Key West is a fun city with some interesting history, lots of attractions, good shopping and good food, so here is our list of Things To Do in Key West.
If you want to do the road trip from Miami to Key West, check out our Miami to Key West Drive: The 20 Best Stops here.
Where to Stay in Key West
Parking is very difficult in Key West, so we opted for a hotel that was close to Mallory Square and close to most of the restaurants, shopping and main attractions. If you choose a hotel farther away from the main attractions, that is fine, but I would plan to use Uber instead of looking for parking.
We stayed at the Opal Key Resort and Marina and loved it.
Click here for other hotels in the area to consider.
For most of our time, we left our rental car in the hotel parking garage and walked around, but if it was too hot or we were in a hurry, then we would call an Uber and that worked great.
When to Go to Key West
Key West has great weather all year; however, consider these when planning your trip:
- Hurricane season starts June 1 and ends November 30. Historically, the chances of hurricane activity are greater between August 15 and October 15.
- The busiest season is around Christmas into early January.
- March through May is a great time, especially before school is out, because it is warmer, but not too hot and not too crowded with summer vacationers.
Things to Do
Sunset Celebration at Mallory Square
One of the evenings that you are staying in Key West, make sure to go to Mallory Square before the sunset. This nightly event started in the late 1960s! It begins two hours before sunset, and everyone is invited to watch the beautiful sunset as the sun sinks into the horizon.
The nightly festival hosts visitors from all over the world. You will be entertained by the magicians, jugglers, clowns, and local musicians.
You can also shop local artists and enjoy food and drinks from the nearby vendors. It is a fun time to be outside and enjoy the talented performers!
Hemingway Home and Museum
The Ernest Hemingway Home was the residence of American writer Ernest Hemingway in the 1930s. The house is at 907 Whitehead Street, across from the Key West Lighthouse. This home is the most popular tourist attraction in Key West.
The house is also famous for its many cats that live there, commonly called Hemingway cats. Around half are polydactyl, meaning that they have six toes on each paw. The cats are named after celebrities like Humphrey Bogart or Marilyn Monroe. You can see many of them lounging in the house as in the photo below.
The entry fee includes a 30 minute guided tour which is very informative about the history of Ernest Hemingway and the house. The house is open daily, 365 days a year from 9 a.m. to 5 p.m.
You can just walk in for a tour as no reservations are required. Please note that it is currently cash only for admission.
Hemingway’s pool is massive, being 24 feet wide and 60 feet long. It goes from 5 feet deep in the shallow end to a depth of 10 feet in the deep end and holds over 80,000 gallons of water. It was built in 1938 for only $20,000, but that is equal to $414,000 in 2022 dollars! Ernest complained about the growing cost of construction. Supposedly, Ernest was so upset about the costs that he flung a penny on the pool patio and said to his wife, “Pauline, you’ve spent all but my last penny, so you might as well have that!” Whether the story is true or not, you can see a penny embedded in the cement at the North end of the pool and shown in the photo below.
Hemingway’s writing studio is upstairs in a separate building from the main house. You definitely want to peek into his studio, so make sure you go up the outside stairs to see it. Hemingway wrote every day in the morning from first light until about noon. You can see his studio in the photo below.
If you are a reader and interested in Hemingway’s works, here are arguably, his top 3 novels. Pick one up and read it while you are chilling in Key West!
Harry S. Truman Little White House
The Harry S. Truman Little White House was originally on the waterfront when it was built in 1890. It served as the first officer’s quarters on the U.S. naval station. In 1911 the building was converted into a single-family dwelling to house the base commandant.
In November 1946, President Truman had finished 19 months in office, but was physically exhausted. His doctor ordered a vacation somewhere warm. Truman arrived in November 1946 and when he left he promised to return when he felt the need for rest. His next vacation here came in March 1947. Truman had additional visits every November through December and every February through March. Truman realized that where the President was, the White House was. Documents issued from the Little White House read “The White House, US Naval Station, Key West, Florida.” Truman spent 175 days of his presidency at the Little White House.
During the time Truman was staying at the Little White House, various cabinet members and foreign officials were regular visitors for fishing trips and poker games.
The tour is 2.5 hours long and gives you good insight into Truman as a president and the history of the house and naval station. The Truman Little White House is open 7 days a week, 365 days a year including all holidays. You can find ticket prices here.
