Florida to Washington, DC: Great Road Trip Stops

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 drove the scenic route to enjoy the countryside. Savannah and Charleston are typically considered musts, and we stopped in both towns for another visit. But the east coast is packed with wonderful historic destinations and seaside vacation spots. Here are some great road trip stops from Florida to Washington, DC!

If you are short on time, focus on the best stops along I-95. But if you have more time, consider venturing off the interstate. This article covers both options! Some spots discussed here, like South of the Border, are mentioned solely because they are right along I-95. Other destinations, like Williamsburg, Virginia, are well worth going a little off course to experience the best preserved colonial destination in the United States.


St. Augustine, Florida

We departed from Orlando and stopped for our final night in Florida in St. Augustine, the oldest European settlement in the United States. Beautiful Spanish style buildings and cobbled streets take visitors back centuries. Stroll through the beautiful Flagler College campus, then wander through the streets toward the old city gates and on to the Castillo de San Marcos, a historic fort with sweeping views of the Atlantic Ocean. It is the oldest fort in the US, built between 1672 and 1695.

St. Augustine was founded in 1565 by the Spanish. Its architecture heavily reflects that influence. The town is also a melting pot of cultures, as many Greek immigrants settled there in the 1800’s after fleeing the New Smyrna colony. A storied history and fusion of cultures equates to a tasty dining scene in the town. Enjoy a charming restaurant in the historic district like The Floridian, packed with internationally influenced southern dishes like shrimp banh mi po boys.

a fountain and palm trees at Flagler College in Saint Augustine, Florida
Flagler College in Saint Augustine, Florida.

For those craving the architecture of Europe, but unable to make a trip, St Augustine is for you. St. Augustine Beach and nearby Crescent Beach are wonderful spots to relax and play, soaking up sunshine and hanging out with pelicans. The beach is just off Highway A1A, a beautiful route to drive along the east coast of Florida. Break up the monotony and hassle of I-95 and take A1A if you have time. You can also explore Anastasia State Park, a protected wildlife sanctuary.

pelicans flying near the pier and beach in Florida
Pelicans fly near the pier on the Atlantic Coast of Florida.

St. Augustine has charming bed and breakfasts great for couples getaways. Carriage Way Inn Bed & Breakfast is a great choice for a couples stay. The adults-only, Victorian-style b&b serves a hot chef’s choice breakfast each morning and offers coffee, tea, and wine throughout the day.Guests can enjoy views of historic Saint Augustine from the verandas, and grab fresh-baked sweets from the lobby each afternoon. Their concierge can assist guests with information about local dining and attractions.

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! 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.

St. Johns River Ferry

4675 Ocean Street
Atlantic Beach, FL 32233


Monday –  Thursday 6:00 am – 7:00pm. Ferries depart every half hour, with the final departure at 7:00 pm.

Friday: 6:00 am – 8:30 pm.
Saturday & Sunday: 7:00 am – 8:30 pm. Ferries depart every half hour, with the final departure at 8:30 pm.

It costs $7 on weekdays and $8 on weekends for cars to utilize the St. Johns River Ferry to cross from Mayport to George Island.

Check their website for the most up to date ferry schedule and fares.


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 a delicious meal at Skipper’s Fish Camp overlooking the Darien River. Their grilled shrimp sandwich, served with a side of okra is excellent. After lunch we strolled around the small quiet town. Then we grabbed some takeaway cappuccinos before getting back on the road.

shrimp sandwich at Skipper's Fish Camp in Darien, Georgia
Lunch at Skipper’s Fish Camp in Darien, Georgia.

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.

Bell posing in front of Tybee Island Light Station and Museum in Tybee Island, Georgia.
Tybee Island Light Station and Museum in Tybee Island, Georgia.

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. Visit the impressive Tybee Island Light Station, which dates to 1736. It is one of only seven remaining colonial era lighthouses. Weather permitting, grab a delicious to go order from Sundae Cafe and enjoy it at the lighthouse or on the beach. The owners used to operate 80 East Gastropub, which was excellent for craft beer and a creative casual menu.

