Florida Keys – which key is right for you?

Welcome to part 2 of our guide to moving to the keys! If you missed part 1 you can find it here: is living in the keys right for you?.

It’s time to pick an island! Don’t be overwhelmed by the number of keys in the Florida Keys. Of those connected by bridges only a handful are likely to be contenders as your future home. A few major factors will help you narrow down which area is best for you: what you like to do, what you need access to and what kind of job you’re hoping to find will all help you zero in on the best key for you!

Let’s get started …

Who are you?

  • You’re a diver: While there’s great diving to be found up and down the keys, Key Largo is known as the diving capital of the world. We have multiple wrecks and gorgeous reefs including the Molasses Reef sanctuary. If you decide to settle further south you’ll find Looe Key just south of Big Pine, Alligator Reef off of Islamorada & wrecks to explore such as the Vandenburg (Key West) and the Eagle (Islamorada).
  • You’re a foodie:  Key West definitely. No other key has the quantity or variety of restaurants that Key West has. When we bring friends to visit Key West they want to drink and explore the bars while we have a list of food we want to eat. If you don’t mind driving an hour for your foodie adventures, then Key Largo is a good choice too with Miami just an hour away. That might sound appealing now but if you’ve never driven around the Miami area you might want to reconsider. Traffic + crazy drivers = a less than relaxing night out for me.
  • You’re a fishermen/fisherwoman: Islamorada is known as the sport fishing capital but there’s great fishing up and down the keys, I don’t think you can go wrong anywhere in the keys.
  • You’re a kayaker/SUPer: There’s great paddling to be found all over the keys but I love Key Largo and the paddles I go on here. That said, I haven’t explored the others by kayak like I have Key Largo. I’m out there exploring as often as conditions allow which ends up being 4-5 days a week. I don’t regret splurging on a canal front home for one second. I love getting lost in the mangrove tunnels and exploring the ocean flats just outside the protection of the mangroves. Check out my post about paddling the Rock Harbor mangroves to see what it’s like out here.
  • You’re a party animal & love an active nightlife/social scene: Key West is the winner for this! A lively, quirky island with nightlife options for everyone!
  • You’re a nature lover: Big Pine Key down south is known as the nature lovers key. It’s also home to the adorable key deer, a tiny species of deer about the size of a medium sized dog. So cute. There’s great nature along all of the keys. I’m a nature lover and I’m very happy in Key Largo.
  • You’re a shopper and love a variety of stores: You’ll have to leave the keys to shop but just north of Key Largo is an outlet mall with pretty good variety, about a 30 minute drive.
  • You’re a beach lover: I hate to be the bearer of bad news but beaches are not something we have a lot of. Sombrero beach in Marathon is a nice little beach and I do mean little. Bahia Honda and Boca Chica state parks have nice beaches too.  I was also surprised by Smathers Beach in Key West. It’s a nice stretch of beach but again that’s looking at it through the lens of beaches in the keys. If beaches are really your thing the keys might not be for you but come down and check out what we have and see for yourself.


What do you need?

  • Do you travel a lot for work and need easy access to an airport? Key West or the Upper Keys are your best options. While Key West has an airport, flights to Key West are a lot more expensive than flights to Miami or Fort Lauderdale both of which are easily accessible from the Upper Keys. If cost isn’t an issue (work is paying!) and you don’t mind fewer direct flight options, then Key West is a great choice.
  • Do you need easy access the high quality/high tech medical care? The Upper Keys. Miami is your best option for medical care.


What type of work do you do?

  • You work in hospitality: Key West has more lodging per square mile than any other key. That’s not to say that you can’t find work on the others, it’ll just be more abundant there. I met a woman the other night at sunset who just got a job at the Key Largo Marriott. High season for tourism down here is winter, November-March, so keep that in mind when you head down. The downside of coming for high season is that the rental market is very tight with everything being snapped up by snowbirds. More on that in a future post.
  • You work in food service or you’re a bartender: See the answer above – same applies here.
  • You work in the dive industry: Key Largo & the Upper Keys has more dive operators than any other key. High season for diving here is the summer, opposite of the general tourism high season.
  • You work from home: Awesome! Move to any key you like!
  • Other jobs: Of course we have a little of everything down here, the key word is “little.” It might be best to secure your job first and let that drive your location.


I hope this helped narrow things down a bit for you! Stay tuned for more posts on everything you need to move to the keys. If you have any questions email me or leave a comment and I’ll be sure to answer it!
What are you waiting for? Make your move to paradise!


Until next time …


Stay warm friends!


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  1. Pingback: Florida Keys – Housing Costs & Considerations | Go Where It's Warm

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