Five Unexpected Places to Stop on a Road Trip from Chesapeake, VA to Hilton Head Island, SC

Driving from Chesapeake, VA to Hilton Head Island, SC takes about 8 hours. This trip will take you through several states, each with its unique attractions, landscape, and cuisine. However, to ensure that you do not miss out on the hidden gems along the way, we have put together a list of five unexpected places to stop.

Halfway point - Saint Pauls, NC

Halfway between Chesapeake and Hilton Head Island, Saint Pauls is a quaint town that is worth exploring. It has a rich history, as evidenced by the many historic buildings that can be found throughout the town. You can visit the Robeson County Museum to learn more about the area's history and see exhibitions on textile Mills, Native American artifacts, African American Culture, and military collections. If you are in the mood for some nature, stop at the Cape Fear Botanical Garden and admire beautiful gardens and unique art displays.

Favorite food to eat in Saint Pauls: Visit The Shell Station, which is a gastropub and brewery. They offer an extensive selection of craft beer and tasty pub fare, like fried pickles and chicken wings.

1. Virginia Beach, VA

Virginia Beach has miles of pristine beaches, lively boardwalk, and a vibrant culinary scene. Start your visit with a stroll on the 3-mile boardwalk, which is lined with restaurants, bars, and souvenir shops. Then, head over to the Virginia Aquarium and Marine Science Center, which has over 300 exhibits featuring sharks, sea turtles, otters, and seals. Before you leave, don't forget to indulge in some fresh seafood at Catch 31, one of the area's top restaurants.

Favorite food to eat in Virginia Beach: Try the she-crab soup at Coastal Grill, which is a creamy, flavorful soup made with crabmeat, cream, and sherry.

2. Wilmington, NC

Wilmington is located on the Cape Fear River and boasts a charming historic district, fantastic beaches, and excellent dining options. Start by exploring the Riverwalk, a 1.75-mile-long boardwalk that runs along the waterfront and features quaint shops and boutiques. If you're a fan of TV shows and movies, you can also visit the Wilmington Film Museum, which has exhibits showcasing the area's history as a movie-making destination. When it's dinnertime, head over to PinPoint Restaurant, which serves up fresh, locally-sourced seafood and Southern-style cuisine.

Favorite food to eat in Wilmington: Have the shrimp and grits at Indochine, which is a fantastic fusion of Southern-style grits and Vietnamese flavors.

3. Charleston, SC

Charleston is known for its stunning architecture, rich history, and world-class cuisine. Start your visit with a stroll down the picturesque streets of the historic district, which has over 300 years of history. Then visit the iconic Charleston City Market, where you can shop for handcrafted art and goods made by local artisans. For dinner, make reservations at Husk, which is known for its innovative take on Southern cuisine.

Favorite food to eat in Charleston: Have the fried chicken and biscuits at Hominy Grill, which is a classic dish done right.

4. Beaufort, SC

Beaufort is a charming, historic town located on Port Royal Island and is known for its antebellum architecture and stunning natural scenery. Start your visit with a stroll down the main street, which is lined with art galleries, boutiques, and antique shops. Then, visit the Santa Elena History Center to learn about the area's history and explore interactive exhibits. Before you leave, stop by the Old Bull Tavern, which is a gastropub featuring a rotating tap of craft beers and tasty pub fare.

Favorite food to eat in Beaufort: Have the Lowcountry boil at Plums, which is a classic Southern dish featuring shrimp, sausage, and corn on the cob.

5. Savannah, GA

Savannah is a city of stunning architecture, historic squares, and fantastic dining. Start by taking a stroll through Forsyth Park, which is one of the city's most iconic landmarks, featuring beautiful fountains, flowers and plenty of greenery. Then, take a walking tour of the historic district, with stops at must-see landmarks like the Cathedral of Saint John the Baptist and the Juliette Gordon Low Birthplace. For dinner, make reservations at The Grey, which is a James Beard-award-winning restaurant housed in a restored Art Deco Greyhound bus station.

Favorite food to eat in Savannah: Have the fried green tomatoes at The Olde Pink House, which is a classic Southern dish with a savory twist.

Conclusion

A road trip from Chesapeake, VA to Hilton Head Island, SC is full of unexpected surprises, from hidden gems in historic towns to fantastic seafood restaurants. By exploring these five stops, you'll experience a unique mix of natural beauty, rich history, and Southern hospitality.