How to Spend a Long Weekend in Key West, Florida

Last week, I mentioned that I had recently returned from a long weekend in Key West. It was the first time that I had ever been there, but I really hope it won’t be the last! It’s a beautiful place with fantastic food, yummy tropical cocktails, and tons of fun stuff to see and do. If you think you’d like to head there sometime yourself, check out my tips for making the most of your long weekend in the paradise that is Key West!

Key West Fun Facts


Before you make your way to Key West for the first time, there are a few fun things you should know about this quirky and interesting island. First, Key West is only about 90 miles from Cuba, which means it’s actually closer to another country than it is to the mainland U.S.! Fortunately, that proximity to Cuba and the rest of the Caribbean means Key West has amazing culture and food.

Next, you should be prepared for the fact that there are chickens EVERYWHERE. They are also protected, so don’t try to pet, feed, or harass them because you can be fined for doing so. We had all heard there would be a lot of chickens, but I don’t think any of us expected to see them literally everywhere. Like walking across your toes while you’re having brunch outside, for example!


And finally, Key West actually once declared independence from the U.S. on April 23, 1982. After the U.S. Border Patrol had set up a roadblock on the only way in and out of the Keys, creating traffic jams and hindering tourism to the Keys, the people of Key West decided to secede and even “declared war” on the U.S. (though it was really more of a PR stunt than anything).

Their independence was short-lived, but Key West became the Conch Republic (pronounced “conk”) that day and the joke still lives on. You’ll see Conch Republic flags all around the city, and you can even buy a souvenir passport for the Conch Republic! And every April, they hold a multi-day celebration in honor of their independence day.

How to Get To and Around Key West

Ok, so how do you get to the Conch Republic? Well, if you want to drive to Key West, you should know that it’s about 160 miles from Miami so it’s not exactly a short drive. However, if you enjoy a good road trip, there are plenty of places to stop on your way down south. Once you get to Key West, though, parking can be tricky (and expensive) so you may either want to look for accommodations that include parking or just plan to drop off your rental car when you arrive.

The fastest and easiest way to get to Key West, though, is by plane. Only four airlines are flying in and out of Key West at this time: American, Delta, United, and a small airline called Silver Airways. I had actually booked tickets with Jet Blue and they partner with Silver, but it was all very confusing. I can’t say I was thrilled with the experience, so maybe just stick with one of the other three airlines.

Direct flights are very limited unless you’re flying from somewhere in the South (or willing to pay a whooole lot more money!) I actually ended up booking two one-way tickets on separate airlines, saving about $100 in the process. We all also added travel insurance since we booked our trip at the tail end of hurricane season and didn’t want to take any chances.


The Key West airport is tiny! There’s just one terminal and fewer than 10 gates. There is a small bar with snacks past security and next to the gates, but if you have to kill some time inside the airport, I’d suggest hanging out in the restaurant you’ll encounter before going through security (you can’t miss it, it’s literally the only one). It’s a bit roomier and looked far more welcoming.

When you arrive in Key West, there are taxis lined up outside the airport, but they operate more as shuttles. It’s $9 per person, and you’ll need to be prepared for multiple stops. We took this when we arrived and ended up having to drive north with a group going to Stock Island before being dropped off at our own hotel. On the way back to the airport, we took a Lyft, which was far more efficient!

One of the many beautiful houses in Old Town Key West!

Once you’re in Key West, there are several options for getting around town. Walking is certainly the easiest and most economical, but it can get pretty toasty walking around mid-day in the hot, hot sun. Lyft was readily available, and we never waited more than three or four minutes for a car. One of the best options, though, is the FREE Duval Loop Bus. It’s very well air-conditioned, and you can even track its location online so you know when you can expect it to arrive.

If you want a guided tour in addition to your transportation, you can also check out the Old Town Trolley or the Conch Train. Both have hop-on/hop-off options, though we found it a little challenging to hop back on to the trolley after we hopped off the first time, leaving us standing around and waiting for far longer than we would have preferred. I’d suggest just staying on the trolley or train for the whole loop if you want to hear the commentary and then use the loop bus, Lyft, or a rented bike for actually getting around town.

Where to Stay

If you’ve never been to Key West, I highly recommend that you stay in Old Town. The airport is closer to New Town, and when we took the trolley through the area, we were very happy that we weren’t staying there! New Town does have larger, more affordable hotels, but the cuter and quainter hotels are all in Old Town. Yes, you will pay a bit more to stay in Old Town, but it was worth it in our opinion since you’re able to get around more easily and find more amenities within easy walking distance.


