The Perfect Weekend in Downtown Charleston

Advisor - Katherine Duggan
Curated By

Katherine Duggan

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  • Charleston

  • Arts & Culture

  • Boutique Travel

  • City Travel

  • Couples Travel

  • Domestic Travel

  • Group Travel

  • Luxury Travel

  • Historical

  • Local Culture

  • Foodie

two people walking next to colorful buildings during daytime
Curator’s statement

After living in Charleston for five years, I think I have finally eaten, drank and experienced everything the city has to offer (although there is always something new opening up). The city is historic and quaint by day and the life of the party by night with something for everyone no matter your interests. As long as you love eating, drinking and exploring, this itinerary is the perfect way to spend the weekend in Charleston!

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Insider knowledge

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Where to stay

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.

Zero George

Sophisticated chic Charleston home with an air of Southern charm perfect for laying back on the balcony or enjoying a bike ride around town.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

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

The Charleston Place

Iconic Charleston landmark with lavish accommodations, legendary service and experiences to elevate your experience in the Southern city.

Fora Perks
  • $100 food / beverage credit.

  • $45 daily breakfast credit.

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

Advisor - Katherine Duggan

Unlock perks by contacting Katherine to book your trip.

Day 1: Arrive in Charleston

two people standing on a balcony overlooking a city

1pm: Check in to your hotel/new home for the weekend, drop off your bags and begin exploring all that Charleston has to offer. Walking to the centrally located Waterfront Park to see the famous pineapple fountain and views of the harbor is a great start. You may even be lucky enough to see dolphins swimming by the pier.

3pm: If you need something to quench your thirst, the Rooftop at the Vendue is a two-minute walk away and offers casual drinks and food with a great view (head to the upper level for an even better view).


If you need a sweet to bring your energy up, visit Carmella's Cafe and Dessert Bar. Yes, they have a full bar including chocolate martinis and drunken shakes!

4:30pm: On your way back to the hotel to get ready for dinner, walk through the Charleston City Market that stretches four blocks in the center of Market St. With over 300 local vendors selling their handcrafted items it's the best place to find souvenirs to bring home to friends and family.

7pm: Dinner at Malagón. A locally owned authentic Spanish tapas restaurant and mercado. The menu is designed for small plates to be shared by everyone at the table to experience a wide variety of flavors. If going with a larger group the paella is a must.

Notes: The restaurant is small and very popular, so make your reservation on Resy 30 days in advance. Only wine and beer are served.

Bonus: If you still have room in your stomach for a nightcap, I recommend The Belmont for some of the best cocktails in town.

Day 2: Historic Adventures

two people sitting at a wooden bar

9am: Free breakfast at your hotel if staying with one of our amazing partnered hotels. If not, no worries, there are countless cafes to grab the perfect latte and pastry.
Some of my favorites are Babas on Cannon, Harken Cafe, Second State and La Pâtisserie.

10am: Start off at the Saturday Farmers Market in Marion Square. Walk through the city's central meeting spot to see local vendors selling food and crafts and meet the adorable local dogs.

10:30am: Since most of the hotels in Charleston have free bike rentals it's the perfect opportunity to ride through the South of Broad neighborhood to admire the historic mansions and cobblestone streets. Stop by Rainbow Row for a photo op of the most colorful houses in Charleston.

1pm: After working up an appetite, arrive at Gaulart & Maliclet known as Fast and French. Popular with locals for their informal bistro menu and pet-friendly outdoor tables on picturesque Broad St.

3pm: Tour the historic Nathaniel Russell House to learn about Charleston's rich history and admire its beautiful garden.

6pm: Cocktails at The Citrus Club on the rooftop of the Dewberry Hotel. The highest rooftop bar in Charleston with views of both downtown and the water. In colder months they have cozy blankets and fire pits.


If the weather doesn't allow that, try the Living Room, their mid-century modern downstairs bar with live music starting at 7pm on Saturdays.

Bonus: if you are staying at The Dewberry you can request one of their complementary Volvo cars to take you to your next stop.

8pm: Dinner at The Restaurant + Bar at Zero George (A must for foodies or if you are celebrating a special occasion). It's one of the only tasting menus in Charleston and consists of six courses plus a number of surprise amuse bouches by Executive Chef Vinson Petrillo.

Day 3: Shopping and Admiring Art

two people walking in front of brick wall next to a palm tree

11am: Brunch at The Darling Oyster Bar for classic Charleston brunch dishes and the most extravagant Bloody Marys in town -overflowing with shrimp, a hushpuppy and full crab claw!

1pm: Walk down King Street for boutique shopping and if it's the second Sunday of the month the lower part of King St. becomes pedestrian only with musicians, vendors and outdoor dining. This is also where you will find some great art galleries.

And if you are a real art enthusiast check out the Gibbes Museum of Art.

3pm: Time to say goodbye and begin planning your next visit to Charleston after falling in love with this charming yet electric city.

Advisor - Katherine Duggan

Travel Advisor

Katherine Duggan

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This guide is part of our ongoing series on travel to South Carolina.