Great Road Trip Stops from Florida to Washington, DC

By Bell & Alex: When we moved from Orlando to Washington DC we decided to turn the 850 mile drive into a week’s vacation. Rather than bang it out in a day or two, we took the scenic route that had us on the road exploring the east coast of the US. Most people recommended stopping in Savannah and Charleston along the way, and we did stop in these towns, but the east coast has so many other great places that are worth checking out. So here are some awesome road trip stops from Florida to Washington, DC.

Saint Augustine, Florida

We departed from Orlando and stopped for our final night in Florida in one of America’s oldest towns, Saint Augustine. The architecture of this town along the Atlantic Ocean is unlike anywhere else in Florida, with beautiful Spanish style buildings and cobbled streets. Take a stroll through the beautiful Flager College campus, then wander through the streets toward the old city gates and on to the Castillo de San Marcos, a historic fort facing the ocean. The fort was built between 1672 and 1695 and is the oldest fort in the US.

Saint Augustine is the oldest European settlement in the US. It was founded in 1565 by the Spanish and the architecture heavily reflects their influence. The town also is a melting pot of cultures, and when you have that, you can always find great places to eat! Check out the Travelling Foodie’s post on the culinary scene in St Augustine.

For those craving the architecture of Europe, but unable to make a trip, St Augustine is for you. Also, as you are in Florida, there’s several great beaches nearby. Saint Augustine beach is a wonderful spot to spend a few hours soaking up sunshine and hanging out with pelicans. The beach is just off Highway A1A, which is a beautiful route to take along the east coast of Florida.

Highway A1A – Florida

Getting off the major American highway system is always a good idea if you have the time. This way you really get to explore the US. We highly recommend taking highway A1A up the Flordia coast. It runs from Key West and ends on Amelia Island. You will drive through small coastal towns, with the opportunity to stop for coffee, lunch or snacks and support a multitude of small businesses. There are beautiful beaches and national parks that you will be able to stop at to stretch your legs. That’s so much better than the rest spots along the major highways! Also, fun fact about A1A, at Mayport you will have to drive up on the ferry to stay true to A1A and cross the Saint Johns River. Cars are $6 and be sure to check the schedule.

Saint Simons Island and Darien, Georgia

Both of these spots are great for a stop. Saint Simons Island has some amazing oak trees draped in the iconic Spanish moss of the south. On some of these beautiful old oak trees, spirit faces have been carved into the trunks. You can search these out using this map as they are spread all over the island. The beach and lighthouse on this island is also a beautiful spot to explore and before heading off the island stop in to grab a bite at Southern Soul BBQ.

We recommend stopping in Darien for lunch. We enjoyed our lunch at Skipper’s Fish Camp overlooking the Darien River. After lunch we strolled through this small town and before jumping back in the car grabbed cappuccinos from Zio Carlo Cafe.

Nineteen miles up highway 17 is America’s smallest church. We almost drove by and didn’t turn around, but Alex knows how much I love checking out the quirky roadside attractions such as this on road trips, so he swung the car around so we could pop in. This church was recently rebuilt due to fire, and it is indeed tiny, very cute and worth stopping for 10 minutes. Alex even gave it his signature thumbs up!

Tybee Island, Georgia

Tybee Island is just east of Savannah, and technically a little out of way on a drive from Florida to DC. But it’s worth going out of your way for, and in the off season, you will certainly find cheaper accommodation as Savannah is always a happening spot and hotels prices reflect the popularity of a southern gem.


This is also one of the last chances to really enjoy a beach unless you really plan to go out of your way for it. Follow highway 17, it is perfect for a morning run or swim, and most of the hotels are within walking distance. We also recommend a visit to the lighthouse and a meal at 80 East Gastropub.

But let’s be honest being so close to Savannah, you didn’t think we’d leave it off from this trip, did you?

Savannah, Georgia

Savannah is a charming southern town, with cobblestone streets and a relaxed vibe. Taking a stroll down by the Savannah River is a lovely way to spend a lazy afternoon. Or check out one, two or a bunch of the 22 beautiful public squares that can found in Savannah. The most famous is arguably Chippewa Square. This is where Forrest Gump sits on the bench waiting for bus number 9 for most of the movie. There is no bench in the spot, but you can sit in the square itself and enjoy a coffee from Gallery Espresso.

While on the topic of movies, we also made a stop at the Bonaventure cemetery, which dates back to 1846 and became famous after the premiere of Midnight in the Garden of Good and Evil. There are a number of historical and beautiful cemeteries around Savannah, but the old hanging moss and statues make this one particularly picturesque.

From Savannah we didn’t take highway 17, we decided to jump on highway 95 as it is a more direct route up to Washington DC, though we did get off and go out of the way for both Beaufort and historic Charleston.

