Key West…the land of breath-taking sunsets, great live music, Hemingway’s legacy and the backdrop to some of my favorite Kenny Chesney songs.
One of my favorite places to visit on Earth, my home away from home and I am always longing to get back. I hope this travel guide helps make your trip to Key West an experience of a life time and you fall in love with this place like I did.
First, let me start off by saying I have been to Key West three times and there is so much to do. If you go to Key West and you are bored…ya doing somethin’ wrong. As I mentioned there is a lot to do but in this travel guide I am only going to focus on the things I have actually experienced.
When to Visit
I have been to Key West twice in June and once in January. I don’t recommend either of these times to visit. It is so hot and humid in June and January is a little cooler then I prefer for a vacation. Spring (March – May) and Fall (September – November) will be better times to visit but keep in mind hurricane season is June through November.
How to Get There
There are a few different ways to get to Key West. First, you can book a flight into Key West but most likely you will have a layover in Miami. The airport in Key West is very small and the flights tend to be a little expensive.
You can also fly into Miami or Ft. Lauderdale and drive to Key West. It’s about a three and a half hour drive. I recommend getting a convertible and cruising down Highway 1, also known as A1A with the radio blasting. Highway 1 is famous and while it's one lane the whole way down, it’s a beautiful scenic route.
A more unique way to get there is to take the Key West Express from Ft. Myers to Key West. You can fly into Ft. Myers and take the three and half hour ferry ride down. The ferry has a full service bar and food, plays movies and has an outside deck to soak up the sun with a beautiful view of the ocean. You do need to make a reservation in advanced for the ferry and check the schedule because it only runs at certain times of the day. The ferry does a Black Friday sale every year and the deal is so worth it. You can buy a round trip ticket for $99 and I believe the ticket is good for two years.
Where to Stay
Most of the action is on the southern end of the island so I recommend staying on that side to make exploring easy. Most of the hotels are small boutique hotels so they are unique and focus on hospitality.
This most recent trip we took to Key West we stayed at the Lighthouse Court Hotel and it was really nice. The room was very clean, the staff was friendly, they had free breakfast by the pool and a mojito bar that was awesome.
I have also stayed at the Wicker Guest House right on Duval Street, smack dab in the middle of the action. The hotel was nice and had a pool but I would not recommend staying here if loud noises throughout the night bother you. Since you are on the street with all of the bars, it can be loud into the later hours of the night.
Papa’s Hideaway is where my friend’s have stayed a few times and they love it. They like to rent out the whole place (about 6-8 rooms) to have it to themselves, which was a lot of fun. The pool is really nice and it’s very close to the southern most point, tucked away on a little side street. It offers more privacy than some of the other hotels.
We’ve also rented a house before which was so fun. It had an extra outdoor shower and a hot tub. We stayed there in January so a hot tub was very nice because it was cooler then. I would recommend renting a house with a pool if possible to cool down if you go during the summer. Trust me, you’ll thank me later.
How to Get Around
If you stay on the southern end of island close to Duval Street, you definitely do not need to have a car. You can walk to pretty much anywhere.
We rented bikes through Island Safari Rentals and it was extremely convenient. They drop off and pick up the bikes right at your hotel and I believe it was $13 a day per bike. We kept the bikes a few days and used them to get around everywhere. They provide a bike lock and bike racks are all over the island. You won’t have any trouble finding a place to lock it up while you are shopping, bar hopping or out exploring.
Another way to get around is to rent a moped. While these are fun, they are a little more expensive and can be dangerous. Normally, I wouldn’t say mopeds are dangerous but when I rented one I broke my knee. Yup, you read that right. On my first trip to Key West we rented mopeds and on the very first turn I hit a curb and broke my knee. I turned a little too quickly and that put a little damper on the trip but still lots of fun. So be careful if you rent one of these.
What to Do
As I mentioned earlier, there is so much to do in Key West. You can shop on Duval Street, bar hop, eat delicious food and find some great live music.
Something I think everyone should experience is the sunset in Mallory Square. I recommend going to Mallory Square about a half hour to an hour before the sunsets to get a good spot. A lot of people gather every night to watch the sun sink down into the ocean and it is spectacular.
We booked a Cruisin’ Tiki sunset tour, which was so fun. It’s BYOB and you go on a tiki boat for three hours to see the sunset from the water. It was beautiful and I can’t recommend it enough. They also have day trip tiki boat tours where you can go snorkeling and swimming as well.
