Key West and the Florida Keys
The Florida Keys are a collection of 800 islands that cover over 180 miles of beautiful sub-tropical coastline. Home to some of the best fishing in the world, the 3rd largest living coral barrier reef in the world, and brings in over $1 billion in tourism revenue a year. Key West is ripe with Spanish, British, Cuban and Bahamian architecture, food, and culture. The historic city was officially founded in 1828 and at one time was the biggest and most prosperous city in the United States due to the wrecking industry. This island is full of history and is home to some of the most fun memories I've ever made.
When you’re planning a trip to the Florida Keys you need to ask yourself; what do you want to do? Key West is obviously the most popular island in the Keys but Key Largo, Islamorada, and Marathon all have their special perks that make them special.
Key Largo
Key Largo is the first key in the island chain. It’s home to amazing fishing both “out front” in the Atlantic, and “out back” in the backcountry of the Gulf of Mexico. I was a mate on a sport fishing boat for a year and met a lot of amazing captains and was fortunate enough to catch some trophy fish. If you’re looking for an awesome backcountry guide, or wanting to go out front I suggest Saltwater Cowboy Charterz with Captain Anthony. A 12 year Coast Guard Veteran and avid fisherman, he will get you on the fish and you’ll be in for a great time. Check him out on Instagram!
It is also home to the beautiful John Pennenkamp Coral Reef State Park, which offers incredible snorkeling and diving, as well as famous “Christ of the Abyss” statue. The Park is open from 8-8 and even has a dive shop on site to help with any questions!
Islamorada
Islamorada is considered the “Sport Fishing Capital of the World” and is home to some delicious rum and beautiful sandbars. If you’re looking for a fishing charter look no further than the famous Captain Nick Stanczyk out of Bud and Marys Marina. He is an amazing captain and has an awesome YouTube channel called StanzFam, check it out!
Since you’re in the islands you need to get some local rum! Be sure to check out Islamorada Brewery and Distillery for delicious craft beer and refreshing mixed drinks. My personal favorite is the Pirate Punch, don’t have too many of these because they’re super strong! Guaranteed to make your next sandbar trip a wild one! Their house made Spiced Rum is really good too and my favorite beer of theirs had to the Islamorada Ale. Be sure to check them out on your way down to Key West!
Marathon
This key got its name from the rail line that used to run through the entirety of the keys. At the time the Overseas Railroad was considered one of the most ambitious engineering projects ever be attempted. Business tycoon Henry Flagler was told it could never be completed, but in 1912 the last section of track was laid and the railway was completed. Marathon got its name from both sides racing toward one another when they were building. One team was in Key West, and the other way coming down from Islamorada. It was a race to see who could make it first! There’s a great restaurant in Marathon called Porky's Bayside Restaurant and Marina. They’re known for their amazing BBQ, seafood, and unique sushi rolls! It was definitely a place for me to enjoy some guilty pleasures and leave absolutely stuffed! Marathon is also home to the Turtle Hospital and the Florida Keys Aquarium Encounters.
If you’re looking for an adventure you should take a day trip to Pigeon Key right in the middle of the old Seven Mile Bridge. This key is now a historic landmark and has some really cool tours about the history of the island, the railway, and the wildlife of the Florida Keys. I took my mom on the island tour they have and it was pretty cool! We learned the island was also the finish line to Season 18 of Amazing Race! The old bridge has just finished restoration in 2021 and is open for tourists once again.
Key West
I truly don’t even know where to start. Key West is an amazing key and was where I called home for 4 years of my life. The people are amazing, the bars are so much fun, and the food is just as incredible as the views. We’ll start off by talking about a true passion of mine; fishing! The boat I worked for is no longer in business, but fortunately I know some awesome captains that I recommend to everyone! Boa Vida Charters with Captain Mary Ann and Sean is my personal recommendation to anyone looking to make a memory that’ll last a lifetime. I was fortunate enough to become friends with both of them and see them turn their 20+ years of passion to their dream job. They just upgraded boats and they’re ready to get you hooked up! I was fortunate enough to catch my biggest Mahi Mahi with them on the last trip I ever had in Key West. Their personality and good vibes makes catching fish and enjoying the sun on the water even better! Be sure to check them out on Instagram and tell them I sent ya!
