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Key West is my absolute favorite beach town in the United States. Its unique mix of charm, inhibition, beauty, and character set it apart from any other Florida vacation spot – and, quite frankly – any other beach on the East Coast. This blog post will cover the Best Things to do in Key West, Florida, including my top recommendations for food, bars, and activities. I also talk about the various transportation options, so you know the best ways to get to the island in the first place.

To put it simply, Key West is a party town. There is live music everywhere, bars on every corner, and the rules are incredibly lax (if existent at all). If you want a place to escape the real world, sing at the top of your lungs, and stumble into your cabana bed at the end of the night, Key West is the place for you.

Best Things to do in Key West
Table of Contents

Getting There/Getting Around
When to Visit Key West
Where to Stay in Key West
Key West: The Bars/Nightlife
Key West: The Restaurants
Key West: The Activities

Website Disclaimer: my most recent visit to Key West was in October 2019. Although everything is accurate as of the publication of this post, it is important to keep in mind that prices, attractions, and other things may change with time.

Getting There/Getting Around

Getting There

Option 1: Fly into Ft. Lauderdale or Miami and Drive

This is what I have always done and what I would recommend doing.

The drive from the Ft. Lauderdale or Miami airport to Key West is about 4 hours. It sounds exhausting, but it is TRULY one of the most gorgeous drives you will ever embark on in your life. You can also make an adventure out of it by stopping at one or more of the Keys on the way down. If you really want to be boujee, it’s the perfect excuse to splurge and rent a convertible.

A couple years ago, my aunt and I stopped at Islamorada and walked around the village where the tv show “Bloodline” was filmed. The resort was stunning, as was the beach.

Islamorada (on the way to Key West)

You also will NOT starve on your 4 hour journey. There are various tiki restaurants to stop at on the way down and back, and every one I have tried has been amazing. They will be visible from the side of the road and they are SO cute.

One of the tiki restaurants on the drive to Key West
One of the tiki restaurants on the drive to Key West

Option 2: Fly Directly Into Key West

Flying directly into Key West has its advantages from a saving-you-time perspective, but it will likely be more expensive since the airport is small. Also, most flights will NOT be direct, and could have multiple layovers.

  • At present time, Allegiant has cheap flights directly into Key West, but you have to fly in and out on certain days.

Getting Around

One of my favorite things about Key West is that it’s an incredibly walkable island. You are essentially able to walk to almost anything you want to do or see. The entire island is a little over 7 miles long, but Duval St, where the majority of the attractions are, is only 1.25 miles. A lot of places to stay will also have bicycles that you can rent and ride around the island. When I visited, I walked or rode a bike everywhere.

When To Visit Key West

I suppose a better thing to know would be “when is hurricane season?” In Florida, hurricane season can run from June to November, with the MOST hurricanes being recorded in September.

The best time to visit Key West is usually in the spring (March-May). The weather is warm but not overly humid, and you’ll likely have days with little rain and lots of sunshine.

  • I have visited Key West in April and in October, and had great weather experiences both times. Sometimes the evenings can get chilly, but you shouldn’t need more than a light jacket.

Speaking of October, every year around the week of Halloween, Key West hosts Fantasy Fest, an adults-only party where I’ve been told literally anything goes. I haven’t gotten to take part in this festival, so I can’t elaborate much more than that – but believe me when I tell you it’s on my list (and, obviously, there will be an entire blog post dedicated to the experience).

Where to Stay in Key West

If you’re an avid reader of my blog, you’ve heard me talk about the “vibe” and the “aesthetics” of a place on multiple occasions. One of my favorite things about Key West – and why I recommend it to so many people – is the vibe is unlike any other beach town I have encountered. It is the perfect mix of laid back meets boujee meets hippie meets tropical oasis. Many of the hotels, inns, and cabanas you can stay in capture this essence and elevate your overall vacation experience.

To experience the best of everything, I recommend staying on or as close to Duval Street as possible. This is the main street that runs through Key West and sequentially where you will find the majority of bars, restaurants, shops, and nightlife.

The accommodations in Key West range from your typical hotels to boutique hotels, inns, and guest houses. Don’t let the simplicity of some of the places fool you – it can get expensive to stay here. The two places I have stayed in (and really liked) are:

  • La Concha (location: Duval St.)
    • This is a more traditional, boujee hotel that includes a spa, a rooftop pool and a wine bar
  • Eden House (location: Fleming St.)
    • This is a more “Key West-esque” guest house with a pool, tiki bar, and relaxing vibe that is located a down a side street (15 minute walking distance to Duval).

