Exploring Florida with a Pensacola to Key West Road Trip

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A Pensacola to Key West road trip lets you soak up nearly everything the Sunshine State has to offer. From picturesque beaches to thrilling theme parks to sizzling nightclubs, Florida mass-produces tropical fun on a scale no other state can really emulate.
If you were taking a direct driving route, the distance from Pensacola to Key West would cover more than 830 miles. But this road trip guide, presented by the car insurance comparison shopping and brokerage app Jerry, is less about the destination and more about the journey.
Before you depart, make sure you have everything you need. Bathing suits, sunscreen, beach towels… and Jerry’s cheap and comprehensive roadside assistance coverage! With tire, fuel, battery, towing, and lockout services, Jerry’s roadside assistance provides everything you need to keep an automotive issue from ruining your Florida vacation.
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Start: Pensacola, Florida

Your adventure begins at the Western Gate into the Sunshine State. Pensacola is a beautiful, tourist-friendly city at the westernmost end of the Florida Panhandle. With white sandy beaches, terrific views of the Gulf of Mexico, and lots of great restaurants, Pensacola is the perfect city to kick off your Florida adventures in.
The white sand of Pensacola Beach meets the light green water in this aerial shot.
Pensacola Beach, Florida

What to do

Pensacola is home to America’s oldest Naval Air Station, and the primary base of the storied Blue Angels stunts and flight demonstration group. With this aviation pedigree, it’s no wonder Pensacola has a really fun National Naval Aviation Museum.
If you enjoy historic sights, check out Fort Pickens. Pensacola is also known for having great fishing and hiking, as well as mesmerizing sunsets.
A blue and yellow jet flies in a clear sky at a Blue Angels airshow.
Blue Angels show, Pensacola

Leg 1: Pensacola to Tallahassee

213 miles, 3.5 hours
Your first destination is Florida’s capital: Tallahassee. It’s roughly three to four hours away, though if you want a more scenic route you can follow US 98 onto US 319. This will double your drive time but the views are spectacular.
The Florida State Capitol building in Tallahassee. Sprawling tree branches partially obscure the building.
Tallahassee, Florida

What to do

Tallahassee is landlocked, but there’s still more than enough to fill a day or two of vacation time. Tallahassee has lots of great museums, including the nature-themed Tallahassee Museum and the Tallahassee Automobile Museum.

Where to eat

There’s great shopping and dining throughout the city. Be sure to check out local favorite 101 Restaurant, offering all-American cuisines with only the freshest ingredients. For bold dishes inspired by the tastes of Mexico, you can’t go wrong with El Jalisco.

Leg 2: Tallahassee to Jacksonville

166 miles, 2.5 hours
Your next stop is the bustling city of Jacksonville, home to some of Florida’s most beautiful and accessible beaches. And whether you’re traveling with kids or seeking out the Florida nightlife, you’ll be happy to have added Jacksonville to your Florida tour.
Lazy waves roll up the shore on a beach of Jacksonville, Florida on a clear day.
Jacksonville, Florida

What to do

Kids are going to love the Jacksonville Zoo and Gardens, the Hands On Children’s Museum, and the Museum of Science and History. Bigger kids can try surfing and go on an airboat tour.
Jacksonville also offers modern art museums, nature centers, and lots of outdoor activities like hiking.
The main draw in Jacksonville is the city’s numerous beaches. They’re less crowded than the beaches in the other locales you’ll visit following this Pensacola to Key West road trip, so this is a great opportunity to break out your bathing suit!

