Will your next cruise vacation or land vacation take you to beautiful Key West? If so, you may be wondering what you should do while your ship is in port. The possibilities are endless and more than one trip to this beautiful paradise is needed.
The first time that I had the pleasure of visiting Key West, I was overwhelmed in the most wonderful way. I wasn’t sure what I wanted to do. I just knew that I wanted to see and experience everything.
It doesn’t matter if you are a Key West newbie or experienced visitor, you might need some suggestions for your next visit. Keep reading for 12 of the best things to do in Key West while on a cruise.
1. Make the Trek to the Southernmost point
When visiting Key West, you might as well go as far south as possible, right? If that is your thought process, don’t miss a trip to the southernmost point.
Most have seen photos of the southernmost point buoy. It’s practically a rite of passage to visit the buoy and have your photo taken. While you are here, you are a mere 90 miles from Cuba.
Is this a tourist trap? Of course. Will you be waiting in line a while to have your photo taken? You better believe it!
2. Visit the Hemingway Home and Museum
It was practically unheard of to have an inground pool in Key West in the 1930’s. You’ll find that here and other luxuries of the legend, Ernest Hemingway.
The most unique element of the home is the presence of the six-toed cats. Ernest Hemingway was gifted a six-toed cat by a sea captain. The cats that live at the home today are descendants of the original pet of Hemingway.
To be fair, I cannot stand cats and six-toed cats sound like something out of an 80’s sci-fi film. But guess what? These cats guard the legacy of Hemingway and all things “Old Man and the Sea”.
3. Check out Captain Tony’s Saloon
If you want to indulge in a few drinks and eats where past local celebrities liked to hang out, be sure to visit Captain Tony’s Saloon. This location was originally built in 1851 and served as an icehouse. In fact, the icehouse doubled as the local morgue and is supposedly haunted.
Grab a pint and sit in the same spot as Jimmy Buffet, Truman Capote, Ernest Hemingway, and Tennessee Williams once sat. Don’t forget to pick up your very own Captain Tony’s Saloon t-shirt’s, books, koozies, and more.
I personally think this is the perfect dive bar for reasonably-priced, potent drinks. Pair a beverage and the chance at seeing a ghost. What more could you need?
4. Stroll Down Duval Street
The “key” to Key West’s party scene is Duval Street. This street is a mile long and was named after the first territorial governor of Florida, William Duval.
You can find almost anything on Duval Street. Souvenir shops are plentiful and local restaurants line this area with an abundance of choices. The world famous Sloppy Joe’s Bar is here and other favorites like Green Parrot Bar and Cowboy Bill’s Honkey Tonk Saloon.
Of course, there are plenty of options besides bars on Duval Street. A yearly Key West Food & Wine Festival is held here, amongst other events. We definitely recommend using the Old Town Trolley while visiting. This is a great hop-on, hop-off option for seeing Duval Street.
It’s pretty much a guarantee that you will not see the same sights twice on Duval Street. I remember wandering down Duval Street thinking, “This may be the funkiest and coolest street, this side of NOLA”.
5. Explore Mallory Square
At the center of Key West’s social scene, you will find Mallory Square. Surrounded by local merchants, restaurants, and museums, Mallory Square is an open-air plaza adjacent to the beautiful Key West waters.
There is truly something for everyone in Mallory Square. Check out a cup of specialty coffee at Cuban Coffee Queen or grab a bite to eat at Aqua D’Keys. If you have the chance to stay later in the day, sunsets are unforgettable here.
Wandering out to Mallory Square while visiting the shops is an incredible experience. Some of my best vacation photos were taken here and I cannot wait to return.
6. Take a Day Trip to Dry Tortugas National Park
For longer trips to Key West, visiting the Dry Tortugas National Park should be at the top of most lists. Located 70 miles to the west, this 100 square mile park is truly paradise.
You will need to ride a ferry to explore this oasis. It takes approximately 2 hours and 15 minutes to get to the park. You can explore Fort Jefferson, snorkel, or visit pristine beaches.
