The city on an island! Roosters roam free, the nightlife is incredible, and you get to live the island life.

Key West, FL, USA

Key West in 4 Days

American Airlines Flight

American Airlines has a direct, roundtrip flight to Key West. This is the flight I took, and it ended up being the cheapest.

I stayed at the Hyatt Centric, and the ocean views were amazing! At the front lobby they had turtles you could feed and a parrot named Odie. Celebrities eat dinner at the restaurant on the resort called Shor. They also had excursions and bike/golf cart rentals available. You can even get breakfasts from Shor included in your room as well as a complimentary 2 hour bike rental. They also have a spa attatched.

Blue Heaven is an open air restaurant. There is live music, an artist in a small open studio within the restaurant's yard, a gift shop attatched filled with local art, and the Blue Heaven cats roam around to greet customers. The food was exceptional and lives up to the amazing reviews. There can be a long wait (ours was 1 hour and 25 minutes), so put your name in early.

Shopping we did while waiting for our table

Right across the street from Blue Heaven.

Here you can meet the famous six-toed cats. They were the highlight of the tour, but you also get to see Hemingway’s House and writing studio where he wrote some of his most famous works. It is cash only entry.

This is the Southernmost point of the U.S. It is a frequent tourist spot, and it is one of the most common photo ops in Key West. This means get there early because there is usually a long line to take a picture with it. I recommended going to look at it and then walking a short way down the street to take a picture with the replica at the Southernmost Point Bar located at the Southernmost Point Guest House.

This was a beautiful, botanical conservatory located near the Southernmost Point. It was filled with butterflies, birds, and two flamingos who are famous on the island. The gift shop was also super cool.

This place was awesome for a light lunch and amazing smoothies. It was an open garden seating area tucked away with an RV in the back with a service window where you place your orders. The owner has a French Bulldog who comes out to greet customers and is so so sweet.

This place had fresh seafood and was on the water. You can walk the docks to see all of the nightlife while you wait for your table.

On the same docks as The Conch Republic Seafood Company, there is a station where people clean the fish they catch for the day. Watching them feed the pelicans and the HUGE tarpons was pretty neat.

The cuban food here was to die for. Also the interior was so cool. It was modeled like an outdoor market. There was a dance floor and stage right off of the Historic Mallory Square leading to the restaurant which was so much fun. Make sure you try the cuban bread here!

The Haunted Tour was on the Trolley of Doom. It takes you through the island, revealing haunted stories about the historical bulidings and destinations, including entry into the Shipwreck Museum with Spanish cursed treasure.

This was the restaurant at our hotel. The food was so good and the ocean views were beautiful. The Duval Crawl Relief drink was great for hangovers.

Dry Tortugas Is one of the most inaccesible national parks in the U.S. On the island Dry Tortugas there is an old military fort called Fort Jefferson which you can wander through and explore. The snorkeling there is amazing, and the views from the top of the fort were incredible.

There is a ferry you can take, but it takes around three hours and is packed with people. The seaplane takes a private or semi-private group over to the island as a guided tour. It only takes about 45 minutes. Also, it can take you at a time when the ferrying is leaving with all the people, that way you get the island mostly to yourself. On the plane ride you get to see all kinds of sea creatures and two shipwrecks. It was so fascinating. Try to get pilot Kris because he was awesome! The seaplane also comes with a cooler full of waters and sodas of your choice and snorkeling gear.

Explore Fort Jefferson, Snorkel, and Get your National Park Passport stamped at the bookstore

We went on a Saturday night so Duval was packed. Duval Street is the main party street on Key West. It is reminiscent of New Orleans French Quarter. The Duval Crawl is a tradition of the island where you do a bar crawl down Duval Street. These are the bars we went to.

Amazing band, some good dancing, & great vodka crans! It's an open air bar and the crowd was so energetic. It is a small dance floor, but that did not stop anyone from getting down.

Can you say Rock N' Roll? This place had an awesome rock band with classic rock tunes, an amazing stage with great lighting, and a spacious dance floor.

This place had THE BEST losbter roll. It was expensive but totally worth it. It was also featured in Diners, Drive-Ins, and Dives.

They have a fresh coconut bar where they pierce a coconut open to drink from. They were so refreshing.

A local artists sits out front of The Crowne Plaza and makes custom wire art. He makes it in less than ten minutes and can recreate an image from your phone. He accpts cash, paypal, and payment methods that can be used with Square. He recreated my dog for me!

This is the rum distillery on the island which is dedicated to Ernest Hemingway. They do a tasting of their in house rums, both the light and the dark, which was entertaining. They also do specially crafted cocktails using the rums. You can even take a tour of the distillery. Don't forget to pick up your own bottle while you're there. Maybe you'll get lucky and catch them when they are selling limited edition bottles.

Island Jane Charters picked us up at our hotel's Hyatt Centric Dock. We took a beautiful, peaceful sunset sail on the glistening, blue waters. We had a first stewart who was so sweet. She brought us drinks during our sail including champagne, margaritas, wine, and of course ice-cold waters.

The food here was phenomenal especially the mac and cheese. The vibes here were super chill and laid back.

Activity: Sailing Sunset Charter with Island Jane

Dessert before Dinner: Kermit's Key Lime Shoppe

Make sure you get key lime pie from Kermit's. Try their pie on a stick and their key lime ice cream. All super delicious.

This place was right on the docks and had the best bar snacks! Also try the Chocolate Covered Pretzel Shooter (it tasted just like one). There was a great singer, but the coolest part was siging a dollar bill to staple up in the restaurant. It is an open air resaurant, but the entire interior is covered is signed dollar bills.

GET THE KEY WESTER AND A FRAPPE WITH VANILLA & CARAMEL! The key wester is an amazing breakfast sandwhich made with the most delicious cuban bread.

Key West in 4 Days

Buy to unlock full guide