Miami was a massive surprise to me. Florida never held much interest for me as a vacation destination, and I don't love beaches, but planning wintertime vacations during Covid restrictions was rough. Direct flights to Miami were ridiculously cheap, and the weather would be hot, so that was my four night February destination of 2021. I actually loved it! Miami has such great energy and Latin flair. Party vibes every night. I then ended up going back to Florida four months later (post-vaccination) when my friend Jackie and her husband moved to the Keys, and again the following year for Key West Fantasy Fest.
Since visiting the Keys requires a flight to Miami anyway (unless you want to pay the absolutely insane prices to fly directly down to the islands), it's the perfect combo blog.
If you can't find good flights into Miami, it's equally as easy to get to Miami from the Fort Lauderdale airport, which is what we did on my first trip. From there, you can take the Tri Rail for a few bucks down to Miami, and we ubered for the rest of the week wherever we couldn't reasonably walk. Our first two nights were spent in Wynwood followed by two at Miami Beach, and I'm definitely glad we got the full experience of both areas.
Wynwood
Wynwood is Miami's art district, evidenced by the murals painted on absolutely everything.
I booked us a private room at a hostel called the Magical West World Inn attached to the Golddigger Saloon and Boho House. I'm happy I stumbled across this hostel on AirBnB because it isn't listed on Hostel World or any other booking site that I saw.
It was super quirky with a courtyard area full of colorful randomness, and our room - the Miner Room - was on the first floor of the little hostel.
At night, this place was such a party! The hostel courtyard had a DJ playing and a bar cart (although drinks were expensive, like $12 for a Corona), and just on the other side of the building was the Boho House with more outdoor live music and a packed full courtyard with an open-air lounge vibe.
The Wynwood Walls are the main tourist attraction, a collection of murals you can pay to see. They were impressive, but so is the vibrant street art all around the district in general, so it's up to you if you want to pay for something you're seeing for free all over. (Not meant to discourage anyone - I'd do the Wynwood Walls again.)
Wynwood also just had the absolute best bars and nightlife! We were out on a Thursday night, and it was popping everywhere. There are bars and clubs lining both main streets all the way down. Spots we hit included Dirty Rabbit with a huge outdoor patio area and stage, Marketplace which was decent, and Miyami where about every five minutes they'd release so much fog from the giant machines up on the walls that the entire place was encased in a white haze. You couldn't see an inch in front of your face. That with the music and dancing made it feel like a dream. Definitely my favorite!
We also during the day hit the Miami Mojito Company across from the Wynwood Walls where they had a dozen mojito flavors to choose from on a cute tropical patio, and then the Astra rooftop bar with lots of plants and nice cocktails.
Astra rooftop
Food-wise, we tried out the Bagel Club (hard to go wrong with bagel sandwiches and coffee), Versailles out in Little Havana (Cuban food is great but I will say this very popular restaurant had the vibes of a Cuban Denny's), and the all-vegan Love Live Cafe which was absolutely amazing whether you're vegan or not. Very much recommend the choripan - Beyond sausage on a baguette with chimichurri, avocado, aioli, pickled onions, and a parm crumble - and an oat milk latte. So good.
Miami Beach
The highlight of the Miami Beach area was our hostel, Generator. Not only one of the best hostels I've stayed at in the US, but the world. The back patio area is just fantastic. So spacious, super social with travelers of all ages, and it features a pool and a little indoor bar (serving some basic food) which leaves its doors open during the day making it feel connected to the party. Loved the bartenders who made quality drinks, were very sociable, and would do shots with the group. On my last morning when I was pounding back gin and cranberries before my flight and very much underestimated the price of them (their beers are cheap, liquor is not!), the bartender even knocked $30 off my final tab while I was having a heart attack looking at my bill.
Just inside the hostel is also a sunroom full of plants and comfy chairs, and our private room was nice as well. We made so many friends here and stayed up drinking by the pool the first night until they kicked us out, after which time we spent a night on the beach until 4 AM. Felt like I'd returned to my backpacking days!
The beaches in Miami were definitely nice. We were only two blocks away from the mid-beach, so that's where we hung out mainly, but we also went down our last day to check out South Beach and its art deco buildings. South Beach was busier and also PRICIER. At a South Beach vegan spot called Planta, I ordered an amazing bloody mary and followed up with a second assuming standard cocktail prices, so I ended up shocked when the two drinks cost me $40 total. Ouch.
Mid-beach
Aside from Planta, we also ate at The Tavern (great mac n cheese), Sweet Liberty which has great brunch and cocktails (also a fun bar at night), and I had a brunch at the Edition in a fancy hotel when I returned to Miami for a night after the Keys.