As for where to stay in Old Town, it really depends on what kind of vibe you like. We prefer a quieter and less crowded scene, so we stayed near the southern end of Old Town, just a block away from busy Duval Street. We stayed at the Best Western Hibiscus, which was clean, affordable, and very spacious, and I’d definitely recommend this hotel to anyone looking for a place to stay in Key West.

There were four of us, all women, staying in one room together, and we had two queen beds and an extra vanity and sink outside of the bathroom which made getting ready in the morning much easier.

Our room rate included free breakfast which had the usual continental breakfast staples, as well as hot waffles, eggs, and either bacon or sausage. There was a beautiful pool, and we were able to eat our breakfast next to it every morning and soak our tired feet in it at the end of the day.

The pretty pool at the Best Western Hibiscus. We had our breakfast here by the pool every morning!

But if you want to be closer to the action and excitement, you’re going to want to pick something on the north side of the island, close to Mallory Square or right on Duval Street. To me, though, Duval Street and the Mallory Square area feel a bit like Times Square in NYC. More national chains, more people, more chaos, MORE. It’s fun to visit for a little while, but it was super nice to go back to our hotel in the evening and enjoy the peace and quiet!

I will say, though, that everything seems to be more concentrated toward the middle to northern section of Duval Street, so we did have to walk a bit further to get to all the action. So, pick the area that makes the most sense for you depending on what kind of experience you hope to have!

What to Do

Since we were only in town for three full days, we barely scratched the surface of things to see and do in Key West. However, we did still cover quite a bit of ground!

On our first full day, we started the morning by grabbing the hop-on/hop-off Old Town Trolley just a block from our hotel. We had pre-booked tickets online since you get a little discount that way, and then we just showed the driver our receipt when boarding the trolley. We wanted to start out our trip with the trolley tour so we could get the lay of the land and take note of anything we would like to stop back and see later.

Scenes from our trolley tour
Key West Pride
This beautiful old theater, sadly, is now a Walgreen’s.
Jimmy Buffett’s recording studio.
So many beautiful houses tucked away!
I loved this mural – it highlights some of Key West’s local celebrities.
This beautiful old church is a private home now.

We hopped off a couple times during our trolley tour, and the first stop was at the Hemingway Rum Company since your trolley ticket includes a free tour and tasting at the distillery. Unfortunately, we learned that the guided tours don’t start until noon, and we had arrived right when they opened at 11. They did let us wander through on our own, though, and we got to do the tasting at the end, so it was still a win in our books!


We tried to hop back on to the trolley and ended up waiting about half an hour before we could catch one that would fit all four of us. At this point, we decided to just stay on the trolley until the last stop before our hotel so we could finish the loop. And at that last stop, we found ourselves at Higgs Beach and the beautiful Key West Garden Club.


The garden is free (though you should leave them a donation), and it is located in an old Civil War-era fort, the West Martello Tower. There are lots of shady places to sit and enjoy the beautiful and peaceful space, and it’s situated right along the ocean so you’ll feel the nice sea breeze blowing through as you wander in the garden. It is truly a hidden gem in Key West and it’s a bit on the outskirts of Old Town, but it’s definitely worth a visit.

The Key West Garden Club is located in the remains of a Civil War-era fort.


As far as hidden gems go, the Key West Garden Club is pretty high on the list of great places to seek out in Key West. It’s a little off the beaten path, but as you can see, it’s well worth a visit!




Later in the day, we set out on the Southernmost Food Tasting and Cultural Walking Tour. On our girls’ trip to Scottsdale last year, we did a food tour on the last day of our trip and had a blast. This year, we decided we should do it on the first day so that we could find some places we might want to go back to for a full meal.

This tour definitely did not disappoint! Our guide was interesting and informative, and all of the food we sampled was soooo good. Bring your stretchy pants, though, because you will be so full by the end of this tour.

On our second full day, we started our morning with a half-day tour of the Keys. We were the only four people on the tour, which was fun, and we were driven all the way up to Bahia Honda Key which is nearly 40 miles from Key West. Along the way, we stopped in Big Pine Key to look for the miniature-sized Key deer (and we saw several!) and got out at the Blue Hole to look for alligators (and saw none).

Key Deer


The Blue Hole

As we drove up the Keys, we were able to see some of the various neighborhoods on the different Keys, and our guide, Kim, pointed out tons of different birds and plant life that we could see from the van’s windows.

This was a fascinating neighborhood. All of these houses have huge garages because the people who live here all have their own planes! That’s actually a landing strip you see out the window.
Just casually leaving the airplane in the yard…

At Bahia Honda State Park, we were able to wander the park for a while and visit the old bridge that was once used for carrying trains down the Keys and then later had a roadway built on top of it before it was eventually closed in the 70s. It was fun getting to see more of the Keys and learn about the history of this unique section of the United States!

