4 Days in Historic Charleston, South Carolina

Travel advisor Ronit Margolis standing in the door in yellow top
Curated By

Ronit Margolis

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  • Domestic Travel

  • USA

  • South Carolina

  • Charleston

  • Boutique Travel

  • Couples Travel

  • Food & Wine

  • Historic

  • Local Culture

  • Local Cuisine

Road lined with cars, trees and buildings during daytime
Curator’s statement

From swanky architecture to hidden gardens, Charleston is where history meets modern. The city is like a living painting, with its cobblestoned walkways and old world charm. You are sure to love this vibrant, foodie city!

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Where to stay

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The Dewberry Charleston

Charleston’s reigning style stay overlooking Marion Square, with a popular terrace lounge and must-visit rooftop bar.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Hotel Bennett

Named #1 luxury hotel in the US, this chic Charleston hotel is perfect for romantic and girls trips with private club experiences.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

The Ryder Hotel

Trendy boutique hotel with an outdoor pool and retro restaurant close to Charleston's shops and restaurants.

Fora Perks
  • $25 food / beverage credit.

  • Welcome treat in room on arrival.

  • Upgrade & guaranteed late check-out.

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Travel advisor Ronit Margolis standing in the door in yellow top

Unlock perks by contacting Ronit to book your trip.

Day 1: Explore Rainbow Row and visit the Pineapple Fountain

Pineapple shaped fountain during daytime

See and be seen at the Restoration Hotel, a restored boutique property in the heart of downtown. Grab a coffee at the Rise Coffee Bar before heading out for the day. Plan on visiting Rainbow Row, this famous collection of 13 pastel homes creates the longest line of Georgian row houses in the country, so plan plenty of time for admiring the houses and then make sure you visit the famous Pineapple Fountain at Charleston Waterfront Park. After all that walking you'll be hungry for Leon's Oyster Shop and its famous mouthwatering hush puppies and fried chicken.

Day 2: Walk around the City Market

Street lined with buildings with cloudy skies during daytime

Wake up early and take a walk to the City Market, a historic four block city market that is over 200 years old and has vendors of food, art and crafts. Explore historic downtown Charleston for a horse drawn carriage tour and visit a civil war monument. Then walk down King Street for some of the best shopping and have lunch at 167 Raw — a line starts half hour before opening, no wonder the po'boys and oysters are the best in town! After a nice nap, head over to The Hotel Bennett for champagne and cocktails at Fiat Lux, a great place for date night or a drink with the girls, and have their signature drink, Don't Kale My Vibes.

Day 3: Enjoy a Beach day at Sullivan's island

Aerial view of land with houses next to body of water during daytime

Head north out of downtown Charleston to Sullivan's island, one of the three area beaches in Charleston. Sullivan's Island is known for its impressive beach homes, smooth sand beaches and popular restaurants on its main streets. My favorite is The Obstinate Daughter — try the gnocchi or go downstairs for a gelato after exploring the beach. After a long day at the beach, unwind for happy hour at The Citrus Club At The Dewberry, this modern chic rooftop bar is perfect with its unobstructed views of the city and sea, and enjoy citrus-inspired cocktails and some appetizers before you hit the pillow.

Day 4: Visit Merion Square and the Haunted Historic District

White tables and chairs in a room with green walls during daytime

Start your day at La Patisserie Bakery at the chic and charming Hotel Bennett and enjoy the fresh pastries and strong coffee which people watching with the locals and out-of-towners. If you are in Charleston on the weekend you can enjoy its farmer's market in Merion Square. Book a Charleston Ghost and Graveyard Walking Tour to view famous tombstones and explore the streets and alleyways in the Haunted Historic District at night while listening to stories of ghosts, haunted houses and superstitions. End your day at Poogans Porch on Queen Street for low-country cuisine — order the fried green tomatoes and fried pickled okra and save room for their famous pecan pie.

Travel advisor Ronit Margolis standing in the door in yellow top

Travel Advisor

Ronit Margolis

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