Another popular hotel is Ocean Key Resort & Spa, which is located right next to Sunset Pier – the most popular place to watch the sunset in Key West. It is (understandably) pricey for this reason, but a good place for those “special occasion” trips when you want to splurge. It also has a restaurant right on the dock that you can visit even if you aren’t staying at the hotel, and you can eat and watch the sunset from there.

Despite the abundance of options, for the most authentic Key West experience, I would recommend trying to find a boutique hotel or guest house like Eden House to stay at.

Key West: The Bars/Nightlife

My favorite thing about Key West is the nightlife. It’s got the Vegas essence of “anything goes” mixed with the laid-back essence of a chill beach town. When I was there, you could walk down the street with a red solo cup and nobody batted an eye. Everyone’s there with the intention of partying and having a good time. There’s live music EVERYWHERE – and sometimes, you even get invited to sing along…👀

Singing with David Bryce Warren – one of my favorite Key West entertainers – at Tiki House (confession: I’m a horrible singer)

There are a plethora of bars on Duval St. to explore. and they’re all a blast. Some of my favorites include:

Sloppy Joe’s – food/drink/live music/dancing; there is also a separate room to watch sports

Tiki House – this bar is my favorite, partially because of – you guessed it – the aesthetics. It’s Hawaii-themed with multicolored string lights, and they ALWAYS have good music

Irish Kevin’s – listen…you have to go. It’s SO fun. There’s always live music, they have a great food/drink menu, and the people talk to you like you’ve been friends for years.

Willie T’s – another great spot for live music/food/drinks. Their decor includes countless dollar bills that cover the ceiling and part of the walls.

The Bull/Whistle Bar/Garden of Eden – a “3-in-1” building that has a different bar on every floor. The Bull & Whistle are similar – The Bull has live music and is one of the last remaining “open air” bars in Key West. The Whistle has pool tables and games, plus a balcony where you can people-watch on the streets below.

  • The Garden of Eden is, ahem, an experience – and one that I don’t want to ruin the surprise for you. It’ll be much more memorable that way. Remember how I said anything goes in Key West? You can call me a lot of things after you go here, but in this case, you can’t call me a liar 😉

Key West: The Restaurants

You know how it is VERY hard to find bad food – especially seafood – in a beach town? Key West is no exception. I can’t remember going to a restaurant that I did not like. Having said that, there are a few that stand out:

The Breakfast Club Toomy favorite. You can get the french toast of your dreams here. Oh – and they make 11 different Bloody Marys.

French toast at The Breakfast Club Too

Sunset Pier Cafe – part of Ocean Key Resort & Spa. This one is extremely popular for the reason that you are able to have dinner with a prime sunset view. Expect to have to wait, unless you get there early.

Moondog Cafe – their eggs Benedict is a LOT better than their omelettes, IMO.

Hogfish Bar – this one is actually located in Stock Island, FL, so you have to drive or Uber to get there. This place has somewhat of a “dive” feel and is widely known for their seafood dishes. I can’t remember the exact meal I got, but I definitely remember it being 100% worth the drive.

Key West: The Activities

Believe it or not, there’s more to do here than just drink and party.

Key West, like many other beach towns, can be as relaxing or as fun as you want to make it. My top recommendations for things to do outside of exploring the nightlife are below:

The Southernmost Point in the USA
  • Check out Fort Zachary Taylorthis place allows you to experience a lot of civil war history in Florida. There is also a nearby beach where you can snorkel, fish, grill, bike, etc.
  • See the sunset at Sunset Pier/Mallory SquareKey West is so well known for having epic sunsets that people routinely flock to Mallory Square to take part in watching the sun go down. All the sunset photos in this post are from Mallory Square or the Sunset Pier restaurant.
  • Visit the Southernmost Point in the USAthe monument for this was vandalized a couple years ago, and I’m not positive if it’s been restored. Regardless, you can say you’ve been as South as it gets in the USA and revel in the fact that you are 90 miles from Cuba.
  • Visit the Key West Butterfly Conservatorya 2 minute walk from the Southernmost Point in the USA, this conservatory is home to butterflies, flamingos, fish, and more.
  • Tour Ernest Hemingway’s house if you are a book nerd, you will love this. If you are an animal lover, you will also love this, as there are a TON of cats all over the property.
  • Take a ghost tour with Ghosts & Gravestones – I did this last time and loved it. They take you in haunted buildings, and you get to ride around in a trolley as the tour guide points out historically creepy things around town.
  • Go there during Fantasy Fest in October and live your best life – and know I’m jealous.
  • Have a pool day at your hotel/inn (despite being a beach town, I found that most people gravitated towards spending time at the pool vs. the beach. The beach near Ft. Zachary Taylor that I mentioned above was probably the best one I found.)
  • Rent a jet ski through Viator tours – there are multiple options, and they all have great ratings.

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