Let’s be honest, any excuse to hop on a plane to the Florida Keys is a good one. Kevin and I recently decided we needed a quick getaway, and naturally, Key West was calling our names. If you’re lucky enough to live near an airport that offers direct flights straight onto the island, do yourself a favor and book it. The new airport terminal is incredibly efficient, and getting off the plane and straight into vacation mode has never been easier.

We used our sister company, Out A Here Travel, to put this little adventure together. While we don’t always book airline tickets through our travel business because airlines can be, well, a giant headache, we definitely take advantage of it for everything else. Key West is known for its stunning sunsets, roaming chickens, and a solid dose of island weirdness. But figuring out where to stay, what to eat, and how to avoid the obvious tourist traps takes a little bit of insider knowledge.

Whether you are heading down for a weekend of frozen cocktails or a week of deep-sea fishing, having a game plan is essential. We hit up some of our favorite haunts, tried a few new spots, and survived a five-drink cocktail class. So, grab your café con leche, and let’s get into the recap of our latest Key West trip.

Finding the Perfect Home Base: Coconut Beach Resort

For this trip, we decided to stay at the Coconut Beach Resort on the southern end of the island. Why the southern end? Because Kevin is slightly obsessed with sunrise photography, and being on this side of the island makes catching those early morning rays a whole lot easier.

Now, full disclosure: this is a timeshare property. Because we booked through a third party (Expedia), we actually had to switch rooms midway through our stay. If you can handle a little flexibility, it is totally worth it. It is a no-frills kind of place, meaning you won’t get daily housekeeping, but the location is practically unbeatable. You get a private beach, a pool, a hot tub, and stunning ocean views.

The absolute best part? There is a secret gate that leads directly into Louis’s Backyard. You just punch in a code, walk right up to their outdoor patio, and order a drink. You are also right next to Dog Beach, where locals bring their pups to play in the surf. It is a much more low-key vibe compared to the wild energy of the Gulf side, making it the perfect spot to unwind.

Dining Experiences You Can’t Miss

We take our food very seriously when we travel. Key West has a massive culinary scene, and we made sure to eat our way through some of the best spots on the island.

The Flaming Buoy Filet Company

We hit up this spot on Eaton Street for dinner, and it completely blew us away. It operates like a classic supper club—dinner only, and they only serve beer and wine. The menu is small but mighty, featuring incredibly fresh fish and unique flavor profiles. If you love Star Wars, you are going to lose your mind over the memorabilia in here. Pro tip: definitely check out the bathroom. I won’t spoil the surprise, but just trust me. It is a tiny place with a huge local vibe, so reservations are highly recommended.

Key West Cooking Show

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If you think a cocktail class means sipping on tiny little thimbles of alcohol, think again. We took the “History of Key West in a Glass” class at the Key West Cooking Show, located upstairs at the shops near Mallory Square. Michael, our storyteller and bartender, served us five full-size cocktails while walking us through the island’s wild history. The Hurricane and the Curry Old Fashioned (made with Pilar Dark Rum and tobacco bitters) were absolute standouts.

We also went back for their lunch cooking show. Come hungry, because they serve massive portions while teaching you how to make Cuban chimichurri, mojo roasted pork, and a chickpea soup that will knock your socks off. The grand finale? Key lime pie topped with a dense, sweet Italian meringue. We even walked away with their Key West Classic Spice to take home.

Miso Happy

Miso Happy is easily one of our favorite spots, but getting a table in their tiny Simonton Street location during the dinner rush used to be a nightmare. Thankfully, they now offer outdoor seating with four high-top tables on the sidewalk. The service is incredibly fast, and the food is just as tasty as ever.

Conch Republic Seafood Company

It wouldn’t be a Key West trip without our mandatory fresh fish sandwich. We stopped by Conch Republic and ordered the mahi-mahi catch of the day. Paired with a great craft beer, it is exactly what you want after a long day of walking around in the sun.

