Key West Travel Guide 2023: A June Weekend in Key West, Florida

Earlier this summer, I headed down to Key West, Florida for a friend’s wedding and, of course, I couldn’t pass up the opportunity to pull together a weekend in Key West travel guide while I was in the area. I’d been to Key West once before for a day trip from Miami and even during those few hours I fell in love with the tropical, world away vibe that has made the Conch Republic a destination for travelers, artists, and writers alike.

The Southernmost Point

Key West is the absolute southernmost point in the continental United States – located just 90 miles from Cuba. It’s a bit of the Caribbean in the United States with the humidity, flora and fauna, and laid back attitude to prove it. There’s a bit of a lawless feel, that you’re totally removed from the trappings of your usual busy life, and it’s that indulgent retreat that keeps so many people coming back to the Florida Keys again and again.

Visiting Key West

Key West isn’t the easiest place to visit since there aren’t many direct flights into the area from places outside of Florida, but it’s well worth the trip – and you can even turn the trip there into an amazing Florida experience.

How to Get to Key West

You’ve probably heard of those iconic road trip drives that you should probably do at least once in your life – and Florida’s Overseas Highway is one of those drives. Running 113 miles through the Florida Keys, you’re surrounded by water on both sides for the entirety of the Route 1 drive from Miami all the way down to Key West. To go this route, you’ll ideally want to fly into Miami before you hit the road, though Fort Lauderdale is also an option.

Interesting fact: when we stopped by the Key West Art and Historical Society at The Custom House, I learned that the original Overseas Highway was actually built as the Overseas Railroad, however the 1935 Labor Day Hurricane destroyed much of the original railroad – it was rebuilt as the highway.

You can also get a flight on Silver Airlines into Key West from Miami. It’s a quick 45 minute flight.

When to Go to Key West

Rumor has it, the best time to visit Key West is between February and May. I can’t vouch for that since I’ve been in October and June, but I can tell you, it’s pretty much always hot, so just expect that. I would, however, advise that you avoid hurricane season if you can just to stay on the safe side.

Where to Stay in Key West: The Marker Reosrt

I did a post last month all about my stay with The Marker Resort and I’d absolutely recommend it to anyone visiting Key West – it’s a gorgeous, bright resort right next to the Historic Seaport. However, the island of Key West is so small that almost anywhere you stay downtown will be perfectly located for exploring.

How to Explore Key West: Do You Need to Rent a Car in Key West?

Of course if you’re driving the Overseas Highway, you’ll most likely rent a car, but if you’re flying directly into Key West, I would advise skipping the car and instead commuting via bike, foot, and uber. Uber drivers are always easy to find, though you’ll be fine walking or biking almost anywhere you need to go.

What to Do In Key West

While you could easily spend an entire weekend eating, drinking, and laying by the pool in Key West, there’s so much to do in the just over 7 miles that make up the island that you could easily spend a week here and never find yourself at a loss for places to discover.

Dive Into History In Key West

If history is your thing, then you’re in luck! There are several historic houses and museums dotting the downtown area and, since everything in Key West is within a few blocks of each other, it’s easy to squeeze a museum in as you’re heading from breakfast to the pool or lunch to shopping.

The stunning Spanish colonial Ernest Hemingway Home and Museum is an absolute must for an Ernest Hemingway fan – or anyone who wants a peek into life in Key West in the 1930’s. Every tour guide seems to be fabulous (and dedicated to their craft – read this article) and, by the end of the tour, you’ll want to take up writing, drinking, and cavorting around with various lovers. Oh, and don’t miss the six-toed cats that roam the property!

Presidential history buffs will want to make a stop by the Harry S. Truman Little White House for a look into this office far away from the rules and regulations of Washington. Then, stop by the Custom House to learn a bit more about the history of Key West since its’ earliest American days and to view some inspiring local art.

We didn’t make it to the Tennessee Williams Museum, the Audobon House and Tropical Gardens, or the Key West Lighthouse, but those are definitely on the itinerary for a future trip.

Explore the Conch Republic

I could have spent days just strolling around Key West taking in the Caribbean influenced charm. It seems that each house is brighter and more charming than the last. Add in all of the big, leafy tropical plants and palm trees and I’m in a colorful heaven. You’re lucky that only 5 house pictures made it into this post. And while I love being able to take pictures during the day, there’s also something so peaceful and inspiring about walking the quiet streets of Key West at night – so take the long way home from dinner rather than grabbing an uber.

Whether you’re looking for daytime shopping, a bite to eat, or hoping for an after hours bar crawl, you’ll most likely find yourself on Duvall Street at some point. The main drag running through Key West, Duvall Street shifts from a lively town center during the day to a raucous party at night.

Make sure you grab a drink one night and watch the sunset from Mallory Square. There’s a nightly “Sunset Celebration” festival where everyone gathers to toast to another day.

And, on another night, make a reservation for a Sunset Sail. There are several companies that operate sailboats out of the Historic Seaport, but we went with Sebago Watersports’ Catamaran Champagne Sail. It wasn’t too crowded, the open bar was flowing, and it was a gorgeous night – this was definitely one of the highlights of my time on the island.