Being so close to Savannah, you didn’t think we’d leave it off from this trip, did you?

Savannah, Georgia

Savannah is just off I-95 making it one the best and most convenient stops driving from Florida to Washington, DC. It is a charming southern town, with cobblestone streets and a relaxed vibe. A stroll along the Savannah River, with a delicious lunch, is a wonderful way to spend an afternoon.

Enjoy some of the 22 beautiful public squares 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 award winning film. There is no bench in the spot, but you can sit in the square itself and enjoy a coffee from Gallery Espresso.

Alex posing with the Chippewa Square sign in Savannah, Georgia
Chippewa Square in Savannah, Georgia.

While on the topic of movies, we also made a stop at the Bonaventure Cemetery, which dates back to 1846. It 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 Bonaventure Cemetery particularly picturesque.

Where to Stay in Savannah

The Drayton makes for a great couples stay in historic Savannah. Comfortable rooms await guests, along with an onsite restaurant, bar and room service. The hotel is close to popular attractions like City Market, River Street Train Museum and Owens-Thomas Museum.

Upon leaving Savannah, we didn’t take highway 17. We briefly got back on I-95 to shave some time, as it is the fastest route from Florida to Washington DC. But we quickly exited I-95 and ventured to both Beaufort and historic Charleston, South Carolina.

Charleston, South Carolina

Alex and Bell at Rainbow Row in Charleston, South Carolina
Rainbow Row in 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. As Charleston is not too far off I-95, it is one of the best stops from Florida to Washington, DC.

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. This is a great area to stroll and take in some fresh seaside air.

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 to use their shuttle, and the service is tip based at the Hilton Garden Charleston Waterfront. That also means the additional money goes to employees, and not a huge corporation. 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.

Beaufort, South Carolina

Beaufort is a picturesque town on Port Royal Island, one of South Carolina’s Coastal Sea Islands. The historic town dates to 1711 and is the second oldest city in South Carolina.

We didn’t have much time in Beaufort, but it is a charming town to stop on an east coast road trip. 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. Beaufort is a charming stop from Florida to Washington, DC.

sunset in Beaufort, South Carolina
Sunset in Beaufort, South Carolina.

South of the Border: Florida to Washington, DC

As you approach the border of South Carolina and North Carolina on Interstate 95 you are going to see 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 in Dillon, South Carolina has seen better days.

Alex posing at South of the Border in Dillon, South Carolina
Mexican themed South of the Border in Dillon, South Carolina.

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. It’s only a quirky highlight of the Florida to Washington, DC drive if you never get off I-95.

Chapel Hill, North Carolina

The beautiful Administrative offices at UNC-Chapel Hill, the USA's oldest public university.
The beautiful campus of the University of North Carolina in Chapel Hill is the oldest public university in the United States, dating to 1789.

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. Built in 1897, it was inspired by the Temple of Love, in the gardens of the Palace of Versailles, just outside Paris.

students mingling around the Old Well at UNC-Chapel Hill
Students mingling around the Old Well at UNC-Chapel Hill.

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.

Where to Stay in Chapel Hill, North Carolina?

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.

A collage of photos at the Carolina Inn across the street from UNC - Chapel Hill.
The Carolina Inn dates to 1924 and is right across the street from 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

Bell posing with flowers along the Blue RIdge Parkway in North Carolina
Beautiful Blue Ridge Parkway vistas in North Carolina.

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.

We continued on through the Smoky Mountains to Gatlinburg and Pigeon Forge, Tennessee. Pigeon Forge is a spectacle of attractions that includes amusement parks like Dollywood. Read more about the drive in our article Blue Ridge Parkway: What to Expect.