Key West Lighthouse and Keeper’s Quarters
Key West Lighthouse and Keeper’s Quarters opened in 1848 and over the years had a number of upgrades including adding a Keeper’s Quarters and finally, electric light. In 1969, the Coast Guard decommissioned the Key West Lighthouse since new technology made the lighthouse obsolete. Today, this lighthouse stands as a museum dedicated to Key West’s maritime heritage.
You can walk up the 88 steps to the top of the light as well as explore the belongings, photographs, and words of the lighthouse Keepers.
If you are interested, you can schedule a Key West Lighthouse Sunset Experience. The price is not cheap, but available for small groups (2-4 people), large groups (5-8 people) or a proposal package if you want to propose to your significant other.
Dry Tortugas National Park
We so wanted to spend a day at Dry Tortugas National Park, but the transportation to this island gets booked up months in advance, so if you want to do this you will need to plan in advance. If you can’t do it, don’t be too discouraged, as we did a wonderful full day Sail, Snorkel and Kayak tour that was fabulous! You will learn about it in the next section.
You can get to the park by ferry boat or seaplane.
You can snorkel and swim around various areas.
If you want to dive, you must bring your own equipment with your own boat as pressurized tanks are not allowed on the ferry or seaplane.
While you are on the island you can tour Fort Jefferson. If you get to the island by the ferry boat, you can join a 60 minute tour of the fort from one of their employees.
Sail, Snorkel and Kayak Tour
We had an awesome time with Danger Charters on our Full Day Premium Sail, Snorkel and Kayak tour. The tour was from 10am until 4:30pm and included lunch which served an awesome Curry Chicken Salad.
We sailed the Key West waters aboard a classic 65 foot schooner to the Key West National Wildlife Refuge. In the refuge, we were able to snorkel through the sponge gardens and over coral patch reefs in very clear water. After snorkeling, we then took kayaks to explore around a mangrove island.
Check out this video of our tour and during the snorkel part of the video, you will see many different sea creatures. For the kayak part of the tour, you can see the mangrove island up close.
If you want to take some amazing underwater video, then get an affordable GoPro camera from Amazon. We used a GoPro Hero 8.
Also, you can take your phone on the kayak with this waterproof phone pouch.
Visit the Southern Most Point of the U.S.A.
Visit the Southern Most Point of the U.S.A. and get someone to take your photo!
You can find this buoy at the corner of Whitehead St. and South St.
There is often a line and in the summer, it can be quite hot, so bring a bottle of cold water with you.
Duvall Street
Duval Street is the main street for shopping, bars and restaurants. It cuts across Key West, starting from near Mallory Square to the other side of the island. Make sure you plan some time to just wander around Duval and the surrounding streets to check out the shops, bars and restaurants.
You can visit Sloppy Joe’s Restaurant and Bar at the corner of Duval St. and Greene St. where they have live music daily.
Shipwreck Museum and Tower
The Key West Shipwreck Museum and Tower is well worth a visit to learn the unique history of Key West.
Between the 1850s and 1921, around 100 ships per day passed by Key West. The waters around Key West were well known as some of the most treacherous in the world. On average, at least one ship per week would wreck somewhere along the Florida Reef.
During that time, wreckers as they were called would watch the reef night and day from observation towers. Some were over 90 feet high. When a wreck was spotted, they would yell “Wreck Ashore” and the wreckers would race to the reef to be the first to reach the wreck. This was financially important to the wreckers as the first man to reach the wreck became the “wrecking master” who controlled the salvage operation and got a larger share of the salvage. The goods salvaged were sold at auction and the wrecking courts awarded between 25 and 50 percent of the profit to the wreckers. This made Key West one of the richest cities in America.
In this museum you will learn about the wreckers and see some of the treasure that has been recovered.
You can also go to the top of the tower and get a great view of Key West.
Mel Fisher Maritime Museum
The Mel Fisher Maritime Museum gives a view of the life of a treasure hunter along with many exhibits on shipwreck archaeology. You will get to see a variety of treasures recovered from the treasure and slave ships that once sailed the waters near the Florida coast. You will definitely want to see the magnificent gold, silver and jewels of the Spanish Treasure Galleons galleries.
The museum is open 365 days a year and is located at 200 Greene Street.
Key West Post Card Photo Spot
This Key West Postcard Photo Spot is on the side of the Cuban Coffee Queen. Ask someone to take your photo and take this postcard home.
This is the place for great Cuban coffee, so buy some to enjoy while you are there and buy some to take home. There are a few difference locations, so make sure you go to the waterfront one at 284 Margaret Street.
