Weekend in Key West Itinerary

Planning a trip to Key West should be on everyone’s Florida bucket list! With tropical vibes, lively scenes, and blue waters, it’s a place you may never want to leave. I have been going to Key West since I was a kid. During those days, it was mainly fishing trips with my family.

Now, as an adult, I got a chance to re-experience Key West and all it has to offer. That is why I am sharing my ultimate weekend in Key West Itinerary, which includes the best things to do when touring this little slice of paradise. This weekend itinerary is perfect for anyone visiting Key West for 2-3 days – the day of the week doesn’t matter! A map with everything is at the end of this article!

If you didn’t already know, Florida has a strip of islands called the Keys. Key West is at the very tip of those islands. Some even say you can see Cuba from here, but I tried, and you can’t, lol.

Weekend in Key West itinerary - Smathers Beach
Smathers Beach – Weekend in Key West itinerary

Key West Itinerary Quick Overview

In case you’re in a rush, here is a quick overview of what to expect from this itinerary. Below, I will go into detail and add travel tips!

  • Day 1: Classic Key West landmarks and attractions, including The Hemmingway Home, the Key West Lighthouse, Duval Street, and more.
  • Day 2: A day trip to Dry Tortugas or a Road trip to Nearby Keys.
  • Day 3: Hit the beaches in Key West, Mallory Square, and more.
Rooster on Higgs Beach in Key West
Key West is known for having a large population of Chickens everywhere

Brief Key West History

Ponce de León initially founded Key West while he was in search of the Fountain of Youth. However, the Calusa Indians had inhabited this land way before. After years of Spanish Rule, Key West became a part of the United States by 1822. At one point, Key West even declared independence from the USA and called themselves the Conch Republic. However, we know that didn’t last.

Big names like Henery Flagler, President Truman, Ernest Hemingway, and Jimmy Buffet have played roles in shaping Key West into the bustling tourist island it is today.

Beach sign from Fort Zachery Beach
Fort Zachary Beach

How to Get to Key West

There are 3 main ways to arrive in Key West. One of the most popular ways to arrive in Key West is by doing a road trip from Miami to Key West. I can attest that driving through the Keys is incredibly scenic, and driving over the 7-mile bridge is one of my favorites.

Another popular way to arrive is by flying to the Key West International Airport (EYW). This is a tiny airport about 20 minutes from the Old Town Key West Historic District. When we visited, it was around a $20 Uber/Lyft ride. We rented a car because we planned on driving to some of the islands, although it is not necessary to do so. I will explain in more detail below.

The last way to arrive is by boat. I did this countless times as a kid, but unless you’re from Florida, bringing your own boat might not be an option. However, Key West is also a very popular cruise ship port. So, this itinerary will be perfect for you if you come to port here.

Once you’re in the Historic District of Key West, it is very easy to get around by foot. You will be able to either walk, rent a bike, or golf cart to all these locations. Alternatively, you can also rent a scooter. If you drive, the parking meters are around $5 an hour, but parking can be tough to find. That is why we left our car at the hotel most days and walked instead.

Plane flying over Key West while cruise ship is docked in the water overlook of Key West

Day 1 in Key West

On our first day in Key West, we will see most of the famous landmarks and attractions. I have organized the activities that are near one another, making it easy to visit each one.

Southernmost Point of the Continental USA

Probably the most famous landmark in all of Key West is the Southernmost Point Concreate Bouy. This is considered the Southernmost Point of the Continental United States. There are also rumors that you can see Cuba 90 miles away, although it’s not true.

Anyway, everyone wants to take their photo here… like everyone! But, in my honest opinion, it is a little overrated. However, it is one of those spots you feel you need to see in Key West if it’s your first time.

So, if you want to see the Southernmost Point Bouy Landmark, I suggest going early in the morning. We were there at 7:30 AM and still had to wait around 8 minutes in line. During the middle of the day, the line is down the block! I honestly feel like it’s really not worth it, but to each their own. This is a free attraction in Key West, so there’s that.

