The Best Charleston Weekend Itinerary
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The Best Charleston Weekend Itinerary

Charleston, South Carolina is a city steeped in history, charm and exceptional cuisine. Whether you’re wandering its cobblestone streets, admiring its classic architecture or indulging in its renowned culinary scene, you’ll find a rich tapestry of experiences in Charleston.

It’s easy to spend weeks in this unforgettable city and have something new to do every day. But if you only have a weekend to explore Charleston, you don’t want to lose a single moment. Follow our Charleston travel guide for our favorite things to do in Charleston, SC, including the best hotels, eateries, and once-in-a-lifetime experiences.

Hotels in Downtown Charleston

Before you set the rest of your Charleston weekend itinerary, start your weekend adventure by checking into one of the best hotels in downtown Charleston.

The Dewberry is a modern classic, blending mid-century design with Southern charm.

The Restoration is an upscale, boutique option that focuses on comfort and local culture. 

For a touch of modern luxury, The Loutrel presents a stylish, relaxed atmosphere with a spacious rooftop terrace featuring panoramic views of the city. 

Zero George Street Hotel offers a historic feel with contemporary touches. 

The Charleston Place and Hotel Bennett provide elevated sophistication and Southern hospitality.

The Dunlin provides a relaxing oasis only a short drive from the city. 

Stay at the Palmetto Inn for an authentic downtown Charleston experience.

The Cooper , a newer waterfront option, is a stylish boutique hotel situated along the Charleston harbor.

The French Quarter Inn  an award-winning downtown hotel, is a popular luxury boutique located in the heart of Charleston's French Quarter.

Where To Eat and Drink in Charleston

Walkable and draped in Southern wisteria, downtown Charleston is a great place to start if you’ve never been before. Here are the top restaurants in Charleston for any meal of the day.

Coffee and Breakfast Options in Charleston

After settling in, grab a sweater or pullover and head downtown for breakfast, or stop by one of the best coffee shops in Charleston.

The Daily offers a delightful array of pastries, sandwiches and coffee. 

Kudu Coffee is a cozy coffee shop known for its charming courtyard—perfect for laid-back mornings.

Welton’s Tiny Bakeshop is a cozy neighborhood bakery on King Street known for their bread, pastries, and seasonal treats made with local ingredients. Make sure to try their signature salted honey pie! 

If you’re downtown, stop in Spread Bagelry to enjoy freshly made bagel sandwiches and coffee. 

Island Provisions is a casual and community-oriented neighborhood market where you can grab anything from excellent coffee and fresh pastries, or a laid-back lunch with delicious sandwiches. 

Babas is a neighborhood cafe inspired by European cafes, serving espresso, house-made pastries, and breakfast downtown.

Best Lunch Spots in Charleston

If you’re ready for lunch, you’ll find a host of distinctly Charleston dining experiences to enjoy.

For a relaxed lunch, head to Sullivan's Fish Camp, a casual neighborhood restaurant serving classic seafood dishes and raw bar favorites with a modern Lowcountry touch. 

For lunch, visit Lewis Barbeque for some of the best Southern barbeque in town.

Berkeley’s is a laid-back lunch spot known for creative comfort food, from shareable small plates and fresh salads to hearty sandwiches and pastas. 

Perfectly capturing the rich history and charm Charleston is known for, Poogan’s Porch is a Southern cuisine restaurant set inside a beautifully restored Victorian house in the heart of downtown. 

If you’re looking to enjoy fresh, local food in a bright but relaxed setting, Basic Kitchen is the spot to go! 

If you're craving something lighter, Brown Dog Deli is a casual spot with a fun atmosphere. 

For something more casual, head to Island Cabana Bar for stunning water views and a relaxed vibe.

Home Team BBQ offers an upbeat, lively atmosphere with a laid-back barbecue experience that’s perfect for gathering with friends, watching sports, or listening to live music.

Where To Go for Dinner in Charleston

For dinner, explore Charleston's Lowcountry dining scene, from fresh oysters and she-crab soup to low country shrimp and grits and contemporary Southern cooking. 

Located on Sullivan’s Island, The Obstinate Daughter is a casual, yet upscale restaurant with incredible views that’s perfect for a delicious dinner after a day spent on the beach or shopping downtown.

Chubby Fish is a popular Charleston seafood spot known for its ever-changing menu of creative small plates and fresh, locally sourced seafood. It primarily serves walk-ins, with a limited number of reservations available.

Leon's Oyster Shop is renowned for its oysters and fried chicken.