Design District
If you're rich or just want to window shop some jaw-dropping merch that you'll never be able to afford, head to the Design District.
Even if you can't swing the triple-digit price tags at the designer shops (we didn't even step foot inside), there is a ton of cool art to look at all along the strip. Vibrant colors and cool photo ops. Also a weird bubble dome. Don't know what that's about.
Vizcaya Museum & Gardens
Another great way to spend a few hours in Miami is by visiting Vizcaya. It's an old mansion and hugely expansive gardens.
The gardens feature lots of stairways, statues, stone, and greenery, while the inside of the mansion is full of gold, religious murals, and plants. I was sure it had to have been designed by someone Italian. (This claim has not been fact-checked.) All beautiful and worth the price of admission!
Getting to the Keys
On my second trip, I flew into Miami and took a Greyhound from there to the Keys. You'll likely need to spend a night in Miami first, because the buses only run once or twice a day, and any afternoon flights definitely won't land in time to catch them. I stayed at a cheap and really convenient AirBnB right by the airport and was close enough to just walk to the Greyhound station in the morning for my early bus. They were the upscale buses with outlets at the nice leather seats, and my only complaint was how intensely they were blasting the A/C the whole way down. I don't appreciate shivering in a hoodie during June in the south of Florida.
My friends, Jackie and Derek, live in Big Pine Key which was a three hour bus ride with a lunch stop at BK in Islamorada for a 20 minute break. It was only a $10 ticket to Big Pine, but if you're heading to Key West, only an hour further south, they throw a tourist tax on that bitch and double the price.
On my third trip, Mat and I rented a car at the Miami airport because bus schedules didn't align with our flights and dropped it in Marathon. Did the same on the return, picking up in Key West and dropping in Miami.
Big Pine Key & Surrounds
Jackie and Derek rent a very nice house right on the water in Big Pine. Two bedrooms, open plan main room that triples as office/kitchen/living area, another office, and a balcony. Derek makes some great tropical cocktails with fresh fruit, so the first thing I did upon arrival was drink one out of a coconut cup on the hammock.
They also own kayaks and paddleboards, so we could wake up in the morning and just hop right out on the water. There were baby sharks and nurse sharks out by patches of underwater foliage nearby which I kayaked out to see on my last morning, and a nurse shark that was right next to their house another day.
On the wildlife front, we also saw a manatee in a canal while stopping for coffee, more sharks next to a restaurant pier, a gator swimming by their house at night, and a ton of dolphins at the Dolphin Research Center in Marathon. The research center dolphins swam up to see us, and we caught bits of shows where they flipped, painted portraits, or just were being fed by keepers. There were sea lions here too but they were all inside during our visit.
I have two restaurant recommendations in this area of the Keys. One is Square Grouper in Cudjoe Key. The food is absolute quality, and upstairs they have a bar with a huge craft beer selection. The other is Irie Island Eats in Marathon. It's a food truck next to a farmer's market with a large fenced in seating area full of tables and couches, all surrounded by leafy palms with chickens walking around and Jamaican music. The build your own bowls/wraps/sandwiches were also awesome. I had a bowl of cilantro noodles, avocado, pickled onions, jalapenos, beans, and more. Healthy and delicious.
I also enjoyed the Islamorada Brewing Company up in Islamorada. They have an amazing back patio with live music, lawn games, and fairy lights.
The big activity we did up this way was an afternoon snorkel tour in Looe Key. If you've read any of my blogs featuring water-related activities, you will know that this is not an environment in which I shine. Even with a life jacket here, it took me two false starts and a bout of hyperventilation to jump off the boat and calm myself once I was in the sea.
Jackie, who is an expert swimmer, was nice enough to stay near me while I was in the water, and I floated around the reef to see a decent amount of fish, but - uncommonly, for me - it was actually seasickness that did me in. The water was pretty choppy that day, and after about 20 minutes, I got out for a break and it just worsened from there on the rocking boat. The only way I felt better was by lying down on my stomach, but I felt like I was wasting time and money, so I got back in once more before we switched sites.
At out next spot, I was even more nauseous and only managed a brief and final foray back into the ocean before retiring onto the boat to buy a ginger ale which worked wonders. I missed seeing multiple sharks and manta rays because of this weak human failing, but I did see a hammerhead from the deck on the ride out, so we'll call that the highlight. That or finally reaching dry land again and getting a free cocktail at the attached tiki bar.
Also, if you're driving down to the Keys, I definitely recommend pulling off in the Everglades and going to the alligator farm. You can ride an airboat, watch alligator feedings and demonstrations, and see a bunch of other animals like owls, iguanas, porcupines, and an emu.
Also hold a baby gator!
