2 Days in Key West | Travel Guide

April 15, 2017

Key West is a beautiful island city in South Florida, lying 90 miles north of Cuba. Planning a trip can first seem a little overwhelming when you first arrive in Key West. There is so much packed on such a little island that you may not know where to start. This is a great travel guide for how to spend 2 days in Key West. If you have more time in Florida, Naples is a great area to explore. Read my two posts on what to do in Naples here and here.

getting here

The three ways to get to Key West are: car, plane, or boat. Each way has positives and negatives. A flight can be much quicker than boat or car depending on where you are, but is fairly pricy. A car allows you to take your time and visit the other Key islands on your way down, but be forewarned. The drive is long and the majority of it is on a long highway through the ocean; it’s quite a boring drive despite what you may initially think. Since you’re heading out to a fun island, I think the most adventurous way is via boat. This is incredibly easy if you’re in Southwest Florida.

We didn’t want to deal with the stress of driving 5 hours to the tropical island, so we hopped aboard the Key West Express. The Key West Express is a high speed ferry departing from either Fort Meyers or Marco Island taking you directly to Key West in about 3.5 hours. Roundtrip ticket prices range anywhere from $62 for children to $155 for adults. The ferry itself is completely stocked with food, a bar, clean bathrooms, and plenty of seating. They even play a movie onboard each way, which helps the trip go much faster.

Boarding the Key West Express
Tyler and I about to board the Key West Express! Such a great sunrise too.

where to stay

If you love being in the center of the action you should stay on the north end of Duval Street. It’s the Bourbon Street of Key West. Party central at its finest. I highly recommend La Concha Hotel & Spa. It was the perfect location for us – everything we wanted to do was in walking distance. This area is a bit more pricy for a hotel, but since you’re only here for 2 days in Key West, it’s worth a splurge!

For those looking to escape the bustle, try looking for hotels on the south shore, specifically near the Southernmost Point monument. This way you can still be in a great, central location but it will be much quieter. There are also some beautiful beaches nearby.

where to eat

Red Fish Blue Fish – We ate lunch here the day we arrived. The dolphin sandwich was amazing Keep in mind there are chickens and cats everywhere on this island! They may even show up when you least expect it….like when you’re eating lunch!

Photo at the restaurant

A chicken and her chick interrupting our lunch!

Amigo’s Tortilla Bar – They have great tacos and margaritas! It’s small and gets crowded fast so be prepared to wait.

Sloppy Joe’s – Sloppy Joe’s in probably one of the most famous restaurants/bars in Key West. It’s a fun atmosphere and everyone always seems to be having a good time.

Sloppy Joe's

Key Lime everything, specifically pie – So many good selections on yummy slices of Key Lime Pie. It’s a staple dessert here and you’ll get the best! It’s served at nearly every restaurant and there are even several key lime shops. For the best deal, go to the bakery section of a grocery store to buy it by the slice for much cheaper than at a restaurant. I promise it tastes just as good.

where to drink

Where not to drink here? Seriously every other building on Duval Street is a bar and people keep rocking through all hours of the night here. Plus, even though you only have 2 days in Key West, doesn’t mean you can’t have a great time. Some of the bars we checked out:

Flying Monkeys – This spot is famous for their frozen drinks. We stopped by shortly to sit at the bar and try one. Every couple of minutes a new person was coming up to the bar to refill their souvenir cups.

Willie T’s – GO GO GO! This was hands-down our favorite bar on the island. The live singer was great – super engaging with the audience, hilarious, and had a great voice. This place is famous for their mojitos and after having one several, I know why! My favorite was the Key Lime Mojito.

Capt Tony’s Saloon – This bar is pretty empty during the day compared to others but once the sun sets it gets crowded! We ended up having a beer here while we waited for a table to open up at Amigos across the street. Oh, and I should mention. One of the gimmicks here is that some lady’s choose to hang up their bras here. Yes, literally. There are bras hanging all over this place.

what to do

There is a lot to do besides eating and drinking your way through this town!

Jet Ski – One of the coolest activities to do here! We did an hour and a half jet ski tour where we were able to explore all the way around the entire island. The morning we went was a bit overcast and the waves were HUGE which made this a crazy and somewhat scary adventure at time. We used the Fury Key West company and it was fantastic.

Wetsuits before jetskiing!


Take a picture at the Southernmost Point – It’s a bit of a madhouse trying to get a picture here. There is a long line of people all waiting for their turn to take a picture. However, it is cool to say you were in the southernmost point of the continental US!

Southermost point in continental US

Sunset at Mallory Square – This is probably the most popular spot on the island when the sun is about to set. That means you’re bound to get some of the most interesting people-watching Key West has to offered. Every five feet there seems to be street performers – even a man chopping up coconuts with a machete for you to have fresh coconut juice!

Machete-chopping coconuts!

Sipping coconut juice

Sipping coconut juice!

Buy some art! – There are fantastic art galleries and shops throughout Key West. I love buying prints from different cities I visit – soon I’m going to run out of room on my walls for all of them!

Find quirky photo ops – There is so much to explore in this city. Just wandering you’re bound to stumble upon lots of cute streets to take photos on.

Cheesy photos

Alas, our 2 days in Key West have come to an end. And although it was a blast, I’m sure you’re as burnt out as I am.

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