The bar scene is incredible in Key West. The famous Duval Street is home to over 40 bars, and even more line side streets! When I was a tour guide I always told my guests that Duval is as close as you can get to Bourbon Street without going to New Orleans. I’m going to restrain myself and only talk about my top 4 bars in Key West. Coming in at #1 is the famous Sloppy Joe's Bar. Sloppy Joes is more famously known for being the favorite bar of author Ernest Hemingway. Today it is always full of people and known to have great live music of all genres as well as good DJ’s later into the evening. On the backside of Sloppy Joes is Joes Taproom, kind of like a bar inside of the bar. It’s small, but it is a nice place to sit down and escape the loud craziness of the main bar and stage. If you’re lucky you’ll see my friend Chris behind the bar serving drinks and sharing stories. He’s also a certified dive instructor and is truly passionate about it so I’m sure he’d love to talk about all the best sites, or even certify you while you’re in town!
Coming in at #2 is my personal favorite on the entire island, and that’s The Retro Room! This bar is just a block away from Duval Street and has this awesome nostalgic pop culture theme. This is a craft beer and wine bar only, but don’t let this discourage you. They have an amazing selection and some of the best bartenders on the island! The selection changes all the time but there’s some favorites they always keep on stock. The bar is also jammed packed with board games, arcade games, and the TV’s are always rocking the classics. I’ve had so many amazing memories made at this bar, as well as seeing two of my friends having a successful proposal here! If you’re lucky you’ll see my friend KP who just so happens to be Chris’s wife! They both do shifts at the bar and are amazing people. They also have super fun trivia nights on Sundays at 7:30 and Happy Hour is every day from 4-6.
#3 is Rick's Bar. Rick’s is actually 8 bars in 1; 4 downstairs, and 4 upstairs. The main bar that’s my favorite is Durty Harry’s, and home to the Durt Bags! They are an awesome cover band who do all sorts of rock music from the 80’s, 90’s, and 2000’s. I have definitely lost my voice singing along to the band after way too many rum and cokes. Upstairs has a dance club, martini bar, daiquiri bar, and a really chill bar in the corner called the Crows Nest. Attached to all of these bars is the Red Garter Saloon. If you can guess by the name it is an adult entertainment club. I’ll leave it at that, lots of fun times had there too! Also at the entrance of Rick’s is Angelina's Pizzeria, the BEST pizza in Key West hands down. It comes in very clutch after a night of bar hopping Duval!
#4 is actually off of Key West on an adjacent island called Stock Island. This is another famous local spot called Hogfish Bar and Grill. Hogfish is known for its delicious food, great atmosphere, and they do have great live music as well. A great friend of mine who was actually my roommate for a few years works there as a server, her name is Rachel! She’s an awesome person and great diver, be sure to stop and say hi. Hogfish is a super flaky white meat that is very delicious. Directly next door is the YankeeCapts, a famous giant fishing boat that does 3-5 day trips to the Tortugas and beyond to catch trophy queen snapper, grouper, and much more. If you want a wild experience look them up online.
Key West really isn’t known for their beaches, in fact every beach in Key West has sand imported from the Bahamas! There’s no natural sand because the barrier reef stops any natural waves from occurring. That being said, Fort Zachery Taylor State Park is a nice beach and a great place to watch a famous Key West sunset! A better option is to go to a sandbar! There’s a lot of ways to get to the sandbar. You can take a charter or if you have a boating license you could always rent a boat, however if you don't know the waters I really recommend you don’t rent one. Barefoot Billy's Boat Cruises do some great sandbar trips that are always a lot of fun. Boca Grande is a super popular sandbar that a lot of people go to, and Snipes is also a really cool spot to check out or ask about when you look for a charter.
A key West sunset is a bucket list item for a lot of people. The Saharan Dust in the summer and early fall make the sunsets super vibrant and a must see for all photographers. You can always see the sunset from Mallory Square and their nightly sunset festival, or Fort Zachery Taylor like I mentioned above. However if you wanna get an on the water view it is hard to beat a sunset sail on Fury’s Commotion on the Ocean. All you can drink and eat for $70 is well worth it. They're also my recommendation for snorkel tours!
