The Ultimate Guide to Key West

I recently went down to Key West for a friend’s wedding and I had such a great time! It was my first time in Keys, so I wanted to make sure I knew where to go, what to see, etc. Just a heads up, since I was there for a wedding, I wasn’t able to see and do as much as I would’ve liked. I definitely think I should’ve stayed an extra day (oh well… next time). So parts of my guide will be based off of recommendations and research I’ve done. Ok, let’s get to it!

How to Get to Key West

These are the ways I recommend getting down to Key West:
1. Fly straight into Key West Airport (EYW) – This option can be pricey depending on the time of the year. This airport is tiny with only a few airlines, so honestly, it’s probably always going to be a little more $$$. Definitely the most convenient though! You can then take a cab or Uber to your hotel.
2. Fly into Miami (MIA) or Ft. Lauderdale (FLL) – If you’re on a budget, I’d recommend flying into one of these airports and renting a car. Yes, not as convenient, but the drive isn’t awful. Our car cost about $120 for the weekend (then split between the two of us). The drive is about 3 1/2 hours from either of these airports, depending on traffic of course. Driving along the coastline and over the ocean makes for a beautiful view. Honestly, it just got us more excited to be on the beach! Definitely not the worst drive I’ve done.

Where to Stay

My friend and I decided to book a room with Vacasa Vacation Rentals for our stay. We were in the Sunrise Suites, which was the perfect location – close to downtown and all the fun, but also close to where the bride-to-be and bridal party were. If you check out Vacasa’s website, you’ll see there are TONS of options for all price points.

I would love to come back one day and stay at one of the below – more of a true vacation-type stay.

Other options are: Chelsea House Hotel (cute historic hotel downtown) // Havana Cabana (close to restaurants & attractions) // Southernmost Beach Resort (pricier, but has private beach & right by Duval St.) // Oceans Edge (located further from downtown, but has 6 pools!) // Orchid Key In (located in the Historic District) // Key West B&B (close to Duval St and multiple attractions)

Things to Do & See

Tour the Hemingway House – Known as one of the greatest American journalists, novelists and short-story writers, Ernest Hemingway lead quite the eventful life. Stopping by his Key West house is a must-see in my opinion. There are guided tours that last about a half-hour and no pressure, you can leave whenever you want. But trust me, you’re going to want to stay. We enjoyed learning about his wild life, his wives (4 in fact), and the famous 5 toed cats that roam the property. Tip: the tours are cash only!

• 

• 

Southernmost Point – This is the southernmost point in the U.S. – it’s very close to Cuba! The line for a picture can be super long, so get there early or be prepared to stand in line. We skipped the line and I snapped a pic as we walked by. It was just cool to see and be there!

Mallory Square – We missed this and I’m so sad! I’ve heard that Mallory Square has the best sunsets, so if you want to watch the sun go down, check it out here. The square has street performers, vendors, restaurants and stores – quite the busy little area!

Duval Street – This is where a lot of the action is! There are so many fun bars (we’ll get to that later), shops and restaurants. The street spans a little over a mile long and is definitely the center of all the fun.

Butterfly Conservatory – We did not get to check this out, but I saw tons of people walking around that had visited (they had little butterfly stickers). We have a butterfly conservatory in the Detroit Zoo and it was my favorite thing growing up. There’s something magical about visiting and seeing butterflies flit around – you may get lucky and have one land on you! I’d definitely recommend visiting if you have kids.

Sunset Key for Dinner – If we had more time, I would’ve loved to take a boat over to Sunset Key (small island) for dinner at Latitudes. The views and food are supposedly breathtaking! (Reservations are required)

Barefoot Billy’s Jet Ski Tour – Our friends took this tour and had such a great time! It’s a two hour tour that takes you around the island. Billy’s also has snorkeling, sunset cruises and so much more!

Little White House – This was the winter home of President Harry S. Truman. Truman stayed 175 days over the course of 11 visits during his presidency. It’s now a certified presidential museum and open to visitors!

Walk around the Historic District – One thing on my list was to go see the historic house that has been nicknamed the Calvin Klein House. I’m telling you, just walking around and looking at all the houses is worth it. There’s so much inspiration all around and everything is just so beautiful. Also, I’ve officially decided that my future house has to be pink!

• 

• 

• 

Go to the beach – There’s a small beach at the southernmost point that rents umbrellas and chairs. There’s also Smathers Beach, which is on the Atlantic side. Key West isn’t known for their beaches, but they do exist! Smathers is the largest and is about a half-mile. You can also rent chairs and umbrellas here.

A few more ideas are: Eco Discovery Center // Champagne Sunset Cruise // Dante’s Pool // Shipwreck Travel Museum // First Legal Rum Distillery // Key West Aquarium // Fury Water Adventures //

Restaurants & Bars

Recommended restaurants:
–DJ’s Clam Shack – (alllll the seafood)
–Blue Heaven (brunch here was so delicious)
–Two Friends Patio (had dinner here and it was good! It was also karaoke night, so that was entertaining!)
–Caroline’s Cafe (had the blackened chicken pasta and damn… it was good! Definitely spicy, but delicious. Everyone was extremely happy with their dinner here)
–Lagerheads Beach Bar (definitely want to check this out next time, sits right on the beach)
–Off the Hook Grill
-Sloppy Joe’s Bar

• 

• 

There are sooo many more – but those are a few that I recommend and have been recommended!

Bars for a good time:
-General Horseplay (such a fun atmosphere. Come here for some fancier cocktails)
-The Rum Bar
-Sloppy Joe’s Bar
-Smallest Bar (not the best tbh, but it’s fun to see)
-Tipsy Rooster
-The Abbey
-Irish Kevin’s
-Maryellens
-Garden of Eden (this is a clothing optional bar… quite the experience. You’ve been warned haha)

What to Wear

I’d say that the vibe in Key West is definitely casual! You can see what I packed in my previous post – Key West – What I Packed

I would love to hear any other recommendations you have – leave it in the comments! Like I said, I definitely wish we had at least one more day, but that just means I get to go back!

Thanks for reading!

xoxo,
Katelynn Ann