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A boisterous Southern burg with a heart of gold, the Holy City of Charleston is full of fun and epic adventures. From a historic downtown to a bustling waterfront, beautiful beaches to Civil War sites, this SC gem is the perfect place to spend a weekend.

With so much to see and do throughout both the downtown area and the seaside, first-time Charleston visitors may have a hard time planning an itinerary that best showcases the city’s charms—but with this two (or three!) day itinerary, both first-time travelers and return visitors will find something to suit their fancy. A choose-your-own-adventure that spans centuries and roams neighborhoods by foot, bike, ferry, and car, this epic guide has enough Southern-style stops and distinctive destinations to fill a weekend (long or otherwise). From hotels to eateries to outdoor attractions and historic haunts, there’s something here for every vacationer looking for an unforgettable trip to Charleston.


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Where To Stay In Charleston

One of the best things about Charleston is its walkability (or bike-ability)—exploring the downtown area is a snap on foot; while the city’s relatively small size means that visitors are never more than a hop, skip, and a jump away from a number of diverse and exciting experiences. This also makes setting up camp relatively easy: with plenty of top-notch downtown accommodations that put vacationers in the heart of the city’s hustle and bustle and a number of nearby beach stays offering unique seaside escapes, there’s something for everyone looking to experience the best of the Holy City.

  • The French Quarter Inn A stunning boutique retreat, this French Quarter gem is one of Charleston’s best hotels Rates start at $439 and up per night.
  • Zero George Hotel is A historic hip haven that’s oh-so Charleston Rates start at $499 and up per night.
  • The Dewberry is A mid-century landmark re-imagined as a stylish; sumptuous stay Rates start at $436 and up per night.
  • Tides Folly Beach Oceanfront views meet resort-style luxury that’s only minutes from downtown Rates start at $229 and up per night.
  • Emeline is A chic and timeless property tucked away in the heart of downtown Rates start at $369 and up per night.
  • The Spectator is all Southern glamour and charming Charleston style Rates start at $579 and up per night.

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Day One: Go Downtown

Start an epic weekend in Charleston by taking a stroll (or bike ride) through its bustling and oh-so-historic downtown area. Whether visitors decide to neighborhood hop, see the sights, and stick to the basics, or get adventurous and go off the beaten track, there’s plenty to see and do in this distinctive downtown to fill any first day in Charleston.

  • Grab a morning brew at Second State Coffee, then take a leisurely stroll on a 20-minute walk to Babas on Cannon for a late breakfast/brunch/early lunch and soak up the friendly vibes—or take a bite to go at Battery & White Gardens
  • Rent a bike and head across the Ravenel Bridge to Mt. Pleasant (and spend the afternoon, see below), or sign up for a Walking Tour to hear all about Charleston’s hidden histories and stories. For bike rental, use the local bike share or rent local; and for walking tours, Charleston Sole hits all the city’s best attractions.
  • Spend the day in Mt. Pleasant A waterfront gem just over the bridge from Charleston, Mt. Pleasant has plenty of history and charm—stroll the Mount Pleasant Pier, visit Memorial Waterfront Park, and hang out harbor side or get historical with a visit to the Charles Pinckney House, Boone Plantation, or Old Village District.
  • Stay in Mt. Pleasant for a tasting at Westbrook Brewing Co., then head back over the bridge. Stayed in Charleston for the day? Then head to The Ordinary for early-ish Happy Hour oysters and a classy, curated cocktail.
  • Early evening is perfect for a walk, and The Ordinary’s sister restaurant FIG is just 20 minutes away—plenty of time to work up an appetite for the fresh, bistro-style vibes and eclectic menu.

Day Two: Historic Haunts Or Outdoor Adventures?

The second day of this Charleston itinerary is a choose-your-own-adventure that gives vacationers the chance to further customize their trip--and gives those with an extra day a great way to explore even more.

Historic Haunts

History buffs will revel in Charleston’s myriad of diverse attractions that are an intrinsic part of the city’s identity and cultural heritage. From its Civil War past to its stately architecture, to its museums and carriage rides(!), there’s an adventure around every Charleston corner.

  • Explore Edmondston-Alston House and Middleton Place for a taste of Charleston’s Civil War-era history. Optional Stop: Magnolia Plantations and Gardens (transportation necessary)
  • Head down to the Battery for lunch at Amen Street Fish & Raw Bar; afterward, visit the Patriots Point Naval & Maritime Museum.
  • Return to the French Quarter and explore the Charleston City Market and stroll Rainbow Row, home to some of the city’s most iconic historic homes
  • Have an amazing dinner in one of Charleston’s most historic properties, Charleston Place, home to the elegantly upscale Charleston Grill

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Outdoor Adventures

Charleston is not only known for its stunning seaside and scenic waterfront but for its plethora of parks and green spaces that make it easy to find both relaxation and recreation.

  • Explore Charleston’s Parks One of the city’s largest, Hampton Park is a beautiful spot to pack an afternoon picnic, walk, ride, or simply soak up the scenery. Optional Stop(s): Charleston’s smaller parks are also a great place to spend some time, both Washington Square and Chapel Street Fountain Park are close to Charleston’s best neighborhoods
  • Have Happy Hour snacks and drinks at Butcher & Bee
  • Charleston at Night Take the long way to dinner at the swanky, 1920s style-spot Prohibition. Optional Stop: Charleston’s nightlife is just as happening as its daytime destinations. Head over to nearby King Street spot Ink Cocktail Lounge & Nightclub for a rooftop nightcap, dancing, and vibes

Charleston is the epitome of large-town/small-city Southern vibes. Its laid-back, relaxed atmosphere is simply a scenic and historical backdrop to its bustling, exciting vibes filled with a plethora of fun attractions and destinations. And this two (or three) day itinerary is the best way to make the most of the Holy City and truly get a taste of what makes this South Carolina town so very special.