Tips For Moving to Key West From Local Experts

July 17th, 2015

Thinking of moving to Key West? Follow these tips from our local experts to make the process smooth and seamless—Welcome to paradise!

Consider a temporary rental first
While the island is relatively small at only about eight square-miles, deciding on a rental property or a house to buy is no small task. Give yourself some time to search and feel out the island and its neighborhoods before you sign a yearlong lease or put a mortgage down. This is a vacation destination after all, so month-long vacation rentals are easy to come by.

New Town or Old Town?
When it comes to moving to Key West the biggest decision you’ll have to make is whether you want to live in New Town or Old Town. For many, Old Town and its tight knit community, charming bars and restaurants and easy maneuverability is the ideal choice. The only drawback is that it’s often more expensive and more crowded with smaller lots and outdoor space. It all depends on the lifestyle you’re after and your budget. Midtown, in between Old and New Town as the name suggests, is also a good middle ground for Key West newcomers.

2 story key west home

Grab a copy of Quit Your Job and Move to Key West
Need some sage advice and a crash course into life in Key West? Grab a copy of the latest edition of Quit Your Job and Move to Key West by longtime locals Chris Shultz and David Sloan. Pairing humor with practical advice this slim volume is a good companion for any newcomer on the island.

Buy a bike
One of the best things about life in Key West is that you can do it sans automobile, especially if you’re living in Old Town. In fact, it’s easier to get around on bike on the island’s narrow streets with little available parking. It’s the preferred mode of transportation for most locals, so if you’re planning on meeting up with your new friends at Nine One Five for dinner or Agave 308 Tequila Bar for a cocktail, plan to meet them on your bike. You can go fancy and customized or buy a rusty, old used one—anything goes in Key West.

Go where the locals go
It’s time to abandon the tourist haunts you once frequented before you lived here and go where the locals go. And where might that be? Any spot that’s locally owned. Remember Chris Shultz, the guy who wrote Quit Your Job and Move to Key West? Well, today he owns a slew of bars and restaurants with a strong local following, including The Porch, The Other Side and Two Cents with Waterfront Brewery on the horizon.

Brush up on your Key West history
Maybe it was the laidback lifestyle and beautiful island scenery that initially drew you to Key West, but this island also has a fascinating history that might tether your heart to this anything-goes island all the more so. This is your new home, so you might as well learn about its history. From pirates and bootleggers to literary legend Ernest Hemingway and poet Robert Frost, there are many fascinating Key West stories through the ages.

You won’t need an alarm
As if the promise of another beautiful, sunny day in paradise wasn’t enough to make you spring from bed at the first sight of dawn, then the crows of Key West’s resident chickens sure will. Don’t be surprise by the free-range chickens roaming the island or their early morning wake up calls, they’re as much a part of this colorful population as anyone else living here.

Old Town Key West house with pool

Incorporate the water into your lifestyle
You’ve moved to a tiny island at the crossroads of the Atlantic Ocean and the Gulf of Mexico. That means tranquil blue waters surround you at every angle. Get out there and enjoy nature’s bounty as often as you possibly can. Whether that means daily swims at the beach the way playwright Tennessee Williams once did, or stand up paddle boarding, kayaking, fishing, snorkeling or boating, you owe it to yourself to get salty and stay salty.

Where to grocery shop and go to the movies in Old Town
If you’ve made the move to Old Town and ditched your car while you were at it, you might be wondering where to get the bare necessities and creature comforts without hitching a ride to the strip malls of New Town. Never fear, Old Town has everything you need from two Fausto’s grocery stores to the art house Tropic Cinema. What more do you really need?

Ditch the suit and tie and high heels
This one may seem obvious, but Key West is a dressed down, laidback place to live. Even at the finest restaurants (you’re in luck—there are plenty of those!), shorts and a t-shirt will typically suffice. This doesn’t mean you can’t get dolled up, but you don’t have to. It won’t take long before you adapt to Key West’s own brand of island style.