Article updated March, 2022.

I’ve recently returned home from my second ever trip to Key West and wanted to highlight even more fun things you can do in the area!

I originally posted this blog after I visited Key West in 2019 for my brother-in-law’s destination beach wedding at that time, I had never been to Key West before, so I wasn’t quite sure what to expect. I did a little bit of research from other bloggers, but honestly I just wanted to go and be surprised. I let my husband do most of the trip planning because we were there for his brother’s wedding, and he knew more of the types of activities we would be doing before and after the big day.

So if you’re planning a Key West vacation of your own, keep reading for some ideas of places to stay, where to eat and fun things you can do.

Ryan and I have been on a lot of trips together, but going to a warm destination was a first for us. He’s a Northerner, through and through. So for him, going anywhere hot is pretty much the last place he wants to go. But we were both pleasantly surprised by how much we enjoyed Key West!

We had an excellent trip, and I want to share with you everything we did so you have an idea of what adventures you can find if you ever make a journey down to the Southernmost Point yourself!

I hope you love the products that I recommend! Just so you know, I may collect a share of sales or other compensation from the links on this page.

The Key West airport is one of the smallest I’ve ever seen. There isn’t even a gate, you literally walk off the plane directly to the tarmack.

One of the first things I heard from a local was “Wear sunscreen! You want to go home looking beautiful, not burned.” And frankly, I think that is some quality life advice. I’ll store that quote in my mind with another I heard a few years ago while visiting the Vegas strip - “Don’t ruin your vacation with dehydration!” Listen to the locals friends, they are full of the best advice!

What To Expect in Key West

Key West is absolutely beautiful, and actually quite small. It’s only a few miles across in either direction, which is fantastic if you only have a short time to visit and want to see all of the things. It’s small size also means you don’t really need a car. In fact, it’s actually easier to not have a car because parking is so limited.

It’s one of the southernmost places you can visit in the continental US, which is amazing when you’re trying to escape winter like I did. The weather rarely dips below the 60’s, and for the most part hangs around 80 degrees. Although it is worth nothing that Hurricane season is June - November, so keep that in mind while planning your visit.

It’s also, like most islands, pretty expensive. Hotel lodging during peak season will easily run you at least $500/night (if not more) and expect to pay around $15-$20 per meal (per person.) There are of course ways around this like pooling your resources with other members in your group to book a vacation home, using credit card points for hotel stays, and buying groceries instead of eating out for every meal.

Where We Stayed

The entire wedding party booked rooms at the Southernmost Beach Resort, a stones throw away from the airport, Duval street and of course, the landmark for the Southernmost point of the US.

Like most resorts, the Southermost Beach Resort had a variety of rooms available for different price points. Our room faced one of the many pools, while others in our group had ocean-view rooms.

After a long first day of travel (thank you MN winter for the flight delays) we dropped off our bags and made our way immediately to the pool bar for a few pre-dinner cocktails.

We had our first of many meals at the resort restaurant, The Southernmost Beach Cafe. The food was absolutely delicious, but I will say that after about 2 days, the non-stop live music was too much for me. I think if we hadn’t have been with a large group of people for a celebration, I would’ve been pretty annoyed by just how loud the resort was, like, all the time. Personally, I don’t need live music at 2pm at the hotel pool every day. Your girl just wants to chill, have a cocktail or two and have a moment of quiet, like the old fart she is. ha!

On my most recent Key West trip, I stayed at the Coconut Beach Resort, actually just down the beach from the Southernmost. This resort is unique because it’s actually more of a time share instead of a hotel. When the owners of the time shares decide to give up their week, they can rent out their unit to guests like me.

If you’re looking for a more quiet stay than the Southernmost Beach Resort, but still want to stay on that end of the island, the Coconut Beach Resort is just that! It was very chill. The hotel didn’t blast music all day so I actually could sit around and enjoy the waves crashing like I had really wanted on our first trip out to Key West.