If you’re a diver Key West is probably the best place do dive in the Continental United States. A couple great options are Captains Corner or Finz Dive Center. I was certified by Captain Nick Balfour of Finz Dive Center and took an awesome day trip with him on their beautiful Freeman 34. By far one of the most memorable experiences I've had in Key West. Their dive shop is awesome and they have great selection of spearguns and equipment, probably the best in the Lower Keys.
For food there is so many places I recommend. For Cuban food I love El Siboney, a very small local place with the best prices and huge portions. A more upscale Cuban place to check out is El Meson De Pepe right on Mallory Square. They currently hold the title for the best mojito on the island and have some great food too. For breakfast my favorite place to go is Goldman's Deli, an awesome little Jewish deli in a strip mall. Don’t let that discourage you from trying it out because the garlic bagels are to die for! I always get the hash and eggs with a garlic bagel, and they change what specials they have daily. These include banana pancakes, smoked salmon or French toast and they are all too die for! For lunch Bo's Fish Wagon has a great fish sandwich, Kim's Cuban has an awesome cuban sandwich, and Smoked BBQ are all great places for a good local bite. For dinner Hogfish like I mentioned above is probably my go to for great sit down food. Half Shell Raw Bar is my favorite seafood restaurant to go to, and has a great happy hour. Waterfront Brewery has some delicious beer and entrees. It’s hard to beat any of their sandwiches with a cold Crazy Lady Honey Blonde Ale or a Lazy Way IPA. Don’t forget to try conch fritters while you’re in Key West too! Probably the most popular food on the island that every tourist needs to try!
If you’re looking to be adventurous while in Key West there’s more than just bar hopping. You should look into taking a trip to the Dry Tortugas National Park. This is one of the most isolated national parks to get to in the entire country and arguably one of the most beautiful places I’ve ever been so far. You’re only able to get there by plane, which is super expensive, or boat. The Yankee Freedom is a ferry that does trips directly to the island and back as day trips. The ferry is also expensive but is definitely the most affordable way to get to the historic fort and experience the crystal clear water. I went the first year I lived in Key West and it was probably the best snorkeling I’ve ever done from shore so it’s definitely worth the trip! You can also Check out the “jumping bridge” on Sugar Loaf Key. It’s a short walk and if you type it in on Google Maps it’ll take you right to it! Another cool spot is the very end of the road on Geiger Key. There’s a hidden beach behind NAS Key West that’s super cool to watch the jets take off, swim, and chill without being bothered. Just keep in mind the very end of the beach is a “nude beach” so maybe don’t take the kids. There’s also a real cool tree fort called Red’s Place. Great spot for photos and to hang out just watching the water. Just look it up on Google Maps, you’ll figure it out!
If you believe in such a thing Key West is also considered very haunted. There’s an awesome book you can get in any tourist shop called Haunted Key West and it's super cool to read and go to the locations. Key West Ghost and Mysteries Tour is by far the best on the island if you want to experience it first hand. Ted is a super awesome guy and will put you on an awesome tour. Going to see Robert the Doll at the Fort East Martello Museum is also a recommendation of mine for anyone who’s into the supernatural. He’s a haunted doll that was actually the inspiration behind the Chucky movies! He’s been on TV a lot and is world famous for both his story and the terror he’s still causing today. I’ve seen him several times but there are rules you have to follow if you see him. Be sure to say hello and goodbye, ask permission to take his photo, and to share it. If you don’t you will definitely regret it. There are thousands of letters written to the museum asking for Roberts forgiveness for treating him poorly because bad luck and misfortune followed them home. Don’t be scared though! It’s definitely worth the visit.
There’s a few really cool museums on the island that are worth checking out like the Hemingway House and the Little White House. The Key West Lighthouse also has an amazing view from the top if you want to see the whole island. There’s dozens of awesome shops and art galleries up and down Duval that I could talk about forever, but I’ll leave that up to you to explore! Living in Key West was one of the best experiences of my life. I met some amazing friends, had some once in a lifetime experiences, and it is where my sense of adventure really started. If you go have fun, be safe, and enjoy the Conch Republic!
