Disclosure: This post may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no extra cost for you!
Heading to Florida soon and looking for an awesome Key West Itinerary to help you plan your stay in the Keys? We are here to help! Key West is a magical place.
There is nothing quite like it. It’s lively, vibrant, fun and has loads to offer. If you love water activities and historical landmarks, you will also be in for a treat! Basically, there is a bit of everything for everyone!
🗒️ Planning a trip to Key West?
Whether you are already in the Key West or just want the short version of this article, here is the practical information you need to know.
☀️ Top Experiences To Book in Advance in the Key West:
- Ghost and Gravestones Trolley Tour in Key West (fun and top-rated)
- Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres (most popular cruise)
- Dolphin Watching and Snorkeling Eco Cruise Tour
🛌 Top Hotel in the Keys:
- Luxury: H2O Suites
- Mid-range: Courtney’s Place Historic Cottages & Inns
🚗 Need a car?
Click here to see the best car rental rates in Key West.
In this ultimate Key West weekend itinerary, we tell you exactly how to spend a 2 days in Key West.
Day 1 focuses on Old Town, Duval Street and the famous sunset celebration. Day 2 takes you to Key West’s most iconic landmarks.
✈️ How to get to Key West
Key West is located at the very end of the Florida Keys.
There are 2 ways you can get there.
- Flying to Key West Airport. There are many flights going there every day. You should be able to find direct flights from all the main cities in the US. This is best for people coming for a weekend and who don’t have time to spare in transport. It’s also worth noting that it will be more expensive than flying to Miami.
- Flying to Miami and going on a road trip to Key West. Miami Airport is ideally located near the beginning of the keys. This is particularly convenient especially since there are loads of cheap flights to Miami (domestic and international).
From Miami, rent a car and go on a road trip through the Florida Keys.
Not only is this a cheaper option but it’s also an incredible trip! The keys are known to be one of the best road trips in America.
There is a lot to discover along the way and you can be sure to have a great time.
🛌 Where to stay in Key West
The best neighborhoods to stay in Key West are the Old Town and Duval Street.
If you truly want to experience the local atmosphere, that’s where you will find it! That said, these are considered as luxury locations so they won’t be ideal if you are on a budget.
Here are some recommendations of places to stay in Key West for all budgets!
💲 💲 💲 Luxury accommodation in Key West: H2O Suites is a luxury resort located in the southern part of Key West, near Duval Street. It’s perfect for people who want to be in a quiet location while still be very close to the main attractions. The suites are fantastic and even have a private pool!
💲 💲 Mid-range: Courtney’s Place Historic Cottages & Inns is a cute guest house in the Historic center with outdoor pool.
💲 Budget accommodation: There is no such thing as cheap accommodation in Key West. Even a bed in a dorm can cost as much as a hotel room elsewhere in Florida. The best option for travelers on a budget is Authors Key West Guesthouse. It’s a bit out of town but it’s great value for money.
The Ultimate Key West Itinerary for 2 Days
Let’s dive into the good stuff now and discover the best things to do in Key West!
Key West Itinerary Day 1: Dolphin Cruise, Downtown Key West, Duval Street & Sunset Celebration
The first day in Key West starts on the water and then continues on foot around town. It’s a vibrant and lively place. You will feel like being in the Caribbean! Key West is a small town so once you are back on land you can do everything on foot! We’ve packed quite a few sites on this first day so be ready for a full one!
Stop 1: Dolphin Cruise
Key West is a paradise for water lovers and one of the best places in Florida to see dolphins.
For this reason, I’d recommend starting your trip with a dolphin Watch and Snorkel Eco Tour.
It’s a 3-hour cruise which means it will keep you busy the entire morning. The first cruise starts at 9AM and that’s ideal.
You will be able to see wild dolphins (or at least it’s very likely but nobody can really make promises when it comes to wildlife).
You will also be provided snorkeling equipment and should be able to see loads of different fish.
Make sure to take a waterproof camera or bag for your phone.
Alternatively, there are plenty of other water activities you can do. Here are some ideas:
- SNUBA. This is a unique activity that you don’t get to find everywhere. It’s basically a hybrid between scuba diving and snorkeling. You don’t need a PADI to do it, you just need to know how to swim. You will be given a mask but instead of having a tuba, you will be connected by a long tube. This is great as you can stay underwater for longer (as you would if you were scuba diving) but don’t have to deal with the hassle of carrying the equipment.
