Ah, the Florida Keys. Driving the 100+ mile stretch off the southern tip of Florida is a bucket list item for most. And when you add a convertible (or jeep) to the mix, it just ups the ante.
Here is our key to the Keys:
How To Get There
It really depends on where you’re coming from and where you’re staying.
Fly into Key West: if you’re staying in Key West, or the Lower Keys, this is your most direct route. Also, if you’re looking to road trip through the island chain, we also recommend this option. The drive from south-to-north through the Lower Keys is gorgeous and offers big water views!
Fly into Miami: if you’re staying in the Upper Keys, Miami is the shortest distance to your destination.
Fly into Ft. Lauderdale: if you’re up for a longer road trip, this is another option that sits about 30 minutes north of Miami and provides another great city to explore (if flights are cheaper or you are a Southwest Airlines fan).
Rent a car: we highly recommend a convertible or a Jeep. If you don’t, you’ll regret it. Trust us!
Private transportation
What To Pack
Sunscreen. Lots of sunscreen. Especially if you’re road tripping in a convertible or Jeep, you’ll want to immediately apply some SPF. And, of course you’ll need it during your time at the pool, on the beach, or just out & about.
A hat and/or bandanas. The road trip is windy (but amazing!).
A floppy beach hat for sunbathing.
Good reads and listens: books, magazines, e-books, podcasts, music.
Bathing suits and swim trunks.
A mobile travel charger: you’ll be stopping to take a lot of pictures and will likely need to recharge your mobile devices.
Flip flops.
Clothes for riding bikes, vespa scooters, boating, or walking the island.
A thermal cup: we recommend taking a Yeti or insulated cup for drinks in the sun.
Where To Stay
It depends on who’s going and what your travel style is.
Divers, fishermen and boaters: The Perry Hotel is an adorable hotel located on Stock Island, one island north of Key West (@10 minute Uber ride to Key West). It’s situated on Stock Island Marina, so you have great views of the marina. And it’s a quick walk to your dive boat, fishing charter, or sail on When & If.
Party time: if you’re looking to do “The Duval Crawl”, you’ll want to stay in Key West. There are plenty of accommodation options, ranging from luxury to boutique.
(The Perry Hotel – image above)
How To Get Around
Bikes, Vespa Scooters, Uber, Hotel Shuttle
Where To Beach
The Keys offer some beach areas, and if you’re a total beach person, this may not be the place for you. However, you can find some beach areas:
The water is stunning. The drive is surreal. The people are lovely.
Ready to book your getaway to The Keys? It’s simple – click here!
Your out-of-the-box vacation
in a box!
Delivering out-of-the-box travel experiences, we take your bucket list ideas, pair them with round-trip travel, accommodations, and experiences to create an itinerary worth boasting about.
Isn’t it time you let someone else handle the planning?
Whether we’re sending you to your dream destination or off on a surprise getaway, our mission is to remove the stress of planning and deliver a vacation package to create lasting memories—all boxed up and TSA approved.