Charleston, South Carolina

Charleston consistently ranks as one of the top destinations to visit in the United States. The first shots of the US Civil War were fired at Fort Sumter in 1861 so the town is packed with history and some of the best preserved antebellum architecture in the US. It’s also a fantastic foodie destination, with a New York style fine dining scene condensed in a small town.

Rainbow Row features the longest collection of Georgian row houses in the United States. There are thirteen colorful houses side by side near the waterfront beginning at the end of East Bay Street.

We stopped in Charleston on our road trip from Florida to DC but spent more time there during another visit. You can read more about Charleston in Alex’s article Charleston, South Carolina: A Top US Destination.

Where to Stay in Charleston, South Carolina

We stayed at the Charleston Marriot, which hosted a conference I attended. When the conference ended, we used Hilton Honors points from previous business travel to stay at the Hilton Garden Inn Charleston Waterfront. If the price is similar, the Charleston Marriot is a better choice. Both hotels are over a mile from the historic center, but both also offer shuttle services. The Marriot charges $6 per person per day to use the shuttle, and the service is solely tip based at the Hilton Garden Charleston Waterfront. Rooms at both hotels are comfortable and modern.

Charleston has several historic grand hotels. The French Quarter Inn has been ranked among the world’s best hotels by Travel + Leisure. So luxury travelers are well covered in this southern gem.

If you’re traveling to Charleston on a budget, you’re probably best off booking an Airbnb apartment or house. If you’ve never used the service, sign up here to receive $40 off your first stay over $75!

Beaufort, South Carolina

Beaufort recently was hit hard by hurricane Michael. Unfortunately, we didn’t have much time in Beaufort, but it is a nice town to stop on a road trip up the coast. It has a pretty coastline and a charming historic town. We’d planned to have a little more time there but arrived just as the sun was setting. We grabbed a bite at Duke’s BBQ of Beaufort, which is a great spot for some old school BBQ and friendly service.

South of the Border

As you approach the border of South Carolina and North Carolina on Interstate 95 you are going to see so a bunch of billboards telling you to stop at “South of the Border.” It definitely catches your eye and even Alex was excited to pull off the highway to check it out. But don’t get too excited, South of the Border has seen better days.

There used to be a Mexican themed amusement park there. It closed years ago but many of the rides still remain, collecting dust. While South of the Border falls way short of awesome, it’s a convenient stop to grab a coffee, maybe a bite to eat and to stretch your legs. You can even purchase some fireworks if you have something to celebrate. Don’t plan to spend too much time there.

Chapel Hill, North Carolina

Chapel Hill, North Carolina is home to the USA’s oldest public university, UNC-Chapel Hill. UNC Chapel Hill was founded in 1795 and particularly excels in medicine, law and basketball. The symbol of UNC-Chapel Hill, and its most famous landmark is the Old Well. The Old Well is a small neoclassical rotunda supported by doric columns. It was built in 1897 and was inspired by the Temple of Love, in the gardens of the Palace of Versailles, just outside Paris.

The Carolina Basketball Museum is a memorable stop for sports fans, featuring memorabilia from one of the countries most successful basketball programs. All five Tar Heel national championship trophies and rings are on display. Don’t wear your Duke gear there – though you probably wouldn’t anyway.

During our visit we stayed at the Carolina Inn, right across the street from the UNC campus, which is owned by UNC-Chapel Hill. The hotel was established in 1924 because back then there wasn’t comfortable accommodation to house visiting professors and returning alumni. In hallways and even in our room there were pictures of notable alumni and informative history associated with the school’s programs. There is no better place to stay in Chapel Hill for convenience, comfort and history.

Carolina Inn, UNC- Chapel Hill

For more on what to do in Chapel Hill, read our article UNC-Chapel Hill: Best Things to Do.

Blue Ridge Parkway: North Carolina & Virginia

The Blue Ridge Parkway spans 469 miles from the North Carolina border with Tennessee northeast through Virginia in the Blue Ridge Mountain section of the Appalachian Mountains. The stretch of the highway we drove in the summer of 2015 was from Asheville, North Carolina to Tennessee, before continuing on through the Smoky Mountains to Gatlinburg and Pigeon Forge, Tennessee (a total spectacle of attractions that includes amusement parks like Dollywood). Read more about the drive in our article Blue Ridge Parkway: What to Expect.

Annapolis, Maryland

Annapolis is a 45-minute drive east of Washington, DC. While it’s not quite on the way from Florida to DC, the capital of Maryland is well worth visiting. We frequently take day trips to Annapolis from Washington and have taken our parents there during their respective visits from Australia and Florida.

Annapolis has a lovely historic center with a lot of good restaurants, cafes and ice cream shops. A visit to the US Naval Academy is a major highlight, where you can walk around the grounds of a picturesque campus on the water. After taking in the beautiful campus you can stroll around the Maryland State House, the oldest state capital building in the US, which has been continuously in use since 1772.

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