Key West
The place to be on the islands is obviously Key West, and since Jackie and Derek are elderly in their sleep schedule, I even looked at booking my own accommodation down there for the weekend when I first visited so I could take advantage of the 4 AM club closing times. Quickly noped out of that idea once I saw the prices for a bed, so I begrudgingly accepted my free midnight rides back to Big Pine Key.
The second time, we booked a place for five of us at Kimpton Ella's Cottages for Fantasy Fest, and it was much nicer being able to stay out and drink as late as we wanted with an easy walk home. This was a nice hotel too - separate cottages around the property, free breakfast, a communal pool, and the coolest cat named Jeffrey.
Bars
Key West houses an overwhelming amount of bars to choose from, but I valiantly took on an in-depth research project to determine the best.
Places I recommend: First Flight - a very cute brewery which is the building where Pan-Am first started selling tickets in 1927. It still has an aviation theme which you can celebrate with a flight (of beer).
Tiki House - on the smaller side, but the cocktails were good and the bartenders were great. One of them gave me a to-go cocktail and helpfully informed me that it was pretty acceptable to just drink on the streets if you behave yourself.
Dante's - if you want a big pool party with loud music and floating beer pong, this is the place.
La Te Da! We went to the Sunday tea dance at La Te Da which takes place weekly from 4-6:30, and it was so much fun! Mainly an LGBTQ+ crowd. It was pretty dead at the start, but more and more people joined as the afternoon went on. There's an outdoor and an indoor bar, as well as a pool, but they said it was for hotel guests only (unsure of whether that's standard or a Covid-specific policy). The whole deck turned into a dance party with a DJ spinning, and I also had the best cocktail of my trip here, some kind of cherry iced tea that was absolutely incredible. I'll be back to tea dance again if I ever return!
22 & Co - do you like glitter? Are you ok with being covered in glitter for a week following your bar visit? Find the tiny little 22 & Co where every drink is doused in glitter, the bartender will pour glitter on your heads, and generally everything is pink and sparkly. I highly recommend the peanut butter martini.
Mangoes - nice outdoor patio right on Duval, live music, not overly crowded.
Places that were alright: Sloppy Joe's - very popular bar, busy vibes, not a super impressive drink list.
801 Bourbon Bar - I'll come back to this when I talk about their drag show, but if you're just going in to sit downstairs at the bar, it's not too memorable aside from the stiletto chandelier and Drag Asylum mural on the mirror.
Old Town Tavern - English pub feel, decent beer/cocktail list.
Wine-O - liked the decor, didn't love the crowd (could have just been a bad time with Fantasy Fest on).
The Roost - cozy little cocktail bar if you want to get away from the party scene for a classier drink.
Waterfront Brewery - large location on the docks, but they wouldn't let you create your own flight outside their two preset ones, and I didn't enjoy the beer I ordered.
Champagne Room - cute spot serving, obviously, champagne, but at 2 PM on a Sunday, we were the only ones in there (although I was on time for a $3 happy hour rose!).
Places I do NOT recommend: Irish Kevin's where the worst musical performance was taking place and I had the literal worst cocktail I can ever remember ordering at a bar made with tropical Red Bull. I had to choke it down. Jackie and Derek were equally disgusted. 10/10 would not return.
Rock Place - Maybe my review is skewed because it was Fantasy Fest, but this was very bro-y and nothing about it said rock n' roll. There was country music downstairs and super clubby music upstairs. Meh.
Restaurants
To start, you definitely should try to make a reservation (far, far in advance! Months in advance!) for Better than Sex, a dessert restaurant. Just go look at their menu. It has pictures. We had about five desserts between the table, and all were amazing. I ordered a red velvet cheesecake and Oreo bread pudding with cheesecake ice cream, along with a Delirium Red that came in a vanilla rimmed glass. Also, the place is glass-chandelier-and-candle swanky.
My favorite meal I've had in Key West was at the Moondog Cafe. Awesome brunch menu - I had the caprese benedict. MisoHappy Thai is a great call to soak up all your day drinking (drunken tofu noodles saved my life), Old Town Mexican provides awesome pico with their chips, Firefly does Southern food, Two Friends has a big brunch patio, and Ram's Head has a build your own bloody mary bar and a heroic bartender who rescued me from a hangover-induced panic attack by allowing me to stand in the walk-in cooler and relocating us from the 90 degree outdoor patio inside to a table in an empty air-conditioned room so I could work through my mental and physical breakdown in privacy. He also brought me a bucket of ice to cool down! What a guy. He earned my eternal gratitude, a generous tip, and a 5-star TripAdvisor review.
Tourist Spots
My top recommendation, if you like cats, is the Hemingway House. At the time of our visit, they had 58 cats on the property, a good handful of which are polydactyls.
