The Best of Key West - 5-day Itinerary

I recently turned 30 and when we were in search of someplace warm and sunny to celebrate - Key West was calling our names! Key West is part of the Florida Keys archipelago and is also Florida's southernmost point located roughly 90 miles north of Cuba which means lots of sunshine (it was in the 80s when we went in March). We flew direct from Chicago to Key West but many people also access the island from the mainland via the Overseas Highway. We didn't rent a car during our stay and found everything to be very walkable (aside from our Uber to and from the airport). Scooters, golf carts, and bike rentals can also be found on nearly every street corner. Keep reading to find out how we spent five days in the Conch Republic! 

Disclaimer: We were hosted for our stay at Best Western and on several of our activity tours. As always, all thoughts and opinions are my own.

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Where to Stay

We stayed at the Best Western Hibiscus which was a gorgeous property located along the Southernmost side of the island. The rooms were spacious and beautifully decorated and centered around the star of the show - the pool! Not being used to the Florida heat, we spent a lot of time in the pool and lounging in the cabanas. The hotel offered complimentary breakfast each morning which saved us a ton of money and was a great way to start our mornings without feeling rushed to beat the crowds at some of the most popular spots. 

The Best Western Hibiscus was also in such a great location for exploring the entire island. It was only a short walk from the many restaurants and bars along the famous Duval Street. A lot of our activities and tours were located in the Historic Seaport area which was a bit longer walk (around 1 mile each way) but still totally doable and I actually really enjoyed walking along the streets and admiring all the colorful houses and flowers. I can't recommend this property enough if you're looking for something that is both budget friendly and offers all the amenities for a relaxing getaway. 

Day 1 

We flew direct into Key West which I preferred as opposed to driving the 3+ hours from Miami. I do want to go back and explore more of the Florida Keys but I felt this option allowed us to really maximize our time in Key West. From the airport we took an Uber to Best Western to drop off our luggage and then walked to Moon Dog Cafe to grab lunch. Moon Dog is located in an adorable garden cottage next door to the historical Hemingway House if you wanted to stop there before or after your meal. There is a patio out front and a larger garden seating area in the back with fun and colorful murals on the walls and fence. They also have a bakery on site which had an amazing selection of pastries and other yummy baked goods. 

After lunch we walked down Whitehead Street which has some of the most beautiful houses to view the Key West Lighthouse. For $17/pp you can tour the museum on site and walk up the 88 steps to the top of the lighthouse which offers stunning panoramic views of the entire island. We continued our walk down to the iconic Southernmost Point buoy which is one of the most photographed spots in Key West. If you want a photo of yourself with the buoy expect to wait in a long line (or go early in the morning). I just snapped one from the side. 

That evening we tried Sinz Burritos for dinner as we were looking for something quick and easy. Sinz offers counter service with build your own burritos, tacos, and quesadillas. It was all very good and the servings were HUGE! In celebration of my birthday we ended the night at Better than Sex Desserts. This is an adults-only dessert restaurant with an intimate vibe. I highly suggest making reservations in advance if you can. They are known for their chocolate rimmed drinks and mouth-watering desserts which are definitely big enough to share (with names that are sure to make you blush).

Day 2

Most of our mornings were spent at the Best Western enjoying breakfast by the pool and lounging in the sun. In the afternoon we walked to the Historic Seaport area of Key West which is full of shops and restaurants. Stop by Cuban Coffee Queen to snap a photo with the famous "Greetings from Key West" mural. Next we went to Dante's Restaurant and Pool Bar and discovered this is where the party was at. The pool is available to use free of charge and they have several different tiki bars as well as a DJ most days. I was a bit skeptic to eat here because let's be honest, it's a pool bar, but the food was surprisingly good and the shrimp po boy was one of my favorite meals from our entire trip. We walked next door to Waterfront Brewery to check out the local craft beer scene. There was a wait but see if you can grab a seat at the bar if you're just getting a drink. I loved the Key Lime Pie beer on tap. 

We ended our evening aboard the Marquesa with Sebago Watersports for their Land's End Sunset Sail. Upon climbing aboard the catamaran you're greeted by the friendly crew members serving premium drinks from the open bar and Chef’s Selection of Hors d’Oeuvres. As you sail away from Historic Seaport you'll pass many famous Key West landmarks while enjoying live music from local musicians. And of course you can't forget about the star of the show as you watch a famous Key West sunset fade into the horizon. We had so much fun on this tour and the crew was fantastic! 

