• Janessa

East Coast Family Road Trip: Florida to Maine

Updated: Jun 28, 2019

10 Great Stops Along I-95

So, you'd like to take your family road trippin' along the East Coast but you're unsure where to go. Luckily, that's where I come in. The East Coast of the United States is known for its port cities on the water, many of which were founding American cities. Most of these major cities are located right off of Interstate 95. When planning a road trip, time is obviously a factor and a lot of people don't have the luxury of time to get off the main path. Here's a a list of ten great stops you can make right along highway I-95. Stop for lunch and play or stay for a few days. Make the road trip your own by choosing the best destinations for your family.

*Please note, this article contains affiliate links. If you click through and make a purchase, I receive commission at no additional cost to you. The revenue I make helps keep this website active and free content flowing! Know that I only recommend brands that I love and believe in.

Thanks for your support in this way!

1. St. Augustine, FL

The Fountain of Youth in St. Augustine FL, located on the famous Magnolia Avenue

St. Augustine is the nation's oldest settlement and one of my all-time favs! Here, you and your family will have a plethora of things to do in this historic town. Take a guided tour, ride the trolley, walk down the famous St. George Street, and eat eat eat! Since you'll have your vehicle, drive down one of the most photographed streets: Magnolia Avenue. The towering moss oaks will take your breath away. If you're like me, you'll park and get your family out for an awesome keepsake photograph. And, The Fountain of Youth is located on Magnolia Avenue so go ahead and plan a visit and meet the peacocks who reside there. Don't forget a beach day and all your sunscreen! For more about what to do with kids in St. Augustine, check out this blog post.

2. Jacksonville, FL

my son riding the animal themed carousel at the Jacksonville Zoo and Gardens, there is also a playground, petting zoo, 3-D theater and splash park for the kids!

My hometown. Jacksonville is a city on the rise with hip urban projects propelling it into the modern day. It's a nice stop if you need a cheap hotel and you started your road trip father down I-95, say in West Palm Beach or Miami. The St. John's Town Center, the biggest shopping mecca in the Southeast, would be your best bet if your family is just stopping for rest and fuel. It has every restaurant and store and accompanying hotel chain imaginable.

But, if your family is looking to take advantage of the Jacksonville sights, I would recommend a family day excursion at the Jacksonville Zoo & Gardens. We are annual members and we think it's the best place to take your kiddos (totally NOT biased!)Your family can also take advantage of the Florida sun with a family beach day at Amelia Island or try a hip excursion to one of the many family-friendly breweries in town such as Engine 15 Brewing. They have a pirate ship playground for your littles. You're Welcome! ( in my Maui voice)

3. Savannah, GA

Forsyth Park in Savannah, GA, a perfect family stop for your east coast road trip

I would buy a house in Savannah Georgia! That's how much I love this city. Although there is lots to do, you don't have to do much to enjoy this gorgeous Southern destination. It is so lush and beautiful. There are parks on parks on parks, twenty-two historic squares ready for your enjoyment to be exact. Save money and take a self-guided walking tour with your family. Make sure it begins or ends at Forsyth Park, which is the perfect place for a family picnic. Stroll through town, take in the historic architecture and grab lunch at City Market, near Broughton Street or on the Riverfront.

4. Richmond, VA

view of Richmond Virginia, an east coast road trip stop along I-95

If you just can't make it all the way to D.C. or you need a cheaper alternative for lodging, stop in Richmond, VA along I-95. Richmond was a major player in the Civil War and there's lots of American history to take in there. Richmond also has a super trendy population (you know, lots of hipsters) They've got a nice foodie scene and you and your family can stop for breakfast, lunch, or dinner and check out the hipster vibe in the Carytown, the Fan, and the Church Hill neighborhoods. When I hear hipster neighborhood, I always have to stop for a latte at a local coffee shop. In Richmond, there are lots of museums to see but The Virginia Museum of Fine Arts is completely FREE (except for temporary exhibitions) It's where we stopped and spent a few hours walking with my son in the stroller before getting back on the road.

5. Washington, DC

The Lincoln Memorial located on National Mall is a popular tourist destination and east coast road trip stop

Oh, the nation's capitol. We've taken so many east coast road trips and this has always been our most trusted stop. Why? Well, logistically it's about the half-way point along I-95 between Florida and Maine. Truthfully though, we love this place! It's easy to find on-street parking, almost everything is free and it's a great walking destination to tire out little people! Some of our favorite popular museums and monuments to enjoy with kids are The National Air and Space Museum, The National Museum of Natural History, the Lincoln Memorial, and the Washington Monument. We've been to these again and again and they never get old. But, get your family to the National Mall and choose one of the dozens of FREE options that match your family's interest. Remember, you can always go back so just decide what you'll see THIS time (it's tempting but don't overbook your family!) For a nice family walk, my favorite starts at the Lincoln Memorial, snakes around the Tidal Basin and ends at the Jefferson Memorial.

