Key West Florida NYAH hotel
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July 10, 2022

How to Live Your Best Life in Key West

By Ashley Hesseltine

My first time in Key West was sophomore year spring break. I was 19 and got into every bar, rocked the shit out of some Bebe tube tops and Abercrombie jean skirts, and fell in love with a local, who I ended up going back down to visit after the semester was over.

Fifteen years later, I would still rank it in my Top 10 Most Fun (and Fashionable) Vacations. The few times I visited Key West after that inaugural trip were just as memorable, and it is definitely one of my favorite places on Earth.

You feel so carefree and relaxed when you’re there, yet the uplifting energy and charm of the island push you to experience all it has to offer.

So when I got invited to check out the NYAH hotel and experience a “Key West Your Way” trip this winter, I was beyond excited to get back down there and find my long lost love revel in my happy place again, and escape the NYC winter.

Your ultimate guide to Key West, Florida

where to eat, stay, play, and soak up this magical place.

(As for the romance, just stand on Duval street in a tube top with a cocktail, and you may just get approached by a drunk 25-year-old looking for love).

Where to Stay

Look, if you’re going to Key West on your honeymoon, ball out and stay at Casa Marina (the Waldorf Astoria property). But if you’re going on a girls or guys trip, NYAH (short for “Not Your Average Hotel”) is where it’s at. The ADULTS ONLY hotel (God bless them) is designed for groups with large rooms sleeping up to 6ish people, and you essentially “build your own room” with a mix of single beds and convertible kings.

NYAH Not your average hotel Florida

There are personal closets/lockers for each person in the room and every bed has its own reading light and charging station. I love this concept because when I’m traveling with a group, I want us all to be together, not split up in separate hotel rooms (you never want to miss hungover morning recap sessions with the whole squad!).

And it’s so affordable — the room price stays the same no matter how many people are in it. As for the property, it’s a historic property right in the heart of the island with two pools, has amazing rooftop views, Starbucks coffee in the lobby, and HAPPY HOUR EVERY DAY AT 4:20: Very #OnBrand.

Where to Eat

I’ve never had a bad meal in Key West (that I remembered). You can eat fresh seafood at a casual hang on the water, fine dine downtown, or walk around scarfing down a slice of Key Lime Pie like it’s pizza (don’t judge me), and it’s all delicious.

For a more upscale experience, Azur is a must. We feasted on their airy patio, tasting nearly everything on the menu, and I was blown away.

For fish tacos and gallons of killer guac on the water, hit Turtle Kraal’s.

And if Beyoncé and Jay Z’s yacht is docked in plain view from the upstairs patio, the owner might just give you a pair of night vision binoculars to spy.

True story, guys. (And no, I never saw Bey and Jay and I don’t want to talk about it.)

Conch Republic and Waterfront Brewery are two other waterfront spots I love. Conch Republic is always a lively scene where you can watch boats come in and out of the harbor, and if you hit Waterfront Brewery, I recommend a cold pint (and an Insta pic) of the Crazy Lady brew.

Waterfront Brewery Key West Florida

And last but never least is the one place you cannot miss if you go to Key West. As in, if you go to Key West and don’t eat here, your trip doesn’t even count. And that place is Blue Heaven (which I also would have been in had I run into Bey, Jay, and Blue Ivy, but I digress).

The food at Blue Heaven is hands-down the best breakfast/brunch food I’ve ever had in my life, plus chickens and cats casually roam the property, and the al fresco setting is like something out of a whimsical fairytale.

If you’re like me, you’ll order the lobster Benedict with banana pancakes on the side (casual), and a slice of Blue Heaven’s sky-high Key Lime Pie…then have to be promptly rolled off the property.

Also, serenade a cat if you can (for the ‘gram, of course).

serenading a cat

What To Do in the Daytime

Key West days are the best days — the island is full of life around the clock and if you head down to Duval Street at any time of day, you’ll hear live music pouring out of the bars and see people living their best lives. One of my favorite low-key activities is exploring the island by bike, so lucky for me, NYAH has beach cruisers available for guests.

Hire a bike for the day Florida NYAH

And the basket was just large enough for me to carry back the lifetime supply of products I bought at Key West Aloe (they make the best smelling lotions on the planet, fight me if you think I’m wrong).

For water activities, you can take your pick. On this trip, I really got to treat myself and experience two incredible excursions — a jet ski tour and parasailing. The jet ski tour set out from the Casa Marina hotel and we rode through the waves all around the island, including the Gulf of Mexico.