Day 3

We were back on the water today for an action-packed Ultimate Adventure with Fury Key West. If you're looking to get the best of all water activities in a short amount of time, this is the tour for you. The Ultimate Adventure includes jet skiing, parasailing, snorkeling, banana boat rides, and a water obstacle course. You'll also enjoy breakfast, lunch, and happy hour throughout the day. After checking in at the Historic Seaport dock we boarded the Fury Key West catamaran to take a short ride out to what they called their "playground" while enjoying a delicious spread of breakfast sandwiches, fruit, and yogurt. Once you arrive at the playground you'll rotate through each activity (aside from snorkeling) over the course of a few hours. We had SO much fun and the crew hosting each activity was fantastic. My favorite had to be parasailing - it felt like you were floating in the sky. 

Next, we enjoyed lunch during the hour boat ride to our snorkeling spot located at Sand Key which is part of the third largest living reef in the world. You're supplied with all your snorkel gear and reef-safe sunscreen and then get to hop in the water and take in the living wonders of the ocean. There was so much coral here and lots of species of colorful fish. On the boat ride back it's officially happy hour and you can enjoy and open bar serving up wine and beer - including a Key Lime lager. One of the most memorable days I've ever had - don't miss out on booking this tour!

While in Historic Seaport, be sure to stop by Kermit's Key Lime Shoppe for a slice of their famous key lime pie. You'll also find the chocolate covered pie on a stick here. Trust me, you can't visit the island and not try this famed dessert. For dinner, we had reservations at Nine One Five which is located in a stylish old house along Duval Street. They make all their own pastas and the lobster ravioli was so delicious. We were seated in the garden patio area out front of the house which had such a romantic vibe. If you don't have a reservation, you can also visit Point 5 which is located on the second level and is first come, first serve. End the night walking along Duval Street and popping in and out of any bar that catches your eye (trust me, there are a lot to choose from!) You can also take your drink to go and sip it while you walk to your next stop. I loved the house sangria at Old Town Tavern.

Day 4

This afternoon we were off to explore the Mallory Square district. First, we grabbed lunch on the colorful dock at Sunset Pier. The tables all line the water so you have a great view of the boats and jet skis while you enjoy your meal. From there we walked to Key West Aquarium where you can get up close and personal with some of the most fascinating creatures who call Key West home. While we were there we got to watch a live feeding at the Atlantic Shores Exhibit and learn more about the different species of fish. You'll also see turtles, sharks, jellyfish, and can interact with the live touch tank. Located right outside the aquarium is another Key West foodie find that you much try - conch fritters! These little balls of delicious are served fresh with a key lime mustard.

During the evening we stopped at Seaside Cafe at the Mansion for dinner. I had heard amazing things about their signature lobster pizza and it did not disappoint. You'll also be dining right on the water and if you're lucky enough to grab the table in the far corner you can claim you've ate at the Southernmost table in the US. They are also known for their mojito bar on site. From there we walked down Duval Street back to Mallory Square to catch the sunset. This is the place to be when the sun goes down in Key West and you'll find large crowds with street performers, food and drink stands, and live music. Be sure to claim your spot along the water if you're set on getting a front row view. 

To end the evening we boarded our Ghost and Gravestones tour to take a ride on the dark side of Key West. The tour takes you past a number of haunted homes as the guide tells you spooky tales of the island's history. You'll also drive past the African Slave Cemetery and get to go inside the Shipwreck Museum. Reservations are required and I recommend booking after the sun goes down. Don't worry, if you spook easily this tour rates higher on historic ghost tales as opposed to jump scares.

Day 5

We were scheduled to fly out later in the afternoon but had some time to kill before we had to check out of our hotel and couldn't let it go to waste. The Key West Butterfly House wasn't originally on my must see list but it was right down the street from the Best Western Hibiscus so I decided to walk over and was so glad I did. It was magical and I couldn't believe how many butterflies were flying around overhead. Try to go when they first open in the morning as it was so peaceful to be able to walk along the path with only a few other people. The Butterfly House is also home to several species of birds including two flamingos who were very vocal.

From here, walk down Duval Street to grab an iced cafe con leche from the famous Cuban Coffee Queen. You'll order at the walk up counter but don't let the line scare you away - they were very quick! For our last lunch on the island we tried Southernmost Beach Cafe. Key West certainly isn't known for its beaches but there was a small slice of sand here if you're looking to catch some sun. This spot was a little pricey for lunch in my opinion but has great views and is conveniently located if you're on the Southernmost side of the island. And that's a wrap on our trip! We took an Uber back to the airport and were on our way back to Michigan.