The family road trip is the classic Americana travel experience. We’ve all imagined one with our family and then we drive 5 miles to Target with fighting kids and the dream is dead.

Don’t give up yet! A family road trip can be done and should be done, albeit with careful planning. Lucky for you, we’ve already planned this adventure and have most of the leg work done for you!

Enter The East Coast Family Road Trip

While this itinerary is focused from Southern Florida to New York, many of the ideas can be translated to anywhere. We found limiting drive days/hours is key along with shaping our in-destination days with organized must-do/must-see items, mapped out playgrounds in between, locating children’s museums and planning ahead for dining.

The Plan:

  • 16 days
  • Florida to New York and back
  • 4 people (ages 7 – 40 something)
  • 8 destinations
  • Keep drive days between 6-8 hours
  • Lots of credit card travel points for hotels

The Plan in Action:

Day 1-2: Drive from Southern Florida to Charleston, South Carolina area (7 hour drive). Arrive at our Downtown Charleston Hotel and set kids loose in the pool with Dad while I unpack and set up for the rest of the day. Walk to the waterfront, Pineapple fountain, let the kids run around, climb and play in the park, pick up an ice cream and make it just in time for a historic walking tour.

Travel with kids
Historic cobblestone streets of Charleston

After the tour, it’s back to the hotel for downtime before dinner. Next, head to The Workshop, a trendy family-friendly space featuring pop-up fresh and local chefs. They also offer a sprawling lawn for kids to play and run, outdoor music, an outdoor craft cocktail and beer bar, and hand spun cotton candy!

In the morning we strolled King Street, visited the Marion Square Market for breakfast and live music and then headed to the Children’s Museum of the Low Country for free play time. Next up is Folley Beach, a southern surf town outside of Charleston. Spend the day exploring the area and enjoying the warm waters. Do a quick wet clothes-swap and it’s on to Bowens Island. Hidden down a dirt road, Bowens Island is famous for its locally harvested oysters, fried shrimp, Frogmore stew, cold beer, and its undisturbed view of the river and marshes. The views are spectacular and worth the wait.

Bowens Island deck

Day 3-4: South Carolina to Maryland (8-9 hour drive). This is the long-haul car day I fretted over for obvious reasons. Nevertheless, we made it. Our route took us along part of Virginia’s coast and across the Chesapeake Bay Tunnel. This was super-scenic and helped the kids stay entertained. Once in Maryland, crabs were had all around including at a favorite local spot Crabs to Go (you read that correctly).

Maryland crabs

Now that you are in Maryland I can not recommend enough exploring one of the many scenic byways to customize your experience. From the inspiring history of Harriet Tubman’s life and journey to the serene and authentic Chesapeake Bay area, there is so much to do in Maryland. Each of the byways has mapped it out for you!

Also consider Ocean City, Maryland for a late day boardwalk stroll, ice cream and the ocean front amusement park. The beach is jumping in Ocean City and would be well worth spending the day or longer.

Family Road Trip
Clearly they had fun

Day 4-7: Maryland to Lewes, Delaware (1 hour drive). Lewes is a quiet town located where Delaware Bay meets the Atlantic and Cape Henlopen. Lewes offers an quintessential Main Street, great dining options and one of the best 4th of July experiences you’ll ever, ever encounter.

Lewes, DE

While in Lewes we had a beach day at Cape Henlopen, rented bikes and rode along the various connector trails, visited the Lavender Farm, played for hours at the canal front park, took in outdoor music and of course experienced 4th of July in all its glory. On top of parades and fireworks, Lewes shuts down Main Street starting at 8am for hours of family games like the egg toss, potato sack races, three legged race and pie eating. Best day ever!

4th of July, Lewes

Day 7-9: Delaware to NYC (3-4 hour drive). We drove straight to the city but you can take the Cape May/Lewes Ferry to Cape May and add a day on there. It’s a great experience.

We visit NYC a lot and this time decided to stay in Chelsea’s Meatpacking District. We knew it would be a great jump off spot for walking about and taking in the city. Chelsea Market is the place for all things NY and unique, including feeding the littles. We each fueled up on what we fancied and headed upstairs to The High Line. Walking from 14th-30th was a breeze and led us straight to Hudson Yards. The kids loved The Vessel and we love NYC in the summer (really any time of year). There are quite a few cool things to do for the whole family while at Hudson Yards.

