The Ultimate Guide to Charleston: On and Off the Peninsula
Why the Charleston area?
It’s no secret that Charleston is a hot-spot city right now in terms of both population and tourism growth.
The Southern charm, colorful streets, exciting hospitality scene, and nearby beach access are just a few of the things that make Charleston special and make so many people want to see the city for themselves. Charleston has certainly changed and evolved a lot over recent years, and the city is busier than ever before.
However, despite the crowds and activities that may seem a little too touristy, there’s still a way to experience the classic local charm of Charleston and make the most of your time in the Holy City and the surrounding areas.
This 5-day Charleston itinerary gives you two days to explore the city and its nearby beach neighborhoods before heading out to the barrier islands, combining all of the best things that the South Carolina lowcountry has to offer.
Our 5-Day Charleston Itinerary at-a-Glance
About Charleston | Where to Eat & Where to Stay
Days 1-2:Local Favorites and Best-Kept Secrets in Charleston
Off the Peninsula: Where to Go and What to Do
Days 3–5: Exploring Charleston’s Barrier Islands in Style
ABOUT CHARLESTON
Charleston is one of the oldest cities in the United States, founded in 1670 and deeply shaped by centuries of American history.
Downtown is filled with colorful row houses, grand historic homes, cobblestone streets, and iconic landmarks that showcase the city’s distinctive architecture and Lowcountry charm. From the Battery and Rainbow Row to the charming streets of South of Broad, the city is both elegant and full of character.
With its coastal setting, celebrated food scene, Southern hospitality, and unmistakable architecture, Charleston truly has a personality all its own.
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Where to Stay in Charleston
There are so many amazing hotel options in Charleston, but choosing one that truly immerses you into the city is key for ensuring a truly memorable and personalized experience.
Here are a few of my favorites:
HOTEL BENNETT
Located in the heart of it all on King Street and overlooking Marion Square, Hotel Bennett is a five-star luxury property that looks to combine European influences with Southern hospitality to create a one-of-a-kind Charleston experience for all of its guests.
A stay at Hotel Bennett is designed to be lavish and indulgent in every detail, from spacious rooms and on-site fine dining to the rooftop pool. Guests can also book access to the hotel’s King’s Club, which offers exclusive access to private spaces, all-day dining and an open bar, and a personal concierge.
It’s no surprise that Hotel Bennett is voted the #1 hotel in Charleston by Conde Nast Traveller.
THE DEWBERRY
Maybe you’re looking for a property that has all the luxury of Hotel Bennett with more of a modern look that reflects all of the energy, charm, and color of the city.
The Dewberry is a pinnacle of the Charleston hotel scene and refers to its hospitality approach as “Southern Reimagined,” looking to encapsulate both the past and present of the city in its design and guest experience.
Named the Best Independent Hotel in the World by Virtuoso in 2025, The Dewberry offers truly unique amenities, like complimentary bicycles and mat Pilates classes hosted every Saturday with views over the city. Of course, the rooms are masterful and comfortable, and the service is outstanding.
THE CHARLESTON PLACE HOTEL
The Charleston Place Hotel truly brings you back in time and into the history of the Lowcountry region. The property is modeled after the iconic historic homes and architectural styles that you see in Charleston and throughout the South.
A few things that make this property special are “The Club,” which offers exclusive accommodations, a private lounge, and personalized butler service, and the fact that the hotel has its own shopping center on-site featuring known brands like Johnnie-O and Sezane.
The Charleston Place, as well as the other options listed, are all located downtown just steps from the main streets and sights, making your time in Charleston even more convenient and accessible.
You really can’t go wrong with any of these options, and I’d love to help you figure out which one is best for you!
Charleston's historic streets, ocean views, and green spaces make this city so inviting year round. Photo credit: @leoheisenberg
HOW TO SPEND FIVE DAYS IN CHARLESTON
Days 1-2: Local Favorites and Best-Kept Secrets in Charleston
Charleston has lots of growing neighborhoods, local experiences, and a fantastic restaurant scene.
For your first two days in the city, I’ll be breaking down where to go, what to do, and where to eat, which includes the main can’t-miss sights as well as some options you may not have heard of before.
A great way to plan out your two days would be to explore the main peninsula on day one and venture out to nearby neighborhoods and islands for day two.