The down side to this place however, is there was no bar access. While there is a bar next door (Louie’s Backyard) it is literally walled off by a fence. Apparently hotel guests used to have easy access pre-pandemic, but it has since been removed due to problems with non-guests using the pool area. I literally had to walk out on the street, convince the bartender I wouldn’t be giving drinks to minors, and then walk back when I could’ve just gone through a doorway. Word from other guests is they are working on a hotel key or passcode to get around this issue, but in the meantime, you’ll just have to BYOB.

How to Get Around

One of the things I was most (pleasantly) surprised about Key West was just how easy it is to get around! The island is small, like, just a few square miles small.

Taxis / Ride Shares
Pink taxis are everywhere, as well as Lyft and Uber, but I should note the prices are higher than you’ll normally pay back home. It’s common to spend around $10-15 to just go for a 5min ride.

Rentals:
If you want a little more control, there are scooter, golf carts and bicycle rental companies everywhere. You can easily rent a bike through your hotel, or just walk for a minute down Duval street and you can have your pick!

Car Rentals:
Personally, I feel that having a car on Key West is unnecessary. The island is so small, parking is very limited and probably more hassle than it’s worth. We found ourselves choosing to walk everywhere in order to really take in the sites.

Tour Trollies:
There are so many options for sight-seeing tours from old school trollies to train cars. This type of activity is something I usually avoid, but it’s a great option if you have limited mobility and want to see the entire town and to learn all of the history of Key West.

Things To Do in Key West

Duval Street

Duval street runs the length of the island and is completely packed with shops, bars and restaurants. We found ourselves walking up and down the street a couple of times because it really is worth checking out more than once if for nothing else all of the amazing food!

There are also stands along the way where you can sign up for various activities like parasailing, fishing, snorkeling, ghost tours, etc.

At night, the street transforms into a total party scene with live music at nearly every bar. Hosting mostly cover bands, I found that we would walk out of one bar into the next and they were more likely playing the same songs. I’m glad we did the pub crawl thing at least once with the wedding party, but I certainly didn’t feel the need to do it more than that.

Key West Butterfly & Nature Conservatory

When we discovered there was butterfly garden, my mind first went to the butterfly house at the State Fair, but I couldn’t have been more wrong!

The conservatory is home to hundreds of tropical plants, birds and amazingly unique butterflies, some of which I’ve never even heard of before, let alone seen IRL. Following a winding path, we watched as vibrant colored butterflies floated past like something out of a fairytale. It was amazing, and definitely worth checking out!

I actually enjoyed this so much, I made sure to visit it a second time on my return visit!

Mallory Square

Mallory square was located on the opposite end of Duval street from where we stayed. We walked down to check it out and you could easily spend an entire day seeing everything from the Aquarium, to art museums, countless tourist shops and cafes along the water. We skipped most of it having already had our fill of touristy stuff and just wandered around.

Mallory Square is also home to the official ‘Sunset Celebration’ on the island. Starting about two hours before sunset, the area is filled with local artisans, food, street performers, and live music. The celebration is located right on the edge of the water with great sunset views. If you want a great seat, make sure to get there early as the pier fills up pretty quickly!

Smather’s Beach

One thing I realized very quickly about Key West is it really feels like a non-stop party town, which is great when you’re there with a large group of friends, but not so great if you just want some down time.

Smather’s beach was everything we needed to have some time to ourselves, and for once not have to listen to anything other than the wind and waves.

It’s also the beach where my Brother-in-law married the love of his life, so I’d say it’s a pretty wonderful place!

Key West Garden Club

We stumbled across the Key West Garden club while walking back to our hotel from Smather’s beach. It was closed when we first found it, but it looked so beautiful from the garden walls that we decided to come back the next day.

We packed a lunch and walked back to enjoy our meal in the shade of a banyan tree in the center of the garden. We were pleasantly surprised to find out that not only was the place nearly empty of other tourists, but it is also free!

Southernmost Point

One of the most iconic statues in Key West is the Southern Most Point marker on well, the southern most point!

