A weekend in Key West; a 3 day Key West itinerary

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Key West is the most southern of the Florida Keys, and one of the most popular tourist destinations in the US. Known for its laid back atmosphere, spectacular sunsets, and diverse mix of history and contemporary culture, a weekend in Key West lets you sample everything the island has to offer.

Whether you’re in Key West as part of a Florida road trip or just visiting the island on its own, this 3 day Key West itinerary covers the very best to what to do in Key West in just a few days.

Weekend in Key West – day 1:

Take an Old Town Trolley Tour

One of the best ways to get a feel for Key West is to take a trolley tour around the island. Old Town Trolley Tours have been operating in Key West for over 30 years and the guides are locals who can tell you the history of Key West. Our guide even gave us some great local tips on where to eat!

The trolley tour runs in a continuous 90 minute loop with 13 stops at all of the major sights so not only is this a great way to learn more about Key West through their live narration, but it serves as a convenient hop on hop off way to get around. 

While Key West isn’t particularly big, it can get hot and sometimes you just don’t want to walk to your next stop. I hadn’t planned to use the trolley to get from A to B but in the middle of the day when it’s 90 degrees and your feet hurt, you’ll be glad you got those trolley tickets!

Meet the wildlife

I guarantee that within a few minutes of setting foot in Key West, you will stumble across a chicken – and if you don’t, you’ll definitely hear one! 

The Key West chickens are famous and are protected by the government. Originally bought over from Cuba to be used in fights, once that was made illegal the chickens were set free and still roam the streets today. 

You’ll mostly see the big roosters walking around, but there are hens and babies as well. As I said, they’re legally protected and I swear someone must have told them that because they have no fear.

They’re not aggressive so don’t worry if they approach you, but if you’ve got food you might want to keep your eye on it!

Once you’ve gotten used to sharing the sidewalk with a bunch of chickens, you might notice another resident of Key West as well. 

Green iguanas are an invasive species that some believe first came to the Keys as stowaways on ships. Although the tourists are generally fascinated with them, many locals aren’t big fans since they tend to eat the vegetation (including flowers out of their gardens) and dig into the ground.

Welcome or not, I loved seeing these guys walking around! In Central Florida we do have lizards but they’re nowhere near this size – the one pictured above was the size of a small dog and walking around like he owned the place! 

As with the chickens, they’ll mostly keep to themselves but they seemed a little more nervous around people (maybe someone told them they’re not federally protected?) so don’t expect to get too close and obviously don’t try to pick them up or feed them or anything – they can bite!

Southernmost Point

Is it even a trip to Key West if you don’t take a picture here?! The Southernmost point buoy is one of the most photographed tourist attractions in the US and was established in 1983 purely as a tourist attraction. The buoy is also about 90 miles from Cuba.

If you want to take pictures of the buoy without having to wait in line, then it’s best to get there as early as you can. Lines can get long and there is very little shade, but the lines do at least move quickly.

If you’re traveling solo then don’t worry; if you’re comfortable handing your phone over then people are more than happy to snap a picture of you. 

Key West Lighthouse 

Walking back from the southernmost point towards the main area of Old Town, you’ll pass a couple of historic places that are definitely worth a stop. The first is the Key West Lighthouse.

The lighthouse was first opened in 1848 (with a female keeper, which was a huge deal at the time) and was put out of commission in 1969. Today it stands as a museum to Key West’s maritime heritage with photos and belongings from those who once worked in the lighthouse.

You can also climb the 88 steps to the top of the lighthouse to look out over the Gulf of Mexico for some of the best views in all of Key West. The steps are a little on the steep side and going down was a bit of an adventure, but the views are absolutely worth it. 

Hemingway House and Museum

Next up on your historic tour should be the Hemingway House and Museum. Found on the same street as the lighthouse (Whitehead Street), the Hemingway House was somewhere I was really excited to go, not just as an English literature fan – but as a huge cat lover!

