The keys are a famous area at the very bottom of the state of Florida. Known for their relaxed atmosphere and gorgeous blue waters. It’s not hard to see why Ernest Hemingway made this his home after visiting. Much of your visit will probably revolve around water activities and Duval street mischief. Either way, it’s a place to relax and enjoy the sun and water. There’s a reason why the beach boys added the keys to their famous Kokomo song! Whether you are celebrating a wedding, heading down for a relaxing weekend or maybe a great fishing trip, it’s got plenty of options for everyone.

Top 5 Things To Do

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1. Sloppy Joes
2. Ernest Hemingway Museum
3. Jet Skiing
4. Fort Zachary Beach
5. Butterfly Conservatory

Sloppy Joes: The Original watering hole and a frequented place by Ernest Hemingway himself. This bar is rich in tradition and fun. As soon as you make your way through one of the many entrances, you are instantly greeted with music and laughter. It’s a large bar area and has pretty basic food for the most part. It’s really the atmosphere that you should come to experience. Anyone that makes their way down to Key West will tell you, you’ve got to stop at Sloppy Joes.

Ernest Hemingway House: This house isn’t overly extra exciting with extra bells and whistles, but is still an icon in the area. It has a lot of interesting history in and around the house. You really get a good feel for who Ernest Hemingway is and why he was so important to the the Key West area. You also get a chance to meet his many descendants of cats from while he was alive. Cats are scattered all over the grounds lounging and waiting for your affection! It’s easy to see who took over the house, when the owner left!

Jet Skiing: There are many jet ski companies around the area and I’m sure you can’t really go wrong with one. I’ve been with multiple companies and will say that this has come up both times as one of the favorite things that we did on our trip. There’s something so cool about jet skiing around the entire island of Key West. You see the island from a different angle, but also get the beautiful views of that crystal blue water as you dash around the island at top speeds. I would recommend this over parasailing also.

Fort Zachary Beach: This last trip was my first time going to this beach area and I’m unsure why I hadn’t gone in the past. This beach is a really pretty area to go to, where you often don’t find an excessive amount of beaches in the keys. It’s easy to ride your bike to, they have a great cafe for drinks and food and also some areas to go snorkeling. My favorite part about the area was after hours when the sun is about to set, you get one of the best views of a sunset on Key West.

Butterfly Conservatory: Right off of the back end of Duval street is the butterfly conservatory. It takes you away for a brief moment in time. Duval street can get a little crazy and to step into their world and just relax and watch butterflies and birds flying around you, it’s a very peaceful situation. We stumbled upon this and were a little uncertain of what to expect going into it, we found that this was actually one of our favorites on the island. It’s just so relaxing to step a way, even if it is for only an hour or two. The ticket prices aren’t too bad and its easy walking from Duval.

Itinerary

Day 1

• Ernest Hemingway Museum
• Green Parrot Cafe
• Island Massage
• Hogs Breath Saloon
• Key West Rum Distillery
• Sunset Cruise
• Alonzos Oyster Bar 

Ernest Hemingway museum: Known to many as one of the greatest American writers, Hemingway wrote many historic stories like the old man in the sea and for whom the bell tolls. Tour through his house, which is now a museum. General admission is only $16 dollars. The house has many items from his past and you will also see his love of cats! Cats are all around the property lounging, which also adds something extra to your visit. Take some time strolling through and you’d be surprised at some of the facts you learn. It’s a quick tour and shouldn’t take over an hour to two at most, unless you would like to relax in one of the many gardens around it.

Green Parrot Cafe: The next block over you will find another famous bar. The Green Parrot dates back to 1890 and stands as a locals bar. A much smaller atmosphere than Sloppy Joe’s, which makes a bit more intimate. Live music happens often here, but the people watching is also a wonderful thing. You see all walks of life come into the bar, and it never really seems like there is judgement of anyone. This staple of key west really shows just what this island is about. They do have craft beer options or a full liquor bar. Stop in at the bar and have a beer after touring the Ernest Hemingway house. 

Island Massage: While you are in Key West, you’re more than likely on vacation right? Why not stop off and have a relaxing massage in the middle of it? We stopped at this local massage spa and loved the kind people and kind hands! There are several places to go and enjoy a massage, this one is just right across the street from the Green Parrot and they did a wonderful job. Stop in for a 50 or 80 minute massage. Not bad prices for being right off of the main area of Duval. We had a couples massage and both people did a wonderful job in making us feel comfortable and were very personable with us. It’s a small location, but it was a great break from the Key West party scene. 

