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. In fact, the Miami to Key West drive is one of the most scenic road trips in the USA and one of our personal favorites!
** This post was originally published in 2013, but updated most recently in 2019.
Getting from Miami to Key West, Florida
The great thing about the Florida Keys is that you have multiple transportation options, unlike many other island destinations. Travelers have the option to flying directly into the Keys, driving, or going by boat (from Fort Meyers on a high speed ferry or you can rent a private boat).
While flights directly into Key West are convenient, they can be a bit spendy. Plus, if you fly you will miss out on the beautiful drive from Miami to Key West. So we actually recommend you fly into either Miami or Fort Lauderdale, renting a car and drive down to the Keys.
As most of you know, Josh and I are suckers for a road trip! So during our trip we actually flew to Fort Lauderdale (better flight prices) and rented a convertible for the drive all the way down to Key West. It was an awesome road trip! But if you decide to rent a convertible…don’t forget the sunscreen (yup…we forgot)!
Driving the Florida Keys Overseas 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 Florida City 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).
How Long is the Drive from Miami to Key West?
The time to drive from Miami to Key West varies. You GPS may say that it takes a little more than 3 hours, but we can assure you that it will take longer than that. If you are like us, then 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 driving down to Key West can go quite slow because it’s a narrow road for the most part. It’s especially slow 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.
Popular Stops on the Drive from Miami to Key West
One of the first keys you will arrive at is Key Largo. And Mrs. Mac’s Kitchen is a popular place to stop for a bite to eat. The walls are covered with license plates from various states and people like to tuck dollar bills on the ceiling.
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! If you don’t know what that is, then check out our post about what Geocaching is.
Islamorada is a popular island that is famous for a few things. You can stop off at the diving museum, which is really cool if you are interested in scuba diving and learning more about the history of it. Also, if you visit the Theater of the Sea then you can even watch seals paint! Yes, you heard me right. I actually had a roommate years ago who bought a painting there made by a seal!
If you’ve worked up a thirst, then before leaving Islamorada you can stop off at the Florida Keys Brewing company for a drink.
When you enter Big Pine Key definitely be on the lookout for the deer — yes, deer! This island is famous for their little four-legged residents, and if you are driving at night then be super careful as they do cross the highway!
Things to Do in Key West & Why We Love It!
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 “Conch Republic.”
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 “Conch Republic” and holds a celebration each year (for a humorous read, click here to read the official “Brief History of the Conch Republic”).
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 Key West is where all the action is, so it is most convenient to stay in this part of town.
Beaches, History, and Duval Street!
Relaxing on the beach in Key West is a great way to spend the day, or out on the water. There are a number of water rentals available as well as snorkel tours and catamaran rides. History or culture buffs in Key West will enjoy the rich history of the area, numerous museums, 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. In fact, most of the establishments on Duval Street have live music or some type of act playing nearly every night. Some of our favorite watering holes in Key West include: Sloppy Joe’s & of course the original Margaritaville!
Our Top Picks for Things to Do in Key West
Water Activities
- Beaches: Smathers and Fort Zachary are known to be 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.
- Visit the Key West Aquarium (if you want to check out sealife without getting in the water)
- Rum & Reggae Snorkel & Sunset Cruise
- Dry Tortugas (awesome day trip & an amazing US National Park!)
Culture / History
- Old Key West Trolley (tour around town)
- The Ernest Hemingway house
- Harry S. Truman “Little White House”
- The southernmost point in the continental US
Nightlife / Entertainment
- Live music (almost everywhere!)
- Bar-hopping up and down Duval Street nightly (AKA “The Duval Crawl”)
- Nightly ghost / mystery tours
- Sunset at the nightly party in Mallory Square (Or you can go to the top of the Crowne Plaza hotel)
Accommodations in Key West
Depending on the type of Key West vacation you are looking for, then there may be different accommodations to suit your needs. But for us, we believe that staying in the heart of Key West is the best way to go. We enjoy having access to restaurants, live music, and all the other fun. Plus, there is public transportation that can get you to the beaches or boat docks. Also, driving and parking can be quite difficult in downtown Key West — which is we we have found that staying in that area so you don’t have to move your car is the best option!
- B&B’s – there are a bunch of them around here, providing great value and service!
- We recommend The Old Town Manor (where we had our weekend wedding extravaganza!) – it’s 1 block to the heart of Duval Street, and it’s a gorgeous and historic B&B!
- Andrew Inn and Cottages is another beautiful B&B right in the heart of Key West’s entertainment area.
- 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! If you use Airbnb be sure to check out our coupon!
- There are many other hotels in the Key West downtown area to choose from as well.
Word to the Wise When Visiting Key West
- Limited parking is available in downtown Key West, 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
- They like to party. Fantasy Fest is held in October…and it’s 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.
Getting Married in Key West
Oh, and one other thing you can do in Key West…throw an awesome weekend-long party and get married, like we did! Being the travelers we are, of course we had to have a destination wedding! And we picked Key West because people could choose to fly, or even drive. It’s a tropical island destination, yet no one needed to get a passport to travel to Key West.
Plus, there are so many things to do in Key West everyone enjoyed themselves — because we figured if people had to travel to our wedding anyway (because all our friends and family are from all over the place…and even from other countries) so we wanted them to have a great vacation too! Lastly, we knew that we could throw a great party and make it into an awesome vacation for everyone.
And in fact, years after our wedding many of our friends and family tell us it was one of the most fun vacations and weddings they attended. We often joke about doing an anniversary trip with everyone back to Key West in the future, because it would be a fun party to relive!
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