Miami to Key West Road Trip: A One Week Florida Keys Itinerary

When my boys turn 13, I offer them a trip in the US alone without brothers. My middle son wanted good fishing, so we decided to spend our time exploring the Florida Keys. Since we didn’t want only to visit Key West, we rented a car and drove from around Miami to Key West with many great spots in between. We weren’t interested in the big city this time, so we only used Miami as a starting point for points farther south. If you are planning a road trip from Fort Lauderdale or Miami to Key West, you are in the right place to help plan your trip.

What is the Closest Airport to Fly into for a Road Trip to the Florida Keys?

There is a small airport in Key West, but it is more expensive to fly into. Our goal was a road trip for the whole Keys, not just Key West, so it made more sense to fly into southern Florida.

The closest airport to the Florida Keys is Miami International Airport.

About 50 minutes north of Miami is Fort Lauderdale International Airport. Because my son wanted to see the marina at Fort Lauderdale and the tickets and car rental were cheaper, we actually flew in and out of this airport.

What Are the Florida Keys?

Florida Key road trip itinerary
Not only does Key West have chickens, but they are also beach chickens and tree chickens!

The Florida Keys are a coral archipelago (chain of islands) almost 120 miles long. Alongside the Florida Keys runs part of the Florida Reef, the third-largest reef system globally and is the only living coral reef in the Continental US. The Keys are also full of military and literary history.

The Keys are connected by the Overseas Highway, a series of 42 mainly low-lying bridges connecting the islands. The longest is the Seven-Mile Bridge. Many of them were built over old railroad bridges. In some areas, you can see the decaying railroad bridges of the past.

The Atlantic Ocean surrounds them on one side and the Gulf of Mexico on the other. The islands have both tropical beaches with palm trees and lush mangrove forests teeming with life.

Most people visit the Keys to dive, boat, fish, and drink.

Florida Key Road Trip Itinerary

things to do in Key West, Florida
Edward B Knight Pier, Key West

Key West

We started our trip by making the longest drive, about three and a half hours from Miami to Key West.

Key West is probably the most famous of the Florida Keys and is all the way at the end. It contains the southernmost tip of the continental US. You will notice it demarcated by a large colorful buoy, the Southernmost Buoy, at the end of Simonton Street.

Parking in downtown Key West is pretty horrific. This is why you see a lot of golf carts. My recommendation is to find a hotel that has a shuttle or Uber around.

Things to Do in Key West

southern Florida road trip

There are so many things to do in Key West, but here are a few of my highlights.

Mallory Square

The sunset is celebrated each night in Mallory Square, so be sure to get there and enjoy this vibrant scene. While there, check out Pier 245 for dinner, but you will need reservations.

Visit the Ernest Hemingway House

Ernest Hemingway made Key West his home; you will find many remnants of him here, including his home and six-toed cats.

Walk the 1.25-mile length of Duval Street.

If you visit Key West to eat or drink, Duval Street is the place to be.

Blue Heaven

Enjoy Key Lime Pie at the bar of Blue Heaven.

Enjoy an Evening at the Edward. B Knight Pier
Miami to Key West Road Trip
Conch are so important to Key West locals are called by this name. Like my Florida nails? Check out travel nail designs for more.

Honestly, I prefer quiet over rowdy, so this was my favorite time we spent in Key West. Key West has random chickens, and this beach is loaded with them- beach chickens who roost in trees! If you enter the water from the stairs on the right of the beach, you can walk very far out on the sandbar. Since it is clear and shallow, you can see many conchs and perhaps even a nurse shark.

While I waded in the water, my dad and son caught fish off the pier. After sunset, the pier came alive with bike riders and people walking dogs.

The Dry Tortugas

Fort on dry tortugas
Fort Jefferson and its moats on Dry Tortugas.

Did you know the most remote National Park in the US lies off of Key West? The Dry Tortugas are a few small islands sitting in the middle of the ocean with a huge fort (Fort Jefferson) on the largest island. Many birds use this stop as a breeding ground. There are also turtles, as the name implies, and great snorkeling.

It is an expensive day trip from Key West, but a unique way to spend the day. You can take a seaplane or ferry to the island. If you take the ferry it takes 2 hours each way. Be sure to take bonine ahead of time as the ride can be pretty rough. If you would like to stay overnight in the national park you can book a camping spot.

We then headed back up the Keys with a few fun stops.

Big Pine Key

Things to Do in Big Pine Key

Bahia Honda State Park

Stop to kayak or take a boat out to snorkel in this state park.

See Key Deer

where to find Key Deer

These endangered relatives of the whitetail deer are unique to the Keys. They are the smallest deer species in North America. Big Pine has a refuge for these cuties, although you are likely to run into a couple if you drive around Big Pine Key’s side roads.


Take a Sailing Tour to Sombrero Reef.