The Southernmost Point Continental U.S.A. buoy in Key West
The Southernmost Point Continental U.S.A. – Weekend in Key West Itinerary

The Key West Butterfly and Nature Conservatory

Nearby is the Key West Butterfly and Nature Conservatory. While small, you get to walk through a greenhouse with thousands of butterflies and birds. I thought it was pretty cool, but I also love butterflies.

If you are visiting with children, they will definitely love this as well. If you don’t care much about butterflies and birds, you can skip this since the tickets to enter are around $17.50 per adult.

Also, keep in mind they open at 9 AM, so if you go to see the bouy first, you will want to get breakfast before visiting.

Butterflies on leaves at the Butterfly and Nature Conservatory in Key West
Flamingo at the Butterfly and Nature Conservatory
The conservatory has two flamingos Rhett and Scarlett

The Hemingway Home and Museum

The Ernest Hemingway home is probably one of the most popular attractions in Key West, Florida, but what really drew me in was being able to see the 6-toed cats that grace his property. I know; shame on me.

While we were there, we overheard the free tour that goes into depth about his home and life. From what I heard, it really sounded interesting, so I would recommend waiting for it when visiting. They happen about every 30 minutes. The property is also really nice, with beautiful lush gardens. I love the balcony with the lighthouse in view.

The Admission is $18, and they open at 9 AM.

Green balcony with 6-toed cat and white lighthouse in the background covered with trees. The Ernest Hemingway home is a must with a with a weekend in Key West
Outside the Hemingway home and Museum. Yellow shutters, white home and bushes and trees around it

Blue Heaven for Breakfast

Whether you’re a Hemmingway fan or not, the Blue Heaven Key West is famous. It is near the Hemmingway Home and a place that he frequented often. However, it was a brothel when he visited.

Now, they serve up breakfast, lunch and dinner. Because it’s famous, you can expect crowds. It is first-come, first-serve for breakfast and lunch, but for dinner, it is best to make a reservation. They also have some great key lime pie.

Key West Lighthouse & Keper’s Quarters Museum

Directly across from the Hemmingway Home is the Key West Lighthouse. I love lighthouses, so I always visit one when given the opportunity. We climbed up the 88 stairs to the top for a nice view overlooking Key West. The stairs are very narrow, so it makes it hard when people are passing in the opposite direction.

I must admit, while nice, this is not the best view in Key West, especially if climbing stairs is difficult for you. So, if you’re on a budget, you might want to skip this viewpoint.

Key West Lighthouse - white with black top
View from the Key West Lighthouse

Fort Zachary Taylor

After, make your way to Fort Zachary Taylor Historic State Park. If you don’t rent a car, you will need to get transportation here. This is one of my favorite spots in Key West because they have really nice beaches, the Fort is cool, and this is where you will see some of the best sunsets in Key West.

First, I suggest starting off with touring the Fort. Named after President Zachary Taylor, this fort was built in 1845 to protect the coastline after the War of 1812. It has the largest collection of Civil War armament in the world and was the longest-serving US fortification.

When visiting, make sure to climb up the stairs for some beautiful views of the ocean. Also, wander down the corridors where you can see some really epic cannons!

After, head to the beach! What I really like about their beach is that it offers umbrellas and has a beach bar. The sand is a little rocky at some points, but I don’t mind. If you love snorkeling, you can see some really great fish up against the rocks as well.

The picnic area is really nice too, and you can even fish over here if you bring your own pole. You can also watch a famous Key West sunset here. If you arrive earlier in the day, like we did, you can leave and re-enter as long as you keep your receipt for the same day. I know every guide says Mallory Square for sunset, but it felt more like a tourist trap than anything else when we went.

Fort Zachery Beach area in Key West
Fort Zachery Taylor Fortification with cannons
Fort Zachery Picnic Area
Fort Zachary Picnic Area

Day 2 in Key West

Key West is not a very large island, so today, I am recommending some day trips to consider.