Travel with kids
Hudson Yards

The rest of the trip was filled with walking from one point of interest to another. The best part of the city is walking it and feeling it. We mapped out public playgrounds along the route to keep the kids entertained and motivated. There are quite a few good ones around Chelsea, the Pier and along the walk Downtown, including Washington Square Park. Use your maps and pinpoint the playgrounds that pop up. You can route yourself around them seamlessly.

Nothing like a NYC park

If you’re looking to stray from traditional tourist spots like Times Square or Lady Liberty and find yourself mid to uptown, there are plenty of local/tourist mix places just for you! Manhattan is for Art and Culture – you would be remiss if you didn’t visit at least one of the many museums. Here’s a comprehensive link to Manhattan’s Museum Mile. Our children love the Museum of Natural History, MOMA, and our favorite for kids, the Children’s Museum of Manhattan. For brunch, Sarabeth’s is in the same neighborhood at the Children’s Museum and walkable. After brunch, you’ll want to make your way to Central Park’s Heckscher Playground for excellent free play. In the park you’ll also find the Central Park Zoo too! Remind them of Alex the Lion from Madagascar and everyone will be thrilled. The Museum Mile also borders the park. Across the street from the base of the park you’ll find FAO Schwartz and the must-do Fifth Ave walk straight to Rockefeller Center.

Check out our full 3 days in NYC with kids itinerary!

Day 9-11: NYC to Washington DC (5 hour drive). There is A LOT to do in Washington DC for families. The key for us was making it manageable. My husband wanted to visit every landmark but that wasn’t going to happen. Their legs can’t do it and with children gravity must have an affect on them- too much walking seems to keep them low to the ground, slow paced and typically they will lay down anywhere…

We chose to stay in Georgetown for the ease of accessibility, family feel and great dining. The Metrorail and electric scooters are an excellent way to take on the city and keep the kids engaged. We chose to keep close to The National Mall and pop in and out of the 15 free museums. We did Natural History, Air and Space, Botanical and American History – spending about 1 hour in each.

Family Road Trip Washington DC
Museum amazement

Many of the monuments and memorials you’ll want to see are located by the mall including: Martin Luther King, Jr., National World War II Memorial, Washington Monument and the Lincoln Memorial. Another great option is a night carriage ride or pedicab around DC. Everything is amazing at night and walking is eliminated!

Family Road Trip Washington DC
Picnic lunch on the lawn

For dining we stayed close to the Fairmont, Georgetown. Popping in and out of local favorites along M street. We like Kafe Leopold, Filomena and Farmers Fishers Bakers located on the bustling waterfront, an awesome place to visit with kids.

Day 12-14: Washington DC to Savannah, Georgia area (7 hour drive). Savannah is one of my favorite US destinations and I was thrilled to experience it with my family. Our first stop was to eat because Savannah has one of the best culinary scenes. You will eat a lot in Savannah. We went to Traylor Park and devoured the waffle fries and chicken and waffles.

We stayed at the Perry Lane, a relatively new hotel that boasted all the amenities you need, including a treasure box for the kids they dove into each time we entered. They also brought the children milk and cookies every afternoon. Everyone enjoyed the rooftop pool in between exploring.

Perry Lane roof top

I recommend the Trolley Tour Pass which will get you from each point of interest smoothly and complaint free. You can hop on and off as you please and your drivers will entertain/narrate along the way. In the middle you can meander the 22 squares unique to Savannah and pristine Forsyth Park. Aside from the familiar fountain in the center of Forsyth Park, it also boasts a rocking playground our kids enjoyed for over an hour.

Forsyth Park, Savannah

Book a ghost tour offered by Blue Orb for some fun in the evening and by day try a walking tour for quirky history and city familiarization. Hit the waterfront for cobblestone streets and the kids will admire the massive barges and ships that pass through.

Do not leave Savannah without shopping around the SCAD area and Broughton Street, and enjoying an ice cream (sundae) from 100+ year old Leopold’s and brunch at Soho South.

Day 15: Tybee Island, Savannah’s Beach Town neighbor. While you’re in Savannah do not skip visiting Tybee Island. We were so glad to spend time on the island, walk the beautiful beaches and have this be our last stop on our crazy adventure. Tybee is one of Georgia’s barrier islands offering ultra wide beaches, warm waters and extremely gentle waves. Photos do not due the beach justice, although, they made our holiday card!

Tybee Island

Day 16: Savannah to Home

We hope this itinerary makes planning a family road trip more attainable for you. The time we spent together was irreplaceable and the children constantly talk about this trip above others. In retrospect, it was a manageable way for the kids to really experience travel in the US. We’re already booked for our next one this summer!

Stayed tuned for our Car Ride Essentials post to learn how we got through the long drive days…