Vacationing in Key West? Here Are the Best Things To Do!

Jennifer MeyerDestination GuidesLeave a Comment

Key West is iconic.

Are you ready to plan an unforgettable vacation?!

This guide will inform you of fun things to do in Key West!

Learn exactly what you need to know when planning your vacation in Key West!

And, if you’re not already planning a vacation there, you definitely should!

I was in Key West, FL over the 4th of July this year (2017), and I loved every moment! The town is cute, small, and beautiful. Along with some famous landmarks, Key West has tons of fun surprises!

Sleeping Accommodations

One of the most important factors of any trip is deciding where to stay. You have to choose something affordable, clean, and in the perfect location! If you are planning to make a trip down to Key West, I would definitely recommend booking your sleeping accommodations sooner rather than later, especially if you are going during a popular travel time–like the 4th of July. As you may have guessed, I learned this the hard way (oops), but you don’t have to!

I booked the Blue Marlin Motel. It was within walking distance of Duval St., which is the main street in Key West, and by “main street,” I mean that it is the one with the majority of the bars and nightlife.

Granted, the Blue Marlin Motel was not the hotel/motel in the best location, but it was the best location that I could find for the price!

Although, had I looked a little further ahead of time, who knows what I could have found. Still, no regrets. The hotel was clean, easy to find, and had a great pool.

If you want a neat experience, quite a few people rent out their boats just like someone might rent out their condo! So you can rent a boat to sleep on! While this is totally awesome, make sure you don’t mind being in close quarters with those you’re traveling with! Check out Airbnb and Home Away from Home and other sites like that! Plus, it can actually be pretty expensive.

To save some money, check out motel information and booking options on for the Blue Marlin Motel on!

(Disclaimer: If you book a room at the Blue Marlin Motel from the link above, I do receive a commission. However, I recommend this motel because of my wonderful experience!)

If you want some tips on booking sleep accommodations, check out my other blog post called Top 10 Tips: Effortlessly Book Your Ideal Hotel for Cheap!

Bars and Nightlife

I visited four bars in the two nights I was in Key West: Rick’s, Irish Kevin’s, Sloppy Joe’s and the iconic Margaritaville. Some bars are open until 4 am there, which is crazy to me considering that bars where I live close at 2 am at the latest. Also, alcohol can be openly carried on Duval St.! Yes, Key West might be a booze lover’s dream vacation spot!


This bar had such a laid back atmosphere. We didn’t wander into this bar until 3 am, and it was a Monday night, so unsurprisingly, it was relatively quiet. But, get this, they had karaoke! My boyfriend and his friend are suckers for karaoke! So we, of course, participated! I sang “Before He Cheats” by Carrie Underwood, and a very nice, very intoxicated lady absolutely adored me for it. (Meeting people on trips is always so fun!) Also, there was another lovely lady in the bar who brought her French Bulldog with her! The dog was so sweet, and it went up on stage with her when she sang! (I’m a sucker for French Bulldog’s, if you couldn’t tell.) Everyone that worked at Rick’s was incredible! The bar owner was there serving drinks, and she was so sweet! The Karaoke DJ (I may have just offended anyone who  does this for a living by not using the correct title, and for that, I’m sorry!) was phenomenal. His personality was so great. He was nice, funny, and quirky!

Irish Kevin’s

This bar was crazy and completely packed. I’m not sure what the maximum occupancy is at this bar, but it seemed like we had reached it. We had a difficult time making it from the entrance to the actual bar to order a drink! I have had to work my way through tight crowds before but nothing like this. There was just nowhere for anyone to move in certain parts–make that most parts–of the bar.

The decor was pretty much exactly what you would expect from an Irish bar. But they did have an awesome Jameson chandelier. Yeah, you read that right!

On another, more fun note, Jared and Jim, the band that played that night, were incredible. They were fun to watch, and their crowd interaction was perfect. They played tons covers and said that they would play any request, which they held true to, and you could tell that people were trying to throw them curve-balls.

 Sloppy Joe’s

Imagine Sloppy Joe’s as a mixture between Rick’s and Irish Kevin’s. It was busy and there was live music, but it definitely had a more relaxed atmosphere than Irish Kevin’s. You didn’t have to elbow your way through a dense sea of people in order to get a drink, but you also didn’t have a French Bulldog wandering around the stage either. The live music wasn’t as awesome as over at Irish Kevin’s, but it was still enjoyable! Philo was the band that played while we were there. They were definitely great and fun to watch.


My parents are huge Jimmy Buffett fans, and as a result, I also enjoy


Buffett’s music. I have fond childhood memories that are brought back when I listen to his songs. And now, I can actually relate to them–it’s 5 o’clock somewhere! So, of course, I had to go to Margaritaville while I was in Key West!