Attractions & Activities Worth the Sweat

Yes, the humidity is trying to eat your soul, but you still have to get out and explore. Here is what we got up to when we weren’t eating or drinking.

Mallory Square Sunset

Sunset at Mallory Square is a Key West staple. Right now, a large chunk of the seawall is under repair and blocked off. If you want a stellar view without fighting the crowds, walk toward the pier near the Truman Annex. You will get an unobstructed view of the sunset, completely free of the massive crowds.

Key West Candle and Bath Company

DeeJay Peak finally opened her brick-and-mortar store on Whitehead Street, and it smells like absolute heaven. She makes everything in-house, and her travel tin candles are the perfect souvenir. She is closed on Sundays and Mondays, so plan your visit accordingly. (Click here to check out her website)

Key West Island Bookstore

If you follow our Fun in Key West Book Club, you absolutely must visit Suzanne at the Island Bookstore. She actually created a dedicated end-cap just for our book club picks! It is a fantastic local business, and there is nothing better than supporting independent bookstores.

San Carlos Institute & Shipwreck Museum

We soaked up some history at the San Carlos Institute, which offers free admission and an incredible look into the Cuban influence on Key West. Later, we hit the Shipwreck Museum. If you aren’t terrified of heights, climb the wrecker tower for a crazy panoramic view of the island.

Sloppy Joe’s

Standard tourist stop? Yes. Did we go anyway? Obviously. The drink cups seem to be getting a little smaller these days, but the people-watching is unmatched. We even ran into someone from our home state of West Virginia, because Key West really is the biggest small town in the world.

Nightlife & Relaxing Spots

When it’s time to grab a drink and listen to some live music, you have to branch out past the main drag.

Bali Bar

Tucked behind a hotel right on Duval Street, this spot has a fantastic tiki bar vibe. They feature live music, cornhole, and a super relaxed atmosphere that makes you want to stay for hours.

Tipsy Rooster

Located over by the Southwinds Motel, Tipsy Rooster is quickly becoming one of our favorite hangouts. It is a liquor store with a full bar attached. You can sit outside on barstools planted in the sand, listen to live music, and enjoy a beer on tap.

Green Parrot

You can’t skip the Green Parrot. Great music, free popcorn, and a perfectly gritty, authentic Key West vibe.

Coffee & Treats for the Morning After

I’m not saying I plan my vacations around coffee, but let’s be honest—I totally do. We stumbled across Doing Work Coffee, which operates inside the Wicked Lick nitrogen ice cream shop near Eaton and Duval. The owner, Daniel, actually roasts beans that have been soaked in rum from Key West First Legal Rum. The flavor profile is wild in the best way possible. They also bake their pastries fresh every morning.

Travel Tips for Your Next Trip

A few quick things to keep in mind before you pack your bags:

• Get off Duval Street! Wander the side streets, especially in the spring when all the orchids are blooming attached to the trees.
• The actual Southernmost Buoy is currently boarded up for foundation repairs, but they set up a temporary replica at a pocket park near South Beach so you can still get your photo.
• Skip the taxi line at the airport and order a Lyft. It is usually about 50% cheaper and gets you a much nicer ride.
• The free Duval Loop bus lost its funding. There is an on-demand city bus for a small fee, but you are generally better off using rideshare apps.
• Hydrate. Drink water between those rum runners, folks. The sun down here does not mess around.

Ready to Book Your Island Escape?

Key West is always a good idea, whether you are celebrating an anniversary, catching the Songwriters Festival in May, or just escaping the cold. We had an absolute blast supporting local small businesses, finding new cocktail hideaways, and soaking up the sun.

If you want more Key West tips, sign up for our newsletter—you might even win a swag box filled with goodies we brought back! And if you are ready to book your next adventure, reach out to Kevin at OutAHereTravel.com. He will get you set up with everything you need for the perfect trip.