Exploring Florida with a Pensacola to Key West Road Trip

From cities to beaches to theme parks, this Pensacola to Key West road trip will showcase nearly everything the Sunshine State has to offer.
Written by Matt Terzi
Reviewed by Carrie Adkins
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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
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Before you depart, make sure you have everything you need. Bathing suits, sunscreen, beach towels… and
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Key trip details

Pensacola to Key West
Distance: 904 miles
Driving time: 14 hours and 47 minutes
Suggested length of trip: 2 to 3 days

Itinerary

  • Pensacola, FL
  • Tallahassee, FL
  • Jacksonville, FL
  • Orlando, FL
  • Miami, FL
  • Key West, FL

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.

What to do in Pensacola

Fort Pickens
  • National Naval Aviation Museum
    : 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.
  • Fort Pickens
    : If you enjoy historic sights, check out Fort Pickens.

Pensacola to Tallahassee

196 miles, 2 hours 55 minutes
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.
For a quicker route, take I-10 E to get to Tallahassee.

What to do in Tallahassee

Tallahassee Museum
  • Tallahassee Museum
    : 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.
  • Tallahassee Automobile Museum
    : For some unique antique car viewing, check out the Tallahassee Automobile Museum. You can imagine yourself cruising to Key West for the rest of your trip in one of these babies.

Where to eat in Tallahassee

  • El Jalisco
    : There’s great shopping and dining throughout the city. Be sure to check out local favorite El Jalisco for bold dishes inspired by the tastes of Mexico.

Tallahassee to Jacksonville

166 miles, 2 hours 30 minutes
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.

What to do in Jacksonville

Jacksonville Zoo and Gardens
  • Jacksonville Zoo and Gardens
    : Kids are going to love the Jacksonville Zoo and Gardens, one of only seven U.S. zoos with an animal wellness team.
  • Kid-friendly museums: Got kids with you? Make the trip an educational one with the
    Hands On Children’s Museum
    and the
    Museum of Science and History
    .
  • Hit the beach: 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! Get started with
    this beach guide
    .

Jacksonville to Orlando

141 miles, 2 hours and 10 minutes
This next destination needs no introduction! Orlando—a city your kids will surely want to spend at least a few days in.
For Orlando, take I-95 S and then I-4 W.

What to do in Orlando

Cocoa Beach Pier
  • Hit the theme parks: The greater Orlando area has 10 theme parks to visit (yes, really!), including
    Disney World
    ,
    Universal Orlando
    , and
    Legoland
    , just to name a few.
  • Cape Canaveral
    : Also within driving distance is NASA’s rocket and shuttle launch site, Cape Canaveral, which everyone should try to visit at least once.
  • Cocoa Beach
    : If you missed the beaches in Jacksonville, luckily the renowned Cocoa Beach is nearby.
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Orlando to Miami

235 miles, 3 hours and 38 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.
Take Florida’s Turnpike to get to Miami.

What to do in Miami

Everglades National Park
  • Kid-friendly spots: 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.
  • Experience nightlife: If you’re traveling without kids, be sure to experience the famous Miami nightlife. Start with
    Sobe
    or
    VIP South Beach
    if you’re into boat parties.
Pro Tip A Miami night done right is sure to be a highlight of your trip. Just remember never to drink and drive if you’re going to be back on the road.

Where to eat in Miami

  • Versailles Restaurant
    ($$): 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 Versailles Restaurant to indulge in tasty Cuban specialties at budget-friendly prices.

Miami to Key West

166 miles, 3 hours 26 minutes
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.
Follow US-1 S to get to your destination.

What to do in Key West

Southernmost point of the United States
  • Explore the towns: 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
    , and
    Marathon
    are all great towns to stretch your legs in and explore**.
  • Southernmost point of the United States
    : 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.
  • Fort Zachary Taylor
    : Got a history buff in the car? Visit the historic Fort Zachary Taylor which houses the largest cache of Civil War Armament.
  • Truman Little White House
    : Make some time for the Truman Little White House, the only presidential museum in Florida.
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
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, 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!
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