Dry Tortugas National Park

On your second day in the Keys, I would highly recommend visiting Dry Tortugas National Park. It is located about 70 miles off of the Keys and is one of the least visited National Parks due to how remote and pricey it can be to visit.

The most important thing to know about visiting is that you must book this far in advance, and there are two ways to do it. One is by Ferry, and the other is by Seaplane. Both have to be booked through the National Park Service.

At the time of our booking, the ferry was around $220 per person, and the seaplane was around $450 per person. We booked the seaplane, but unfortunately, it was too windy to fly out, so we didn’t get to go. We hoped that there might be a cancellation, but that didn’t happen.

Even though I didn’t get to visit, I am still recommending it to you because it is a really unique experience. You get to see a 19th-century fort, crystal clear water, and snorkel. There is also some excellent fishing around here.

Dry Tortugas Ferry
Dry Tortugas Ferry

Bahia Honda State Park

If Dry Tortugas is not in the cards, consider a visit to Bahia Honda State Park. This is what we did when our seaplane got canceled. It is just past Big Pine Key, and the drive takes about an hour from Key West.

Aside from the stretches of the beach, you can see what is left of Henery Flagler railroad tracks. This is considered more of a local place, so if you want a break from normal tourist activities, this is a great place.

Bahia Honda State Park Weekend in Key West Itinerary
Bahia Honda State Park is a great day trip from Key West - Samantha Oppenheimer on the beach with blue water wearing a hat and red bikini

Water Activity

The last option to consider on day 2 of your Key West weekend itinerary is doing a water activity out of Key West. Some great options for Key West tours include:

  • Jet Skiing (you need to do a quick boating license test online)
  • Kayak or Paddle boarding through the mangroves.
  • Snorkeling the Florida Keys National Marine Sanctuary (3rd largest coral reef in the world).
  • Boating (sail or dolphin tour).
  • Fishing
Sailboat in Key West from Fort Zachery

Day 3 in Key West

To end this weekend in Key West itinerary strong, we will be checking out some of the other awesome beaches around Key West, visiting the famous Mallory Square, and more!

Cuban Coffee Queen Waterfront

Start the morning off at Cuban Coffee Queen Waterfront. This is where the famous Key West mural is, and they have some amazing Cuban coffee and sandwiches. It really is a must to taste some Cuban food and coffee while in Key West.

Key West Travel Tip: This coffee shop is very popular and has a couple of locations around Key West. I suggest going early to avoid crowds.

Cuban Coffee Queen

Duval Street

Once you’re in Key West, you will probably head down Duval Street on your first day, but if not, this is the time to make sure you head down and around Duval. Duval St. is the most famous street in Key West. This is a lively area with dozens of restaurants and shops. At night, it becomes a little more adult-rated.

Did I mention this is a popular Bachelor and Bachelorette party area?

Duval Village in Key West

Mallory Square and Key West Shipwreck Museum

Next, head to Mallory Square and the Key West Shipwreck Museum. Remember when I told you there are better viewpoints in Key West? Well, it can be seen at the top of the Key West Shipwreck Museum!

Mallory Square is known for its sunset celebration, and almost every person I know who’s been to Key West recommends it. I prefer a more local spot with better sunset colors. However, that doesn’t mean you shouldn’t explore the area. It is really cute and a good place to grab some souvenirs.

Mallory Square in Key West
The top of the Shipwreck Museum View in Key West with blue ocean and palm trees
View from the top of the Shipwreck Museum

Key West Water Activity

If you haven’t done any water activities up to this point, you should definitely add one in! These usually need to be booked in advance, which can change up your Key West itinerary a little bit, but that’s ok! Just get out on the water.

Kayaking in Key West - colorful kayaks lined up

Hit the Beach

You can never go wrong with visiting some of the other beaches in Key West. In all honestly, Key West is not known for its sandy beaches. This is because the island has more mangroves. However, the list of beaches below are quite nice, in my opinion.

