Going Coastal: Weekend Road Tripping Through America’s Southeast

From Hilton Head to Savannah to Jekyll Island, this road trip is a true Southeastern joy ride. Few itineraries offer as much handmade charm, natural beauty, delicious food and rich history as an expedition along 100-plus miles of the Southeastern coastline. This trip is romantic enough for couples and engaging enough for families.

As always, check for travel restrictions and closures before planning your trip. Now, let’s get rolling.

Hello, Hilton Head, SC

Your journey begins in this island resort town. Named for Captain William Hilton, who discovered it while sailing from Barbados, Hilton Head brims with history, culture and natural beauty. The beach town centers around the restaurants, music, dancing and theater of Coligny Plaza. The Coastal Discovery Museum offers a full history of the island’s heritage as well as nature tours on land and by boat. And what’s a beach with no lighthouse? The privately owned Harbour Town Lighthouse has a museum, restaurant, shopping center and, of course, a gorgeous Atlantic Ocean view.

Away from town you can bike along Hilton Head’s miles of trails and go for a swim at one of 12 local beaches, where dolphins are a common sight. Get up close with Island Explorer Boat Tours, or careen through the trees with Zipline Hilton Head.

For great local eats, look no further than Bluffton Oyster Co. The last active oyster operation on the island, this 200-year-old company offers the freshest seafood around. Enjoy a taste of seaside living as you watch your food go from hook to table. End the day with a cocktail on the terrace of Skull Creek Boat House, which often has live music and almost always a spectacular sunset.

South to Savannah, GA

Next stop on your road trip: Savannah, located just 45 minutes south of Hilton Head by way of May River Road.

In Texas, they ask who your family is. In Boston, they ask what you do. In Savannah, they ask what you drink. Yes, the Garden City has a lust for nightlife, and the epicenter of the revelry is just across the river from The Westin Savannah Harbor Golf Resort & Spa. This downtown area is packed with boutiques, restaurants, antique shops, artist studios, local dives, crab shacks and Savannah’s famous candy shoppes. It also offers world-class people watching with a mix of locals, tourists, students and military visiting from nearby bases.

The Historic District makes Savannah one of the most beautiful cities in the country. Stroll through its fairytale-worthy squares, taking in classic buildings in the shade of moss-draped oak trees. Get a peek inside these ornate abodes on the Savannah Tour of Homes & Gardens. For a bit of contemporary culture, visit the Telfair Museum and the SCAD Museum of Art.

When you’ve worked up an appetite, grab lunch at Zunzi’s, a South African-owned eatery that brings exotic flavors to American-style sandwiches. (Best when savored in the sun on a picnic in one of the historic squares.) For Southern-style home cooking, visit Mrs. Wilkes Dining Room. Known for the best fried chicken around, Mrs. Wilkes serves meals family-style, with a menu that changes daily. For dessert, stop at Lulu’s Chocolate Bar for house-made truffles.

Head uptown to Broughton Street for shopping. This fashionable part of town has the perfect blend of chic home-goods shops like 24e Design Co. and DC2 Design and local boutiques like Zia Couture Jewelry and Satchel.

Find all your kitsch and candy on the riverfront at the River Street Market Place, an open-air market of handcrafted gifts and imported goods. Make sure to visit dueling candy shops River Street Sweets and Savannah’s Candy Kitchen—just follow your nose to the thick slabs of fresh fudge.

Onward to Jekyll Island, GA

Less than two hours south of Savannah is Jekyll Island. With The Westin Jekyll Island as your base, you can step back in time with a carriage ride through the island’s 250-acre historic district and cool off with a hand-dipped cone from Island Sweets Shoppe.

Jekyll has three main beach areas: secluded Glory Beach, sociable Great Dunes Park with its bustling restaurants and Driftwood Beach, where you can hop on a horse for a sunset trot past the gnarled remains of live oaks that have washed upon the shore.

The island is home to a lot of wildlife, and the state does a good job of preserving the environment for its feral friends. With development limited to only 35 percent of the island, Jekyll has become a sanctuary for birds and bird-watchers alike. Explore this pristine stretch of coast with 4-H Tidelands Nature Center, which offers live animal exhibitions, nature walks and kayak and paddleboard lessons. Once a power plant, now a safe haven for endangered species, the Georgia Sea Turtle Center is a year-round attraction for animal lovers.

Of course, there’s no better way to end a road trip than with a great meal. Enjoy shrimp and grits, pan-fried red fish and a classic Low Country boil—all with a view—at Beach House Restaurant+Tap Room.

Pristine nature. Historic architecture. Contemporary culture. Savory seafood and sticky sweets. This road trip has it all, whether you’re traveling for romance or family fun. For the perfect way to unplug in the Southeast, go coastal.