Guided tours are included in the price of admission or you can simply tour the house yourself. I chose to tour solo since the next available tour wasn’t for over an hour but it would have been great to learn more of the details of the property from the experts.

One of America’s most famous and respected authors, Ernest Hemingway lived in this very house for nearly 10 years. The house is set up to look as it would when he lived there with photos and newspaper articles on the walls detailing his life.

While I knew about his published work, there was a lot of his early life I wasn’t as familiar with so I found all of this fascinating. 

Once you’ve toured the main house, you can also tour the grounds, which include beautiful gardens and a magnificent pool (which was considered a huge architectural feat when it was built in 1938). There is also his study, where his typewriter is on display. 

As you walk around the house, you’ll notice the cats everywhere. Fast asleep on the bed in the bedroom, snoozing in the sun in the kitchen, sleeping halfway up the stairs (we were told to just step over him!) Outside in the grounds, there are cats absolutely everywhere you look!

The story of the Hemingway cats begins with a six-toed cat called Snowball. Snowball belonged to a highly respected shipwreck captain who had noticed Hemingway admiring Snowball on the docks, so he gifted him with a kitten from Snowball’s litter.

The 40 or so cats that now call the Hemingway House their home are descended from Snowball and carry the polydactyl (extra toes) DNA so even if they don’t have six toes themselves, they can produce kittens that do. 

I am a huge cat lover and I could have walked around petting the cats all day! Some obviously didn’t want to be disturbed, others looked totally oblivious to the fact that there were people walking all around them, and others very much wanted the attention.

The one pictured above enjoyed his ear scratches very much and meowed indignantly when I walked away!

This is one of my most recommended places to visit in Key West, it was absolutely fantastic (and not just because of the cats!)

Weekend in Key West – day 2:

Truman’s Little White House

On day two of your weekend in Key West you have a little more history in store before discovering what else Key West has to offer. Truman’s Little White House should be your first stop of the day because they offer scheduled tours and the early ones are usually the least busy.

The Little White House is Florida’s only Presidential Museum and runs 30 minute guided tours where you can learn more about President Truman and his relationship with Key West. There are no photos allowed inside but the tour was incredibly informative and the stories and anecdotes our guide told were fascinating. 

There is a gift shop on site that had some great books if you’re a history buff as well as other souvenirs.  

The Little White House is inside the Truman Annex, which is a beautiful, peaceful (and shaded!) area that was quiet every time I walked by. This would be a great place to sit and cool down for a few minutes if you needed a break from the heat. 

Shipwreck Museum

I was really excited to visit the Shipwreck Museum, and it ended up being even better than I thought it would be! I’ve always been fascinated with shipwrecks but even if you’ve never really given them a second thought, this museum is wonderful and I’d definitely recommend stopping in. 

The museum starts with a 10 minute video presentation (it’s not mandatory to sit and watch but I don’t think you’d get nearly as much out of the museum visit if you didn’t.) The video discussed how shipwrecks in Key West were actually considered a good thing as long as no lives were lost.

A lookout would stand at a tower and watch for boats coming in; at the sight of a wreck they could call out “wreck ashore!” and everyone would flock to their boats. The first person to reach the wreck would be considered the ‘wrecking master’ and would pretty much be in charge from there on out.

The goods rescued from the wreck would later be sold at auction and around 25% of the profits would be split equally between the people of Key West. These fortunes could be quite extensive and made Key West one of the richest cities in American until the wrecking courts were closed in 1921.

The museum holds some of the treasures found in the wrecks and goes into more detail about some of the ships themselves. There is even a genuine bar of silver from 1656 you can try to lift!

After exploring the museum, you can climb 90 feet to the top of the tower to see what the lookouts would have seen as they watched for shipwrecks. It’s fun to imagine what life must have been like back then, and the views out over the water are beautiful.

Key West Aquarium

Just steps away from the Shipwreck Museum is the Key West Aquarium, Key West’s very first tourist attraction. Dating back to 1935 the aquarium was built as part of an effort to attract tourists to Key West after the Great Depression. 

