IF YOU’VE BEEN CRAVING THE KIND OF TRIP WHERE YOUR DAYS START WITH CUBAN COFFEE, END WITH LIVE MUSIC, AND SOMEHOW EVERY MOMENT IN BETWEEN FEELS LIKE A MOVIE… KEY WEST IS THAT PLACE.

WE RECENTLY SPENT A FEW DAYS SOAKING UP THE ISLAND LIFE AND HONESTLY? IT WAS THE PERFECT LITTLE ESCAPE. BETWEEN THE OCEAN VIEWS, PASTEL STREETS, AMAZING FOOD, AND LAID-BACK ENERGY, I ALREADY WANT TO GO BACK.

HERE’S EVERYTHING WE DID ON OUR KEY WEST GETAWAY, PLUS A FEW EXTRA RECOMMENDATIONS IF YOU’RE PLANNING YOUR OWN TRIP SOON!

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GETTING TO KEY WEST ON THE KEY WEST EXPRESS

Instead of driving the Overseas Highway, we decided to take the Key West Express from Fort Myers and I would 100% do it again every time!

The ride was honestly part of the experience. You can sit outside on the upper deck, grab drinks/snacks, watch dolphins, and enjoy the ocean views the entire way down. It instantly makes the trip feel more relaxing instead of stressful travel days.

If you’re staying in Southwest Florida, this is such an easy way to turn your getaway into a full vacation experience from the second you leave.

For more information, check out my blog Taking the Key West Express | Everything you Need to Know.

BREAKFAST AT THE KOFFIE HOUSE

Once we arrived, we headed to The Koffie House, and it instantly became one of my favorite coffee spots in Key West.

The aesthetic alone is worth visiting. It has that cozy café vibe that makes you want to sit there for hours. We grabbed coffee and breakfast before starting our day and honestly… if this was my local coffee shop I’d become a morning person immediately.

CHECKING INTO SOUTHERMOST BEACH RESORT & GUESTHOUSES

Following breakfast, we grabbed an Uber over to Southernmost Beach Resort & Guesthouses and immediately fell in love with the property.

The entire resort has that laid back tropical luxury feel that Key West does so well. Palm trees everywhere, ocean views, pastel buildings, cute pathways through the property… it honestly feels like its own little oasis while still being walkable to everything.

One of my favorite things about staying here was the location. You’re close enough to Duval Street to easily walk everywhere, but the resort itself still feels peaceful and relaxing when you want to slow down.

We spent so much time just sitting by the pools, walking around the property, and taking in the views. It’s definitely one of those places where you immediately understand why people keep coming back.

If you want a full breakdown of our stay at the resort, I wrote a dedicated blog post here.

LUNCH AT BLUE HEAVEN

You absolutely cannot visit Key West without going to Blue Heaven!

This place feels like pure Key West energy in the best possible way. Chickens wandering around, live music playing, colorful outdoor seating under trees and string lights… it somehow feels chaotic and relaxing at the same time.

Everyone talks about the lobster benedict and key lime pie, but honestly the atmosphere is what makes it so memorable. It doesn’t feel like just another restaurant. It feels like part of the entire Key West experience.

WALKING DUVAL STREET

After lunch we spent most of the afternoon walking Duval Street and just exploring with no real plan.

That’s honestly one of my favorite things about Key West. You really don’t need a strict itinerary. Some of the best parts of the trip were just wandering around, popping into random shops, grabbing drinks, and listening to live music coming from literally every direction.

At night, Duval turns into one giant party. Every bar has live music, the streets are packed, and somehow there’s always something happening.

Some of our favorite spots downtown were:

• Rick's Bar (our top fave!)

• Irish Kevin’s

• Sloppy Joe’s

• General Horseplay

• Capt Tony’s

• Hank’s Hair of the Dog Saloon

• Whistle Bar

Each one has a completely different vibe which makes bar hopping in Key West so fun.

RESORT DAY

Our second day in Key West was definitely our slower paced vacation mode day and honestly… it ended up being one of my favorites from the entire trip.

We spent most of the morning enjoying Southernmost Beach Resort & Guesthouses and fully taking advantage of everything the property had to offer. Between the pools, ocean views, palm trees, and frozen drinks, it was the perfect excuse to slow down for a bit and just enjoy where we were.

One thing about Key West is that it somehow makes doing absolutely nothing feel productive enough. We spent hours lounging by the pool, walking around the property, and soaking up the sunshine before heading back out to explore more of the island.

BREAKFAST AT MOON DOG CAFE

Before heading out for the day, we grabbed breakfast at Moon Dog Cafe and immediately understood why so many people recommend it.

It has such a cozy tucked away feel and honestly felt a little more local than some of the bigger tourist spots around Duval Street. We tried the berry tart, Elvis French toast, fish tacos, and eggs benedict and I genuinely don’t think you can go wrong here. The Elvis French toast was SO good and an island staple you have to try at least once. Between the cozy atmosphere and amazing food, Moon Dog Cafe ended up being one of our favorite spots from the trip.