Williamsburg, Virginia

Williamsburg, Virginia is the best preserved colonial town in the United States. Colonial Williamsburg was the capital of the colony of Virginia from 1699-1780. Along with nearby Jamestown and Yorktown, it is part of a “historic triangle.” The historic town serves as a living museum. Actors dressed in colonial attire provide insight into colonial life along the streets, stores and workshops.

There is a lot to do in the area, but plan to spend at least a couple hours strolling the historic center. Highlights include the Governors Palace and Visitors Center, housed in an 18th century mansion. There is even a Busch Gardens amusement park in Williamsburg.

While Williamsburg is very touristy, it has a surprisingly excellent culinary scene in its historic center. If you enjoy craft beer, go for brews and bites at Amber Ox. Their fried wings, prepared Alabama style and burgers, are as delicious as they come. For delicious French-American dishes like croque madames and fried oyster po boys, head to Blue Talon Bistro. We loved both of those restaurants during our stay in Williamsburg. They also have nice outdoor terraces to enjoy dining al fresco when the weather is good.

Where to stay in Williamsburg, Virginia?

The Williamsburg Lodge is perfect for a luxurious stay. Stylish rooms juxtapose throwback 18th-century themed coverlet bedspreads and hand painted lamps with plush beds and large flatscreen TV’s. Two on-site restaurants serve classic American cuisine infused with a southern Chesapeake Bay twist. The property also features a spa, swimming pool and golf nearby. This is a popular hotel to get married. On the Saturday we stayed, there were two weddings taking place that evening.

We redeemed an anniversary award stay with our Marriott Bonvoy AMEX card for a free night at the Williamsburg Lodge. This saved us around $249 a night on a weekend stay. Read more of our travel hacks tips to save big money on travel!

Richmond, Virginia

In 1780 the capital of Virginia was moved from Williamsburg to….Richmond! Richmond, Virginia is one of the best stops right along I-95 driving from Florida to Washington, DC. The Virginia State Capitol Building was designed by Thomas Jefferson and features the oldest Greek columns in the United States. The State Capitol Building also houses the oldest statue of George Washington. It was created using a plaster cast during his lifetime! Richmond was also the capital of the confederacy, and you can tour the White House of the Confederacy.

Statue of George Washington at the State Capitol Builing in Richmond, Virginia
The oldest statue of George Washington at the State Capitol Building in Richmond, Virginia, which was designed by Thomas Jefferson.

Read our itinerary on how to spend a weekend in Richmond, Virginia. We celebrated our 14 year wedding anniversary at the beautiful and historic Jefferson Hotel. It’s the only AAA rated 5 diamond rated hotel in central Virginia. Rooms range from comfortable to expansive apartment style suites that are beautifully appointed.

Plan for dinner at Lemaire, one of the premier dining experiences in Richmond. Or enjoy high tea in their foyer, overlooking a statue of Thomas Jefferson that dates to the late 1800’s. They have an amazing Sunday brunch too – where you may feel like you’ve stepped inside The Great Gatsby. It is a wonderful place to experience for a special occasion! For more tips, read our article on Richmond, Virginia restaurants you should eat.

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. The Maryland State House is the oldest state capital building in the US, continuously in use since 1772.

Maryland State House in Annapolis, Maryland, the oldest U.S. state capitol in continuous legislative use, dating to 1772.
The Maryland State House in Annapolis, Maryland is the oldest U.S. state capitol in continuous legislative use, dating to 1772.

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 one major highlight. Tour the grounds of the picturesque campus for military cadets. We took our parents to Annapolis during their respective visits from Australia and Florida. They both really enjoyed the historic waterfront setting and delicious dining.

Recap on Driving from Florida to Washington, DC

There are many wonderful destinations to see, it just depends how much time you have. If you have the opportunity to take your time and not wizz through on busy I-95, do it. But I-95 makes the trip much faster, and there are great destinations right along I-95 or just off it to experience. Savannah, Georgia, Saint Augustine, Florida and Richmond, Virginia are three of the best stops right along I-95. If you’re short on time driving from Florida to Washington, DC, plan to stop in those three destinations!

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