Hogs breath saloon: Another famous bar in Key West, it’s been said that most famous country artists have played here at one point in their career. Outside, you will find a post where you can place your heads into cut outs of pigs dressed in island attire. The inside is a island feel meets rock and roll. The place will normally have some type of band playing when you enter, and more than likely it will be busy. The drinks are pretty normal when you compare the rest of the keys, but the food is actually pretty good. We ordered some stone crab, ceviche and a couple of other seafood entrees. All were actually pretty good for what we thought we would get with the atmosphere. There are also signature shirts for you to purchase to keep that memory of the location. You will see many people with the Hogs breath shirts, so join the club!  

Key west rum distillery: As we walked away from Hogs breath, we were feeling pretty full on food, but still looking for something to do in between our sunset cruise. What we came across as we came up to the harbor was the Key West Rum Distillery. They offer private tours of the distillery and end in the tasting room. The staff is fantastic and give a great history of the place, along with what rum they create as opposed to larger distillers. It was very educational and it gave me a great understanding of how rum is made. They have many different types of rum. One part of a rum company that I didn’t know was if the company doesn’t make a simple rum without the flavoring, you should probably question how they make it. At the end of the tour, taste as many types of rum that you wish, I recommend the bad bitch and cuban coffee rum, but there were plenty of delicious rums to try! The tour was a great time to spend while waiting for the cruise and I honestly didn’t know the differences with rum vs whiskey and other liquors.  

Sunset cruise: After the distillery, we were ready to go for our sunset cruise. We chose to go with the Fury company with this one. There were a decent amount of people joined together at the dock when we got there. There are several restaurants and shops in the area if you get there a little early. As we got on the boat, we were instantly greeted with a choice of beer or margarita. The drinks were actually decent for being a large commercial boat. We made our way out of the harbor and found a place to set up and watch the sunset. Sadly we got out and it was very cloudy so we never got a chance to the see the sunset on the boat. What we did experience was a great time dancing, eating, drinking and listening to a 80’s cover band. The band played various hair band songs from the 80’s the whole cruise. Of course, as the cruise went on, people drank more and more, which lead to more dancing and fun on the boat. We talked with several couples that were on the boat and made some good connections. We enjoyed our time on the boat and would have been even better with an actual sunset to see. Either way, the crew did a wonderful job of helping make sure that the people on the boat were fed and well dosed with alcohol! 

Alonzos oyster bar: After the boat, we decided to finish the night off with a little meal. We stopped in at the oyster bar for some food. We both had some drinks in us, but we decided to take on the seafood tower! The seafood tower comes in various forms, but we got the tower that came with king crab legs, oysters, clams, shrimp, calamari, seaweed salad and fish dip. It was pretty massive and we weren’t able to eat the whole thing, but we did enjoy the food. It was a great location right off of the harbor area and would recommend stopping in for a bite. If you aren’t hungry it’s fine to just stop in for a drink and an appetizer if that’s how you want to end the night.  

Day 2 

• Jet Skiing
• Waterfront Brewery
• Willie T’s
• Wicked Lick
• El Siboney

Jet Skiing: Our morning started early as we grabbed an Uber out to the edge of Key West. There are several jet skiing tours around Key West, we went with sunset water sports. It was located right off of the Parrot Key hotel. The jet ski tour takes you from that area and loops completely around Key West. Depending on your desired speed for the tour, they will break the group up between people that want to go fast and others that prefer a slower speed. We of course had to go with the faster tour! The water was perfect and many places you could see down to the bottom. There are various stops that are made to give you a history of the island and also for others to catch up. They were very accommodating and gave plenty of opportunities to enjoy the ride. The cost wasn’t too bad overall and the passenger rides free with them. The jet skis were in great shape and had some speed to them when you held down the throttle. Overall it was one of our favorite experiences on our trip. Sometimes it’s just fun to get some type of adrenaline rush in your vacation! 