- Sailing cruise. If you don’t want to go in the water, you should consider going on a cruise. That’s a great way to discover beautiful views of Key West and Fort Zachary State Park.
- Parasailing flights. This one is for the adventurers out there! If you want to take a bit of height and enjoy some thrilling (pun intended) views of Key West, parasailing will be perfect for you.
Stop 2: Mallory Square
Once you are back on dry land, make your way to Mallory Square.
This is one of the most famous attractions in Key West however, no need to spend too much time here now as you will come back for the sunset celebration.
Stop 3: Key West Historic Memorial Sculpture Garden
From Mallory Square, walk a couple of minutes to Key West Historic Memorial Sculpture Garden.
You will find busts of some of the most famous Key Westers.
These people have made Key West what it is today!
Under each sculpture, you will find a biography that explains who they were and what they did.
Stop 4: Key West Shipwreck Museum
Keep walking on Wall Street. You will find, just around the corner, the Key West Shipwreck Museum.
This is a good place to visit with kids as it’s very interactive.
That said, even as an adult, you will love it. Key West (and the Florida Keys in general) has always been a paradise for sailors.
Hundreds of boats go by every day and visiting the museum is a unique opportunity to learn more about the history of sailing in Key West.
It is a recreation park set in a 19th-century warehouse. It’s super fun and very cute!
You can buy your tickets on-site.
If you don’t feel like visiting the museum, that’s fine too. Just walk by, take some photos and keep going!
Stop 5: Clinton Square Market
Clinton Square Market is a historic building that used to be a US Navy depot and storehouse, and later the local Coast Guard headquarters. It is now home to loads of shops. If you want to find some unique souvenirs that could be a good place to do so.
Stop 6: Mel Fisher Maritime Museum
Just a minute walk from Clinton Square Market is Mel Fisher Maritime Museum.
This is another museum dedicated to shipwrecks and the maritime industry in Key West.
Unlike the Shipwreck Museum, this one is more of what we can describe as a “normal” museum.
It’s a good place to visit if you want to learn more about this.
If not, just stop for a bit to look at the building and take photos. It is a historic building and it’s quite pretty.
Once you’re done, walk down Front Street for a couple of minutes until you reach the famous Truman Little White House.
Stop 7: Truman Little White House
Located on the edge of the Old Town, this house is one of the most famous landmarks in Key West! It used to be President Truman winter house!
It was built in 1890 but Truman only started visiting in 1946.
He came 11 times altogether to enjoy fishing trips and a bit of a break. He visited both while he was in office and afterwards.
The reason why this house is now so famous is that President Truman wasn’t the only one who stayed in this Key West house.
Thomas Edison stayed in the house back in 1918, while he was working on naval weapons research during WWI. Eisenhower used it too: first for meetings in 1948 and 1949, then as president in 1955 and 1956.
There are many interesting stories to learn at the Little White House which is why we highly recommend going on a guided tour. You will learn so much!
Stop 8: Sunset Celebration at Mallory Square
The sunset celebration is Key West’s most beloved event! It has been going on since the 60s!
Every evening, people gather at Mallory Square to watch the sunset.
It starts a couple of hours before sunset. Sunset times vary a lot through the year, from around 5:40 PM in December to about 8:20 PM in June, so make sure to check the time for your dates.
Try to get there a bit early so you can find somewhere to sit on the edge.
If you’ve been running late and it’s already crowded, make your way towards the bars on the righthand side. It usually is less busy.
Your last option is to go for a drink in one of the bars.
They aren’t the cheapest but you will get to sit at one of their tables and enjoy the view. The sunset truly is beautiful.
The colors are incredible! Also, there is live music and performers on the square. All in all, it’s a magical experience!
Alternatively, you can opt for one of the sunset cruises.
It’s a bit different as you won’t get that “Mallory Square” feels but watching the sunset from a catamaran definitely is something you will love.
Click here to see the latest prices.
Stop 9: Duval Street at night
Duval Street is an incredible place at night and the atmosphere is completely different from the daytime.
Once you are done with the sunset celebration, make your way to Duval Street.
By then, the atmosphere should have gone up a notch.
People are ready to have fun and party!
Walk up and down the street, grab a drink, dance a bit (in a bar or in the street, it’s Key West, nobody cares!), sing a bit. Have fun!
You will be back on Duval Street tomorrow to see it in the daylight, so don’t try to do everything tonight!