Here’s the thing though, there was always a line to snag a photo. I suppose I could’ve woken up at the crack of dawn to snap a quick pic, but I didn’t think it was worth the hassle. If I ever find myself standing in front of the Taj Mahal you bet your ass I’ll be there before the sun is awake,. but I digress. I did ask a nice stranger to snap this gem of me after a few cocktails though… talk about Instaworthy! lolz.

Whitehead St

Whitehead street runs parallel to Duval and is frankly more our speed in a touristy town. Every few blocks there are some really amazing things to see like a historic lighthouse, Ernest Hemingway’s house, the Audubon House, Mile Marker 0 and several amazing cafe’s.

The wedding reception was at the Audubon House and it was one of the most beautiful venues I’ve ever seen! TBH I’m glad I’m already married because they set the bar too high! haha.

On my recent trip, I made sure to get back to the Audubon House and actually do the home tour, because we weren’t allowed inside during the wedding in 2019. I’m so glad I went back!

I learned a great deal about the house, which was actually built well after John James Audubon, a well known and respected wildlife painter, had been in the area. It is believed the house got it’s name because Audubon used a branch from the property in his paintings, and is one of the reasons the house was saved from demolition in the 50’s.

Note: The Audubon house is three stories high with very steep stairways and no elevator access. However, the garden is fully accessible for all mobility types.

Key West Light House

This historical light house is 88 steps up (or about 4 stories high) and has amazing 360 views of Key West.

I will say, after having done it, this is not for the faint of heart (i.e, someone who doesn’t like heights or winding staircases!) The platform up top is not very wide and it was difficult to get around other tourists, so if you can time your visit when there are next to no other visitors, that would be ideal!

Where We Ate

Ana’s Cuban Cafe - $
If you’re looking for an authentic experience and a damn fine cup of coffee, this is for you! The menu is unapologetically simple, the service is fast and the baby chickens run free at your feet looking for crumbs. I recommend the Hangover Breakfast which includes 2 eggs, potatoes, Cuban toast and choice of bacon or sausage with a cup of coffee, all for $8!

Banana Cafe - $$
With literally hundreds of options for places to eat, we went back to the Banana cafe several times because it was that good! If you’re looking for a quieter atmosphere, delectable morning treats like vanilla latte’s and Nutella crepes this is the place for you.

We also went back for a dinner and I gorged myself on truffle fries, mussels and seafood risotto, all while sitting on the roof top and watching the people of Duval St. meander by.

Southernmost Beach Cafe - $$$

Located right on the beach (and at our resort) naturally we ate at the Southernmost Beach cafe a couple of times. I would highly recommend the bacon scallops, but I honestly think you can’t go wrong with any of the options!

We also had the chef specially prepare 2 fish the bachelor party caught the day before. It was once of the best (and bougie) experiences of the entire trip!

Croissants de France - $

I was surprised to see how much of a french influence Key West has and jumped for joy when we found the all of the baked goods at Croissants de France! Give this lady a ham and butter baguette sandwich any day!

Waterfront Brewery - $$
The Waterfront Brewery is literally just that - a brewery right on the water. But don’t let the straightforward manner of the name fool you, their beer is prime, the food is some of the best we had and the view is worth the visit alone!

Moondog Cafe - $$

The Moondog Cafe is located on Whitehead street, about a block from the Key West Lighthouse. They have a lovely back garden patio that is fully shaded to help escape from the heat of the day and had some of the best hueveos rancheros I’ve had in a long time!

Old Town Mexican Cafe - $$

There are no shortage of places to grab a drink in Key West, but if you’re looking for the BEST margarita, head to Old Town Mexican Cafe!

The Raw Machine - $$

If you’re looking for a lighter lunch and some delicious smoothies, head to the Raw Machine. The food is served to you through this adorable vintage airstream trailer and they have the most beautiful little garden patio for you to enjoy it.

The trip was truly amazing! Now that we’ve experienced Key West together, I see more tropical trips in our future. Have any warm, sunny, tropical recommendations for me? I would love to hear them!