Waterfront Brewery: After jet skiing and feeling a bit of pain from sitting for a while, we figured it was time to hit a watering hole. We stopped in at the new local brewery in town. The first thought was that this place was huge! A massive building for the brewery, it has arcade games, pool and various other things to do on one half, and the other half is the brewery. They had good food overall and the beer was pretty good. They only allow you to do their house flight as opposed to creating your own with their beer, which was a little disappointing. Overall it was a good experience and some decent beer. I was surprised that they had several IPA’s as they aren’t always ordered in warm climates. They were actually pretty good, but I would much rather have a lager in this type of humidity. 

*Willie T’s: Off to the strip again we went. This time we wanted to spend some time at a local bar known for placing dollar bills all over and their live music. The place constantly has a decent amount of people at it and the singer always plays to the crowd. The singer will usually play classic rock for the most part, but don’t be surprised if they throw in some type of a jingle from a tv show here and there! The drinks are pretty simple like most of the main bars on the strip, but still it has an outdoor feel to it and live music is really never a bad thing right? 

Wicked Lick: Everyone enjoys a little ice cream right? This ice cream is made with nitrogen so it’s got a different consistency to it. There are a vast amount of ice creams and even more toppings to try. The seating area is small, but if there is nowhere to sit, you can walk with your ice cream. The owners are fantastic and will give plenty of recommendations on different flavors to try. We had a delicious pistachio flavor with a biscotti topping and we were not shy with jumping in to eat it! 

El Siboney: A little ways off the strip is a wonderful Cuban restaurant. It’s a short walk from the middle of the strip or you can drive of course. The restaurant itself is simple and keeps with the family feel. We were greeted kindly and offered fresh Cuban bread, which was amazing! There is a wide array of drinks and Cuban dishes for you to dive into. It’s also plenty of food! My wife got the strip steak and I ordered the enchiladas with yucca and sweet plantains. Both were delicious meals that we loved. The place is highly rated and if you’re in the keys (which is the closest you will get to Cuba without being there) you need to try some delicious Cuban food. 

Day 3 

• Parasailing
• El Meson De Pepe
• Fort Zachary Beach
• Mangoes
• Sunset

Parasailing: Waking up the next morning, we walked down to the main area by Mallory square. The dock where we went with Fury parasailing has a lot of different options for you to take tours from. We got there early and they offered for us to take the early tour since there were less people on the trip. The boat took us out and there was a brief introduction to parasailing and directions on what to do. We were chosen to go first as we were the closest to the back of the boat! Both of us had not parasailed before so we were a bit nervous to go. What I will say is that it is much more relaxed than we expected. Even the initial take off from the back of the boat was much slower than we expected. When you get up in the air, it’s a beautiful view of the entire island. It feels so tranquil as you fly high above everyone. They take you down to dip into the ocean a couple of times but it’s slow enough to where it doesn’t feel like you’re dropping to your death. I was going to take my go pro but wasn’t sure if it would stay on or not. I should have worn it. The crew takes pictures while you are up and charged way too much for pretty mediocre photos. Other than that, we had a fun time, just not sure if we would do it again. I would definitely recommend at least trying it while on the island though. 

El Meson De Pepe: We got down and wanted some more Cuban food from the night before. This time we stopped at a restaurant right next to the square. I had been wanting a Cuban colada since I had been on the island so I ordered it with a mojito. The Cuban bread and food we got was also delicious. The inside of the restaurant was even cooler. Cuban history is sprinkled around the place and has a wonderful decor. At minimum I would say to grab a drink here and see the inside. Regardless, the food was as good as the drinks. 

Fort Zachary beach: After deciding that we needed some form of transportation, we got bikes to ride around the island. We were glad we did and probably should have got them sooner. Either way, you can walk to most of the attractions. We biked over to Fort Zachary beach. The beach was nice and even had a small cafe to get small food items and drinks. We got some and sat on the beach. The snorkel equipment was sold out from the rental area, but the store also sells equipment for the same price! I got a snorkel and went out to the small reef area in front of the beach. There were small forms of sea life around the area to enjoy, but nothing like if you actually go out and snorkel in the much larger reef around key west. The beach and water were perfect though. We relaxed after a couple of days of go go go and enjoyed it. 

Mangoes: Heading back into a town after spending the day at the beach, we went to a restaurant we hadn’t gone to. Mangoes is down in the thick of it, but a bit nicer dining than some others we had gone to, along with the staple live music. We had the maine lobster mac and cheese, tuna poke and the crab fritters. All were delicious. As we ate, it started to get busier and busier. Another band came on and several patrons started to get up and dance. They started to play various classic rock songs and it brought the excitement! Everyone jumped up and started to dance to the music. You could tell the alcohol started to hit! Overall it was a good place and some great music to go along with it. 

