Ultimate Key West Travel Guide

Key West Sunset

So you just booked a trip to Key West and are trying to determine the best spots to hit up for dinner, what to fill your days with and what hotel to book ... I got you covered!

Growing up in South FL, we took countless family vacations down to the Keys & Key West. I loved the area so much that I made a point to go down once a year with friends during college. Then my long-distance boyfriend at the time (now husband =)) decided to take a job in the area and then came many many more trips. Needless to say, I am full of Key West recommendations. 

Where to stay: 

There are SO many boutique hotels, bed & breakfasts and vacation rentals in Key West. These are my top picks!

Truman hotel – this is my top choice every time. They always have great prices, it’s in an amazing location in walking distance to Duval and just the cutest boutique spot! It's perfect for either large groups or couples. My only caveat is the staff is not the most accommodating, so don’t expect VIP treatment.

Casa Marina Resort – love this hotel for the private beach, restaurants and overall great property. It is further from the main area of Duval, but very close to Higgs and Smathers beach. The rooms are pretty standard for the price, but it is great if you are looking for more of a resort feel, rather than a B&B.

Sunset Key Cottages – if you are able to splurge, do yourself a favor and go stay on this secluded island (5 min ferry ride). It is quieter in nature, but beyond relaxing and has the most adorable beach cottages.

Hyatt Hotel or Ocean Key Resort – check these two hotels out if you want a hotel right on Duval / Mallory square. The prices will likely be rather high though. 

The Mermaid and the Alligator – this is right next to the Truman hotel, but if you are looking for a true B&B experience, cannot recommend this place enough. The staff is excellent! Note – they do mention that 2 of the rooms are smaller than the rest (i.e., Key Lime room).

Marquesa Hotel – this is a mix between a B&B and a hotel. I'd recommend this hotel to couples. The rooms are a great size and it's a pretty quiet property. 

Blue Marlin Motel – I would normally not add a motel to the list, but I'd be remiss if I didn't give a shout out to the property I stayed at every time I visited in college. The rooms are actually pretty modern and if you are looking for an inexpensive spot that you can bring a large group, well, you’re welcome. =) 

Truman hotel

Truman hotel

views from ocean key resort

views from ocean key resort

What to do:

Shop and explore Duval street and Mallory Square.

Dante’s Pool Bar – if you are looking to start the night early with a daytime pool party and live DJ, this is your spot!

Dry Tortugas National Park -  this could take a full day, as you have to take a ferry out to the island, but if you have the time, totally worth the trip.

Beach day – while the beaches are not the best in Key West, you can still check out the beach scene which is always full of sunbathers, snorkelers and volleyball players...Fort Zachery State Park (picnic/sunset beach), Higgs Beach(family-esque beach) and Smathers Beach (party beach). 

Snorkel excursion – if you want to get out on the water, I’d highly recommend booking one of these trips. Danger charters and Fury Water are both great.

Sunset Cruises – I’ve probably done one of these on every girls trip. Just a fun way to kick off the evening.

Drag show – while this may not be for everyone, I have the best time at these shows. If you are open to it, Aqua is not to be missed!

entertainment at mallory square

entertainment at mallory square

danger charters

danger charters

Where to eat and drink: 

This list could be endless, so I tried to narrow it down to my favorite spots. My favorite spots are usually more of a locals feel and not the typical tourist traps =)


  • Blue Heaven – if you have to choose one breakfast spot during your stay, go here. Expect a long wait, but grab one of their famous bloody marys to kick off the day! FYI - there are a lot of roosters roaming around, but it adds to the charm. 
  • Sarabeths – such a quaint breakfast spot, within a Key West style home.
  • Pepe’s Café – tiny, old school breakfast place, but they cook up some good food. I always leave here with a bottle of their signature hot sauce.  
blue heaven

blue heaven


  • Southernmost Beach Café – oceanside café, directly on the sand. Perfect spot for a burger and a beer. 
  • Salute – open air restaurant, right on the beach. Great place to relax with a glass of wine. 


  • Louie’s Backyard – fine dining seafood restaurant for Key West, with the most spectacular ocean views. I would recommend sitting outside. 
  • Santiago's Bodega – this is off the beaten path, but one of my favorite spots in Key West. Great tapas and wine bar.
  • Sunset Pier at Ocean Key Resort - more casual vibe with dockside dining. Not the most amazing food, but I just love the atmosphere and sunset views. Great for cocktails and live music at night. 
  • Michaels– hidden gem in KW. High-end steakhouse, located in an old FL home. Get a table in the garden patio. 
  • Latitudes – if you are looking to get away from Duval, hop on the ferry to Sunset Key (through the Westin hotel) and take a 5 minute ride to this amazing restaurant. Luxury dining on the Gulf of Mexico. 
sunset pier 

sunset pier 

stunning sunsets from sunset pier

stunning sunsets from sunset pier


  • Better than Sex – I know I know, the name is comical …and the deserts are to die for! Lives up to the name. =) 


You can see most of the bars on Duval, but these are my go-to: 

  • Irish Kevins - irish pub, with the best nightly live music. 
  • Sloppy Joes - Key West staple that cannot be missed. You never know when a celeb guest may show up to perform.
  • Conch Republic Seafood - great spot for happy hour and live music. 
  • Virgilios - locals hangout, behind the Italian restaurant, La Trattoria. They serve amazing martinis and have a killer salsa night.
  • Vino’s on Duval – cozy wine bar if you want a more relaxed environment and escape from the Duval rowdiness. 
  • Green Parrot - iconic KW locals dive bar, off the strip. 
sloppy joe's 

sloppy joe's 

If you've been to Key West, comment below with your favorite spots. If I haven't heard of the place, I'd be shocked, but I love a good challenge =) 

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