Road Trip Key West - Pinterest

When looking for an island vacation, many people look toward Hawaii, the Bahamas, or the Caribbean; but what if you don’t have a passport or don’t want to fly halfway across the Pacific Ocean?  How about the good ol’ Florida Keys!  With beautiful weather, clear blue water, lots of history and some fun locals, Key West provides a tropical-island vacation that may be more convenient for some of you east coast sun-seekers!

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Perfect weather for cruising in the convertible through the Florida Keys – on the way to Key West!

The Florida Keys

The great thing about the Florida Keys is that you have transportation options, unlike many other island destinations.  Travelers have the option to flying, drive, or going by boat (from Fort Meyers on a high speed ferry or you can rent a private boat).  If flights directly into Key West are too spendy, then you may consider flying into Miami or Fort Lauderdale, and renting a car and drive down.

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Cruising in the Convertible through the Florida Keys

As most of you know, Josh and I are suckers for a road trip!  We recently flew to South Florida and rented a convertible for the drive all the way down to Key West.  It was an awesome road trip!  But if renting a convertible…don’t forget the sunscreen (yup…we forgot)!

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Made it to mile marker zero…end of the highway! Key West, Florida

Driving the Florida Keys Highway

The Florida Keys Overseas Highway is a unique roadway that has the highest recognition as a National Scenic Byway. It begins just south of FloridaCity at mile marker 127 and goes all the way to mile 0 at Key West.  This unique drive takes you island hopping as you cross 40+ bridges along the way; one particular bridge is 7 miles long (aka – 7 mile bridge).

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Enjoying the drive across 7 mile bridge – on our way down to Key West, Florida!

The trip varies in the amount of time it takes to drive it, so allow plenty of time.  You will want to stop and check out some sites along the way, and perhaps dip your feet in the inviting water at some of the beaches.  Also, traffic can go quite slow – especially if you are behind a slow truck and can’t pass, so you do not want to be in a hurry on this stretch of road.  One beach in particular that we loved was Anne’s Beach.  It’s located around mile marker 73 just off the highway.  There are boardwalks, picnic tables, and sandy areas where you can easily get in the water. And there’s a Geocache in the area – if you are interesting in going on a little hunt!

Made a stop along the highway at Anne's Beach while driving in the Florida Keys!

Made a stop along the highway at Anne’s Beach while driving in the Florida Keys!

We Love Key West

What we love about Key West is the character of this unique town; with its quirky, laid back, island vibe.  The town is known for its humor and sometimes off-beat spirit!  A perfect example of this is when they briefly seceded from the US and declared themselves the “ConchRepublic.”

While the citizens concerns stemmed from real issues, the public display has become rooted in their culture.  Even though the secession lasted all of 60 seconds, this area still refers to itself as the “ConchRepublic” and holds a celebration each year.  (for a humorous read, click here to read the official “Brief History of the Conch Republic”)

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You will hear them crowing every morning! Key West Florida – and their Wild Roosters!

There are so many things to do in Key West that a weekend just won’t cut it.  Plan to spend at least a few days in the area so that you have time to relax and take in the sights.  Old town is where all the action is, so it is most convenient to stay in this part of town.

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Duval Street, where all the action is! Key West, Florida

Maragaritaville in Key West

Relax on the beach or play on the water!  Spend your day visiting cultural and historic sights, or listen to old pirate stories.  During the evenings, you can participate in one of the many ghost tours, pub crawls, or just plop yourself down on a barstool and listen to local music or comedians all night!  Some of our favorite watering holes in Key West include: Sloppy Joe’s & the original Margaritaville!

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Of course, those who know Liz know you can find her at Margaritaville! The Original Margaritaville, Key West – Florida

Our Picks

Water Activities

  • Beaches:  Smathers and Fort Zachary are the best
  • Watersport rentals (jet skis, kayaks, paddle boards, etc.)
  • Open water snorkeling! The beaches are poor for snorkeling, but there is an amazing coral reef just offshore, so take one of the many boat tours out there.
  • Full day party boat with unlimited water activities such as kayak, snorkel, etc. (includes lunch)
  • Dry Tortugas (awesome day trip!)

Culture / History

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Have to make a stop at the southernmost point in the continental US, Key West Florida

Nightlife / Entertainment

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In Key West, it’s all about the sunset! Head to the top of the Crowne Plaza for some drinks and a great view!

Accommodations

  • B&B’s – there are a bunch of them around here, providing great value and service!
  • Rentals (homes / apartments) – highly recommended!  There are actually a lot of vacation homes and condos available that you can rent at reasonable rates, depending on the time of year.  If you get a group together, you can get a great house with a pool for a reasonable rate!
  • Hotels – many budget to luxury options available
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Getting hitched in Key West, Florida. The Old Town Manor is a great B&B to stay at, and a great place to have a wedding party!

Word to the Wise

  • Limited parking available, and it’s expensive!
  • Pedicabs are a good value if you are making the long walk up or down Duval, especially on a hot day
  • Fantasy Fest in October…not for kiddos or the faint of heart!
  • And yes, the stories are true.  There is a clothing optional bar – if you want to find it, you will.

Oh, and one other thing you can do in Key West…throw an awesome weekend-long party and get married, like we did!

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Getting hitched in Key West – the Old Town Trolley took our guests to and from Fort Zachary Beach State Park for the ceremony.

For more information about visiting the Florida Keys, click here to visit their tourism website. 

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How about a reception entrance to the Top Gun anthem? Complete with aviator glasses & sparklers – yeah, that’s how we do it!

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