Smathers Beach

Located near the airport, this is at a tie for my favorite beach in Key West with Zachary Taylor. It is a free beach to visit as long as you can score a spot in the parking lot, and it’s a nice strip of sand.

They have bathrooms, a water sports stand, and nets right on the beach. There are also a lot of gorgeous palm trees lining the beach, which I really liked. It is also one of the most Instagrammable places in Key West.

Smathers Beach in Key West - a must with a weekend in key west itinerary

Higgs Beach

This is a smaller local beach that is also really nice. The parking lot is on the smaller side, but free. There is also a restaurant attached to the beach if you’re feeling hungry. We stayed for sunset, and it was really beautiful. There is a small pier you can walk out on for the sunset.

Higgs Beach in Key West covered with palm trees

Simonton Beach (Optional)

I was hesitant to add this beach because it’s really not a beach. It is more like a little square of sand next to the inlet. Simonton happened to be right next to our hotel, so we checked it out. Unfortunately, it was covered in seaweed. They have chairs and a bar, though. So, it can be nice if you’re looking to do something that feels a little more local.

Simonton Beach
Beach during sunrise

White Street Pier and Key West Aids Memorial Park (Edward B. Knight Pier)

Spending a chunk of my childhood in Florida, I love piers, so I had to check out the White Street Pier. This is a large concrete pier near Higgs Beach. It is great for fishing, or if you like to watch others fish.

White Street Pier in Key West

Where to Eat During a Weekend in Key West

Your weekend in Key West itinerary is jam-packed with fun activities to do, and we haven’t even talked about food yet! I should let you know that if you eat seafood, you can expect some of the best and freshest seafood you have ever tasted right here. I would also recommend trying the Conch fritters. Oh, and don’t forget to try some Key Lime Pie!

  • Latitudes at Sunset Key. This is a private island, and reservations are required and need to be booked well in advance. A ferry will bring you to dinner. We didn’t book early enough, but it comes highly recommended for a nice dinner.
  • Cuban Coffee Queen
  • Sloppy Joe’s Bar and offers live music
  • The Breakfast club, too – really great breakfast
  • El Meson De Pepe’s Restaurant
  • Schooner Wharf Bar

Other Places in Key West

With just a weekend in Key West, you’re not going to see it all. I listed what I think are the best ways to spend your time within 2-3 days. Some other popular attractions that you could swap out include:

  • The Truman Little White House
  • USCGC Ingham Maritime Museum
  • Key West Cemetery
  • Tropic Cinema
  • The Key West Aquarium
  • A Trolley Train Tour (Hop on, Hop off, or the Conch tour train) Either of these can be nice if you are with family and don’t want to do so much walking. It’s a little pricey, though.
  • A stop by Mile Marker 0
Tropic Cinema in Key West

Key West Weekend Itinerary Wrap-up

That’s a wrap of how you can spend an awesome 2 or 3 days in Key West. As you can see, this little island packs a punch, so have the best time exploring the island life! If you haven’t already, make sure to check out my Key West travel tips (coming soon)!

You can save this map by clicking on the star. On the left side, the legend will pull out. On the right-hand side, you can make the map larger.

If you have any questions about this Key West itinerary or feel like I missed something, let me know in the comments below!

If you found this Weekend in Key West Itinerary Helpful, I’d appreciate it if you could share it below!

Weekend in Key West Itinerary
Photo of author

Samantha Oppenheimer

Samantha Oppenheimer (Sam Opp) quit her corporate marketing job in 2018 to travel the world and become a travel writer, blogger and content creator. She loves experiencing authentic travel experiences, photography, and nature. Sam shares helpful travel itineraries, travel tips, budget tips, and travel advice from her personal experiences. You can also find Sam's words featured in large publications including Mirror, Thrillist, and Well + Good.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.