So you’re planning a trip to Key West and need a little insider information. You came to the right place. During our two years of living in the Florida Keys, we visited Key West entirely too many times to admit, spent (and wasted due to our ignorance) too much money and had the greatest times too!
Below are some tips and tricks we picked up while down there. My hope is that you will learn from our mistakes and be able to make the most of your time while visiting that awesome island.
Parking is a challenge in many areas of Key West-especially if you want to be near Duval Street. There is no real free parking down there (unless you have a disabled parking pass-then you can park in any public space for free-even if it is not a handicapped spot).
They have parking garages (which are nice when it is August and roasting outside!), public parking lots, private parking lots and street parking. The parking garages cost the most. Oh, stay away from the Westin parking garage as they charge $20 for two hours! Eek! Naturally, it is the parking garage closest to Duval Street and you will probably see it and be tempted. Unless money is no object, there are other more affordable options.
The City of Key West has a parking garage off Grinnell St. It too is in Old Town but a little farther from the action. This is $3.00/hour with an $18/day max. There are trollies, buses and taxis throughout the island so you can easily get transported to your next destination if you do not want to walk. For reference, Sloppy Joes is 0.6 miles from the garage.
If you want to park on the street, the side streets are (versus trying to park on Duval) your best bet. If you arrive early enough in the day, you should be able to find a spot with some diligent hunting. We generally had good luck finding spots by checking out the side streets off Front Street near the Truman Little White House.
If that did not work, then our go-to parking lot was the one in front of the Conch Republic Seafood Company at 540 Greene Street. Of course, I cannot remember how much the parking was there but it was more reasonable than at the Westin.
One last thing on parking. Do NOT park in any of the lots that are labeled as Residential. You will get towed! Those are meant for Florida Keys residents only.
If you are staying overnight, make sure your hotel offers a shuttle to and from the various Key West attractions. Those shuttles are worth their weight in gold!
Eating in Key West can be quite the costly endeavor. Especially if you’re in Old Town. I relied on Yelp a lot. The best tasting and least expensive meals we had were at the Cuban restaurants. Cuban Coffee Queen was one of our most economical and yummiest places. We would hit them up for some black beans and rice, a glass of iced tea then head down to Smathers Beach for lunch. Seriously now. Does it get any better?!?
Another Cuban place we loved in a big way was Juan Loves Lucy on Duval Street. They do cost more. I paid $10.00 for a plate of black beans, rice and plaintains. It is in an interesting little spot stuck between two buildings. You walk between them and a courtyard opens up to the restaurant-that is basically open air. The manager was hysterical and sassy and I loved her the moment I saw her. Tip from Amy: Order a mojito! You cannot go wrong.
One of my favorite café’s (for the ambiance not the food) was Southernmost Beach Café. Man, did I love that place! The food. Eh. The service. Eh. The ambiance and the view. Woot!
We also loved Fogarty’s on Duval Street. Not the cheapest. Not the most expensive. Basically, all the tables are outside so you get a great view of everybody walking by. The menu is super extensive and even vegetarians like me can find something (not an easy thing in Key West).
We visited various museums and local attractions while down there. (you can’t just sit and drink ALL day!) Custom House, Mel Fisher Maritime Museum, Truman Little White House, Ernest Hemingway’s house, etc. I will go through some of them and give a very short blurb on each.
Mel Fisher Maritime Museum: Mel Fisher was the very focused guy who spent 16 years searching for two Spanish galleons off Key West. In 1985, he found the Atocha and a cool $450 million in treasure. Some of his treasures and artifacts from the sunken ship are displayed at the museum. Definitely a fun diversion.
Ernest Hemingway Home and Museum: If you’re an Ernest or cat fan, then this place is worth a visit. We went once since it cost $14 per person to get in. Ernest and Key West have quite the history together. The six toed cats are everywhere. The house is gorgeous and fun to wander through and dream about the old days.
Truman Little White House: What a great house and property! We took the free guided tour (there is an entrance fee) which was excellent and gave great information on the history of the house and who has visited over the years. The property is beautifully landscaped and kept up too.
Custom House: The Custom House is across the street from Mel Fisher’s museum. It is four floors of gorgeous architecture and artwork.
Not to be missed things to do
Old Town Trolley Tours: This hop on, hop off trolley tour is the most efficient and economical way to see Old Town. We have taken many friends on this guided tour and they all loved it. Big hint. They usually have a coupon available on Groupon that will save you some money.
Mallory Square: Sunset at Mallory Square is one of those staple things a person does when in Key West (similar to getting your picture taken next to the Southernmost Point buoy which frankly I do not see the appeal). Mallory Square though, has lots of free entertainment every evening. Locals are there with their acts hoping you’ll be so enamored you’ll throw a few bucks in their hats.
This can be anything from the unicycling duo, to the guy with trained cats, to a sword swallower. There are also street vendors with lots of fried foods for you to try. If you want an unhindered view of the sunset, go approximately an hour early and stake out your spot.
Smathers Beach: Smathers Beach is gorgeous and the reason we go to tropical islands. There is quite a bit of parking (and quite a bit of beach). Restrooms in multiple locations (consider bringing your own TP with you). And plenty of palm trees to hide under. The water is quite warm and has that wonderful Caribbean turquoise color we all drool over.
Some links for additional ideas on things to do in Key West
- https://www.lonelyplanet.com/usa/key-west/top-things-to-do/a/poi/361914 - Lonely Planet’s list is a long and detailed one.
I hope this list provided you with some ideas on what to do and how to do it down in the Conch Republic. It is one of the places you visit and never forget. Enjoy and vow to go back!