Leg 3: Jacksonville to Orlando (141 miles, 2 hours and 15 minutes)

This next destination needs no introduction! Orlando—a city your kids will surely want to spend at least a few days in.
A swan glides through a river streaming by Orlando with tall buildings in the background.
Orlando, Florida

What to do

The greater Orlando area has 10 theme parks to visit (yes, really!), including Disney World, Universal Orlando, and Legoland, just to name a few.
Also within driving distance is NASA’s rocket and shuttle launch site, Cape Canaveral, which everyone should try to visit at least once. The renowned Cocoa Beach is nearby, too.
A pastel-colored sky tints Cocoa Beach a light blue. A pier nearby casts light onto the sand.
Cocoa Beach
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Leg 4: Orlando to Miami

266 miles, 3 hours and 40 minutes
At nearly four hours, the drive from Orlando to Miami seems long—but you’ll get some decent views along the Florida Turnpike. And at the end of this leg, you’ll find yourself in one of Florida’s most famous tourist hotspots.
A tall Miami apartment building casts a shadow over beachgoers and a blue sea.
Miami, Florida

What to do

Miami’s legendary nightlife is something adults simply must experience.
If you’re traveling with kids, Zoo Miami, the Miami Seaquarium, Miami’s several water parks, and the Everglades National Park are definitely worth seeing.
A man bikes down a white path in the Everglades National Park, Florida.
Everglades National Park, Florida

Where to eat

Miami is a hotspot for great food, and you’d be remiss not to try some Cuban dining in Little Havana before you leave. Try the family-run Exquisito Restaurant to indulge in tasty Cuban specialties at budget-friendly prices.

Leg 5: Miami to Key West (166 miles, 3.5 hours)

The final leg of this journey will take you down one of the most famous highways in the world: Highway 1. This massive highway runs the full length of the east coast, but the most iconic stretch is between Miami and Key West where the highway is built over the ocean itself. The views from US 1 are simply unforgettable.
The sun dips below the horizon line with the silhouette of US Highway 1 in front of it.
US Highway 1

What to do

A lot of people think US 1 is a continuous run from the mainland to Key West, but it actually stops off on a chain of islands. And that means there are plenty of places to stop for food (and fuel) along the way.
Key Largo, Plantation Key, Lower Matecumbe Key, and Marathon are all great towns to stretch your legs in and explore.
A small bright blue building sits on a Key Largo beach. The wind blows palm trees on the shore.
Key Largo, Florida

Welcome to Key West!

This awesome Pensacola to Key West road trip will finally take you to what many refer to as the Conch Republic. Key West is a tropical paradise with great food and excellent beaches. You’ll also find lots of family-friendly fun here, even though Key West’s bar scene is famous around the globe.
An expanse of sand and bright green grass jut out into the blue water of Key West.
Key West, Florida

What to do

While visiting Key West, it’s customary to head down to the southernmost point in the continental United States and have your photo taken alongside the famous buoy there. You should also visit the historic Fort Zachary Taylor and the Truman Little White House.
Like most of the other cities you’ll visit during this Florida road trip, Key West has awe-inspiring beaches and some of the best ocean swimming in Florida. You’ll also find boats and seaplanes to charter. If you’re outdoorsy, try night kayaking.

Don’t let a roadside emergency ruin your Sunshine State adventure

Going on a lengthy Pensacola to Key West road trip is going to expose your car to more than its fair share of stress. You’ll cover a lot of ground—probably over 1,000 miles when you factor in city driving and detours. And much of this will happen in Florida’s tropical heat.
Don’t let a roadside dilemma ruin your otherwise perfect Florida road trip! With cheap and comprehensive roadside assistance from Jerry, you can confidently explore Florida knowing you’re fully prepared for whatever the highway throws your way.
And hey, since you’re downloading the free Jerry app already, why not take advantage of the 50 free quotes on car insurance it offers? Jerry users save an average of $879 per year on car insurance—and Jerry eliminates the frustrating paperwork and phone calls, leaving you with huge savings and zero headaches. That’s not bad for an app that takes less than a minute to start using!
“Wow, straight to getting what I want! Where was this app all my life? Jerry is easy to navigate. You can edit your preferences of coverage and their team searches for the best in all insurance companies. Best of all, they will cancel your old insurance and set you up with the new one. I am happy to have found this app!” —Jerry user
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