We didn’t get to do this tour, but a friend says it’s the best snorkeling that she did on the Keys.


I wanted a more low-key town for a few days and am so glad I picked Islamorada. My whole family preferred it to Key West. It is near many reefs and mangrove forests, with a gorgeous oceanfront, so it has many active things to do.

Things to Do in Islamorada

La Siesta Resort

I lucked out finding this family-friendly resort on the water. The rooms are big, it offers free water activities such as kayaking and paddleboarding, and it is conveniently located. Staying at this resort, you also have access to its sister properties, which have different vibes.

Book a room at La Siesta Resort now.

Meet a Manatee

Paddle! The Florida Keys

where to kayak with manatees

Take a Kayak through the mangroves looking for manatees. One of my goals for this trip was to meet a manatee face to face, and mangroves are one of my favorite places to explore by kayak. They are teeming with life and tend to have calm waters. As a side note, my favorite mangrove kayak was an evening paddle to a bioluminescent lake in Puerto Rico. When I heard a trip combined mangroves and manatees, I knew it was for me.

Brittany guided us across a harbor into a sheltered mangrove forest where we saw jellyfish and crabs. In the middle of our paddle, we took a cool dip in a quiet cove. You may want to wear water shoes for this part. Since we had not yet found our manatee, we paddled in the marina looking for one and found a humongous one! Bucket list check for me!

Book your Paddleboard or Kayak Ecotour with Paddle! The Florida Keys now.

Check the waters at a marina.

Manatees, tarpon, and nurse sharks can be found hanging around marinas, drawn by water and the remnants of fish cleaning. Feeding manatees freshwater or feeding them lettuce can hurt them, so please don’t participate in that activity.

I saw another manatee at the Post Card Inn marina.

Watch a Tarpon Feeding

This activity happens at pretty much any marina when fishers are cleaning their catch. These huge white fish can weigh as much as 250 lbs and reach 8 feet long and hang around docks or feeding stations. When fish is thrown in the water, the water comes alive with the fish attacking the bait.

I loved the tarpon feeding at The Post Card Inn because one brown pelican had a raft in the middle of the feeding. One of the more popular places to do this experience is at Robbie’s, where you can buy anchovies to feed the tarpon yourself.

Join a Party Boat Fishing Charter

My son was the king of the boat with this almost 20-pound amberjack!

My dad and son wanted to catch some big fish. They joined a party boat from Bud’N’Marys just down the road from our hotel. For just $70 apiece, they spent all day catching fish. My son was king of the boat, catching an almost 20-pound Amberjack. They both caught a lot of yellowtails as well.

After returning to shore, the crew filleted our fish for us. We then headed right next door to Lazy Days.

Eat Fish You Catch at Lazy Days

Even if you don’t bring in your own catch, this is a great seafood restaurant on the water. They also have a station where you can feed the tarpon.

Key Largo

John Pennecamp’s Coral Reef State Park

Visit the US’ first underwater park. You can see what is underwater with a glass-bottom boat tour, snorkeling, or SCUBA. If you want to stay above water but not go on a boat tour consider, renting a canoe or kayak.

Everglades National Park

Boating along the Everglade’s waterways

The Everglades is a diverse park on the southwest coast of Florida. The entrance is only about an hour out of the way on this trip, so if you are crazy about US National Parks like I am, be sure to spend some time here.

Take an airboat tour through the swamps.

You will see signs for companies on your way into the park. The tickets usually include an alligator show of some kind.


As I said, there are so many different areas to explore in this National Park. You can hike in a cedar forest, along boardwalks through swamps and grassy fields. Visit a visitor center or the park’s website for more information.

birds in the Everglades
An Osprey in the Everglades

Rent a Boat.

Since the Everglades are mainly water and my dad and son are obsessed with boats and fishing, this is how we spent our day in the Everglades. We did a lot of fishing, got a closeup look at the mangrove banks of waterways, and were even visited by a friendly pod of dolphins on an inland lake.

All boat rentals happen with Flamingo Boat Rentals, although you also could take a fishing charter or a guided boat tour.

Grab a Bite on your Way Back to Miami at Yardie Spice

This whole-in-the-wall restaurant run by a husband and wife team has incredible Haitian and Jamaican food. I am even considering returning to it if I have to drive from Fort Lauderdale or Miami. Be sure to save room for the coconut rum cake.

We had a wonderful time exploring the Florida Keys. So good that I would love to return with the whole family one day.

Have you been to the Keys? Is there anything you would add as a must-see? Please let me know below.

If you liked it, please share it. Thank you!

3 thoughts on “Miami to Key West Road Trip: A One Week Florida Keys Itinerary”

  1. Wonderful recap. Glad you liked our little paradise. One change. The Southernmost point is at the end of Whitehead and South streets, not Simonton.


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