One of my favorite places on this planet is Key West, Florida. It’s by far my most visited place and is a special to not only me but my family as well. I wanted to put together a little (or rather fat) guide to help anyone planning a trip to the FL Keys! For anyone not familiar the Keys are a string of islands on the southernmost tip of Florida. Key West is the most bustling of the islands and the southernmost of them all.
Some Background
Like I said before, KW is my most visited place and it’s because I have been coming since I was quite literally born. Some background. My grandparents (Dad’s side) bought a house in Key Largo in the late 80’s. When my parents were first dating they would go visit them in Key Largo for a few nights then drive down to Key West for the remainder of their trip. They loved it there so much that it soon became a tradition, so much that my parents legit got engaged on one of the rides there.
After I was born, they kept the trips going. Since my mom was an elementary school teacher, we would end up going every single Easter/spring break from the time I was in Kindergarten into my High School years since we all had the same week off. My parents have built friendships/connections there and although it is out of their price range to buy property, they are now only a ferry ride away in Fort Myers. Soooo now that you know I am somewhat of a Key West expert (kidding), I hope you will trust me with your trip!
How To Get There
There’s 2 main ways of getting there (if you are flying).
Fly Direct to Key West: If you’re lucky depending on where you live you can fly directly into Key West airport. It’s tiny and the flights from where I live tend to be infrequent and pricey.
Fly to Miami and drive: A method I have more commonly taken but I have done both. If you have the time I recommend doing this and making a roadtrip out of it with stops throughout the different keys. It’s about 4-6 hours depending on traffic without stopping so don’t forget to factor that in!
“I’m driving from Miami. Where do I stop for lunch?”
I won’t pretend I’m an expert in this specific department BUT I did just go on a lil roadtrip myself and every single spot was excellent so I’ll share.
Stop 1: Robert is Here Fruit Stand (Florida City)
Go here if you are into tropical fruits. The place is filled with exotic fruits you've probably never heard of. They offer to cut the fruit for you so you can enjoy right away if you please.
They’re whipping up fresh milkshakes and smoothies to order with whatever fruits you want. They also have quick bites like guac to grab.
If you are an animal person… they have an entire rescue farm where a ton of different animals all live harmoniously together.
Stop 2: Key’s Fisheries (Marathon)
A small little restaurant on the water serving up freshly caught seafood.
They are known for their lobster reuben and it was genuinely one of the best sandwiches I have ever consumed. It comes packed to the brim with fresh lobster.
If it’s stone crab season (Oct-May) get an order! If it’s after 5 you can enjoy them straight off the boat. I found out they are the supplier for Joe’s Stone Crab!
Stop 3: Paradise Flavors (Marathon)
Ice cream shop serving up cases and cases of paletas.
Straight off the main road so the ambiance is lacking but the Key Lime Pie Pop is wonderful.
There are soooooooooo many places I missed on the drive from Miami that are worth going so this is not the end all be all, but I can’t wait to expand on it in the future!
ALL THINGS KEY WEST
First and foremost here are some fast facts you should know before you go.
The island is NOT known for its beaches. They do have public ones and some hotels will have them but this is NOT a beach destination. The seaweed here is absurd (not to mention the red tide).
It’s only 95 miles from Cuba.
The entire island is around 4 miles long and a mile wide. Tiny.
Having a car is not necessary. Especially if you are flying in direct.
They are known to get hit very heavily with hurricanes so make sure to plan around this.
Key West is a place for quite literally any and everyone with a large LGBTQ+ presence. You will find many LGBTQ+ hotels and drag bars. I know that the majority of FL is very conservative but luckily Key West is one of the more accepting places out there.
It has a HUGE drinking culture. However, if drinking isn’t your thing there are plenty of other things to still do.
As much as it is a party place you will find plenty of families as well. Everyone is welcome!!
Places To Stay
There are plenty of ranges ($, style, location) of places to choose from. I am not necessarily an expert in hotels here because my parents are loyal to the same few places. Some spots I have been to their properties and used the amenities but have not actually stayed so I’ll do my best.
Southernmost Point Guest House
About: My most stayed at spot in KW! I grew up going to this B&B and it is absolutely gorgeous. It’s at the bottom of Duval St. opposite of Mallory square. Over the years they’ve really added to this historic property. This is a fabulous place to stay we just have since shifted away due to the increasing cost of rooms! Since we typically go on holiday weekends, the prices spike. On avg. the rooms range from $300-400/night during non-peak times.
