Charleston Itineraries

Island Hopping Adventure

5 Days to Discover 5 Beautiful Beach Towns

Island Hopping Adventure

Day One: Isle of Palms

In the five days ahead, you will learn that no two beach towns are alike, discover that life is better with a bit of sand between your toes and taste fish so fresh you'll swear it swam onto the plate. First up on your seaside sabbatical: a visit to Isle of Palms.

Bike the Breach Inlet

Isle of Palms is home to beautiful beaches that stretch as far as the eye can see - and a mesmerizing inlet between it and its neighboring town of Sullivan's Island. Get your bearings at Breach Inlet by bike, where you'll cruise past green marshland and ocean views in every direction.

Serve up Sandy Spikes

Isle of Palms' Front Beach, located between 10th and 14th Avenue, offers three lively volleyball courts, open year-round. Hit the courts to work on your spike and make friends with other beach-goers.

Tee Off Oceanside

Pay a visit to the Wild Dunes Harbor Course for a round of seaside golf. Tee off near serene lagoons, lush marshland and the winding Atlantic Intracoastal Waterway. This varied, and stunning, course will keep you on your toes at every hole.

Seafood On The Terrace

Dine on the terrace overlooking the pool at Wild Dunes Resort’s Coastal Provisions. Inspired by Charleston’s rich sailing history, Isle of Palms’ signature restaurant and bar features weathered driftwood floors, a colorful coastal palette and fresh seafood plates.

Island Hopping Adventure

Day Two: Sullivan's Island

For your second beach day, head to Sullivan's Island, an idyllic beach town with a storied shore waiting for you to explore.

Historic Morning

Start your day at Fort Moultrie, one of the oldest remaining forts on the Eastern Seaboard. Originally constructed in 1776 to protect Charleston, the fort has an illustrious military defense history spanning the American Revolution through World War II.

Go Crabbing

Try your hand at crabbing from Station 16's community dock. Its intracoastal waterways are a favorite for local crabbers.

Sunset Stroll

Take a sunset stroll with pastel homes and lush gardens to your right and waves lapping at your left. No sight on Sullivan's Island is more memorable than seeing the sun slink into the Atlantic Ocean.

Barbecue Dinner

Close out your day with a visit to Home Team BBQ for slow cooked, scratch-made barbecue. We recommend you order collard greens, smoked gouda mac and cheese and a frozen Game Changer on the side!

Island Hopping Adventure

Day Three: Folly Beach

Spend the day at Folly Beach, a funky and carefree outpost nicknamed "The Edge of America."

Cast Your Line

Try your hand at fishing off Folly Pier with the locals. This popular spot jets a thousand feet into the Atlantic Ocean, making it a popular fishing spot for those who don't want to find their sea legs. Even if nothing bites, you'll enjoy breathtaking views from the East Coast's second-longest pier. *PLEASE NOTE: THE PIER IS CURRENTLY CLOSED FOR REPLACEMENT CONSTRUCTION UNTIL SPRING 2023.

Lunch With A View

BLU combines spectacular oceanside views with a menu dominated by sustainable seafood, regional flavors and local ingredients. Enjoy local favorites and seasonal specialties including Baja Shrimp Tacos and Shellfish Mac & Cheese.

Shop Center Street

Walk off your lunch with a stroll around town. Hit Center Street's funky surf shops and bohemian boutiques to grow your beachwear wardrobe, find a new pair of shades or a souvenir to commemorate your time here on Folly Beach.

All Aboard

Climb aboard the Carolina Skiff with Charleston Outdoor Adventures where you'll embark on a six-mile cruise to Morris Island. Keep your eyes peeled for dolphins playing in the waves, osprey diving for fish and, of course, the historic Morris Island Lighthouse, your stopover on this excursion.

Island Hopping Adventure

Day Four: Kiawah Island

Escape to Kiawah Island, an unspoiled barrier island boasting 10 miles of stunning beachfront, championship golf courses and more.

Fore!

Over 90 holes of golf await both beginners and novices on Kiawah Island's five championship courses. Each offers its own breathtaking view and a claim to fame, like the Ocean Course - host to every major PGA event in the U.S. and a recently redesigned Jack Nicklaus course.

Shopping Excursion

After a scenic drive onto Kiawah Island, you'll stumble upon Freshfields Village, where you can refuel at a variety of cafes, coffee shops and restaurants - or refresh your beach wardrobe at one of the area's countless boutiques and outfitters.

Relax and Rejuvenate

If four days at the beach wasn't relaxing enough - a spa day should do the trick. Kiawah Island is home to one of Charleston's most special and lauded spas. Receive five-star treatment and a full menu of services at The Sanctuary while surrounded by the gentle sound of ocean waves.

Dinner is Served

Don't leave Kiawah Island without one final indulgence at The Ocean Room. An opulent evening awaits, complete with white tablecloths, steaks and seafood that is just about as fresh as it gets.

Island Hopping Adventure

Day Five: Seabrook Island

Seabrook Island is your final shore to explore. Tucked away and home to a lush maritime forest, serene marshes and pristine beaches, this island is your quiet getaway for the day.

Saddle Up

Develop your horse sense and enjoy a scenic three-mile, coastal ride along the Atlantic Ocean with Seabrook Equestrian. If you've maxed out on sun, trail rides through the maritime forest are also available.

Cruise the Island

One of the best ways to explore this beautiful barrier island is by bicycle. Peddle down winding streets lined with majestic live oaks and keep an eye out for white tail deer, turtles, rabbits and the many other creatures that call the island home.

Hit the Tennis Courts

Head to the tennis courts at The Seabrook Island Racquet Club to work on your tennis game. Choose from a variety of clinics offered by the pros or reserve a court for a few matches with your vacation party.

Dine Dockside

Enjoy dolphin sightings and breathtaking sunsets while dining oceanfront at Pelican's Nest. Daily features highlight fresh, local seafood and refreshing drinks at the open-air bar. Visit between Memorial Day and Labor Day to catch live musical acts every Friday and Saturday night.

Explore More Charleston Itineraries

24 Hours in Charleston

Holy City Honeymoon

Luxurious Getaway