6. New York City

you can rent bikes and bike around Central Park in NYC with your family

If you're on an east coast road trip and you don't stop in New York City, have you even lived...I kid! But, New York City is a spectacular destination unlike anywhere else. I think it would be hard for any other east coast travel destination to match this city's energy (or expense!) We've stayed overnight and also just stopped for a lunch in Central Park. There is just so much to do but I think everyone should walk over the Brooklyn Bridge and take in the sunset over the NYC skyline from DUMBO Brooklyn. Afterwards, grab a taxi and head back over the bridge to see the shimmering city lights. Trust me, you won't regret it. If you have your kids, a family visit to Central Park is obligatory fun. Go to the Central Park Zoo, have a picnic, paddleboat on the lake, walk over the famous bridges, play chase, dream, have fun. If you're brave (and crazy) like us rent bikes and ride miles around Central Park. They have baby carriers and helmets!

7. Boston, MA

The Boston Public Garden on a beautiful summer day, a great tourist destination with your family

We lived outside of Boston for a few years and I love this city! It's a smaller city and oh so walkable, you can see almost everything on foot with your family. Leisurely walk along the Charles River or walk yourselves along the historic Freedom Trail. End your walks at the gorgeous Boston Public Garden. Feed the ducks, listen to a street musician, and ride on the famous Swan Boats! The ride is so cheap, under $5/per person! You and your family can also take guided tours of the city by tour guides in historic garb.

If you'd rather spend the day inside, museum hop around Boston with the kids. I'd suggest the New England Aquarium, the Museum of Fine Arts Boston and the Museum of Science. If you need more reasons why Boston, MA is great with kids, read my blog post here.

8. Portsmouth, NH

This New England town is like a mini Boston, with free parking and no crowds. It's super adorable. Grab coffee and an outdoor seat and people watch at Market Square, the center of town. Then stroll through the paved streets and little alleyways. Get wonderfully lost. Snap some photographs and buy little trinkets and gifts at the local shops. Let the kiddos run off some steam at Prescott Park on the riverfront. There are gorgeous manicured gardens and music festivals throughout the summer season. Grab lunch or dinner on your way up to Maine, some of our favorites are Portsmouth Brewery, Lexie's Joint, Thirsty Moose Tap House, The Kitchen, and Popovers on the Square.

9. Ogunquit, ME

a view of Perkins Cove in Ogunquit Maine, a perfect east coast road trip stop

If you want to experience quintessential coastal Maine, then you have to make a road trip stop in Ogunquit, Maine. It has sailboats, rocky cliffs, stately homes, oceanfront dining, and charming shopping centers. A family walk along the mile long Marginal Way is a must do! It's partly paved and partly dirt path but easy to maneuver with a stroller. The picturesque views are not to be missed!

Eat lunch in Perkins Cove, a pedestrian friendly spot with waterfront dining, tourist shops, and ice cream parlors. Our favorite restaurant was Barnacle Billy's a family-friendly seafood place with patio dining. There is also Ogunquit Beach, another outdoor option for you and your family.

10. Portland, ME

Portland Maine is a hip city with parks, art, eats and a working fishing wharf. It's a great east coast road trip travel destination

You've traveled all the way from Florida and you've made it to Portland, Maine. Something important to note when planning your trip, Portland is very far north and doesn't warm up until about June. It is a super hip and up-and-coming city often referred to as the "other" Portland. Downtown there's a healthy mix of big-chain retailers and local shops. One of my favorite local eateries is The Holy Donut on Exchange Street. They're donuts made from mashed potatoes and so freakin' delicious. Use the donuts as incentive for your kids' good behavior, I won't judge!

Portland is located in Maine and Maine is known for its local seafood! As such, there's a working wharf downtown with fishing boats galore. There's also many restaurants along the wharf, Flatbread Company is our all-time favorite! And, of course, you must visit at least one lighthouse while in Maine. The world famous Portland Head Light is located on the coast right outside of Portland Maine.


Have any questions about this route? Comment below and I'll get back to you...

Want more road trip itineraries? Subscribe to get my monthly newsletter with new travel guides, road trip itineraries, and journal entries from the road.

Many Blessings and Happy Travels,


We're the Martin family and we're in love with family road trips and family travel! We're currently renovating a 1974 Airstream Sovereign so we can continue our family road trippin' adventures across North America! We're hoping to inspire others to pack up and head out on the road! 


Hey There!

Thanks for submitting!

Want to get the latest updates on #NellietheAirstream renovations? Follow her progress from start to finish? See where we choose to travel and why?


Tip Jar

Enjoying the Airstream renovation and travel tips? Want  to buy us a cup of coffee, a tank of gas, or supplies for the renovation...three of our favorite things! We'd be deeply grateful for your support.