Type: Bed and Breakfast
Price: $$-$$$
About: The place we have been staying the past few times just because it’s a bit more affordable than above. It is also a B&B centrally located on Duval St. It’s not the fanciest of places but for the price, location, pool, and breakfast, I would say this is a great place to stay.
Type: Bed and Breakfast
Price: $-$$
About: A beautiful property with both hotel offerings and guest houses. They have a restaurant on property as well as multiple pools, a gym, and spa.
Type: Hotel + B&B
Price: $$
About: If I was going to KW alone and not with my family this is where I would stay. It’s not too far away from Duval with a private beach and lovely pool. I just love the property in general and the restaurant on site. It’s on the smaller side!
Pls note I haven’t stayed here overnight but this is the primary location where my family comes to spend our days so I do think I can speak to it.
Type: Hotel
Price: $$$-$$$$
About: One of the most gorgeous hotels I have ever been to. I haven’t stayed but have been to the pools, restaurants, and beach here. If you are looking for an elevated hotel stay this is the place for you. On avg. the rooms run around $500+ a night.
Type: Hotel
Price: $$$-$$$$
There are soooooooo many other hotels and B&B’s that you should explore these are just the ones I am familiar with!
Dining
Key West thrives in the casual dining department. Please note they are not a food destination. I’ve done the fancy and will probably continue to do the fancy once or twice while there but IMO your best bet is so stick to the less flashy spots. Here are my opinions on literally everywhere I have ever eaten in KW.
Half Shell Raw Bar - A go to classic for the Lavery’s. This is a great place to order a pitcher of beer and some freshly caught seafood.
Garbo’s Grill - One of my favorite lunch spots. It’s a food truck with permanent residency at Hank’s bar. It’s dog friendly and a great place to hangout. Get the Korean BBQ tacos. Trust meeee.
Bagatelle - Not to be confused with the club like Bagatelle in Miami. Was once one of my favorites to go for an upscale dining experience but their quality has severely gone down hill over the last 5-10 years. I do love their lobster mac though.
Louie’s Backyard - One of the more $$$ restaurants but you are bound to have a good meal here. If you are looking to ball out one night this could be an option for you.
DJ’s Clam Shack - Go to spot for a pre-dinner bite. Get the clams, some beers, and a lobster roll. This is a spot that was on Triple D for any of my Food Network ppl!!!!
A&B Lobster House - Another fancier spot which is solid but like I said before the island is a place for casual eats. I do love it for their deck though and the Key Lime pie is solid.
Blue Heaven - A staple for breakfast and their Key Lime Pie. Great place to start the day.
Seaside Cafe at the Mansion - Only went for their “famous” lobster pizza and drinks but it was super disappointing. The lobster was not fresh.
Southernmost Beach Cafe - My dad’s favorite spot for breakfast. They do a house-made corned beef hash that is extremely heavy but super delicious.
Conch Republic - Overpriced and overrated. This is nottttt the place for you.
Fogarty’s - Casual vibe with okay food. Only go here if you are in a pinch.
Mangoes - I actually mix Fogarty’s up with Mangoes because they are both pretty forgetful. This is on the “classier” side but the food is always so underwhelming. There tends to be live music here though which is nice.
Latitudes - The fanciest restaurant in KW. You have to take a 10 minute boat to get there. I thought the octopus was inedible tbh. The fish was nice but nothing you can’t find elsewhere. If the ambiance is most important to you then this is a place to book for sunset. If food is more important I would avoid.
The Lobster Shack - A quaint little shack for some lobster rolls if you’re in the mood.
Banana Cafe - Cutest little cafe!!! You can get crepes, regular breakfast, eggs benny, and some French classics. Favorite spot for crepes.
Le Creperie - OOP I think Banana Cafe is slightly stronger in the crepe department. That being said Le Creperie is also great and their sweet crepes are sugary goodness. Their house-made salted caramel sauce is incredible.
Dante’s - My parents enjoy this place for lunch. They have a pool at the property you can pay for a day pass to go to. In my experience this is more of the hangout and party vibe than the sit and relax vibe. Could totally have just been when I went though.
Grand Cafe - One of the better restaurants I have been to in KW. The outside dining is really nice as well.
Jack Flats - Sports bar! I would only recommend hitting here if you are trying to watch a sports game.
Four Marlins - Favorite spot on the island for lunch ever. It’s a restaurant at The Reach that I think is worth hitting even if you aren’t staying in that area. The conch fritters, fish dip, fish tacos, key lime pie are ALLLLL amazing.
Old Town Tavern - Not the best food in town but a spot to get some casual food and beers and hangout.
Key Lime Pie + Desserts
I almost exclusively eat Key Lime Pie anytime I want something sweet in Key West but occasionally I’ll stray LOL. This is partly because it’s rare to find good Key Lime pie is rare outside of the island and also its legit everywhere. I don’t think there is a single restaurant that doesn’t offer it in some form. Without further ado here are my favorite spots for a sweet treat.
Kermit’s - A classsssic. The slices are super tiny but they are worth it. Some people like to get the chocolate covered pies on a stick but for me I like the classics.
Four Marlin’s - My favorite. The lime flavor is more mild so if you like it more tart this won’t be for you. The crust is the perfect balance to the creamy custard and the whipped cream is THICK.
Blue Heaven - Get the Key Lime pie here no matter that time of day. I promise it is acceptable. It is piled high with meringue which isn’t my preference but
Matthessen’s - Their Key Lime pie is skippable IMO. The whipped cream is from a can which a miss for me too. INSTEAD come for the monster size cookies and ice cream.
Publix- Probably not what you would expect to make this list but they do have a fantastic key lime pie. Well the filling is fantastic. If you are stopping here for other groceries you should pick one of these up as well.
Activities + Things To Do
Key West has a ton of things to do to keep you busy whether it’s a family trip, a bachelorette, your honeymoon, or just a fun trip. There’s also plenty of family friendly activities as well. Have no fear you will not be bored.
Duval Street
The main street in Key West that's filled with restaurants, bars, and shopping. You can easily spend a few hours popping into the different stores here, which range from cute boutiques and T-shirt shops to art galleries and more well-known brands like Birkenstock. A lot of the restaurants mentioned above can be found on Duval or right off of it.
Mallory Square
The best place to watch a sunset is here. Growing up, this was a nightly spot for my family and me. Before dinner, we would head to Mallory to watch the street performers, eat some guac or conch fritters, and catch the sunset. I will say it’s currently under construction, and a lot of the old vendors and performers have since moved on. Still somewhere to hit though!
Drag Shows (Aqua + 801)
One thing that I think is essential to your KW experience is attending a drag show!! There are 2 main bars that have them and I have been to both and honestly I don’t have a preference. 801 does a happy hour though which I enjoy if you have night time plans.
If you’re looking to check out the Dry Tortugas, the only way to get there is by boat or seaplane, and a seaplane just sounds more fun in my opinion. The Dry Tortugas are a set of isolated islands and are filled with sea life. Fun little day excursion.
Electric Car Rental
One of my favorite things to do is rent an electric car for a few hours and drive around the island. There are so many spots on the island to get them and it honestly is a must do for me anytime i’m there. You can also rent golf carts, bikes, or scooters too.
A must-hit for me if it’s your first time. Go right in the morning when they open, after a little brunch moment at Banana Cafe. It’s a large nature conservatory with so many different kinds of butterflies flying throughout, and some flamingos too. It’s calming and special in there.
If you’re in the mood for another Museum learning about Ernst Hemingway is the 2nd one I would choose! It’s open 365 and you don’t need to reserve in advance.
Smather’s Beach
Largest public beach in KW that you can go too and doesn’t require $ or a hotel stay. The seaweed goes crazy so just be prepared but they do have public restrooms and showers as well.
So, I did this a few years ago and for me, NEVER AGAIN, but that’s only because I got altitude sickness and a migraine back to back right after. However, the actual skydiving experience and the team were fantastic. Everyone was super experienced, and the views of the turquoise blue waters were everything. So if you're in the mood to skydive, I definitely recommend this as the spot to do it. It’s about a 25 to 30 minute drive outside of Key West, but we Ubered and it was super easy.
If you are in the mood to get in the ocean Barefoot Billy’s is the company to use. They do everything from jet ski’s, fishing boats, private charters and Billy is a long time friend of my parents!
Bar Hop
Plan a bar crawl! There is huge drinking culture here that you can dive into if you please and almost all of the main ones have live music. Irish Kevins, Sloppy Joes, Rick’s, Willie T’s, Durty Harry’s, and Hog’s Breath Saloon are some of the main ones but you don’t even need to have a set plan. Start at one on Duval and make your way down the strip!
Ok hope I didn’t forget anything. Enjoy the Keys hehe xoxo.
Going to the Keys for the 4th this is PERFECT TIMING ❤️
loved this!!!
if you haven't tried irie eats in marathon, i think you'd love it! lunch is slightly better than breakfast, but I've never had a bad stop there.