Let me be clear about three things: 1) This tour is not amateur hour (at least not the one I was on); I was riding at max speed and was still in the back of the pack. 2) Riding a jet ski at top speed through the ocean will knock the hangover right out of you (#thankful for that). 3) Being single is great because you always get your own jet ski.

Jet Ski hire in Key West Florida

I absolutely loved this tour and highly recommend doing it through Barefoot Billy’s — one of their guys even gave me a waterproof lock box for my phone and insisted I take his sunglasses on the tour so I wouldn’t lose mine (I think we’re still dating).

Parasailing with Sebago Watersports was equally as incredible, and something I’d never done before. I set out in the morning with a couple of hot professional guides on a boat and killer tunes, and before I knew it, I was suspended from a parachute 400 feet in the air, with a birds eye view of paradise.

They also take photos you can purchase afterward, because as we all know: If you don’t gram it, it didn’t happen.

Watersport parasailing in Key West Florida

The Ernest Hemingway Home and Museum should always make a Key West to-do list. Where else can you get the rich history of the original Most Interesting Man in the World, stroll the gorgeous grounds, and see dozens of 5-toed cats roaming free?

Not to mention, my cousin and his wife got married there in 2010, and it was the most fun wedding of all time, so it will always have a special place in my open bar-loving heart.

Papa Pilar’s Rum Distillery (AKA Hemingway Rum Company) is one of the newer attractions on the island, and a solid activity for any alcohol lover. Named for Ernest Hemingway (Papa) and his beloved boat/second wife Pauline (Pilar), you’ll gain some additional knowledge of Key West’s most famous man during the distillery tour, do a tasting at the bar, and stock up on swag (and/or rum) in the shop.

Hemingway Rum Company Key West

What To Do in the Evening

The perfect Key West evening always begins with a stunning sunset at Mallory Square. Since there’s no open container law, you can head down there with a cocktail (or two) in hand, grab some freshly made guac if your heart/stomach desires, admire the street performers (sword swallower FTW), and watch the sun dip below the ocean. And look, I’ve never clapped for a sunset, but I’ll admit I’ve been tempted.

And while we’re talking sunsets, I cannot recommend a Danger Charters sunset wine cruise enough. This was probably my favorite thing I did on the trip (maybe in life) because it involved a sailboat, a sunset, and sitting down while cute guys brought me a dozen different wines to taste…. PLUS CHEESE.

Tell me that’s not the goddamn dream. Do this cruise, get buzzed up, post humblebrag pics on social media, and thank me later.

Next up for nighttime: A ghost hunt. If you just rolled your eyes, I get it. But hear me out. We did Sloan’s Ghost Hunt and I was very impressed and entertained. Key West has some WILD and scary stories, and on this tour, you get devices to detect the ghosts and haunted spots, which is a fun element.

And as mentioned before, you can walk around with a cocktail.

And finally, the portion many of you have been waiting for: GETTING WASTED BAR HOPPING. Key West has a ton of awesome bars, so you’ll never be hard pressed to have the most fun night of your life.

Sloppy Joe’s is a MUST — it’s been around since the ‘30s and still maintains this unexplainable ambiance and energy you feel the second you walk in. There’s live music daily on the famous stage, the drinks are always stiff, and if you’re hungry, you can stuff your face with…wait for it…a SLOPPY JOE (for the record, they’re delicious).

Sloppy Joes Bar Key West

Irish Kevin’s is another solid go-to, and they’ve recently expanded so there’s even more room to crush car bombs and sloppily make out with strangers (what?). And fun fact: My brother won a Guinness chugging contest here back in 2010 and literally got a standing ovation (tbh, his picture is probably framed on the wall).

For the true local experience, hit Green Parrot — it’s the oldest bar in Key West and off the beaten path a bit. There’s live music nightly, it always feels like a party you were lucky enough to stumble into, and their motto is “a sunny place for shady people” (perfect).

If you’re getting hot in therrre and need to take your clothes off, visit Garden of Eden, the island’s only “clothing optional” bar. And if you need to work up to that (literally), you can hit the other two historic bars in the same building first, The Bull and and Whistle Bar, as Garden of Eden is the rooftop.

There are plenty of other hot spots, and as you bounce around, you’ll surely discover the ones that speak to you most. On this magical island, everyone has a place.

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