Charleston’s Best Neighborhoods
These three are the classics. If this is your first time in Charleston, you’ll want to start with these neighborhoods:
South of Broad—a largely residential neighborhood, South of Broad is a great neighborhood to wander around and take in all the historic homes that seem to transport you back in time to the Antebellum South. East Bay Street is home to the famous Rainbow Row, and nearby are several old homes you can visit inside, like the Heyward-Washington House.
French Quarter—a very historical area of the city, the French Quarter is where you’ll find a lot of museums and art galleries that pay homage to the city’s establishment and those who defined it. Consider visiting the nation’s only French Huguenot Church or the South Carolina Historical Society Museum. But if museums aren’t your favorite, this neighborhood has lots of other great spots like Charleston City Market and Waterfront Park.
King Street—technically divided into Lower and Upper King, this is Charleston’s hotspot for shopping and dining. You’ll find a lot of name-brand stores here, but along Lower King, you’ll still be able to find locally owned antique stores, galleries, and bookstores.
Familiar with Charleston and looking for something more off-the-beaten path?
Cannonborough-Elliottborough—This neighborhood provides a much better sense of what Charleston looks like in the modern day and helps show the true lifestyle of the city. It’s further removed from the tourist scene but still has plenty of exciting places and new development to offer. This neighborhood is close walking distance from King Street and home to a lot of students and young professionals. There are lots of great boutique and local shops and some of the best restaurants in the city. Enjoy walking around, shopping, eating, and people-watching.
Charleston Restaurant Recommendations
Charleston has lots of great local dining options featuring almost any cuisine you can think of.
Here’s a short list of options:
Felix—French-inspired bistro with a lively atmosphere
Delaney Oyster House—upscale oyster bar and seafood spot
Vern’s—refined neighborhood restaurant with seasonal Southern fare
Bodega—casual sandwich shop and late-night hangout
Babas—cozy neighborhood café serving French-inspired dishes
167 Raw Bar—casual seafood spot known for lobster rolls and oysters
Frannie & The Fox—rustic Italian restaurant with wood-fired dishes
Melfi’s—classic Italian with handmade pasta and a lively atmosphere
The Daily—casual café serving breakfast, lunch, and coffee
Little Jack’s Tavern—a laid-back neighborhood tavern with elevated bar food
Chubby Fish—an intimate seafood restaurant with creative, seasonal dishes
Southbound—casual neighborhood spot with Southern-inspired food and cocktails
Sorelle—upscale Italian restaurant with a stylish, lively setting
Shiki—small Japanese restaurant known for sushi and traditional dishes
Another view of Charleston’s historic downtown. Photo credit: @cssilver
Off the Peninsula: Where to Go and What to Do
For your next full day in the city, take this time to wander out a little further and explore some of Charleston’s nearby neighborhoods off the main peninsula, some of which offer beach access.
Mount Pleasant—just across the Ravenel Bridge from downtown Charleston, Mount Pleasant offers a more relaxed, residential feel while still having plenty to explore. The Old Village is especially charming, with tree-lined streets, historic homes, and locally owned shops and restaurants along Pitt Street. If you’re looking to get out into nature, head to Shem Creek for waterfront views and walking paths, or visit the nearby Patriots Point Naval & Maritime Museum.
Sullivan’s Island—a laid-back beach town just outside Charleston, Sullivan’s Island is known for its wide, quiet beaches, historic homes, and small-town atmosphere. Spend the day walking along the shoreline, exploring the island’s historic sites like Fort Moultrie, or wandering Middle Street, where you’ll find a handful of local restaurants and shops. It’s a great spot for a slower-paced afternoon away from the busier parts of Charleston.
