Here is a complete 6 day Key West Itinerary for you and your family. Follow this itinerary to have the most amazing tropical vacation in America’s little slice of paradise.
Day 1-Arrival Day
Fly directly into Key West airport. We actually flew Allegiant Airlines direct from BNA and it was a short, easy flight.
Check into your hotel. We stayed at Havana Cabana and could not have been more pleased with our hotel choice. It was a very family friendly atmosphere with spacious rooms and an amazing pool area.
Chill out and relax at the resort pool for a few hours to rest up from your travel day and then head to dinner at First Flight. This restaurant is on the site of where the first international flight took off from the US (hence the name). The food and drinks were fantastic.
Day 2-Lunch at the most famous restaurant on the island
Take a slow start to your day and head to lunch at the famous Blue Heaven restaurant in the Bahama Village area of Key West. This restaurant is famous for it’s key lime pie and it did not disappoint. Be prepared for a wait though. We waited around an hour, but there are plenty of shops across the street to keep you busy while you wait on your table.
After lunch, head to the Butterfly Conservatory. This place is great for kids. There are so many beautiful butterflies to see and even flamingos. My kids loved this.
After the museum, we came back to the hotel to enjoy the resort pool some more. There is a pool bar with amazing drinks and food as well as lawn games scattered around the pool. So there is so much to do and keep you busy while at the pool.
That night head to dinner at the Southernmost Beach Cafe. It sits right on the water and has the most beautiful views. The food here was really good as well.
Day 3-Islamorada
We took this day to take a scenic drive up the Florida Keys. We drove up to Islamorada to spend the day at Robbie’s. This place is such a cool spot. They have a restaurant, food trucks, kayaks, paddle boards, etc. It is like a one stop shop for fun activities in the Keys.
You can also feed the Tarpon here, but watch out for the pelicans. Those pelicans are ruthless and will try to steal the fish out of your hand before the tarpon can take it. Andy found this out the hard way.
We drove back to Key West that afternoon and walked up and down Duval Street and shopped around. We stopped in at Kermit’s on Duval and had the chocolate dipped frozen key lime pie and wow…this was AMAZING!
Day 4-Beach Day and Tour
On Day 4, we decided to have a beach day that morning. We chose Smathers Beach. This is a sandy beach with beautiful palm trees lining the beach. You can rent beach chairs, jet skis, paddle boards and several other water sport activities here.
Then head to lunch at Moondog Cafe. We loved this restaurant and this place actually had my favorite piece of Key Lime Pie that we tried on the island.
After a late lunch, we took the Conch Train Tour and this was a definite must do. It was one of our favorite things we did on the island. The train takes you all around the island of Key West with a tour guide showcasing many amazing things around the island. They tell you some interesting facts, the history of Key West and point out things you likely never knew about this fabulous island. The best part is that this train tour is a hop on/hop off tour with many stops where you can hop off and explore.
We hopped off at the Southernmost Point and snapped a quick pic and then headed to the Key West Lighthouse where we were able to climb to the top and see Key West from up high. The views up here are just beautiful.
That night head to dinner at El Meson de Pepe for the most amazing Cuban Cuisine. I love Cuban food and don’t get to have it often, so this is an amazing treat.
Day 5-Boating Excursion
Head to grab some breakfast at Glazed Donuts. These donuts were excellent. Be sure you grab the famous Key Lime Donut that has been featured on the Food Network.
Now it’s time to head to your boating excursion. We booked our excursion with the Get Your Guide app. The excursion was through Sunset Watersports. It was such a unique experience where you actually get to captain your own boat and drive it to a hidden paradise (island) where you will snorkel, explore the island and swim around. This was our favorite thing we did during our time in the Keys.
That night head to dinner at the Seaside Cafe at the Mansion. Get the lobster pizza and enjoy the most beautiful views while you eat.
Day 6-Beach and Hemingway Museum
That morning head to the Fort Zachary Taylor State Beach. The water here is absolutely stunning. I feel like this a bit of a hidden gem for beaches in Key West. There are also picnic tables and grills around so you can have a great beach day here.
After the beach head to the Hemingway House Museum. It is really amazing to read all about his life in the Keys and see where he wrote so many American classics. I don’t think you can come to Key West without doing this. Hemingway is such a staple in our American culture. Remember, the Hemingway Home accepts cash only for entry.
That evening it is time to head home and leave this tropical paradise behind. Until next time Key West. You will definitely want to come back to this beautiful island.
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