Fabulous Long Weekend in Charleston

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Advisor - Angela Marini
Curated By

Angela Marini

  • Charleston

  • Weekend Getaways

  • Food & Wine

  • City Travel

  • Long Weekend

  • Romantic

  • Foodie

  • Sightseeing

A tall, white church in a city street during a sunrise
Curator’s statement

I love Charleston for many reasons. It is a short, reasonably priced flight for all of us in the Northeast. I also adore the Southern culture and the weather and many will agree with me that the food is amazing. Charleston's food scene is off the charts. I am not kidding. It is the perfect escape for a long weekend whether it is a couples trip or a girls trip- you can't go wrong visiting this treasure of a city.

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Where to stay

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Day 1: Arrival

Facade of a red brick hotel from an outside courtyard

Arrive in Charleston after a quick Uber ride from the airport. Check into your hotel.
There are many great hotels in Charleston but the following three stand out in a big way. The Dewberry is hip, cool and in a perfect location. Hotel Bennett is as southern as it gets. It is elegant and classic and right on King Street. My other favorite is Charleston Place which is also on King Street. All three are close to dining, tours and nightlife. If you booked one of these hotels with a Fora Advisor, like me you will be in LUCK because there will be lots of complimentary perks attached to your reservation and you will likely be treated like the rockstar that you are!

Settle in to your hotel and then explore everything Charleston has to offer. Walk King Street and stop in the lovely stores. Stroll through the many parks. Walk along the water front and see Rainbow Row and think about what your next two days will be.

Plan dinner at Sorelle if you are lucky enough to snag a reservation. Have a cocktail at their beautiful bar before moving onto dinner in their dining room. After a long, delicious dinner either walk back to your hotel or hop in a cab or Uber. Have a nightcap in the lobby bar and call it a night.

Day 2: Horse and carriage tour

Aerial view of a city street

After breakfast (part of the perks I was talking about) plan on a horse and carriage tour of Charleston. You can do these tours over and over because they have many different routes. Each tour is unique. I like Old South Carriage Company because I see how well cared for their horses are. They are all clydesdales or strong working horses and they are beautiful. Bart was my horse and he was amazing. After a few tours they go back to their farm for some grazing and rest.

By midday you will most likely be hungry again. Stop in to 167 Raw for some oysters and then take a long walk enjoying the views.

Before dinner stop at one of the many rooftop bars for a cocktails. The Bennett and the Dewberry both have amazing rooftop lounges. Then off to dinner at the infamous Halls Chophouse. Their steaks are to die for. There is music in the bar area and it will be the perfect evening.

Day 3: Day at the beach

Inside dining area of a restaurant

Today, after breakfast, head to the beach. The Dewberry will arrange a beach day for you with a cooler and even provide a car! Sullivan's Island beach is just 20 minutes way. After a long, hot but enjoyable day at the beach you will want to get a bite to eat. I love the Obstinate Daughter and recommend it highly.

Back to your hotel for a quick shower and you're off to dinner. (Are you getting my food theme here?) Most of my trips revolve around restaurants. After a quick cocktail at the pink, elegant champagne bar at the Hotel Bennett, head to Vern's for dinner. This neighborhood restaurant is fantastic.

Day 4: Save room for dinner!

A platter of smoked meats and cups of various sides on a red tablecloth

Today, after breakfast, go for a long, long walk. You are going to need it because you will go for an early dinner at either a southern BBQ (Lewis BBQ) or delight in some fried chicken, champagne and oysters (Leon's Oyster Shop). Then, at dusk, head out on a Ghost Tour for some Charleston haunted sights.

Day 5: Departure

Outdoor sign for Charleston International Airport above a road

After a lovely breakfast, head to the airport for your flight home all while reminiscing about the amazing long weekend you had in Charleston.

Advisor - Angela Marini

Travel Advisor

Angela Marini

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This itinerary is part of our ongoing series on travel to Charleston. Looking for more travel inspiration? Check out my itinerary, Exploring Italy's Amazing Amalfi Coast.