Where to Eat
A few great places to enjoy an easy lunch or go to dinner include:
Obstinate Daughter—popular neighborhood spot serving Italian, French, and Southern-inspired dishes
Saltwater Cowboys—laid-back waterfront restaurant with seafood and Lowcountry favorites
Post House—cozy neighborhood inn and restaurant with elevated Southern fare
The Red Drum—a casual seafood spot with Southern and coastal-inspired dishes
Ruby’s Bagels—local favorite for fresh bagels and breakfast sandwiches
The Wreck—no-frills seafood shack known for fresh local catch
Locals—casual neighborhood restaurant with burgers, sandwiches, and seafood
Cuoco Pazzo—modern Italian restaurant with handmade pasta and seasonal dishes
Boxcar Betty's—a casual spot known for crispy fried chicken sandwiches
The Longboard—laid-back coastal restaurant with bowls, tacos, and sandwiches
Sullivan’s Fish Camp—upscale coastal spot serving seafood and classic beach-town favorites
Co-Op—casual café and market serving sandwiches, salads, and breakfast favorites
Views of the Ravenal Bridge to take you off the peninsula for your next destinations. Photo credit: @cmalquist
Days 3–5: Exploring Charleston’s Barrier Islands in Style
Charleston has great local beach access and so many great nearby barrier islands to choose from for the remainder of your trip. These areas have both iconic established resorts and newly developed, exciting properties for you to choose between, both about an hour outside of the city.
Kiawah Island Golf Resort
Kiawah Island is one of the most popular beach spots outside of Charleston, and Kiawah Island Golf Resort is the crown jewel of it.
This is a classic 5-star resort with every feature and amenity you’d expect. Kiawah offers several world-class golf courses like the famed Ocean Course, as well as other outdoor and fitness activities like tennis, pickleball, padel, and biking.
You can stay at The Sanctuary, the main oceanfront hotel property, or rent a villa or cottage for larger groups. There are several dining options ranging in setting and cuisine from steakhouses to poolside bars and coffee shops, as well as a luxurious spa to enjoy as well.
Something that also makes Kiawah Island Golf Resort unique if you’re traveling with your family or children is the amount of kid and family-friendly activities they offer for all ages. Kids can attend the resort’s various camps and participate in activities like sports, crafting, nature exploration, and outdoor challenges.
There is definitely a version of Kiawah Island Golf Resort for everyone.
The Dunlin, Auberge Collection
The Dunlin, a newer property by Auberge, is unique for its riverside setting along the Kiawah River on Johns Island.
Considered the #1 resort in South Carolina by Travel + Leisure, The Dunlin is truly special and gives you a true Lowcountry experience as though you live in a luxury cottage along the intercoastal waterways.
The resort is designed to feel coastal and cozy with intimate details that make you feel right at home. Choose from a room, suite, or bungalow, enjoy any of the three restaurants on-site, and book an expertly curated, French-inspired spa treatment at Aster.
The property features 20 miles of forested pathways for long walks and offers kayaking and paddleboarding out on the river. For more activities and experiences, The Dunlin has endless options of things to do, from pickleball, mahjong, fishing, horseback riding, wildlife safaris, yacht charters, and more.
Of course, they have a luxury resort pool as well, but if you’re worried about not having direct beach access, the resort offers transportation and chairs to visit any of the nearby shores.
There isn’t an Auberge property that isn’t absolutely outstanding, and The Dunlin certainly seems to be the latest and greatest of them.
Whatever resort you choose, spend the rest of your time in South Carolina relaxing, enjoying nature, and partaking in any resort-offered experiences that you please!
The beautiful beaches and palms of the South Carolina coast! Photo credit: @scafs
Want to Learn More About the Lowcountry in Georgia?
Read my 5-Day Savannah & Georgia Coast Itinerary with hotel recommendations and more incredible local resorts!
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Final Thoughts: Charleston and the Barrier Islands
There’s a reason the Lowcountry continues to grow in popularity, but what I love about this Charleston Guide is that it gives you the chance to experience all that the area has to offer in the city and beyond.
Start in Charleston, where you can walk historic streets, discover locally owned restaurants and boutiques, and experience a city filled with Southern history and culture. Then, head out to the beaches, where the pace slows even more and you can spend a few days enjoying everything the barrier islands have to offer at any of the incredible resorts nearby.
In just five days, you get a little bit of everything: a historic Southern city, incredible food, boutique hotels, beautiful beaches, outdoor activities, luxury resort time, and plenty of opportunities to slow down and enjoy where you are.
And like most itineraries I share, this one can easily be adjusted depending on how you like to travel. Add another night in Charleston, spend an extra day on the coast, make it a couples’ getaway, or bring the entire family.
As a travel advisor, my mission is to help design a trip that is curated to you and your travel companions. Ready to plan a trip to the Lowcountry? Reach out and let’s get started.
The process is easy for you, and thanks to my partner connections, I can ensure a South Carolina adventure that is both special and memorable.
Here are some quick links to help you get started:
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