Key West Itinerary Day 2: Hemingway Home, Southernmost Point & Ghost Tour
Day 2 is all about Key West’s most famous landmarks. Everything is within walking distance again so put your comfy shoes back on. You will finish the day with a ghost tour, so keep some energy for the evening!
Stop 1: Cornish Memorial A.M.E. Zion Church
Start your second day with a stop at the Cornish Memorial A.M.E. Zion Church.
It’s a pretty church completely white.
If you like architecture, you will appreciate it.
Stop 2: The Ernest Hemingway Home and Museum
It would be impossible to put together a Key West itinerary without mentioning the Ernest Hemingway Home and Museum as it is, without the shadow of a doubt, the most famous landmark in Key West.
Ernest Hemingway was a famous American journalist and novelist. He was born in Illinois but lived in Key West in the 1930s.
He served in WWI and was a journalist. Later on, he published novels including the famous The Sun Also Rises and The Old Man and the Sea, which won the Pulitzer Prize in 1953.
The house itself is beautiful and you will be impressed by the interior. You visit on your own or opt for a guided tour.
Quick fun fact: Ernest Hemingway was known for loving cats.
He owned several six-toes cats. The first one was gifted to him by a ship captain. As time went by, he ended up with many of them.
Nowadays, you can still find loads of six-toe cats in Key West and it is believed that it’s where they originated.
Stop 3: Key West Lighthouse
Key West Lighthouse is only a couple of minutes down the street from the Hemingway Home.
The first Key West lighthouse was built in 1825 but it was destroyed by a hurricane in 1846. The tower you can see today was completed in 1848.
With so many ships passing through the Straits of Florida, the need for a lighthouse appeared very quickly and that’s why it was built.
You can now visit the museum and the keeper’s quarters. It’s quite an interesting visit and the views from the top are fantastic!
You will have 88 steps to climb though.
Stop 4: Lunch at Blue Heaven
📍 Address: 729 Thomas St, Key West, FL 33040, United States
Blue Heaven is one of the best places to eat in Key West. It’s a tiny bit hidden which means that a lot of visitors miss out on it but that’s a mistake you won’t be making! It’s a very quirky restaurant.
You will never see anything quite like it! They offer both Caribbean and Floridian dishes.
It’s a great place to try some typical dishes and eat your first Key Lime Pie in Key West!
Stop 5: Southernmost Point
After lunch, head to Duval Street and walk all the way down to the Southernmost Point.
As the name may suggest, this is the southernmost point you can visit in the continental USA!
It is particularly famous for the Southernmost Point Buoy.
This landmark has become one of the most instagrammable spots in Key West.
If you were to only take one photo in Key West, that will be here!
You can enjoy the sea views and also take a look at the cute signs indicating the distance with famous cities in the world.
Once you are done, make sure to walk by the Southernmost House hotel as it’s very cute spot.
If you’d like to grab a coffee on the beach, head to the Southernmost Beach Cafe. They have giant chairs where you can take beautiful photos.
Stop 6: Duval Street
Now is time to discover Key West’s most famous street: Duval Street.
Duval Street is one of the most unique places you will find in the world.
There is no place like it! It’s full of bars, restaurants and shops.
It’s a place where Texan saloons stand next to Irish Pubs and Caribbean bars. Such a unique and amazing feel!
The best thing to do is to walk up the street.
Duval Street is worth exploring during the day and at night. It’s a completely different atmosphere in the evening so make sure to do both.
As you walk up, here are some of the best places to check out:
- The Bull & Whistle Bar: a Key West institution spread over three floors.
- The Strand Theater: the Art Deco facade is still there, though the building itself is now a Walgreens.
- Capt Tony’s Saloon
Make sure to stop in one of the bars along the way to get a drink.
Good to know: you are allowed to walk around with drinks in Key West so don’t hesitate to grab a cocktail and take it with you!
Stop 7: Ghost tour
Key West is one of the most haunted places in the United States.
If you like spooky stories and interesting tales, you will be in for a treat!
The best way to learn these stories is to go on a ghost tour. It’s a very popular activity here and for good reason, it’s amazing!
The best ghost tour in Key West is the Ghosts & Gravestones Tour of Key West. You will be on board of a trolley for about 1 hour. The guide will take you all around town.
It’s a great way to discover Key West at night, the history of the keys and of course, some spooky stories.
If you don’t like the idea of the trolley, you can also opt for a haunted pub walking tour. This one lasts 2 hours and includes both stories and drinks! See prices here.
Map of this Key West 2-Day Itinerary
You may also be interested in:
