Key West has got to be one of my top 10 places in the country to vacation to – I LOVE it here. Not only do you get the most beautiful beaches, but there’s TONS of things to do and so many places to explore! Jared and I have visited here three times already and while I will include everything we’ve done up to this point so far, this past time it was just Jared and I, and we had a HUGE LIST of things we wanted to check off. So get ready, because this is going to be a lengthy one!
Jared and I love to explore, and we challenged ourselves to get the most out of this trip, all while in the midst of relaxing. And I have to say, we accomplished SO MUCH, but don’t be fooled, there’s still a ton of things we didn’t get to do that we will definitely be coming back for! In this blog post you will find, Where We Stayed, Transportation, What To Do, Where To Eat, and Where to Drink/Nightlife.
Before we even got there Jared had ordered us this book, The Key West Bucket List. And while we had every intention of trying to do everything in here, on our own list, and a list we had found on TikTok, there just wasn’t enough time to do it all. It’s safe to say we will definitely be coming back here once again and THAT is why I love Key West so much. There are endless things to do. And luckily for us, we know a few locals here, so we are able to get all the good deets on where to eat and what to do!
Where We Stayed
Airbnbs/Villas
The few times we’ve been here before, we were with a bigger group and stayed at some pretty nice Airbnb’s but these are mostly further away from the main part of Key West. A lot of the houses and rentals are about a 20 minute drive to Duval Street, but are great if you are staying with kids or a large group of people. Here you get the best of both worlds, and of course if you do this, it would probably be in your best interest to rent a car. When renting, we were still right on the water but also had our own private pool and house!
The Southernmost Beach and Resort
This time around, we booked a reservation at The Southernmost Beach and Resort. It was our first time staying at this resort, and it is the place to be if you want to be right in the middle of it all. This is a huge hotel and there is always a lot going on. They do have their own beach BUT, the waves can get very intense. It may not be the best beach to bring your young kids to, but not to worry, there are a TON of other close, calmer, beaches nearby that I’ll discuss later on.
There are three different pool areas at The Southernmost Beach and Resort. There is: Pineapple Pool, Shores Pool, and the Tranquility Pool. Pineapple and Shores each have their own bars and food, while the Tranquility pool is more of a relaxation area where drinking and rowdiness is not so much welcomed. It was a silent ~tranquil~ area for those who want to read a book or relax in the sun and this was my favorite one.
Also at this place there is a really cool tanning pier that LITERALLY stretches out into the ocean. It is lined with chairs and umbrellas and really is a cool spot to spend the morning at. It’s also a beautiful place to go watch the sunset or sunrise. Right off of here is a Sandbar Pavilion and Private Beach where they have yoga classes, cabanas, and hammocks – that are all perfect places to lounge at. Don’t be fooled by the “beach” part of this though, yes, it is on the sand but you cannot walk out into the ocean from here because it is closed off by a huge cement wall that keeps the waves from flooding the area (see photo below).
I will not lie, because I want to always be completely honest and transparent here, these rooms were NOT the nicest we’ve ever stayed at, and are definitely due for an upgrade. HOWEVER, in my opinion, it was worth it anyway. For the view, location, and amount of activities there were, I didn’t mind it. What you pay for is the location and the view. Would I stay here again? Probably. It wasn’t horrible, but we have definitely been to way nicer places, that’s for sure. I think waking up and being directly on top of the ocean and hearing the waves from our balcony was worth it. Jared would still be sleeping and I could sneak right down to the beach area and he could still see me!
Transportation
Although we usually rent a car, you can definitely get away with biking, walking, or even Ubering around Key West, especially if you plan to stay right around Duval Street. Everything is close to each other, and it’s also right next to the airport which makes it nice and convenient to get around. You can also rent scooters, bikes, and golf carts – which you will see a TON of around here! There is a trolly that runs during the day for tours and transportation that’ll take you all around Duval Street. We rented our car right at the airport after we landed which made super easy for us.
Things We Did
Beaches – There are endless beaches to see in Key West. For beaches: Southernmost Beach Resort, Fort Zachary Taylor Historic State Park, South Beach, Monroe Beach, Smathers Beach, Higgs Memorial Beach Park, Rest Beach, Simonton Beach, and the list doesn’t end there. We went to Fort Zachary Taylor Historic State Park this time around and it was gorgeous and might even be my new Key West beach spot.
They have nice hiking trails and big facilities with changing rooms and even a cute little cafe for a good food spot. The water was beautiful and there were tons of people out snorkeling. It wasn’t crazy busy either! It was the perfect beach spot!
Botanical Butterfly Garden – This is one of my favorite places in Key West. The Key West Butterfly and Nature Conservation is the most zen place to go if you want to see some of nature’s purest beauty. I haven’t been to one of these in YEARS and Jared and I had so much fun here. We even circled it twice and stayed in there for about an hour! It was so cool to see such beauty in these living beings and watch as hundreds of butterflies buzz around your head. It is truly breathtaking. They have a ton of plants and other animals including turtles, birds, and FLAMINGOS (Rhett and Scarlett). At the end there is a live view of caterpillars at all stages ready for nature to take its course. I definitely recommend going here if you’re ever in the area, and it is a totally inexpensive activity and great learning experience for all ages.
The Southernmost Point Rock – This is a must-see landmark when you come to Key West. You can’t miss it. It’s a huge rock in the shape of a buoy that sits just 18 ft above sea level marking THE southernmost point in the continental United States (and only 90 miles to Cuba). It is the lowest latitude land of contiguous North American states. It’s such an interesting landmark to see but there is ALWAYS a line (hence why we’re practically in the dark in these photos). The best time to go is at 5:00 when everyone is getting ready for dinner.
Private Boat Charter – This was one of the coolest things we did while staying in Key West. Jared found Fish and Chicks Charters Key West right off of Google and I’m so glad we went with this one! Raquel is AMAZING and she is the one who chartered us on the boat and around the island. Here is her Instagram and I would highly, highly recommend giving this a go while you’re in Key West. She took us to places I have never even thought of seeing or knew existed. The water was absolutely amazing and SO crystal clear.
You know we love our chefs, and we originally wanted to take one out to cook for us on the boat. However, that was a little challenging considering we were on a speed boat with no kitchen. So Raquel had set up to have a chef cook for us beforehand and she had brought the food out with us to eat at one of the most gorgeous places on the island.
Golf – You know we don’t go anywhere without golfing. We went to the Key West Golf Club and got in a quick 9 holes one day. It was super nice out with a slight breeze which made the day really enjoyable. This course was nice and flat which we were not used to here in Connecticut so it was definitely a different experience for sure!
Duval Street Shopping –
I don’t tend to be a huge shopper on vacations, but this place has some of my favorite stores to shop at. There are tons of local art places and gift shops all around Duval Street. We always like to do some gift shopping and art collecting when we come down here. You can find some pretty unique and memorable pieces in Key West.
Then there is Earthbound Trading Company, a super aesthetic crystal shop and most beautiful store ever – I am obsessed with this place. I come here every time and they have tons of crystals, earthy things, decor for the home, and some really cute handmade jewelry. This is one of my favorite shops to stop at.
Jewelry – Then there is my FAVORITE jewelry store EVER. I honestly couldn’t tell you the name of it to save my life, and I know that is so unhelpful, but I couldn’t find it online either. I can say it’s a really tiny boutique-like shop right on Duval Street across from the old Green Room. They have tons and tons of sterling silver and crystal jewelry. I come here every time we’re in Key West and I have never been so in love with a place.
Gladiators Ice Cream – After a long day of walking around in the heat shopping, eating, and drinking, be sure to stop at Gladiators Ice Cream for some refreshing and delicious ice-cream! This is definitely a favorite place of mine to come to. It was so refreshing – sweet AND savory. They have so many flavors to choose from with all of the frozen fruit on top!
Harry S. Truman Little Whitehouse Tour – It’s actually pretty funny how we ended up on this tour. Jared’s niece wanted to go on the Ghosts and Gravestones Tour but it had already closed for the day. So, we decided to go “ghost hunting” at the Truman house on their tour, at the very last minute, before they too were about to close. It ended up being interesting to see and learn about. It was very informative, but probably not on the top of any kids list of “fun things to do” unless, of course, you tell them you’re going ghost hunting!
Trolley Tours – Key West does have a ton of trolley tours you can hop on and ride that run daily all throughout Duval Street. There are a ton of different options that you can choose from for whatever works best for you. You can find a bunch of info about the different tours here.
Other/For Next Time:
Live Entertainment/Nightlife
Uncle Dave – Jared’s Uncle Dave lives and plays music all over Key West. It’s so fun to follow him and the vibes are always great. Follow his Facebook page for live updates! This time around his gig was on the Fury Cat Sunset Sail and it was such an awesome experience. He plays often at a bunch of different places so be sure to give him a follow!
Fury Cat Sunset Sail – This is one of the top sunset cruises and Key West and I 100% recommend doing this if you get the chance while you’re down here. It is so incredible to see and also super freaking fun. The crew was incredible and Uncle Dave and the band made it even better! The sail includes live music, food, drinks, hanging on a boat, AND a crazy sunset view… it doesn’t get any better than that! You check in at 4:30 and set sail at 5:00. Our drinks were never empty and EVERYONE I mean EVERYONE was having a great time!
Mallory Square/Sunset Pier – This place is where you HAVE to go one evening for the sunset. (Same place the sunset cruise goes by) It is a truly incredible sight to see. And I’ve never seen the sunset like this before in my life. There is a whole strip you can walk down with tons of live entertainment, shopping, restaurants, music and more! Once the sun starts to go down, a mass amount of people begin to line the boardwalk. They say the sun flashes green right as it disappears and I can confirm this is true! Once the sun is down people fluster away, off to dinner and the place is empty like it never even happened – it’s so crazy!
Drag Queen Show – Highly recommend going to a drag show while you’re in Key West. We went to the one called 801 Bourbon Bar and WHAT AN EXPERIENCE. I won’t go too far into detail here because you need to experience this one for yourself, but it’s safe to say it was a blast!
DUVAL STREET BARS – WHERE TO DRINK
The Bull / Whistle Bar – Uncle Dave sometimes plays here too! There are three floors to this bar and be prepared for the third floor… it’s a NUDE BAR. It’s not something you see everyday and some may find this a tad uncomfortable, but also you have to experience it once… right? If you do decide to check this out, just brace yourself, that’s all I have to say!
Fat Tuesday’s – This is a classic place for alcoholic slushy drinks. If you plan on spending the day exploring Duval street, go to this place first and you can get free refills all day! There are two locations on Duval street. We love this place and hit it every time we come!
Willie T’s – Willie T’s is a cool hole-in-the-wall bar. This is their infamous bar that is COVERED in dollar bills. They have pool tables and games and I can’t forget the bras hanging all over the walls and ceilings. It’s a cool place to check out and have a drink at for sure! Add a bill to the collection and you’ll always have a memory to look for in Key West!
Island Dogs Bar – This is a very lively bar spot with both indoor and outdoor seating. They also serve food – burgers, wings, and oysters, and have tons of mixology drink options to choose from . Their Key Lime Pie Martini is the BEST. It’s really a fun bar to be at with both vacationers and locals. I loved the atmosphere here. They have a huge bar and some of the island’s best live music.
The Green Room – While I totally wanted to recommend this place, I just discovered it’s permanently closed. So we can just take that one right out of your options but this used to be the SPOT! I am not sure if they have changed it or replaced it but hopefully there is something new here in place of this fun place!
FOOD
There is SO MUCH FOOD to eat in Key West. The options are seriously endless. I am going to cover all of the places we went to the past few times we came so I broke it up into four sections to keep it a little easier to find: Breakfast/Brunch, Lunch/Happy Hour, Dinner, and Dessert. I’ve also included a list of places that were recommended to us that we haven’t gotten to yet!
Breakfast/Brunch:
La Grignote – This French cafe and bakery has some of the best baked goods in Key West. This place was a TikTok find, and a great one too! The menu was pretty big however, we had gotten there at peak hour and had to wait 45 minutes to get in. By the time we had sat down, they were already starting to run out of a few things on the menu. It’s THAT good. Be sure to get here early if you want to be able to choose from their large selection of food. We ordered the Croque Madame, an Egg Bacon Swiss Croissant (which was the freshest, flakiest croissant ever), and a Belgian Waffle. They also have an amazing Key Lime Pie that is a MUST HAVE.
Banana Cafe – Right across the street from LaGrignote – Banana Cafe is open for breakfast, lunch, and dinner. This was another find off TikTok and I am so glad we came across it too! I loved this place a lot and they had some amazing breakfast options to choose from. I, of course, had to try the crepes, and the Eggs Benedict (again). Jared ordered the Turkey Bacon Club and said that it was superb! They also have a bunch of omelettes to choose from and some delicious sides!
Harpoon Harry’s – This place is perfect for a good, inexpensive, brunch. They serve breakfast all day everyday. I got the Fluffy Biscuits with Sausage Gravy – SO FREAKING GOOD, and Jared got the BLT with a Fried Egg. It was a super casual and cute little diner but the food was AMAZING. This place was a little further from the main part of everything but totally worth it. They also make and sell their own hot sauce which is absolutely sensational. I would definitely come here again in fact I am craving those delicious biscuits right now!
Lunch + Happy Hours:
Fogartys/The Flying Monkey – This place is across from The Bull and we stopped here for cocktail hour one day and it was the perfect food to hold us over before dinner. You can fill up on your slushy’s right at The Flying Monkey. They have good finger foods like apps, salads, sandwiches, and sides. They do have beer and wine but the Banana Breeze from The Flying Monkey is my absolute favorite.
Rams Head Southernmost – They have a great happy hour, live music and DELICIOUS bloody mary’s. Their drinks were so good and they had an amazing Crab Dip with Jumbo Lump Crab, Warm Cream Cheese, Jalapeños, and Cheddar Jack Cheese. This one is a little ways down from Duval street and is a great place if you are looking to eat outside!
The Original Sandy’s Cafe – We heard about this place on TikTok and I haddd to try it. It’s safe to say it was WELL worth it and one of the best empanadas I’ve ever tried. We had ordered the Chicken Empanada & Rueben Sandwich – both were super satisfying. Make sure it’s THE ORIGINAL because I believe there are two. Oh my gosh. It was so good I want one right now.
Hurricane Hole – When we first arrived this is the first place we came to. I didn’t really love anything about it except for the cool view. It was crazy busy and I’m not sure I would go back here. The only cool thing about this place was that it was right on the water and you could pull your boat up to it and see all the different boats coming in.
Gates Hotel – One of our good friends from back home works here so of course we had to go check this place out. The drinks were SO GOOD and it was such a fun pool vibe. Definitely a good place to bring the kiddos. They have a food truck right outside the pool area and they have some pretty awesome falafels. They had such good frozen drinks and the bar vibe was awesome.
Southernmost Beach Cafe – HIGHLY recommend this place for a good happy hour. Right on the beach and they have $6 appetizers and $5 drinks which are well worth it. They have these amazing Buffalo Tots that I literally couldn’t get enough of. We also tried the cheese dip and it was so filling! It was a great beach vibe, we did not leave here hungry, and even met some cool people at the bar!
Salute On The Beach – Another great inexpensive dinner spot right on the beach. What we really came here for was the Blue Heaven Key Lime Pie. Apparently this is THE best one in town – boy was it delicious! I never really go for Key Lime Pie but we heard this was a must have and I would totally say the same! We had the Steamed Mussels in Bianco and I had the linguini with muscles, white wine and garlic butter – totally recommend! I loved the scenery here and they sometimes have live music and live shows right on the beach.
Caroline’s Cafe – This was a little outdoor lunch/happy hour spot. We went here for drinks before dinner and it was a super quick meal with burgers, sandwiches, and salads. Definitely a very inexpensive casual spot you can walk to right on Duval Street. You have to try their Key Lime Mojito or Rum Punch.
