The Ultimate Key West Travel Guide: Where to Eat, Drink, Stay and Play in Key West, Florida

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Earlier this Spring, I went down to the Florida Keys with eight of Kenny and my good friends and we had an absolute blast! I had been to the Florida Keys before with my family and knew I loved it down there in Key West, but this was my first time with Kenny and with friends. Key West is funky, colorful, eclectic, beachy, chill, rowdy and wild all at once. 

Key West has so much to offer for every kind of traveler, from families to couples to girls trips and groups of friends! 

Here is the ultimate Key West Travel Guide: Where to eat, drink, stay and play in Key West


Where to stay in Key West

Ocean Key Resort & Marina

Beautiful waterfront hotel with romantic views and chic, island decor and a delicious restaurant called Hot Tin Roof. 

Casa Marina Key West, A Waldorf Astoria Resort

One of the only hotels in Key West with direct beach access, this is one of the luxest places to stay in Key West. 

On a Sailboat

We stayed a few nights on this BOAT – which I highly recommend. We stayed on board took the catamaran sailboat out for the day (they provide you with a captain) but otherwise it was docked in the chic marina.

Even when it’s docked, it’s SO fun to be on a boat, and you have access to the nice hotel right in the marina, too for an easy pool, and a really good bar and restaurant to hang out in. There’s something about a happy hour in the marina that just hits different, ya know??

Our catamaran in Key West – which we LOVED! and slept 9 people

Other boats you can rent:

6 person catamaran in Key West

8 person yacht – sleeps 6 in Key West

Duval House 

Located right on Duval Street – this cute hotel is PERFECT for a group trip to Key West and to be centrally located.

Hanging with my girls in the courtyard at Duval House (wearing our Kenny Flowers bikinis and matching sarongs!)

The Perry Hotel Key West 

This is the hotel connected to the Marina in Key West – so you have access to it if you’re staying on a boat. It was SUPER nice and we ate here a couple nights. The bar makes delicious cocktails, and the pool is a great spot to spend the day. The only downside is it’s 20 minutes from Duval Street and downtown, but it’s kind of nice to be tucked away, too. 

Ocean’s Edge Resort & Marina

15 minutes outside of Key West, which is great to be a little tucked away from the Duval St. craziness. Popular with families, couples. 

Where to eat in Key West

Blue Heaven

You must, must, MUST eat brunch at Blue Heaven – this place is easily one of my favorite restaurants in the WORLD, and it’s absolutely worth the hype. I get the lobster BLT eggs benedict – with avocado instead of tomato – and it is heaven. They home-make all their breads too so make sure you try the banana bread – and a bloody mary – so yummy!

Louie’s Backyard

For the best views and waterfront dining – and the most delicious Caribbean-American cuisine dinner in Key West, Louie’s is the spot! A must stop on any trip to Key West. 

Santiago’s Bodega

Upscale tapas and delicious sangria.

Eaton Street Seafood

Casual seafood market – Go for the lobster roll. 

Misohappy Key West

The best freshest sushi in Key West! 

First Flight Brewery

I loved this little garden restaurant for casual, all-American food. Great spot for dining with a group in Key West. 

What to do in Key West

Rent bikes!

Biking around Key West is a really fun way to see the island. They have bike rentals all over KW- but we rented from Blue Sky Rentals on Duval Street.

Watch the sunset in Mallory Square

Watching the sunset in Mallory Square is essentially a religion in Key West. Every night, street performers, artists, and the like gather in Mallory Square for a sunset celebration. It’s fun to walk around and see! 

Go to the beach!

Check out Fort Zachary Taylor – a Florida state park with great snorkeling. 

The best bars to go out in Key West

When it comes to Key West nightlife, there’s no shortage of fun and funky bars to check out. I loved the live music at Sloppy Joe’s Bar, and my favorite going out spot was the upstairs of Rick’s Key West – which has a huge outdoor space and was super fun. From there, you can walk up and down Duval Street and there’s a ton of fun bars. 

What to know before your trip to Key West

It’s a popular spot! Make your dinner reservations ahead of time – especially if you have a group. I was shocked that we couldn’t get in some of the best restaurants in Key West – even on a weekday! So definitely make those reservations, and you’ll be all set. 

The weather in Key West is amazing year round – but you do have to watch out for hurricane season from June through early November.

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Christina is a leading luxury lifestyle and travel blogger with over 2 million readers. Follow her on instagram @jetsetchristina.