As you might imagine with a more historic aquarium, it’s on the smaller side and you can see all of the exhibits in about an hour. Although I loved the nursing sharks and could have watched the seahorses all day, my favorites were the two rescued sea turtles, Lola and Rocky.

Both had been injured to the point where specialists agreed they couldn’t be released back into the wild so they’re living out their days in comfort in Key West. Both have also been fitted for prosthetic fins by the same man who created the tail for Winter the dolphin in Clearwater! 

If you have a little more time, you can join one of the tours offered by the aquarium. I enjoyed browsing the aquarium on my own but would have liked to have joined a guided tour if I’d had more time – I caught the tail end of one and the guide was extremely knowledgeable.

Watch a famous Key West sunset

Seeing a sunset from Mallory Square has been on my travel bucket list for years and I’m so happy that I finally got to see one! Widely regarded as one of the best sunsets in Florida, Key West is in the prime location for an amazing view. I can say with complete honesty that it totally lived up to the hype and was the most beautiful sunset I’ve ever seen.

You can obviously watch a sunset from anywhere in Key West (and locals told me that Fort Zachary is a great place for somewhere a bit quieter) but I wanted to have the full experience so I went to the Mallory Square Sunset Celebration. 

In the hour or so leading up to the sunset, Mallory Square is filled with various street performers and food vendors. Pick up a cocktail or a bite to eat and find a spot to sit and people watch before the sun goes down. 

About 30 minutes before sunset people do start to claim their best spots so I’d recommend finding a place to sit or stand around that time. I chose the bridge between Mallory Square and Margaritaville, which stayed relatively empty right up until the moment the sun went down. 

When the sun does finally dip below the horizon, a cheer erupts from the crowds before they begin to disperse. Although many people move away at that point, it’s worth staying just a little bit longer to watch the colors of the sky change from orange to pink (which I always think looks particularly spectacular on nights when there are a few clouds).

Weekend in Key West – day 3:

Fort Zachary State Park

Your last day in Key West should probably be a little more relaxed (especially if you overindulged at the Sunset Celebration the night before!) Fort Zachary Taylor State Park is a great place for a little peace and quiet. You can walk to the park from Old Town or hop off the trolley at the closest stop. 

Fort Zachary is a National Historic Landmark that covers over 54 acres. The park features a fort that dates back to 1845 and was used in the Civil War and the Spanish American War. You can explore the fort on your own or take one of the daily guided tours offered (check the website for times). 

As well as the fort, the park offers a beautiful beach. When I was planning my trip to Key West, I was surprised to find out how few beaches there were here; Florida is obviously famous for its beaches and it seemed strange that Key West didn’t have any.

I later found out that the Florida reef off the coast means that no waves have been able to make a beach in Key West, and the only beaches are man made. The beach at Fort Zachary State Park is widely regarded the best in Key West, and it’s the perfect place to lie in the sun, splash in the calm waters, or even go snorkeling. 

Take a boat trip

Getting out on the water is the perfect way to finish your trip to Key West.

Whether it’s a charter fishing trip to catch something for your dinner (restaurants in Key West will often prepare your catch if you show up with it!) or a glass bottomed trip out to the reef to go snorkeling or a sunset cruise to watch the sun go down over the Gulf of Mexico, boat trips are plentiful in Key West. 

Offering just about every trip possible, as well as a commitment to protecting the delicate ecosystem of the Florida Reef, Fury have boats that go out every day so you can explore everything the waters around Key West have to offer. You can also go parasailing or head out on a jet ski!

If you’re in Key West to see the marine life, you might be interested in a dolphin excursion. The top rated eco tour in Key West is with Honest Eco Tours, a family (and biologist!) run company who offer the guarantee of seeing a dolphin on your trip.

They operate an electric boat so the dolphin are disturbed as little as possible, meaning they’re also much more likely to be stay close to the boat. 