Set in a beautifully restored historic home, Husk is a must visit for an elevated yet authentic Charleston dining experience. 

A Michelin-starred recipient, Vern’s is highly acclaimed for its intimate atmosphere and ever evolving menu, providing a fresh and inventive experience with each visit. 

Consider Post House for its refined Southern dishes in Mount Pleasant's historic Old Village. 

Eli’s Table is a lively Charleston staple that focuses on modern Southern cuisine and offers both cozy indoor dining and outdoor patio seating.

Housed on historic Market Street, The Tempest delivers a refined yet adventurous taste of Charleston’s vibrant culinary scene with a seasonal menu curated by acclaimed chefs.

For a sophisticated dining experience, Slightly North of Broad (SNOB), serves elevated Southern cuisine in an elegant setting.

High Cotton is a classic and elevated Charleston restaurant known for its refined Lowcountry cuisine and warm, lively atmosphere in the historic French Quarter.

No matter which spot you choose, you’re in for a treat with Charleston’s seafood offerings — just remember to book your table well in advance to secure a spot!

Where To Grab A Drink 

For after dinner drinks, Charleston offers everything from rooftop lounges to casual waterfront spots.

Enjoy a cocktail at Citrus Club, a rooftop bar known for its citrus-inspired cocktails and incredible views of the sunset.

Located in a former church downtown, Church and Union is the perfect elevated spot to grab a classic or creative cocktail. 

The Rooftop at the Vendue is one of Charleston’s top acclaimed rooftop bars, with stunning views of the city’s skyline and harbor. 

Revelry Brewing Co. is a lively Charleston brewery known for its rotating lineup of craft beers, laid-back taproom, and popular rooftop bar with skyline views. It’s a go-to spot for casual drinks, live music, and sunset views. 

Located in the Ryder Hotel, Little Palm provides a tropical poolside experience in the heart of downtown, with a beach inspired menu and cocktail list.

Saltwater Cowboys in Shem Creek is perfect for those looking to venture closer to the coast to grab a drink in a livelier and more casual spot.

Rosemary Rose is a rooftop bar at The Nickel Hotel, that blends Mediterranean style dishes and artisan cocktails with city views.

Charleston’s cocktail scene is always buzzing, offering everything from historic downtown charm to stunning waterfront views. Whether you’re dressing up or keeping it casual, there’s always a perfect spot to unwind and soak in the city’s atmosphere.

Things To Do in Charleston

Cuisine isn’t all Charleston has to offer (although it’s one of our favorite parts!). Add these activities and excursions to your Charleston weekend itinerary to explore everything the city has to offer.

The Best Shopping in Charleston

Don’t miss out on unique and elegant shopping opportunities on your trip to Charleston! Pick up a few souvenirs for loved ones along the way, and don’t hesitate to buy yourself a little something, too.

Spend the afternoon enjoying historic King Street Charleston shopping, one of the premier fashion districts in the South. 

Detour your walk down Meeting Street and enjoy the Charleston City Market, which highlights the city’s artistic culture through a combination of souvenirs, cuisines, and jewelry crafted by local artisans.

If you’re in the mood for some upscale shopping, Freshfields Village is our favorite pick for the best mix of local shops and your favorite brands.

When you’re ready for a break from shopping, head to 48 Wine Bar just outside of downtown, in Kiawah Island, to enjoy a selection of wines through their automated wine stations.

Don't miss out on a true southern shopping experience. Stop by any Southern Tide or Lilly Pulitzer location in Charleston to add pieces to your wardrobe.

More Activities in Charleston

Take a walk through early American history and Southern culture on an afternoon stroll through Charleston. And while you’re at it, stop by the city's art galleries, historic landmarks and quaint businesses.

Head over to Credit One Stadium on Daniel Island or the Windjammer on Isle of Palms for an unforgettable night of music, where you can discover a new artist or enjoy one of your favorites! 

After dinner, take a boat tour of the Charleston harbor with Daniel Island Ferry and watch the sunset from the water. 

Take a trip to Kiawah Island where you can tee off at one of their seven renowned golf courses. The Ocean Course is our top pick with a celebrated tournament history and challenging seaside layout. 

Snap a few pictures in front of the colorful historic homes on Rainbow Row along East Bay Street.

If you’re visiting in the Spring or Summer, enjoy a day at the ballpark cheering on the Charleston River Dogs! 

Enjoy a hike in the birthplace of Charleston, South Carolina: Charles Town Landing State Historic Site.

