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Key West Travel Guide

I LOVE to travel (who doesn’t?) and when I thought about sharing some of the places I’ve been I knew I had to start with Key West. I have visited Key West six times in the past eight years and I plan on continuing this trend. Many people probably know it as the ultimate party destination (not a bad thing – I love to party), but there is SO much more. When I am in Key West I truly feel like I am on VACATION. Closer to Cuba than Miami, Key West is an island at the southernmost tip of the US. It is easy to see how this magical place has inspired so many including Ernest Hemingway, Tennessee Williams, and Jimmy Buffett.

Welcome to Key West


“It’s the best place I’ve ever been any time, anywhere” – Ernest Hemingway

Anyone who knows me knows that I am a huge Jimmy Buffett fan, which is probably what drew me to Key West first. According to Margaritaville, “A weekend drive down the overseas highway (A1A) landed Jimmy in the town that would prove to be the biggest influence in his musical career, the town that would provide the catalyst for “Margaritaville,” the town that continues to play a large role in his life, Key West.”

home brew

When to go:

I personally believe the best time to visit is in the late fall or the spring. The winter is nice, but there is a chance the weather will be cooler (70’s during the day and you’ll probably need a sweatshirt and pants at night). The summer gets really hot and it brings hurricane season.

How to get there:

You can fly into the Key West airport (usually with a layover somewhere), but it will cost you quite a bit. Instead, fly into Miami and rent a car. The drive takes 90 minutes (another option is Fort Lauderdale with a 2 hour drive) and there is so much to see! I have grown to love the middle Keys just as much as Key West (we even got married in Islamorada) – look out for a blog post soon.

What to pack:

As much as I enjoy getting dolled up once in a while for a night on the town, one of the best parts about Key West is how laid back it is. No need to pack heels or dress shoes – flip flops are the way to go in Key West (even in the more formal restaurants a nice pair of sandals will do, maybe wedges if you’re feeling really fancy).

Christmas gifts for my sister before we brought her to Key West for her 21st bday

What to do:

  • Relax – Believe it or not Key West doesn’t have great beaches, but if you want to beach it the best options are Fort Zachary Taylor State Park, Higgs Beach and South Beach (next to Southernmost Beach Resort).
  • Party – A stroll down Duval Street is a party in itself.
  • Do it for the insta – Stop by the Southernmost Point and the Key West Lighthouse
  • Get some culture – Visit the Hemingway House (watch out for the cats), Mel Fisher Maritime Museum, Harry S. Truman Little White House, Audubon House and Tropical Gardens, plus multiple art galleries (many right on Duval Street).
  • Watch the best sunset – Join the celebration at Mallory Square and get there early for food vendors, street performers and exhibits. It’s tourist central, but it’s fun and a Key West must do.
  • Go for a stroll – The Historic Seaport and Harbor Walk has great little shops and restaurants – seafood galore. There is also a brewery and distillery! Also, if you wander around historical Old Town look out for gorgeous architecture (widow’s walks, tropical and gingerbread accents, etc.), colorful flowers, trees and chickens!
  • Key West Aquarium – Not the greatest aquarium, but a nice option to get away from the craziness of Duval Street especially if you have tiny humans (aka kids) with you.
  • Hit the water – There are many different companies which offer sailing, snorkeling, fishing, or sunset cruises. Another awesome option for daytime is a jet ski tour around the entire island with Barefoot Billy’s.


Where to stay:

  • Southernmost Beach Resort – As the name implies, this hotel is near the Southernmost Point and has one of the nicer beaches (South Beach) I’ve seen in Key West.
  • La Concha – This hotel is right on Duval Street (middle of everything) and recently went through a big renovation adding a wine bar and spa.
  • Casa Marina Resort – The Casa Marina is a Waldorf Astoria resort and is definitely one of the more luxurious hotels in the area.
  • If you have a large group, I highly recommend renting a house (preferably with a pool)!

Where to eat:

blue heaven

  • Blue Heaven – Excellent food in a fun laid back setting. Roosters walk around while you eat and there is often live music. There is usually a long wait for breakfast/brunch so have the least hungover person in your group get there early.
  • Rum Barrel – This is a Philly bar so I guess I have to love it, but the cheese steak spring rolls will make you love it too. (apparently the Rum Barrel has closed since I first started writing this which I am not happy about)
  • Latitudes – Gorgeous setting on Sunset Key (you have to take a boat to get there) and amazing food. Make reservations ahead of time – it books up fast! This is one of the nicer places you could wear sandals as opposed to flip flops too.
  • Louie’s Backyard – Awesome location right on the water. Also, apparently used to be one of Jimmy Buffett’s favorite spots.
  • Salsa Loca – Great for large groups.
  • Santiago’s Bodega – Tapas and excellent sangria.
  • Better Than Sex (dessert) – The name explains it.
  • Kermit’s Key Lime Shop – They have pretty much anything key lime your heart may desire, but the chocolate covered key lime pie on a stick is a favorite. Honestly, there are tons of spots you can grab a slice of key lime pie around the island and you likely won’t be disappointed.
View from the deck at Louie’s

Duval Bar crawl:

I have tried to squeeze more stops into my Key West bar crawl, but it usually comes down to these 6. Hog’s Breath is only a 2 minute walk from Mallory Square if you want to catch the sunset before or after your first stop.

  • Hog’s Breath
  • Smallest Bar
  • Sloppy Joe’s
  • Captain Tony’s
  • Rick’s (you can get slices of pizza downstairs)
  • Irish Kevin’s

If you make it out of Irish Kevin’s (difficult because it is SO much fun) continue down Duval and find even more great spots: The Porch, The Bull/Whistle Bar (hit the Garden of Eden roof top if you’re feeling super adventurous), Margaritaville, Willie T’s. Then make a right on Southard St. for the Green Parrot Bar and some late night live music.