Bahia Honda State Park




Later in the day, we strolled up the northern section of Duval Street and eventually made our way to Mallory Square for the sunset celebration. Every night, an hour or so before sunset, performers and food vendors all come out on the pier to help tourists and locals alike enjoy the spectacular sunset.

We had learned that there was a cat circus and naturally went to watch that, though we found it a little sad and fairly disappointing. We watched some of the other performers instead, several of which were rather entertaining. Sunset, of course, is really the star of the evening, though! 

Watching the cat circus.
This guy was hilarious! He’s balancing on a board on top of a piece of pipe. Eeep! His running commentary was so funny, though.
The sun is starting to set…
…and now it’s gone!

After, we wandered around the Historic Seaport District to admire the beautiful boats while searching for somewhere to have dinner. There was a power-boat race in town during our visit, so some of the boats in the Seaport were pretty insane and there were tons of people milling about to check them out. 

Yes, that’s six outboards…
America 2.0 – this boat sails in NYC in the summer and spends the winter in sunny Key West!

If you want to go out on a boat rather than simply admiring them from ashore, though, there are plenty of options for doing so. We didn’t go sailing ourselves, but I would imagine one of those sunset cruises would be spectacular!

This is just one of the many boats we saw heading out to enjoy the sunset.

And on our final full day in Key West, we mostly just walked from one end of Key West to the other, hitting all the remaining stops we wanted to be sure not to miss before leaving town. We started at the Key West Butterfly & Nature Conservatory, which was wonderful! It’s an indoor tropical garden filled with exotic birds and hundreds of butterflies.




Your ticket allows you to visit as many times as you’d like on the same day, and we actually went through a second time immediately after completing our first circuit. There is so much to see, and we were surprised at how many different butterflies we saw on our second loop through.

We also had to stop and take photos at two very special points in Key West. The first is the Southernmost buoy, which marks the southernmost point in the continental U.S. And the second is at Mile Marker 0, where U.S. 1 both begins and ends! On one side of the street you’ll see the “End” sign and on the other, “Begin”.




Probably my favorite thing we did in Key West was visiting the Hemingway Home and Museum. Not only are the house and grounds beautiful, but the museum is currently home to 59 cats, about half of whom are polydactyl (meaning, they have extra toes!) We took the 30-minute tour of the house and grounds and then spent a bit more time wandering and searching for cats. I loved this place!







Next, the rest of my group declined to join me, but I scaled the 88 steps up to the top of the Key West Lighthouse. The top of the lighthouse is the highest point in Key West and once you make your way up there, you’re treated to a 360-degree view that lets you see for miles.

Naturally, I climbed up on the ugliest of the three days we were in Key West and it was all cloudy and overcast, but I enjoyed the view nonetheless! And when you’re back on the ground, there’s a very interesting museum you can check out in the old Keeper’s House as well.


88 steps to the top!


Not a bad view – too bad there were so many clouds.

A couple places we didn’t get to but that will be on the top of my list if I make a repeat visit are the Dry Tortugas National Park, the Fort Zachary Taylor Historic State Park, and the Key West Cemetery. The Dry Tortugas National Park is about 70 miles from Key West and is quite expensive to get to (and going there is basically an all-day event).

You can only get there by boat or seaplane, and it’s known for its spectacular snorkeling and coral reefs. There’s an old fort you can explore there as well, but my understanding is that the amenities are otherwise limited if you don’t intend to snorkel or tour the fort.

Fort Zachary Taylor and the Key West Cemetery are both in Key West, but we just didn’t have enough time to visit either on this trip. As the name implies, Fort Zachary Taylor also has an old fort you can tour, as well as public beaches and hiking trails. And the Key West Cemetery is said to be very beautiful and also very quirky. If you go, check out their website in advance so you know which gravestones to find.

As you can see, there’s a whole lot you can pack into a three-day visit to Key West, but you’ll need much more time to see and do it all. If you’re like me, though, after you visit Key West once, chances are you’re going to want to go back and do see and do even more.

Where to Eat and Drink

All the sight-seeing you’re going to do in Key West is going to make you work up an appetite, and you’re definitely going to be thirsty! Fortunately, there is fantastic food and drink in Key West to keep you fat and happy.

If you’re looking for excellent Cuban food, head to El Siboney. This was the first stop on our food tour, and it was soooo yummy. We had roast pork, plantains, and rice and beans, and it was really spectacular. They also have excellent sangria to wash it all down with and some extra-potent Cuban coffee if it’s a pick-me-up you’re looking for instead.

