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
’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.
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.
: 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.
’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.
: 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.
: 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.
: 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.
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
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
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
Kid-friendly spots: If you’re traveling with kids,
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.
($$): 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.
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
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.
: 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.
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
, 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?
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
RECOMMENDED
Haven’t shopped for insurance in the last six months? There might be hundreds $$$ in savings waiting for you.