Exploring the East Coast with a New York to Key West Road Trip

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  • New York City, NY
  • Atlantic City, NJ
  • Ocean City, MD
  • Virginia Beach, VA
  • Jacksonville, NC
  • Charleston, SC
  • Jacksonville, FL
  • Orlando, FL
  • Miami, FL
  • Key West, FL
  • Roadside assistance
From Jersey to Virginia to the Carolinas, a New York to Key West road trip explores many top tourist destinations on the east coast of the United States.
Starting in the city that never sleeps and ending in the Conch Republic, you’ll drive along some of America’s most famous and scenic roadways. This massive road trip would take 23 hours if you drove it nonstop!
But if you’re driving from New York City to Key West, why not take your time and explore?
This road trip guide, presented by the car insurance comparison and broker app Jerry, will take you from the intrigue of historic colonial America to the extreme R&R of some of America’s prettiest beaches.
Ready to start exploring?
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Start: New York City

You’ve seen New York City, New York in movies and on TV shows. You may have explored the city in video games, or read about it in books. But until you actually visit the Big Apple and see it with your own eyes, it’s impossible to really get a sense of just how massive it is.

What do to

You probably already know what you want to do in NYC. The Statue of Liberty and Ellis Island, visiting Times Square, strolling through Central Park, taking the kids for a Nathan’s hot dog on Coney Island or a slice of pizza in Brooklyn… the list goes on.
One thing you won’t want to do? Drive. Most hotels in NYC recommend parking nearby, and many have discounts or even validate for you. Park your car and take the subway around town—riding the subway is deeply ingrained in the New York experience and will help you avoid some serious headaches.
Pedestrians walk by the yellow storefront of Nathan's hot dogs at Coney Island.
Nathan’s hot dogs at Coney Island, New York City, New York

Leg 1: NYC to Atlantic City, New Jersey

127 miles, 2.5 hours
Pick yourself up a Joe’s Pizza to enjoy on the road and then make your way toward the Las Vegas of the East Coast: Atlantic City, New Jersey.
Atlantic City is a beautiful seaside resort town with America’s most famous boardwalk. As you head into town, keep an eye on the street names. You probably know them from the board game Monopoly, which takes place in Atlantic City!

What to do

If you’re traveling without kids, Atlantic City is a casino playground. But there’s plenty to do here for the whole family, too.
Steel Pier is loaded with fun games, and a short distance from Ripley’s Believe It or Not. The Playground Pier (formerly known as Ocean One) is a shopping mall built over the ocean, with restaurants featuring beautiful views of the Atlantic.
Two women ride down an Atlantic City pier in a rickshaw.
Atlantic City, New Jersey

Leg 2: Atlantic City to Ocean City, Maryland

141 miles, 3.5 hours
Your next stop on this epic New York to Key West road trip visits another city famous for having a classic boardwalk. Ocean City, Maryland is famed for its tourist attractions and is jam-packed with fun for the whole family.

What to do

Ocean City has a gorgeous beach, perfect for swimming, surfing, or kayaking in the Atlantic.
It’s home to several amusement parks, too. You’ll want the kids to see the Jolly Roger, Trimper’s, and Frontier Town.
If your family enjoys mini golf, be sure to visit Old Pro Golf and Professor Hacker’s Lost Treasure Golf. You can easily spend a couple of hours in Marty’s Playground, too, a vintage old-school arcade.
An Ocean City theme park at sunset. A ferris wheel and rollercoaster stand against the sky.
Ocean City, Maryland

Leg 3: Ocean City to Virginia Beach, Virginia (141 miles, 3 hours)

Leaving Ocean City, you’ll take Highway 13 south and cross one of the most beautiful bridges in America, the Chesapeake Bay Bridge-Tunnel. This highway cruises above the Chesapeake Bay, occasionally dipping below the surface of the water into tunnels so ships can sail past. Don’t worry, it’s not as scary as it sounds!

What to do

Virginia Beach, Virginia is another exciting vacation hotspot, with a beautiful beach and loads of fun places to explore.
Virginia’s Military Aviation Museum, the Cape Henry Lighthouse, and the stunning statue of Neptune are must-see destinations. And like Atlantic City and Ocean City, Virginia Beach also has an excellent boardwalk.
A pink sky descends over Virginia Beach, with beachview hotels near the sand.
Virginia Beach, Virginia
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Leg 4: Virginia Beach to Jacksonville, North Carolina

210 miles, 3.5 hours
This New York to Key West road trip will have you visiting two different cities that share the same name, and your first Jacksonville is in North Carolina. Take Highway 17 South out of Virginia Beach for the best views—the “Great Dismal Swamp” is actually quite pretty to look at).

What to do

Jacksonville is a great city to visit and break up the otherwise long drive to Charleston. There’s lots to do here, including the Hullabaloo Indoor Play Space, the Pine Knoll Shores Aquarium, Jungle Rapids Family Fun Park, and the famed White Lake Water Park.

Leg 5: Jacksonville to Charleston, South Carolina

228 miles, 4.5 hours
Continuing along Highway 17 south you’re going to see some beautiful sights. And you’ll also have an option to extend your trip even further. Do you pitstop in the renowned vacation town of Myrtle Beach or do you continue onward, knowing the rest of this trip is jam-packed with stunning beaches and seaside adventure?
When you’re looking down this list of cities to visit on a New York to Key West road trip, Charleston, South Carolina might not jump out at you as the most tourist-friendly of the lot. And that’s a shame… because it just might be.