Since so many people gather at Mallory Square every night, there are also performers who do shows before and after the sunset. You have magicians, sword swallowers, palm readers, dogs that do tricks, the list goes on and on. Some of the performers have really good shows and some not so much. The one annoying thing I do want to mention is the performers are there to make a living so they do ask for tips. Some of them can be very pushy. Do not be afraid to walk away from their show and do not feel like you need to tip them. If you want to that is ok but do not let them pressure you. Some of them really rubbed me the wrong way.
Key West is not known for its beaches. While they do have some beaches, I do not recommend going to Key West to lay on the beach. I do however, recommend going to Ft. Zachary if you like nature. There is a beach there with a small café that sells concessions. You can also ride your bike through the preserve there. We rode our bikes there and I think it was $2 per biker to get in.
Smathers Beach is an ok beach to visit. If I am remembering correctly, I think we took an Uber to that beach. If you rent bikes, you might be able to bike there.
The Southern Most Point is also a big tourist attraction. Personally, I would recommend riding your bike past it, if you want to see it. There is nothing to do around there. If the cruise ships are at port there will be a line to take a photo. I would recommend getting up early one morning to beat the line for a photo. I also suggest going to mile marker 0 while riding your bike around to snap a quick photo. They are not too far from one another and you can hit a lot of touristy things in a short time.
Hemingway House is a must do. It was right across the street from our hotel and you will learn so much about the history of Hemingway. You do have to pay an entry fee of $14 (cash only), which included a guided tour and I highly recommend it. The tours are constantly running and are about 30 minutes long. After the tour you can roam the property on your own and play with the six-toed kitties. You will learn all about Hemingway’s pterodactyl cats during the tour and yes, you can pet them.
Last but definitely not least, bar hoping and listening to live music is one of my absolute favorite things to do. There are so many talented people hanging in Key West and preforming at some historic bars. If you love live music, this is something you definitely want to make time to do. My favorite place to hangout and listen to music is Hog’s Breath.
Where to Eat
Ok, let’s get to the good part. FOOD!
Moon Dog Café was one of my favorite places to eat. We stopped there on the first day and it was SO GOOD. I had a mahi-mahi sandwich, which is one of my favorite things to order. It was really good. They also had THE BEST key lime pie. Now, I know that is a big claim to make but I tried key lime pie at pretty much every place we ate and this one was by far my favorite. We walked in around 12 or 1 PM when we first got to Key West and we did have to wait a little bit. I would recommend going here for brunch or lunch and making a reservation.
Blue Heaven is a very popular restaurant in Key West and it is worth every bit of hype. I recommend eating here twice, one time for brunch and one time for dinner. They are both so amazing and I couldn’t deprive you of the experience of both. I had the eggs benedict, something else I love to try everywhere I go. I think the hollandaise sauce makes or break the meal and I loved it. I got a side of their banana bread and it is mouthwatering. We also went here for dinner and it was incredible. A reservation is a must for dinner or brunch.
DJ’s Clam Shack was a great little place to stop and grab a snack. It was featured on Diners, Drive-ins and Dives with Guy Fieri. I think we had the cracked conch. It was really good and the perfect little snack while drinking all day. It’s right in the middle of Duval St.
We did eat at two places I don’t recommend and while I normally wouldn’t call out these restaurants, I want to prevent you from wasting your money while on vacation. I do recommend avoiding Sandbar Sports Grill and Bagatelle. No one in our group enjoyed the food at either of these restaurants.
Where to Drink
We did a lot of bar hopping obviously and these spots are so fun to stop and grab a drink or two and then hit another bar. We didn’t eat at most of these places so I can’t speak to their food but the live music and drinks were awesome.
- Green Parrot: had a really good reggae band one of the nights
- Willie T’s: this bar has money stapled to the whole bar, definitely stop for a pic
- Blue Macaw: they have a build your own bloody bar with all the toppings
- Irish Kevin’s: highly recommend this place on a Friday or Saturday night for a great time
- Sloppy Joe’s: famous because of Hemingway, definitely stop in for a drink and some history
- Hog’s Breath: by far my favorite spot for live music
- Garden of Eden: clothing optional at this bar (insert blushing emoji)
- Lucy’s Retired Surfer Bar: if Rob Benton is playing here live DO NOT MISS HIM
Better than Sex is a dessert restaurant that you have to experience. It’s a romantic, dark atmosphere where you can order different chocolate dipped alcohol drinks. I ordered the Sex Appeal, it’s a sparkling white moscato in a red sugar and white chocolate-rimmed glass. Soooo good. They do book up though so make a reservation as soon as you book your trip. So worth it.
All right, if you made it this far I recommend grabbing a drink because you deserve it! That was a lot to take in but I wanted to give you all the details so you can plan an amazing trip to Key West. If you’ve been to KW or plan on going comment below or send me a message on Instagram, I would love to hear about your trip.
xo, stay salty babes