Dinner:
Latitudes/Sunset Key – Latitudes is an ocean front restaurant located on a tiny little private island that you have to take a ferry to and from. They also have a resort on the island that you can stay at – Sunset Key Cottages. Before your reservation, you meet on the dock at Mallory Square and the ferry picks you up to bring you across the water to the restaurant. It was a fancy fine-dining seafood restaurant with indoor and outdoor seating. In my opinion, the food was pretty average, but the drinks were where it was at. There is a fun little bar to sit at while you wait for the ferry to come and pick you back up. Such a cool experience and even though the food wasn’t anything crazy, I would definitely go check it out to see for yourself!
Abbondanza – This might just be my favorite Italian spot in Key West. It’s pretty low-key with very enjoyable food. I had the Lobster Capellini and it was phenomenal. It was a smaller, cute little place, but the definition of a classic Italian restaurant. They have all the good Italian favorites and I can’t say enough good things about this place.
Onlywood Pizzeria Trattoria – We went here for dinner and it was super, super good wood fired Italian food. I had the Gnocchi, Mozzarella, Cheese Board, and a Pizza. That sounds a little crazy, but they had all of my favorites here! I loved this spot and the setup of this place. They have both indoor and outdoor seating, and it’s definitely a popular go-to.
Santiago’s Bodega – This is a popular spot for “Hot Tapas”. They do small plates and there are so many options to choose from. This is perfect if you just want a small meal or to try a little bit of everything. They offer a globally inspired menu that is meant to be shared with the table. For food, we did the Dates, Beef Short Ribs, Roman Meatballs, and Brussels Sprouts. They were so good and SO WERE THE DESSERTS. They only offer beer and wine but you have to try their mouthwatering sangria.
Bagatelle Inn – This is actually a hotel, but their upstairs dining is beautiful. It feels like you’re in a dream. This might be one of my favorites spots, just because it was so pretty inside and I loved the energy in here. They offer indoor and outdoor dining and it’s a pretty casual lunch spot but I would definitely dress up if you’re coming here for dinner. The food, drinks, and service were all great!
Mangoes – This was a cute little outdoor dining spot right one the corner of the street which was able to accommodate our huge party. The food and drinks were delicious! Their menu is inspired by traditional Conch and Caribbean dishes, using local indigenous ingredients. They also have an indoor banquet that hosts private dining and special events. I would definitely recommend this place!
Dessert:
Better Than Sex – Huge dessert place and highly recommended to us. I haven’t been here yet because we always order dessert at dinner or are too full, but I have been dying to go. We were told the Port Wine & Chocolate Rib are the best things on the menu. Definitely on the very top of my list for the next time we come.
Cupcake Sushi – I am so sad we also didn’t get to go here. This is also at the top of our list when we go back. If you click on their website it shows you photos of their desserts and its exactly that – cupcakes in the shape of sushi. They look so freaking GOOD and they are so freaking cute!
For Next Time…
Here is a list of other places we didn’t make it to, but were recommended to us/on our list of places to eat/drink:
- Moondog Cafe – Get Grilled Pizza
- First Flight – Brewery
- Tipsy Rooster – Liquor Store and Bar
- Blue Heaven – For Breakfast
- Glazed Donuts – Crazy Donuts
- Lolas Bistro – A Du Jour Menu/BYOB
- Mary Ellen’s
- Nine One Five Restaurant
- Fritas – Cute Patio, Best Known For Cuban Burger
- Louies Backyard – Fine Dining with Ocean View
To Wrap It Up
I could go on and on about Key West. It’s such a fun and exciting spot to vacation at. There are endless things to do, eat, and drink here. While we had accomplished a majority of our Bucket List while we were here, it’s safe to say there’s plenty more to do. We have a different experience every single time we come here and that’s why it’s so much fun. If you’re a travel or beach lover, then Key West is a must to visit. If you have any other questions feel free to send me a DM! Be sure to follow me on Instagram for daily updates, deals, fashion inspo, influencer tips, travel posts, food spots, and MORE!
UNTIL NEXT TIME,
TAYLOR ONZE
TAYLOR ONZE 
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