The best stops on a road trip from DC to Florida

When I was a child, my family drove to Miami from Washington, D.C. every summer. We’d always divide the 15-hour drive into two days with Florida alone taking up most of the second day.

As fate would have it, I married a Cuban-American from Florida. This means that we go to Miami at least twice a year and still vacation with my family on Miami Beach every August. Usually we fly but this summer, we opted to take a road trip from DC to Florida and explore the South East a bit.

Our journey took us to St. Simons Island, Georgia, Miami, Florida, Key Largo and Key West in the Florida Keys. It was a long trip but we survived and had fun exploring this beautiful coast together.

Guest post and photos by Guiomar Barbi Ochoa. Disclosure: This post may contain affiliate links, please see my disclosure policy for more details.

Driving to Florida from DC

Road trip from DC to Florida
Road trip: Washington DC – Florida Keys

If you have longer then I’d highly recommend adding some more stops to your road trip itinerary. This slice of the country is home to significant historical sites and some beautiful landscapes. Other places to add to your itinerary include:

Richmond, Virginia. This is one of the best stops along the I-95. The Virginia State Capitol Building was designed by Thomas Jefferson and features the oldest Greek columns in the United States. Also in Virginia is Williamsburg, the best preserved colonial town in the country.

Beaufort is another destination worth spending some time in. Located on Port Royal Island, one of South Carolina’s Coastal Sea Islands, it’s a charming place to while away the days and the sunsets are sublime.

The Outer Banks, in North Carolina, are another great place to stop on this Washington to Florida drive. Expect nothing more than beautiful, unspoiled beaches, charming villages and plenty of outdoor activities.

For hiking opportunities you have the Blue Ridge Parkway that spans 469 miles from Virginia to Cherokee in North Carolina. Taking some time out somewhere like Pigeon Forge in the Smoky Mountains (part of the Blue Ridge Mountains) will be a small detour but well worth it.

Unfortunately, time didn’t allow us to add these stops to our DC to Florida drive, hopefully next time!

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Day 1: Washington DC – St Simons Island, GA

Road trip from DC to Florida
‘South of the border’

The drive from Washington DC to St Simons Island in Georgia is a long one, some 656 miles. It takes about 10 hours to drive – which is why I recommend breaking up the trip if you can. Given that we couldn’t explore the east coast, we choose two good pit stops instead.

The first place we stopped was South of the Border, the quirky, Mexican-themed divide between North and South Carolina. The large billboards placed along the border on Interstate 95 may have seen better days but it’s still a good photo op and the kids enjoyed it.

The second place we stopped was Florence in South Carolina. This is a really lovely city and well worth an overnight stay if you have time. There’s a lively arts and culture scene, some wonderful food options and charming Southern hospitality.

The thing my kids loved the most about Florence, however, was Bruster’s Real Ice Cream. You can order from an old fashioned window or even drive thru.

Road trip from DC to Florida
St. Simons Island Morningstar Marina

Overnight: St. Simons Island, Georgia

Our first overnight stop was St. Simons Island, GA. The largest of Georgia’s illustrious Golden Isles, St. Simons is a picturesque seaside resort with family friendly beaches, tons of outdoor activities, fun shops and tasty restaurants.

Because I’m a stickler for learning about the history of places we visit, I made sure our family went on a Lighthouse Trolley tour. The tour was scheduled to last 90 minutes but actually ran over two hours! The kids took a little nap but my husband and I had a great time and feel like we definitely got a great history lesson about the island.

Road trip from DC to Florida
The King and Prince Beach & Golf Resort

Where to stay in St Simons Island

One of the things we loved most about St. Simons Island, GA. was the King and Prince Resort. Our room had a view of the beautiful beaches. We went for a long walk during low tide while the kids splashed each other and took dips when they got hot. It was the perfect way to get rid of energy from being cooped up in the car.

Day 2: St Simons Island – Miami

Road trip from DC to Florida
Palm trees on a beach In Miami, Florida

From St Simons we continued our drive to Florida from DC along the I-95. This drive is about 430 miles and takes around 7 hours. There are lots of places you can stop in Florida along the way; this is a long state to drive from North to South so it’s definitely worth breaking up the journey.

