Tortuga. The water here is gorgeous, and many Americans don’t even know this place exists.

You can thank me later for this piece of advice!

(Photo: Cacinda Maloney / Points and Travel)

3. Wander through Old Town’s prettiest streets and take photos of doors

If you are a regular reader of my blog Points and Travel, then you know it is one of my favorite things to do! I am a door nut and I love seeing how people decorate their front doors, so this is a must if you enjoy seeing different kinds of neighborhoods. There will even be a scattering of chickens or two from the old cock fighting days!

(Photo: Cacinda Maloney / Points and Travel)

4. Attend the Lower Keys Underwater Music Festival

If you’re visiting in July, don’t miss this unique concert at Looe Key Reef. A local radio station pipes marine-themed music under the water while hundreds of divers and snorkelers (in costume, of course) explore the reef. It’s an annual event, so put it on your calendar for next year.

(Photo: Cacinda Maloney / Points and Travel)


5. Stroll down Duvall Street

Shop, eat and drink your way around town at all the local hangouts — and there are many, including the famous Sloppy Joe’s Bar and Jimmy Buffet’s Margaritaville.

(Photo: Cacinda Maloney / Points and Travel)


6. Tour famous houses

From the Audubon House to Hemingway’s home and Harry S. Truman’s winter White House, there is a lot of history here to discover. This visit, I toured Ernest Hemingway’s Home and Museum. You can even pet Papa’s six-toed cats! It is quite interesting to walk around and to see where the writer did his thing. Or visit another kind of house, the Custom House, to learn about Key West’s history of pirates, smugglers, turtle people, artists, and more.

(Photo: Cacinda Maloney / Points and Travel)

7. Have breakfast at Blue Heaven

They put lobster on everything here — and of course, you have to have a slice of their Key Lime Pie!

(Photo: Cacinda Maloney / Points and Travel)

8. Watch the sun set on Sunset Key

Save a special night for dinner at Sunset Key’s Latitudes, located on an resort island in Key West Harbor. You can take the ferry over and stay until the sun sets. (Guaranteed to be a perfect evening!)

(Photo: Cacinda Maloney / Points and Travel)

9. Go to the end

Just do it: Take a photo of where Highway 1 ends!

(Photo: Cacinda Maloney / Points and Travel)

10. And if you get a chance…

You are only 90 miles from Cuba!

(Photo: Cacinda Maloney / Points and Travel)

Two Things You Should Skip in Key West

1. Mallory Square

Lots of people will advise you to go to Mallory Square to see where all the action is, but let me tell you: It is crowded, hectic, and crazy. There is a nice sunset from here, but you’ll have to watch it among the street performers and the crowds.

2. The Southernmost Point of the U.S.

You might also hear that you should drive to the concrete buoy that marks southernmost point of the United States, a popular place for tourist photos. It’s overrated. If you go, be prepared to stand in line in the muggy heat.

(Photo: Cacinda Maloney / Points and Travel)