What to do

Charleston has some of the prettiest beaches on this road trip and loads of attractions worth visiting. With Zoos, aquariums, museums, and amusement parks, Charleston is a city you may want to spend more than just one day exploring. Don’t miss out on the sights, sounds, and tastes of **Charleston’s French Quarter, either.
While there, take in some history with visits to Fort Sumter, the Charleston Museum, the historic naval ships at Patriot’s Point, and the Old Exchange, where kids can visit a creepy real-life dungeon that once housed actual pirates!
Two hotels reflect in the water of Myrtle Beach, South Carolina during the daytime.
Myrtle Beach, South Carolina

Leg 6: Charleston to Jacksonville, Florida

279 miles, 4 hours
This next leg of the voyage will finally take you into the Sunshine State—and to the second Jacksonville on this New York to Key West road trip.

What to do

If you’re only going to visit the beaches in one city during this trip, Jacksonville Florida should be an easy contender. Jacksonville has some of the least crowded, most accessible, and well maintained beaches on the east coast.
You’ll also want to take the kids to see the Jacksonville Zoo and Gardens, the Hands On Children’s Museum, and the Museum of Science and History.
A bridge over water crosses in front of a view of Jacksonville's business buildings.
Jacksonville, Florida
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Leg 7: Jacksonville to Orlando

141 miles, 2.5 hours
Remember when we said earlier that New York City doesn’t need an introduction? Well, neither does the next stop on this trip: Orlando. Orlando is perhaps the best-known tourist destination in Florida and it’s likely the stop the kids are most excited about.

What to do

The greater Orlando area has 10 major, world-famous theme parks to visit. Disney World, Epcot Center, Universal Orlando, and LegoLand are just a few of these famed attractions. You’re also within driving range of Cape Canaveral, where NASA launches rockets.
Need to add even more gorgeous beaches to your itinerary? Daytona Beach, Edgewater, Cocoa Beach, and Palm Bay are all nearby.
Hotels face the water of Daytona Beach, Florida, at sunset.
Daytona Beach, Florida

Leg 8: Orlando to Miami

235 miles, 3.5 hours
If Orlando isn’t Florida’s most famous city, surely it must be Miami. The buzzing seaside metropolis has plenty to offer, from sun and sand to dining and nighttime entertainment.

What to do

Miami is probably best known for its legendary nightlife, but kids will love exploring Miami’s waterparks, the Everglades, Zoo Miami, and the Miami Seaquarium.
You don’t want to miss out on Cuban dining in Little Havana, either!
A pastel rainbow sunset sweeps over an aerial view of Miami's skyline.
Miami, Florida

Leg 9: Miami to Key West

161 miles, 3.5 hours
If you thought the Chesapeake Bay Bridge-Tunnel was cool, wait until you get a load of US-1’s famous bridge over the Atlantic Ocean. The final leg of your New York to Key West road trip will take you over this beautiful highway that runs through the Florida Keys.
You’ll have plenty of places to take pit stops too, namely in Key Largo, Plantation Key, Lower Matecumbe Key, and Marathon.

Welcome to the Conch Republic!

At long last, you’ve finally made it. Welcome to Key West, a tropical paradise that makes all the driving on this New York to Key West road trip worth every second.
While the other cities on this road trip are meant to be thrilling, Key West is all about resting and relaxing. The vibe on this tiny island is upbeat and fun, but also—what other word can you use here?—chill.
You have the freedom to take on Key West at whatever pace best suits your mood. And while that may be true anywhere, it’s never as true as it is here.

What to do

You shouldn’t visit Key West without getting at least one photo of yourself in front of the famous buoy at the southernmost point in the continental United States. You should also visit the Truman Little White House. If you’re feeling more adventurous, try some night kayaking or even charter a boat or a seaplane.
The food, the nightlife, and the fantastic beaches all make Key West the perfect town in which to end any road trip. And with a NYC to Key West road trip, you’re traveling from the busiest city in North America to one of the most relaxed places on Earth. Very few journeys can do the same!
A teal and pink sign in front of the water welcomes visitors to South Beach in Key West, Florida.
Key West, Florida

Roadside assistance you can rely on

This New York to Key West road trip will take you to some of America’s prettiest beaches and the hottest of hotspots. But it’s also going to put your car through its paces, so you’ll want to make sure you prep it for all the stress this trip will expose it to.
Roadside assistance from Jerry includes everything you need for peace of mind from just $6.99 for one car:
  • Vehicle towing up to 10 miles
  • Jump starts
  • Tire changes
  • Lockout services
  • Fuel delivery
  • Roadside reimbursement
  • And more!
It’s also a good opportunity to make sure you aren’t paying too much for car insurance. A licensed broker that offers end-to-end support, the free Jerry app gathers affordable quotes, helps you switch plans, and even cancels your old policy for you.
“I’ve been dealing with agencies and quote websites for the longest time and the Jerry app made it so much easier than it’s ever been. In a matter of MINUTES I was able to get multiple quotes, cancel my policy, start my new one, save $230 a month, AND it automatically does quotes for you every 5 months to make sure you’re paying the lowest possible price. You can do everything within the app there’s absolutely no runaround. And the best part is that I didn’t get 100 calls from random scammers. 10/10 highly recommended.” —Jerry user
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