If you do not have an espresso maker, I would recommend purchasing this affordable Classic Stovetop Espresso Maker from Amazon. It is so easy to use, and you put it right on your stovetop. In addition, it is small so it will store easily, and there are three sizes: 3-cup, 5-cup and 8-cup. This one is a 5 cup. There are several colors to choose from, so you can get your favorite.
Take a Photo of a Key West Gypsy Chicken
There are lots of roosters and chickens that roam around the streets of Key West, and they have been dubbed Key West Gypsy Chickens by the locals. The one below was outside of our hotel room and provided an early wakeup call each morning!
These birds are so prevalent, that you can even get rooster souvenirs in the shops, like the T-Shirt below where the rooster is touting that they own this town! You will certainly see them walking in and out of restaurants like they own this town! They are beautiful and add to the charm of Key West.
Mile Post 0 Photo Spot
If you look closely at the sign on the corner behind us in the photo below, you will see Mile Post 0 for Florida Highway 1. It is a cool spot to take a selfie.
Places to Eat
There are many great places to eat in Key West. Here are the ones that we enjoyed and one that got away! If you plan in advance you don’t have to let the last one on our list below get away.
Bagatelle
The Bagatelle Restaurant is located at 115 Duval Street, close to Mallory Square and is in a historic, architecturally beautiful building, built in the 1800s.
We went here for dinner one night and it was very crowded. We ended up eating at the bar, which was fine, and better than waiting longer.
We started with a Crab Cake, which was delicious!
I had the Chicken Caesar Salad.
My husband had a special salad with apples, cranberries, candied walnuts, bacon and blue cheese and he loved it!
Caroline’s Cafe
Caroline’s Cafe is located at 310 Duval Street. We stopped in for a lunch and enjoyed the outdoor patio.
Try some Conch Fritters if you haven’t ever had them. They are hushpuppies with finely chopped conch meat in them.
We also tried their Macon and Bacon Salad, which was good. It is made with fried chicken, corn, Vidalia onions, crunchy bacon, maple pecans, romaine lettuce, and homemade ranch dressing.
Clemente’s Wood-Fired Trolley Pizzeria
We chose to get wood fired pizza one evening and have a casual dinner at Clemente’s Wood-Fired Trolley Pizzeria which is located at 516 Fleming St. This pizzeria is off the beaten path and we enjoyed a nice dinner at a sidewalk table in the cool of the evening.
We chose to get one pizza with half meatball and half supreme. The pizza was really tasty with a thin crust.
Azur
The Azur Restaurant is a chef-owned restaurant located in Old Town Key West at 425 Grinnell St.
The restaurant serves Mediterranean specialties in their dining room or on their shaded terrace.
I had the special of the day, which was sea bass with shrimp, and it was delicious!
My husband had the branzino which he enjoyed every bit of, even with the work to get it off the bones.
We also had the pecorino-sesame fried cauliflower for a side dish to share.
Cafe Marquesa
The Cafe Marquesa is a small, but cozy, high-end eatery located at 600 Fleming St. It was the fanciest restaurant that we went to during our stay in Key West and included the requisite white tablecloths.
I had the Scottish salmon over asparagus with roasted eggplant and it was very good.
My husband had the filet with asparagus and French fries, and I must say that he devoured it!
For dessert we shared the beignets with powdered sugar, crème Anglaise and fresh berries. The beignets were crunchy on the outside but melt in your mouth soft on the inside and the crème Anglaise on them was awesome.
Garbo’s Grill
Garbo’s Grill is a food truck that makes some tasty tacos, burritos, hamburgers, hot dogs, poke bowls and lobster rolls! It is located at 409 Caroline St, behind Hank’s Saloon.
They have two Happy Hours with the first being 4pm-6pm and the second being 10pm to midnight. Happy Hour is the best time to go because you can get their Taco Trio with 1 Korean BBQ taco, 1 Cayo Fish taco and 1 Yum Yum Shrimp taco for a bargain price!
During Happy Hour, you can also get two Umami Sliders for a deal!
Latitudes
The Latitudes restaurant is the one that we couldn’t get into because all of the reservations were taken, so if you want to go there, make reservations way in advance as reservations are required! Their dinner menu looks fabulous!
And the view out the slide open doors looks amazing too!
This restaurant is not on Key West, but on a small island next to Key West called Sunset Key. So, you have to get there via a small shuttle boat that departs from the western edge of the island of Key West from Opal Key Resort and Marina. This boat travels just a mere 500 yards away, which is about a seven-minute ride to the dock at Sunset Key Cottages.
DID YOU Vacation in KEY WEST?
If so, leave a comment below about what you did and what you loved!