I”m not sure that there is a more beautiful beach in the United States. The water is a color of blue like no other and the snorkeling cannot be beat. My husband loves to snorkel and this would be first thing on his list for our next visit.
7. Grab Drinks at Sloppy Joe’s
The first word that comes to my mind when thinking of Sloppy Joe’s is “iconic”. Just passing by this bar makes me feel like I might run into Ernest Hemingway and join him for a beer. Visit Sloppy Joe’s in July, and you might see the yearly Hemingway Look-Alike Contest.
Music lovers will love spending time here. There is live music every single day of the year. Don’t leave without a souvenir t-shirt to remember this truly unique experience by.
Do not leave Key West without trying the award winning Sloppy Rita – Cazadores Reposado Tequila, Citronage, sour mix, orange juice, club soda, and lime. It is literally perfection in a glass.
8. Visit the Key West Cemetery
For something a little off the beaten path, take a trip to the Key West Cemetery. This historical cemetery was established in 1847 and is located at the corner of Margaret and Angela Streets. The cemetery is nineteen acres and the final resting place for a diverse group of citizens.
If you want to visit the cemetery, there are maps available at the entrance. Horror movie lovers like myself might be tempted to try a Ghosts & Gravestones Tour. I’m always up for a good ghost tour and Key West is no exception.
9. Take an Old Town Trolley Tour
For an easy and convenient way to see Key West, the Old Town Trolley Tour is a fantastic option. They offer a Hop-On, Hop-Off tour that features 13 different stops. After the purchase of a ticket, you can stop and return to the bus anytime that day.
A few of the possible stops for this tour include Mallory Square, Truman Little White House, Duval Street, Bahama Village, East Martello Fort, and the Southernmost Point.
For my family, an Old Town Trolley Tour is a must. We can “hop on” and “hop off” as much as we’d like, without having to worry about paying each individual time. Look into purchasing your tickets ahead of time for additional perks and discounts.
10. Stop by Blue Heaven for Lunch
Blue Heaven is a local favorite serving some of the tastiest, freshest food around. The restaurant is open for breakfast, lunch, and dinner. Reservations are an option for dinner only. The atmosphere is incredibly authentic here. Art in the form of a leopard-spotted mannequin is the norm.
Variety is key at Blue Heaven. The Caribbean “BBQ” Shrimp is a favorite, as is the Famous Key Lime Pie.
Personally, I think Blue Heaven has one of the best vibes anywhere. If you look in the dictionary for “Blue Heaven Key West”, you are likely to see the phrase, “Key West charm and deliciousness”.
11. Pick Out a Perfect Pair of Soles at Kino Sandals
A real treat awaits those who decide to visit Kino Sandals. Since 1966, this Key West establishment has provided the best in handmade leather sandals, created by Roberto “Kino” Lopez himself. Kino moved to Key West from Cuba in the 60’s and along with his wife, created a lasting Key West tradition.
You can visit the store and choose from over 17 different styles of sandals. Plan some extra time for this stop and you may be able to see the artisans crafting the sandals.
For the price and the craftsmanship, Kino Sandals are hard to compete with. I am personally a fan of the “Thin Strap” design in the Ladies line. I cannot wait to add another pair to my shoe collection. My husband doesn’t need to know that.
12. Catch a World-Famous Sunset
Sunsets in Key West are “World Famous” for a reason. They are arguably some of the most beautiful you will ever experience. Visitors will make their way to Mallory Square 1 or 2 hours before the event. Definitely plan to watch the sunset from Mallory Square or on one of several sunset cruises.
A sunset in Key West is something that will live on in your memory forever. For me, it is right up there with the first “Hairy Chest Contest” I witnessed on the Carnival Fantasy.
Hopefully our extensive list will help you to plan your next Key West stop. The possibilities are limitless and there is something for everyone. What do you plan to do on your next trip to Key West?