I will admit, the restaurant/bar was a lot smaller than I imagined! (I have been to the one in Orlando, FL, which is significantly bigger.) Still, the atmosphere is cool and so is the music. If you go and are a margarita lover, I would definitely recommend the Perfect Margarita!

But, not a single one of us ordered a bad drink while we were there, so order whatever strikes your fancy! We didn’t order any food because we were ballin’ on a budget. Yeah, I said that–no regrets! I think…


Okay. First of all, don’t go to Key West for the beaches. They aren’t so great. When I think of a beach, I think of a great expanse of sand and ocean. Sure, there is plenty of ocean, but the beaches were tiny and the sand wasn’t very nice. That doesn’t mean that you shouldn’t spend any time at the beach while you’re in Key West though!

There is a dog beach, so if you take your dog on your trip with you or if you just love seeing other people’s dogs, it’s definitely a neat place to check out! We saw it, but we didn’t spend any time there.

Also, there is a beach at Fort Zachary. I would recommend the beach there because they are trying to rebuild a coral reef, and you can snorkel there! However, when we were there, the current was really rough, which meant that sand was getting churned up, making it difficult to see. So at the deeper parts, you really had to dive down a bit to be able to see much. I would still definitely recommend checking it out! We had a great time there!


There are tons of food options in Key West. Like, oh my gosh, so many.

Jacks Flat’s

This was where we went the first night. We enjoyed some American cuisine (a Burger and Philly Cheesesteak, among many other yummy dishes), but for a restaurant that advertises their food as American, the menu is actually quite eclectic. There was something perfect for everyone in our group! The restaurant had a bar, so if we had wanted a drink, we could have easily order one. Also, they had tons of TVs! We watched American Ninja Warrior while we ate; even though I usually despise TVs in restaurants because of their incredibly distracting nature, it was perfect because we were all exhausted from our day of driving and snorkeling, so creating conversation was outside of our abilities that evening. While the food was good, the service was only mediocre. We ran out of water and our waiter had an occasional attitude. He let what was going on at other tables affect how he treated us. Even though the service wasn’t top-notch, the food was good and reasonably priced, and we would probably go back.

Caroline’s Cafe

We had lunch at Caroline’s Cafe on the 4th of July! While they advertise having the biggest and best burger in Key West, none of us actually ordered it. I know! No one ordered the supposedly phenomenal burger on independence day: embarrassing. I ordered the Dolphin Sandwich–in case you don’t know, it’s Mahi Mahi and not actual dolphin–and it was delicious! My boyfriend ordered the Ahi Tuna appetizer, and it was also incredible. It looked and tasted fresh. It was delightful! In true Key West fashion, I ordered a Key Lime Margarita. It was yummy, but honestly, it tasted like a regular margarita, so I may have fallen victim to some clever advertising.

Mr. Z’s

We went here for dinner one night looking for something inexpensive. It was a cash only joint, and it was tiny. We ordered two pizzas (a white pizza and a philly cheesesteak pizza) and the five of us took up most of their seating. But it worked out perfectly, and oh my gosh, it was delicious!

Biggest Regrets

Now it is time to discuss my biggest regrets about the trip. I don’t regret going to any of the bars or restaurants or beaches or anything like that! We enjoyed everything we did! My regrets lie in missed adventures.

Not Seeing Robert the Doll

I really wanted to see Robert the Doll, who inspired the Chucky movies, while we were in Key West. I am a huge fan of horror movies, and I think that seeing Robert would have been a neat experience!

Not Stopping by Hemingway’s House

I majored in English in college, so admitting that I didn’t tour Hemingway’s house while I was there is embarrassing to say the least. Granted, I believe that I was the only one in my group that wanted to go see it, so even if we had time, I’m sure I would have been out-voted. I did get to see it as we drove past though…does that count?

Not Visiting Mile 0

We stopped at the Southern Most Point and waited in line for a picture, but we didn’t find the Mile 0 mile marker. I don’t know why. I wish I had a picture of us next to it, and maybe we wouldn’t have had to wait in line for that one–I know, crazy thought!

Not Having Enough Time

Above all, my biggest regret was only spending two nights in Key West. I would have loved to stay for longer! I wanted to relax and explore the entire key! There are so many quiet, cute streets, and I wanted to walk down each one of them!

I hope you guys enjoyed reading about my experience in Key West! I hope that all of my recommendations help you when you plan your trip! Are you heading to Key West soon? Do you dream of going one day? Or have you already been? Let me know in the comments below!

Until next time,



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