Art lovers can explore the Gibbes Museum of Art whose collection spans historical, modern, and contemporary works, alongside rotating exhibitions.

A Year of Events in Charleston

There are always exciting events to attend in Charleston, regardless of when you’re in town! Enjoy any of these events depending on which month you will be visiting Charleston.

January: Charleston Restaurant Week running January 7-17, 2027, where various restaurants celebrate the city’s local cuisine by offering limited menus, new items, deals, and more. 

February: SEWE, The Southeastern Wildlife Exposition, (Feb 12-14) is an annual three-day wildlife art and outdoor sporting festival held in Charleston each February that includes art exhibits, live animal demonstrations, sporting events, and more. 

March: Don’t miss driving to Daniel Island for the Credit One Charleston Open taking place March 27 - April 4, 2027. It's North America's largest women-only professional tennis tournament.

April: The Cooper River Bridge Run (April 3rd, 2027) is one of America’s largest 10k races! Enjoy the race even if you aren’t participating, by cheering on the runners or exploring the various vendors! 

May: Spoleto Festival is a performing arts festival held each spring in Charleston, featuring more than two weeks of opera, theater, dance, and live music performances by acclaimed and emerging artists in venues across the city.

June: Party at the Point is Charleston’s beachfront happy hour concert series, held on Friday evenings at Charleston Harbor Resort & Marina and features live music, food and drinks, and sunset views over the harbor. 

July: The 4th of July Fireworks Blast at Patriots Point Naval & Maritime Museum in Mount Pleasant is the largest Independence Day celebration in Charleston, with live music, food vendors, and a 20+ minute display from the USS Yorktown flight deck. 

August: Deep Water Vineyard’s Annual Grape Stomp Festival is typically held in mid-August in Wadmalaw Island, and features competitive grape stomping, live music, and local food trucks.  

September: Attend Dancing on the Cooper, a summer concert and dance series held on Friday nights during summer at the Mount Pleasant Pier, with live music and waterfront views.

October: Riverfront Revival is a two‑day music festival (October 8-9th, 2027) in North Charleston curated by Darius Rucker that showcases country and folk artists on the banks of the Cooper River alongside local food and drink vendors. 

November: The Holy Smokes BBQ Festival in Charleston is a one‑day celebration of American barbecue where more than 50 top pitmasters and chefs serve up a variety of regional BBQ alongside live music at Riverfront Park in North Charleston. 

December: The Holiday Festival of Lights at James Island County Park is Charleston’s beloved annual winter event showcasing millions of lights and hundreds of themed displays. Guests can enjoy festive activities like rides, treats, Santa visits, holiday shopping, and sights for all ages.

What To Wear in Charleston

Southern Tide offers stylish, comfortable clothing that matches Charleston’s laid-back, coastal vibe. From exploring the historic district to spending an afternoon by the water, find easygoing styles for every stop on your itinerary.

Women’s Weekend Outfits 

Ideal for Charleston’s climate, casual dresses or matching sets are perfect for Charleston. Whether you’re exploring the city or enjoying a casual meal, these versatile pieces offer both comfort and style for any Charleston outing. Women's pants are easy to style for a range of occasions. Pair them with women’s blouses in a variety of patterns and colors.

When the evening gets chilly, slip on a classic sweater or comfortable pullover. Timeless and versatile, these pieces provide both warmth and style, making them perfect for layering during cooler weather.

Men’s Weekend Outfits 

Southern Tide Sport Shirts and Skipjack Polos are perfect for Charleston. Lightweight and breathable, these shirts are perfect for transitioning easily from day to night. Pair with performance shorts for warm Charleston days. With a sleek cut and versatile color options, they're a must-have for casual outings or weekend adventures.

For cooler days and nights, men’s casual pants combine classic style with modern functionality. Ideal for transitioning from day to night, they're perfect for everything from a stroll downtown to a dinner date. Choose a performance vest, pullover or quarter-zip for added comfort and warmth.

Southern Hospitality and Southern Style

In just a weekend, Charleston offers a rich array of experiences, from historic charm and luxurious accommodations to mouthwatering cuisine. With so many fantastic dining and lodging options, each moment in this city is an opportunity to savor the best of Southern hospitality and culinary delights. 

Whether you're staying at a hotel in Charleston, SC, or dining at its renowned eateries, Charleston will leave you with lasting memories and a desire to return. And when it’s time to plan your next vacation, whether it’s a trip to 30A or a weekend in Nantucket, remember to bring your Southern charm with you!

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