HEMINGWAY RUM COMPANY TASTING

Later in the day, we headed over to the Hemingway Rum Company tasting which ended up being such a fun experience.

Even if you’re not a huge rum person, I still think it’s worth doing. It felt like one of those classic Key West activities that you just have to experience while you’re there. The atmosphere was super fun, and it gave us something different to do besides just beaches and bars all day.

It honestly ended up being one of the highlights from the trip.

VISITING THE SOUTHERNMOST POINT BUOY

Of course, we also had to stop by the iconic Southernmost Point Buoy while we were out exploring.

Yes… there’s usually a line for photos. And yes… it’s still worth it.

It’s one of those classic Key West landmarks you just have to see at least once. Right next to the buoy is also this gorgeous historic home that honestly caught our attention immediately. The pastel detailing, wraparound porches, and old Key West architecture felt straight out of a movie scene and made the whole area feel even more charming. Definitely don’t rush past it while visiting the buoy because it’s such a pretty little hidden detail right next door.

SUNSET AT MALLORY SQUARE

We ended the night walking around Mallory Square for sunset and honestly it was one of those moments where you just stop and think “okay… this is why people love Key West so much.”

There were people everywhere watching the sunset, live music playing in the background, little stands set up along the water, and somehow the whole area just had this fun laid back energy to it.

The sky kept getting prettier every few minutes and nobody even seemed in a rush to leave. It was the perfect way to end the day.

FINAL THOUGHTS

If you’re looking for the kind of getaway that perfectly mixes relaxing resort days, amazing food, tropical scenery, and fun nightlife… Key West truly checks every box. Between riding the Key West Express, slow mornings at local coffee shops, afternoons by the pool, nights on Duval Street, and sunsets at Mallory Square, this trip honestly felt like the perfect little escape from reality.

What I loved most about Key West is how every part of the island feels different. One moment you’re walking through lively streets filled with music and bars, and the next you’re watching the sunset over the ocean feeling completely relaxed. It’s one of those places that somehow feels exciting and peaceful at the exact same time.

🌊 ☀️ 🌴 🍹

This Key West trip is definitely not the last you’ll be seeing from me because I already have so many more spots, restaurants, and hidden gems I can’t wait to share. Be sure to follow along for more Key West blogs, travel guides, resort stays, and all my favorite finds from the island!

- Travels By Dawn

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GET ALL YOUR KEY WEST OUTFITS!

SHOP HERE!

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FAQ | IS KEY WEST WORTH VISITING?

Absolutely! Key West has such a different vibe from the rest of Florida. It’s laid back, colorful, walkable, and somehow feels both relaxing and lively at the same time. Between the beaches, nightlife, food, sunsets, and tropical atmosphere, it’s the kind of place that’s hard not to love.

FAQ | IS THE KEY WEST EXPRESS WORTH IT?

Honestly, yes! Taking the Key West Express made the trip feel like part of the vacation instead of just transportation. It was relaxing, easy, and way less stressful than driving all the way down the Keys.

FAQ | WHERE IS THE BEST AREA TO STAY IN KEY WEST?

I personally loved staying near the Southernmost Point area. It felt a little quieter and more relaxing while still being walkable to Duval Street, restaurants, and most of the main attractions.

FAQ | HOW MANY DAYS DO YOU NEED IN KEY WEST?

I think 3 to 4 days is honestly perfect for a Key West getaway. It gives you enough time to explore, have a resort day, experience the nightlife, and still slow down enough to actually enjoy the island.

FAQ | IS KEY WEST WALKABLE?

Very! We walked almost everywhere during our trip. Between Duval Street, the Southernmost Point, restaurants, bars, and waterfront areas, most things are super easy to get to without needing a car.

FAQ | WHAT SHOULD YOU NOT MISS IN KEY WEST?

If it’s your first trip, you definitely have to watch sunset at Mallory Square, walk Duval Street at night, visit the Southernmost Point Buoy, and spend at least one full day simply relaxing and soaking up the island atmosphere. Honestly, some of the best moments in Key West happen when you aren’t rushing from place to place.

FAQ | DO YOU RECOMMEND UBERING OR GETTING A TROLLEY PASS?

It depends on your trip style. If you plan to stay mostly in Old Town and near the resort, walking and occasional rideshare is usually enough. If you want to sightsee often and hop around multiple attractions, a Old Town Trolley Tours pass can be a fun and convenient option.

FAQ | WHAT IS THE BEST TIME OF YEAR TO VISIT KEY WEST?

Spring is honestly one of the best times to visit because the weather is warm without being unbearably hot. Fall and winter are also really popular because of the slightly cooler temperatures and lower humidity.

FAQ | WOULD YOU GO BACK TO KEY WEST?

1000% yes! This trip honestly made me want to plan another one immediately. There’s still so much we didn’t get to do, and Key West just has one of those places-you-never-want-to-leave kinds of vibes. 🌴