Speaking of the Key West Historic Seaport, you should also spend a bit of time wandering around that area. There are bars and restaurants to stop into, and it’s a great spot to take in the boating culture that defines Key West.

Breathe in the Salty Air

We did less outdoor activities than we hoped just because of a tight schedule, but, next time we’re here, I plan on working in a day to take the ferry out to Dry Tortugas, which touts that it’s America’s most remote national park. In addition to serving as the home to Civil War era Fort Jefferson, there’s snorkeling, beaches, and more.

You can also spend a morning or afternoon kayaking, fishing, snorkeling, boating, or going on eco-tours.

Where to Dine and Drink in Key West

Oh my gosh, where do I even start with the food in Key West? We had one delicious meal after another and we didn’t even make it to half the places on our list of recommendations.

Breakfast and Coffee in Key West

The very first stop on your Key West trip should be Cuban Coffee Queen. You cannot beat Cuban iced coffee, especially when it comes with coffee ice cubes. The cheesy breakfast sandwiches on Cuban pressed bread are nothing to scoff at either.

I did tear myself away from Cuban Coffee Queen’s iced coffee late one morning (though I’m pretty sure I’d already gotten my CCQ fix first thing, if I’m remembering correctly) and got a tropical macchiato from Coffee Plantation. Also a winner – why aren’t coconut and chocolate in all my coffees?

On our last morning, we grabbed breakfast at Pepe’s Cafe, apparently the oldest restaurant on the island. While I didn’t love what I got (I ordered pancakes, which are so hit or miss for me), Adam got some sort of chorizo breakfast taco special that was mouth-wateringly delicious.

Lunch in Key West

There are quite a few French restaurants in Key West, and Banana Cafe is among them. We’d heard rave reviews from friends who had brunched here, so even though we weren’t exactly hungry, we decided to stop in and grab a quick bite. We split a lobster BLT and has zero regrets about consuming a second lunch that we may not have needed. Hey, we were walking a lot, right?!

A classic Key West brunch spot is Blue Heaven, and while there’s often a wait at this quirky restaurant with a large outdoor space where the wild roosters roam (yes, roosters are a Key West thing). Fortunately, we were able to snag 2 bar seats inside which meant AC and no wait. I had the lobster benedict, and if you go, you better get the same.

On Sunday, we unsuccessfully tried to go to a restaurant that is apparently closed on Sundays. Starving, we stopped at the next place we say – Eaton Street Seafood Market. I have no idea how we hadn’t already found this place on a list of recommendations! I got a shrimp salad roll, Adam got a lobster roll, and both hit the spot for a seafood lunch. We took our sandwiches to go, sat out by the pool at our hotel, and had a lovely afternoon.

After lunch, make sure to save some room for a slice of chocolate covered frozen key lime pie at Kermit’s Key West Key Lime Shoppe. It may sound a bit strange, but this is the best dessert you’ll ever taste. I’m craving another as I type this.

Dinner in Key West

On my last trip to Key West, we ate at Louie’s Backyard Grill, and while I didn’t have a chance to include it this go round, it’s definitely one of the most charming spots on the island. Located in a pink house right on the ocean, it’s perfect for a nice, relaxing dinner out, removed from the craziness of Duvall Street.

While I didn’t officially have dinner there, I did have plenty of passed appetizers at Bagatelle at the welcome dinner for my friend’s wedding, and based on those bites alone and the ambiance within the restaurant, I would definitely return.

Our last night in Key West, we wanted to grab something easy after our sunset sail, and we ended up at the Waterfront Brewery. My expectations were low since breweries obviously concentrate more on the beer than the food, but the fried mahi sandwich that Adam got is one that I’m still dreaming about.

A Few Key West Recommendations We Didn’t Have Time For

So, there were three places on our must-try list that we just weren’t able to squeeze in. Bien, a Cuban- Caribbean sandwich shop that just so happens to be named after me, is closed Sunday-Monday so we missed out, but a few of our friends said it was one of their best sandwiches in Key West. El Siboney is supposed to be a delicious and authentic Cuban eatery, and DJ’s Clam Shack is said to be a great place to get conch fritters.

Stop on the Overseas Highway Drive

If you drive the Overseas Highway, I would definitely include a stop at the Key Largo Conch House. It’s right off the highway, yet it feels like a secluded hideaway. We got the conch fritters and the coconut macadamia panini and both hit the spot on our drive back to the FLL airport.

What to Pack for Key West

Sunscreen. Seriously. Lots and lots of sunscreen. It’s hot in Key West and the sun is beating down on you all day long, so dress appropriately. Lightweight dresses were what I turned to again and again – I even went with a beach cover up that looked enough like real clothing one day. Oh, and a hat. Do not forget a hat.

Beyond that, I went for bright colors and tropical prints the entire time I was in Key West because, why not? 

A Few Final Notes on a Weekend in Key West

Key West is one of my favorite places I’ve visited – I just can’t get enough of the laid-back vibe, the colorful homes, and the amazing food. It’s absolutely somewhere I’ll return again and again. Definitely reach out if you have any questions about my weekend in Key West travel guide and visiting the Conch Republic!

Thank you to the Florida Keys & Key West Visitors Bureau for working with me on pulling together such a fantastic trip! Check out their website for so many great vacation ideas!