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Beach sunset: We finished the night by heading back to the beach to watch the sunset. It was a perfect ending to the night. Several couples joined on the night and the clouds were few. As the sun went down, it was the perfect setting. With palm trees around us and watching various fishing boats, we got to see someone wrestle to bring up an extremely large fish…only for the fish to break the line before getting up to the boat. We noticed several boats going through trying to get their perfect view of the sunset for their riders. We’ve been to many places to watch a sunset including Hawaii and we thought that it was a beautiful view that was hard to beat. If you are looking for a place to watch the sunset while in Key West, we would highly recommend seeing it at Fort Zachary.  

Day 4 

• Rodriguez Cigar Factory
• Sushi Song
• Butterfly Conservatory
• Little Pearl
• Mallory Square
• Irish Kevin’s

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Rodriguez cigar factory: Waking up on our final day, I was excited to finally get the chance to watch the cigar rollers in action! We showed up a bit early and got the fortunate chance to have a tour with the daughter of the creator of the cigar business. She took us around and taught us about the history of the place and showed us the different ways that they rolled cigars. We even got a chance to finish off some wrappers on cigars and roll our own! It was so cool to get the chance to roll cigars. Turns out it was a littler harder than I thought! I have much more respect for cigar rollers now! As she finalized the tour and took us up to see where they stored cigars and showed us pictures of her father upstairs, it was such a cool experience. We bought several types of cigars as we left and loved the experience. I would highly recommend doing this tour of Rodriguez cigars if you have any interest in cigars at all. Most tours never give you the chance to learn how to roll your own! I also usually enjoy a Padron or Myfather cigar and these cigars impressed me quite a bit. Being that they are rolled right here with a Nicaraguan tobacco plantation that the family owns, I would highly recommend supporting them.  

Sushi song: We stopped off for sushi after cigar rolling. Why not keep with the rolling theme and then have sushi rolls right? We had various rolls that were delicious, but we loved the Miso Tom Yum soup. The restaurant itself was smaller, but still had plenty of seating. The service was great and we overall enjoyed the experience. There are many options to choose from if you are going for sushi, if not, they have plenty of other options on their menu that will delight.  

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Butterfly conservatory: Venturing over to the opposite side of Duval street, we stopped in at the butterfly conservatory. It takes you through the cycle of a butterfly to begin with and gives a lot of information about the life cycle. It’s not that exciting until you get into the conservatory. As you enter, you get a chance to enter into their world. As you enter, you are instantly greeted by butterflies all around you. The butterflies are going about their business and flying around in such a positive way. As you walk the pathway they fly all around you. They have several birds also in the area. It doesn’t take you too long to go around the walkway, but take your time and get the full experience in. It’s quite a difference in the conservatory compared to the rest of Key West. I would recommend going in and getting away for just a little bit.  

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Little Pearl: Our reservation for the evening was at a small restaurant just off of Duval street. It was the perfect setting for a romantic meal. The restaurant gets filled quick and it seems like reservations are even harder to get. The cool part about the place is that it has a tasting menu. When you get in, you choose between 2-3 different options for appetizers, main dish and desert. The food was fantastic! Every dish was something that the chef had shopped for at local markets for the day. It was the best meal that we had on the island.  

*Mallory Square: Leaving the restaurant, we finished our night at Mallory Square. The area is special that it used to have navy boats parked all around the area in the early days. Now it is bustling with street vendors and performers. If you want to see someone walk a tight rope and blow fire, you’ve got it! Watch the different performances and finish out your night.  

*Irish Kevin’s: To finalize the night we went to one last bar. An irish themed bar with live music and a wonderful atmosphere. We got in and were already part of the crowd. A group of people sat next to us and enjoyed the evening. As the singer called people up to do contests like chugging Guiness, it almost reminded me of being away on spring break! The atmosphere was electric and a perfect way to end our last night in Key West. 

Day 5

• Snuba diving
• Turtle Hospital
• Keys Fisheries Market & Marina
• A&B Lobster
• Sloppy Joes
• Ricks Key West
• Angelina’s Pizzeria

*Top people watching spot