Roast pork at El Siboney

Bad Boy Burrito was the second stop on our food tour, and they had delicious fish tacos made with the freshest local catch. During our visit, the local catch happened to be black grouper, and it was really tasty. We paired our tacos with margaritas made from fresh lime juice – no margarita mix there!


Black grouper fish taco from Bad Boy Burrito

If you want to dine near the water, both Salute and the Seaside Cafe are good options on the southern side of Key West. Salute is next door to the Key West Garden Club, and we enjoyed appetizers, salads, and drinks on their patio before we visited the garden. The Seaside Cafe is located next to the boutique hotel, the Southernmost House. There are tables on the patio as well as right alongside the ocean. The drinks were good, and I really enjoyed my lobster salad on their honey-butter biscuits!

The Southernmost House
The Seaside Cafe
Now that’s some oceanfront dining!
Lobster salad on honey-butter biscuits….yummmm….

In Bahama Village, we enjoyed both Blue Heaven and the Rams Head Southernmost. Both have outdoor dining with live music, and Blue Heaven is particularly famous for its sky-high key lime pie. So good and SO BIG! We stopped for pie at Blue Heaven on our food tour and returned there for brunch a couple days later.

The Rams Head Southernmost


Blue Heaven is a quirky place…
But it has a great bar outside!
And OMG look at that key lime pie!

We had drinks and dinner at Rams Head twice, the second time because we were unable to get into Santiago’s Bodega down the street. Santiago’s was highly recommended by several people during our visit, but I would suggest you make a reservation if you want to eat there! We didn’t have one and were told it would be 2.5 hours before we’d get a table.

If you’re in the Seaport District, we enjoyed a very lowkey dinner at The White Tarpon Bar & Restaurant. They have several drink and appetizer specials for happy hour, and we ordered a bunch of appetizers to share while sitting outside and admiring all the boats. They also have an outdoor pool table and lots of good craft beer options.

The White Tarpon Bar & Restaurant

If you’re visiting the Hemingway House and the Key West Lighthouse, stop by the nearby Moondog Cafe and Bakery for breakfast or lunch. There is so much good stuff on their menu that you will have a hard time picking just one thing. We all really enjoyed our meals here, and the place is super cute inside, too. All of the walls are painted and everything is bright and colorful. There is a bakery case in the front, too, in case you just want to pop in to grab a treat to go.

My huevos rancheros plate at Moondog

For dessert, you can’t go wrong with either Kermit’s or Duetto. Kermit’s has all things key lime, from cookies and jelly beans to chocolate-covered slices of key lime pie. We stopped in for the chocolate-covered pie ourselves, and it was delicious! The best part is that you can sample all kinds of treats throughout the store, so if you need a snack, stop in and see what they have.


Chocolate-covered key lime pie!

Or just head over to Duetto and grab yourself some of their delicious gelato. The chocolate and peanut butter together was divine! (They sell slices of pizza, too, in case you need something more substantial. We didn’t sample any, but it looked really, really good.)

And finally, if you just need a drink, never fear. Key West has you covered. Did you know that Key West has more bartenders per capita than any other city in the U.S.? Yep, it does! You can also carry alcohol on the street without anyone batting an eye, and on more than one occasion we were asked if we wanted a to-go cup for our drinks! (It’s technically not legal, but apparently no one cares unless you’re acting like an idiot.) 

There are some Key West classics that probably warrant a visit. We went to Sloppy Joe’s twice to have drinks and enjoy the live bands. The place is always packed, and the music is an added bonus. Not far away you’ll find the Hog’s Breath Saloon and Capt Tony’s Saloon, the latter of which is the former location of Sloppy Joe’s. We didn’t make it into Captain Tony’s, but we did venture inside the Hog’s Breath. It was very hot and crowded, so we didn’t stick around but everyone was having a great time!



Finally, further south on Duval Street you’ll find the Speakeasy Inn and Rum Bar. We stopped here on our food tour to enjoy a delicious rum runner cocktail and learned that this location had once, in fact, been a speakeasy. Today, they’re famous for their insane assortment of rums which includes more than 300 different varieties from all over the world. If you’re in need of a tropical rum cocktail or if you just really take your rum seriously, look no further than the Rum Bar!

The Speakeasy Inn and Rum Bar
Rum Runners!


As you can see, Key West has a lot to offer, and you can cover a lot of ground, even in just a short visit. I hope you’ll find this guide useful in planning your own trip to Key West, and if you’ve already been there or are a local, please share any other suggestions or recommendations you may have for first-time visitors to the Conch Republic!