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

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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.
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Key trip details

New York City to Key West map.
New York City to Key West
Distance: 1,561 miles
Driving time: 29 hours
Suggested length of trip: 4 to 7 days

Itinerary

  • New York City, NY
  • Atlantic City, NJ
  • Ocean City, MD
  • Virginia Beach, VA
  • Jacksonville, NC
  • Charleston, SC
  • Jacksonville, FL
  • Miami, FL
  • Key West, FL

Leg 1: NYC to Atlantic City, New Jersey

127 miles, 2 hours 11 minutes
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!
Take Garden State Pkwy to start your trip.

What to do in Atlantic City

Two women ride down an Atlantic City pier in a rickshaw.
Playground Pier, New Jersey
  • Steel Pier: Steel Pier is loaded with fun games, and it's a short distance from the next stop.
  • Ripley’s Believe It or Not: You’ve probably seen the jaw-dropping contents of the books, so why not see Ripley’s oddities in person?
  • Playground Pier: The Playground Pier (formerly known as Ocean One) is a shopping mall built over the ocean, with restaurants featuring beautiful views of the Atlantic.

Leg 2: Atlantic City to Ocean City, Maryland

100 miles, 3 hours 39 minutes
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 in Ocean City

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

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!
Take US-13 S to Virginia Beach.

What to do in Virginia Beach

Virginia Beach Statue of Neptune at sunset on the pier.
Statue of Neptune
Virginia Beach, Virginia is another exciting vacation hotspot, with a beautiful beach and loads of fun places to explore.
  • Virginia Military Aviation Museum: See one of the world’s largest collections of flying-condition warbirds at Virginia’s Military Aviation Museum,
  • Cape Henry Lighthouse: Cape Henry marks the southern entrance to the Chesapeake Bay. See the Cape Henry Lighthouse here for ocean views.
  • Statue of Neptune: This stunning statue by Paul DiPasquale is a must-see at Virginia Beach Boardwalk at 31st street.
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Leg 4: Virginia Beach to Jacksonville, North Carolina

207 miles, 3 hours 41 minutes
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 US-17 S for the best views —the "Great Dismal Swamp" is actually quite pretty to look at).

What to do in Jacksonville, NC

New River, Jacksonville
New River, Jacksonville
  • Pine Knoll Shores Aquarium: Jacksonville is a great city to visit and break up the otherwise long drive to Charleston. There’s lots to do here, including the Pine Knoll Shores Aquarium.
  • Jungle Rapids Family Fun Park: Need some excitement after looking at the road for hours? Hit Jungle Rapids Family Fun Park.
  • White Lake Water Park: If you happen to have packed your swimsuit, hit White Lake Water Park for some more thrills.

Where to stay in Jacksonville, NC

  • Home2 Suites: If you’re looking to wind down before driving more, stay at the Home2 Suites by Hilton. It features modern rooms, free breakfast, and a pool if you’ve still got your swimsuit. Cost per night: from $122

Leg 5: Jacksonville, NC to Charleston, South Carolina

229 miles, 4 hours 32 minutes
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.
US-17 S is your best bet for this route.

What to do in Charleston

Fort Sumter on a sunny day.
Fort Sumter
  • Fort Sumter: While in Charleston, take in some history with a boat ride visit to Fort Sumter.
  • Patriot’s Point: Prepare to be wowed by the historic naval ships at Patriot’s Point. You can step into the ship to view the museum — quite a location!
  • The Old Exchange: Stop by Old Exchange, where kids can visit a creepy real-life dungeon that once housed actual pirates!

Leg 6: Charleston to Jacksonville, Florida

239 miles, 3 hours 53 minutes
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.
Follow US-17 S and then I-95 S to get to Jacksonville.

What to do in Jacksonville, FL

Flamingos at Jacksonville Zoo.
Flamingos at Jacksonville Zoo

Where to stay in Jacksonville, FL

  • Margaritaville Hotel: Get that unmistakable resort feel at this spot right by the beach. You are in Florida after all, right? Cost per night: from $159
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Leg 7: Jacksonville, FL to Orlando

141 miles, 2 hours 10 minutes
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.
To get to Orlando, take I-95 S then I-4 W.

What to do in Orlando

Rocket engine at Cape Canaveral.
Cape Canaveral
  • Hit the theme parks: 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.
  • Cape Canaveral: You’re also within driving range of Cape Canaveral, where NASA launches rockets. Don’t miss this Kennedy Space Center attraction.
  • See Orlando’s famed beaches: Need to add even more gorgeous beaches to your itinerary? Daytona Beach, Cocoa Beach, and Palm Bay are all nearby.

Leg 8: Orlando to Miami

235 miles, 3 hours 36 minutes
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.
Hop onto Florida’s Turnpike to get to Miami.

What to do in Miami

A sign warning of alligators at Everglades National Park.
Everglades National Park
  • Experience Miami nightlife: Miami is probably best known for its legendary nightlife, which you’ll be sure to want to experience. Even if you don’t hit the clubs, make sure to walk around to get a sense of the atmosphere.
  • Everglades National Park: Get your nature fill at the Everglades National Park. Be careful, though—those alligators are real!
  • Miami Seaquarium: Prefer to view animals at a distance? See some aquatic species here.
  • Little Havana: Want to feel like you’ve been transported outside of Florida? This is the spot to do so. You don’t want to miss out on Cuban dining in Little Havana, either!

Leg 9: Miami to Key West

166 miles, 3 hours 30 minutes
If you thought the Chesapeake Bay Bridge Tunnel was cool, wait until you get a load of US-1 S and its 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.

What to do in Key West

Buoy marking the Southernmost point of the U.S.
Southernmost point of the U.S.
  • Southernmost point of the U.S.: 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.
  • Truman Little White House: You should also visit the Truman Little White House, Florida’s only presidential museum.
  • Night Kayaking: If you’re feeling more adventurous, try some night kayaking! This will become a highlight of your trip without a doubt.

Where to stay in Key West

The Gates Hotel: Reward yourself for arriving at Key West with a restful night at this posh hotel. It has a rum bar, cigar lounge, and Caribbean food truck to make you really take in the atmosphere. Cost per night: from $159

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
  • Jumpstarts
  • 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.
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