The house is fine too and you can learn about Hemingway's life as well as visit his writing studio, but don't play - we're all here for the cats.
The main street to wander in Key West is Duval Street, where aside from the bars, you'll also find plenty of souvenir shops and expensive art galleries.
Everyone seems to visit The Southernmost Point in the Continental US, basically a big buoy that you can wait 15+ minutes in line on the sidewalk for a photo with.
There's also Mallory Square which is like, a big thing? For some reason? Everyone gathers here to watch the sunset, and they set up shop stalls and street performers, but in the end, it's just a sunset. People get really hyped over sunsets like they don't happen literally every evening on the earth's daily rotation. And to be honest, I've seen better. However! There is a key lime shop called Kermit's right by the square which fills about every key lime need you could desire.
Drag Shows
Key West has a thriving LGBTQ+ scene, and I love to frequent drag shows, so I was really excited to book tickets for Saturday night at Aqua. There are a few options to choose from around Key West, and I had done a bit of research before picking a show. I'd also like to mention that La Te Da has icon impersonators who are supposed to be very good at their drag cabarets, but it was off season for those shows, so we didn't have the option.
There's a 7 PM and a 9 PM show at Aqua, and we went for the latter. I'd bought tickets months in advance, and we were some of the first people in the club having gotten in line early, so I was super pissed when they sat the three of us in the back, back corner. There were a bunch of long tables near the stage and comfy couch booths on the side, and we got stuck at this shitty little bar table buried against the back wall. I saw people come in with no reservation and get seated at the square bar or alongside the stage, both of which were way better views than we had, so I went and asked if we could be moved - they said no because the place was full.
We just felt very uninvolved and removed from the show, and the queens rarely came around the back, so it was hugely disappointing. About halfway through, I moved up to an empty stool along the stage for a better view, but I had to leave Jackie and Derek back at the table so it wasn't ideal. The show was fine, the queens were talented, and the shirtless bartender at the back was SO attentive and friendly, but this was easily the inferior of our two drag show experiences that weekend.
To make up for it, we hit the 801 Bourbon Bar drag show the following night, and it was a blast! They have it upstairs above the bar in a show room, and it's cozy enough that it still feels like a more intimate show wherever you're seated. (The bartenders were slow, and they wouldn't give out free tap water, but other than that, I won't complain.) The formidable old queen at the door sat us upstairs alongside the stage, so we had great views, and the show in general was just so much more fun and varied.
We had our host, Raquel, who was funny and raunchy and involved the audience members every time she was on the mic, baby queen Eileen Taylor who did some cool, artsy performances ('Creep' in a straightjacket? Yes, please!), and body queen Vicky the Doll. We enjoyed ourselves far more than at Aqua and laughed a whole lot. There was also an 89-year-old woman there with her friends and they were having the most adorable time.
I am, however, happy to amend my review of Aqua as we went again during Fantasy Fest and had the best time. We were seated at a proper table this time in the second row, and the queens absolutely killed it. Our host, Beatrix Dixie, was very charismatic and entertaining (her decision to live sing two Three Doors Down songs in a row had us dying), Jessica Devereaux was campy and fun, and Elle Taylor, who at first seemed like a burlesque queen, absolutely blew my mind with a batshit Joker number that is one of the best drag performances I've seen in my life.
Fantasy Fest
Finally, let's discuss Fantasy Fest, Key West's massive Halloween celebration. This is certainly an experience, but one that I have mixed reviews on. A big thing about Fantasy Fest is that nudity is allowed with body paint, and a lot of people are walking around in very little, if any, clothing. I'm all about liberation and bodily autonomy, but it draws a bit of a sketch crowd, including a lot of older men walking around asking if they can photograph the ladies or just generally leering. One group in a bar was rating women as they walked past the window. There were a lot of pervy older guys and a lot of bro energy from the younger crowd. I would say the first night we did not have the best time.
Street mimosas = good though
The second night was a vast improvement for two reasons: the parade and the fact that we opted to attend a drag show instead of hit the crowded bars at the other end of Duval. The parade was actually fantastic, really impressive floats and costumes, and we got to see a lot of good costumes from the spectators as well.
So go if you want, but do it with realistic expectations and be prepared for the kind of crowd it attracts.
Since my bus back to Miami didn't arrive in until evening on my day of departure from the Keys my first time there, I spent a night back at Generator in Miami Beach where I was poured free drinks and shots all night by one of the bartenders I'd met on my earlier trip and brought a friend along who I'd met on my Greyhound to drink and lay by the pool with me. Ideally, I think combining a Keys trip with at least a few nights in Miami is the way to go.
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