Where to eat in Key West

Blue Heaven

Ask anyone where to have breakfast in Key West, and they’ll tell you to go to Blue Heaven. With tables outdoors amongst the roosters, this is an authentic Key West experience that’s not to be missed.

I opted for breakfast there and was told I had to try the banana pancakes. Richard’s Very Good Pancakes can be made plain or with various different flavors but I went with the recommendation of banana and they were some of the best pancakes I’ve ever had! They also had amazing freshly squeezed orange juice and very importantly, great coffee!

Garbo’s Grill 

On Caroline Street there is a small food truck in the courtyard of Hank’s Saloon. It would be so easy to just walk past it but it’s kind of hard to miss the line out front – and if you walked on by you’d be missing the best fish tacos I have ever had!

Garbo’s Grill has a small menu but the person ahead of me in line was talking nonstop about the fish tacos she’d had the day before so I decided to give them a try.

Soft tortillas filled with fresh mahi mahi, mango, red cabbage, onion, cilantro and their house made Caribbean sauce, these were hands down my favorite fish tacos ever. They come with a wedge of lime and squeezing the fresh lime juice over them definitely kicked them up a notch!

Conch Republic Seafood

Sat right on the water, Conch Republic Seafood is a great place to get really fresh fish – and with a daily happy hour, it’s a great place to grab a cocktail as well!

You can’t go wrong with any of the seafood dishes here, but their raw bar is fantastic and they have an award winning conch chowder that was delicious even in 90 degree weather!

Their key lime mojito is also famous for a good reason (there’s also a key lime colada, a key lime lemonade, and a key lime martini so this is a pretty good place for a key lime themed drink!)

Eaton Street Seafood Market

Eaton Street Seafood Market can be found on a street corner a short walk from Old Town, and the food here was so good that I went back three times in three days! 

From the lobster roll to the conch fritters to the famous Key West pink shrimp, every single thing was delicious and made fresh to order. I asked about just getting grilled pink shrimp (pictured above), which I didn’t see on the menu, and they were happy to make me something. There is very limited seating inside but plenty of shaded seating outside the store. 

Frenchie’s Café

My other recommendation for breakfast in Key West is Frenchie’s Café. The food here was absolutely amazing; I tried the Croque Madame breakfast sandwich which was rich, cheesy and delicious, and the perfect way to start off a day. 

They also have fantastic coffee! I had both a cappuccino and an espresso with my breakfast and they definitely helped get me moving that day! 

Cuban Coffee Queen

Speaking of getting you moving, I think everyone’s morning should start with an iced Café con Leche from Cuban Coffee Queen!

There are two different locations depending on where you are, but both make the same amazing coffee. The secret to the amazing iced coffee is the frozen coffee iced cubes that mean the drink doesn’t get watered down as the ice cubes melt. I added caramel to my drink and it was delicious!

Latitudes 

If you’re looking for somewhere a little fancier for a special meal in Key West, then look no further than Latitudes. Located at the Sunset Key Cottages, which sits on an island that requires a boat trip over, Latitudes offers amazing food in a fantastic location. 

Reservations are required and there is a dress code, so do check the website in advance. If dinner looks a little too fancy, then they do offer breakfast and lunch as well. 

Kermit’s Key Lime Pie 

You can’t come to Key West without trying their key lime pie, and everyone has an opinion as to which is the best. I tried more than my fair share of key lime pie in Key West and came to the conclusion that my favorite was from Kermit’s Key Lime Pie Shoppe. 

If you’ve seen pictures of chocolate dipped frozen key lime pie on a stick then this is where you can get it (although they actually sell this at a bunch of other places around Key West as well) but honestly, I don’t think you can go wrong with just a regular slice of pie. Sweet and tart, this pie was one of the best I tried all weekend.

Kermit’s will also let you sample other key lime flavors so it’s a great place to start off your search for the best key lime pie.

We received complimentary admission for the Old Town Trolley, the Little White House, the Shipwreck Museum and the Key West Aquarium on this visit. Many thanks to Historic Tours of America for hosting us on this trip. As always, all opinions are my own.