For your first two nights, you’ll stay in Charleston’s historic district before you head out to the beach. Shelby books many of her clients at the Restoration on Wentworth Street adjacent to King Street. The Restoration’s suites come with apartment amenities—if you’re moved to turn some of the local bounty at the farmers market on Marion Square into your own farm-to-table feast, you can prepare a meal in your own kitchen. Or opt instead to leave the cooking to the chefs at the Watch, the hotel’s rooftop restaurant and lounge with views of historic streets and the harbor.

After lunch, borrow one of the hotel’s Martone bikes for a tour of the peninsula, riding along the streets lined with historic homes down to the Battery at its southern tip. You’ll not only get some exercise, but also a better sense of how much Charleston has always been oriented towards the sea as you admire the beauty of the natural harbor here.

In the evening, venture over to Shem Creek, on the opposite side of the Cooper River. While you can see the Arthur Ravenel Jr. Bridge from the creek, it feels a world away from the city even though it’s in the heart of Mount Pleasant. Dolphins can be spotted in its waters while a variety of birds rest on the banks of the creek, including egrets, pelicans, and ospreys. Then pull up a seat at Tavern & Table, overlooking the creek, for a dinner of global dishes incorporating local ingredients prepared by chef Katie Lorenzen.

After breakfast at your hotel, set out for Boone Hall Plantation, roughly a half-hour from downtown Charleston. The Avenue of Oaks at this late 17th-century plantation may look familiar from countless photographs, but there is much more to the estate: more than 700 acres of working farmland, a butterfly pavilion, and gardens showcasing native and imported plants. At the end of your tour, you can shop for produce grown on the farm and other gourmet gifts at the Boone Hall Farms store.

Head back to the city and stop at Fleet Landing Restaurant and Bar, not far from the Charleston City Market, for lunch on the restaurant’s wraparound porch overlooking the harbor and Fort Sumter.

You’ll get a closer look at the fort in the afternoon, when you board a Spiritline Cruise. While Fort Sumter, which was the site of the first battle of the Civil War in April 1861, is the highlight, you’ll also sail by the other islands that dot Charleston’s harbor and enjoy stunning views of the skyline punctuated with steeples. Once you have returned back to the mainland, head to High Wire Distilling for a taste of the spirits renaissance that is sweeping South Carolina. Since 2009, when micro-distilleries were legalized here, more than two dozen have opened in the state. High Wire was the first in Charleston since Prohibition. Tours that explain the distilling process are followed by tastings of their small-batch spirits—gin, rum, whiskey, and vodka. Follow up your visit with a meal at Cru Café, known for its classic Southern dishes and gracious Southern hospitality.

You’ll leave this morning for some of Charleston’s seaside playgrounds, it boasts five different beach communities. Sullivan’s Island and the Isle of Palms are to the northeast of the harbor; Folly Beach, Kiawah Island, and Seabrook Island are to its southwest. On this trip, you’ll visit the beaches to the south of the harbor over the next two days.

Start your day on Folly Beach at Charleston SUP Safari—that SUP is short for stand-up paddle boarding. Even if you have never tried the sport before, the experts here will explain the tricks to getting up on your board and you’ll soon be paddling through the calm waters of the Folly River. You’ll have a unique perspective on the marshes and the birds that live here, as well as the dolphins that can often be spotted in the distance.

Dry off and head to lunch at Pier 101, one of the newest additions to Folly Beach’s dining scene. American and Southern dishes are served with panoramic views of the beach and the Atlantic Ocean. There’s live music most days, and cold beers every day.

After lunch, try your hand at a more leisurely outdoor pursuit. Take a short walk along a long pier, when you visit the Folly Beach Fishing Pier. You can cast a line here and give a go at saltwater fishing, hoping that one of the redfish or flounder in the water below takes the bait. If your visit happens to coincide with one of the Moonlight Mixers, held once a month from May to September, stick around to dance under the stars to a DJ spinning oldies and beach tunes.

You’ll then continue on to the next island south from Folly Beach, Kiawah Island where you’ll spend two nights at the Kiawah Island Golf Resort. Shelby can reserve you a room at The Sanctuary hotel or one of the private homes for rent.

Spend your morning exploring Kiawah Island on a bicycle—there are over 30 miles of bike paths that pass through forests and wetlands, and connect most of the island’s best beaches. Or you can trade pedal power for paddle power and go kayaking through the island’s marshes. As you quietly move through the waters, you’ll be able to spot some of the more than 200 different bird species that live here. If you are a serious birder, you may want to opt instead for the 3-hour Back Island Birding tour, on foot, led by an expert who will provide background on the various habitats found on the island and the natural history of its various avian residents.

Kiawah Island Golf Resort counts 13 restaurants and bars, assuring you’ll find a place serving whatever you may crave. A favorite for lunch is Loggerhead Grill, a tropical oceanfront café serving a casual menu of salads, sandwiches, burgers, and tacos.

In the afternoon, take advantage of some of the resort’s world-class facilities, from golfing (there are five courses) to tennis (there are two separate tennis complexes with a total of 12 courts each). Of course if you want to simply lay your towel down on one of the miles-long beaches or claim a chaise by the pool and relax with a good book or a frosty cold drink, the staff at the Kiawah Resort will be happy to assist.

In the evening, toast your trip with an elegant send-off, perhaps at the Atlantic Room, if you are in the mood for seafood, or the Ocean Room, the resort’s steakhouse.

It’s time to head to the airport and begin the journey back home today, though depending on the time your flight is scheduled, you may still be able to squeeze in one last stop en route—maybe at serene Seabrook Island, Kiawah Island’s neighbor, or Magnolia Plantation and Gardens, not far from the airport. Or you can simply save those sights for your next visit.