Ultimate Weekend Getaway in Charleston, SC: Itinerary and Tips

Planning to spend a weekend in Charleston, SC? You’ve got a lot to look forward to. From delicious food to laid-back afternoons at the beach, the best city in the South is rich in history, culture, and natural beauty.

Whether you’re soaking in Charleston’s charm for the first time, making plans for an upcoming vacation, or searching for a site for your future home, this 3-day itinerary gives you a valuable peek into Lowcountry living.

Get ready for a Charleston weekend getaway filled with local experiences and coastal elegance!

Day 1: Historic Charm

Start your weekend off strong by digging deeper into the heart of Charleston. Plan to arrive early and squeeze in as many fun-filled hours as possible.

Morning

First stop, your hotel. We recommend downtown hotels that bring you near the center of the historic district, close to Broad Street. You’ll have easy access to the city’s best dining, entertainment, and historical sites.

Once you’ve settled in, take a stroll through King Street for some shopping, coffee, and city energy. Take in the incredible architecture before checking out the boutiques and antique shops. Along the way, drop by the Harken Café or Sorelle Mercato for a sweet pick-me-up.

Afternoon

You’ll have plenty of options for delicious dining when lunchtime arrives. We suggest checking out the delectable oysters at 167 Raw or some Southern food with a modern twist at Husk.

When your meal is over, take a stroll down Rainbow Row, a collection of 13 colorful historic houses on East Bay Street. After this pastel paradise, wind down with a stroll by the water. Battery Park and nearby Waterfront Park offer scenic views of the Charleston Harbor.

Evening

Kick off your evening with sunset drinks from the Watch Rooftop Bar and Restaurant, located on the 7th floor of The Restoration Hotel. When you’re ready to eat, head to the Basic Kitchen for a holistic dinner made from seasonal, locally sourced produce.

Walk off your meal by wandering the quietest, most picturesque part of town, South of Broad. This neighborhood is home to historic monuments, beautiful homes, and elegant gardens.

If it’s a Friday night, check out a First Friday ARTWALK, where art galleries open their doors for free while you sip wine and relax.

Day 2: Coastal Living

On the second day of your Charleston weekend trip, venture outside the city limits to see the nearby islands. After all, no trip to the area is complete without a visit to the beach.

Morning

Start your day with a Charleston classic at Callie’s Hot Little Biscuit, where you can savor flaky, made-from-scratch biscuits paired with creamy grits and a fresh cup of coffee.

Then, make your way to Isle of Palms (IOP) or Sullivan’s Island, two of the Lowcountry’s most beloved barrier islands. Stroll along the shoreline, sink into the soft sand, watch for coastal wildlife, or take a scenic drive to admire the stunning homes that frame the waterfront.

Afternoon

When hunger strikes, head to The Obstinate Daughter, a local favorite serving inventive New American dishes and craft beers with coastal flair. For dessert, stop by Beardcat’s Sweet Shop for melt-in-your-mouth pastries, creamy gelato, and perfectly brewed coffee.

While you’re in the area, swing by our Mount Pleasant office. We’d love to say hello! 

As South Carolina’s largest coastal town, Mount Pleasant offers peaceful walking trails, beautiful beaches, and some of the most desirable homes in the Lowcountry, making it well worth exploring before your day winds down.

Evening

End your day strong at Shem Creek, which runs through Charleston and Mount Pleasant. Take advantage of happy hour and chat with locals before moving on to your next destination.

Watch the sun go down while indulging in the local seafood at Tavern & Table, a rustic, waterfront restaurant. Finally, spend some time in the heart of Mount Pleasant’s local scene, including the Pitt Street Bridge, a pedestrian walkway with panoramic views of the harbor.

Day 3: Lowcountry Tranquility on Kiawah Island

One of the best parts of the Lowcountry is how easy it is to explore so many different communities. Make the most of the final day of your Charleston weekend itinerary by enjoying the best of both the city and the surrounding towns.

Morning

Get your energy up with a coffee and breakfast at The Daily in downtown Charleston, offering freshly-made pastries, smoothies, and creative meals.

Next, take the scenic 45- to 50-minute drive to Kiawah Island on a route lined with majestic live oak trees draped in Spanish moss. This natural tunnel will make your drive to the coast nearly as enjoyable as the beach itself.

Begin your visit to the island with a peaceful walk or a bike ride along Beachwalker Park, a stunning and often quiet spot. Keep cycling through Kiawah’s residential paths, where you can admire beautiful homes nestled among tree-lined streets and lush greenery.

Afternoon

Make your way to Freshfields Village, the vibrant town center of both Kiawah and Seabrook Islands. Depending on your mood, get lunch at Hege’s for French-inspired fare or Cantina 76 for casual tacos and cocktails.

When your stomach is satisfied, spend the afternoon browsing the area’s many boutiques, where you can buy everything from jewelry to books to pet supplies. If your timing is right, you can also attend a seasonal event, such as Cars & Coffee or Music on the Green.

Evening

Ready for a relaxing evening after such a busy day? Head over to Seabrook Island, Kiawah’s quieter, more residential sister island. Stroll along the marsh boardwalks and soak in the natural beauty and slower pace — perfect for those seeking privacy and a deeper connection to nature.

Wrap up the evening back at Freshfields Village for dinner. If you’re a wine lover, try FortyEight Wine Bar & Kitchen, with dozens of featured wines and interactive wine stations.

In the mood for a cozy, family-style meal instead? Drop in at La Tela Pizzeria for pasta, grinders, and wood-fired pizza.

Enjoy Your Escape to Charleston, SC

Charleston offers a rare blend of outdoor adventures, vibrant city life, and sun-kissed beaches, all wrapped in unmistakable Southern charm. One weekend here is enough to fall in love, but hardly enough to experience everything this remarkable city has to offer.

If the Lowcountry lifestyle speaks to you, why limit it to occasional getaways? As you stroll the historic streets or take in the coastal views, picture what life could be like in a home of your own here.

When you’re ready to turn that vision into reality, reach out to our team. We’re here to guide you every step of the way.