We chose to stop at the Florida Welcome Centre on the I-95 and picked up some freshly squeezed orange juice. If you drive about an hour further south you’ll hit St Augustine, which is a wonderful stop for a day trip or longer. Pretty St Augustine is the oldest city in the US, home to Spanish colonial architecture and some excellent beaches.

Our second pit stop was in La Carreta in Miami to eat good, reasonable and authentic Cuban food.

Overnight: Miami

The drive from St. Simons to Miami was a good nine hours. It’s a long haul but mentally knowing we were beach bound helped get us through it! In Miami, we split our time between Miami Beach and the city itself.

Miami with kids is a lot of fun and you can spend days – or even weeks – enjoying everything on offer. From Cuban croquetas to Colombian carimañolas, there are vast food options to satisfy even the pickiest of palettes. There are many family-friendly beaches too.

Road trip from DC to Florida
The Acqualina Resort & Spa, Miami

Where to stay in Miami with kids

The Acqualina Resort & Spa is a super kid-friendly, luxury seaside sanctuary located in Sunny Isles Beach between Miami and Ft. Lauderdale. Our room was on the twenty third floor so we had a breathtaking view of the Atlantic Ocean.

Kids aged five to twelve can try the hotel’s Aquamarine Day Camp that teaches children about the sea through educational activities. I walked into Acqualina and was afraid it might be too stuffy for our little ones but nothing could be further from the truth. From the foosball table by the pools to the gelato bar near the lobby, this resort is a must for any family visiting Miami Beach.

Day 3: Miami – Key Largo 

Road trip from DC to Florida
Key Largo

Leaving Miami we got on the Highway 1 to drive to the Florida Keys. U.S. 1 is a one lane road so you have no choice but to sit back and enjoy the beautiful views that lie ahead.

Our first stop was Key Largo, about 60 miles south of Miami proper. We opted to spend the night here so we could enjoy the John Pennekamp Coral Reef State Park. This is the first undersea park in North America and is made up of approximately 70 nautical square miles. The coral reefs are spectacular and you can enjoy them either via a glass-bottom boat tour or by getting in the water and scuba diving or snorkelling.

Overnight Key Largo

In Key Largo, we stayed at the Ocean Pointe Suites. We had a kitchenette, pool and even a little private beach which is not always a given in the Keys.

Day 4: Key Largo – Key West 

Road trip from DC to Florida
Beautiful Key West in Florida

It takes just two hours to drive from Key Largo to Key West along U.S. 1. Key West is Florida’s southernmost point and lies just 90 miles north of Cuba.

Key West is a fun, quirky place with lots of Spanish and Caribbean influence. Don’t be surprised to see roosters walking on the streets! Tin-roofed conch houses were once home to Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost and Jimmy Buffett.

In downtown Key West, the Mel Fisher Maritime Museum is well worth a visit. Containing an extensive collection of artefacts from ancient shipwrecks, this is a must see for any family with tiny pirates.

The Ernest Hemingway House and Museum was the famous author’s home, in Key West, from 1931 to 1939. A U.S. National historic landmark, the house is still populated by six- and seven-toed cats that are descendants of Hemingway’s cats.

This post details lots of fun things to do in Key West with kids.

Road trip from DC to Florida
Colourful houses in Key West

Where to stay in Key West, Florida Keys

We opted for the new Hilton Garden Inn. This property is right at the entrance of the island. It’s not right smack in the middle of everything but that might be a better option for families that don’t want to deal with the noise or business of Key West at nighttime. They do have a shuttle that takes you to historic Key West.

3 thoughts on “The best stops on a road trip from DC to Florida”

  1. Congratulations for your Road Trips with Kids but Washington DC to the Florida Keys is too long way. I’m totally shocked to Washington DC to the Florida Keys Road Trips. How would you guys spend all 4days on road trips. Didn’t you get bored on this trip ?

  2. La Carreta, heck yes! Great choice. I like to drive between South Florida and DC every other year or so but I rarely touch I-95. I love to find cool smaller roads. Then again, I am not on a schedule and do not have the kids with me. Nice information!

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