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Long Weekend in Charleston: 4 Days of Dining & Exploring

ByGlenn G.

Savor culinary delights and discover historical sites on this 4-day itinerary in Charleston. Enjoy the rich flavors of Lowcountry cuisine at some of the city’s best restaurants, from classic shrimp and grits to innovative seafood dishes. Each meal is a testament to Charleston’s vibrant food scene, which beautifully complements the city’s charming atmosphere. This itinerary includes leisurely strolls through picturesque neighborhoods and day trips to nearby beaches and historical forts.

Long Weekend in Charleston Itinerary

Day 0: Arrive in Charleston

Day 1: Explore Downtown Charleston

Day 2: Mount Pleasant & Fort Sumter

Day 3: Kiawah Island Beach Day

Day 4: Sullivan’s Island & Fly Home

Itinerary Map

This itinerary spans 4 days in picturesque Charleston, South Carolina, relying on a rental car to navigate beyond the city. Click on the image to launch an interactive map.

Itinerary Snapshot

A quick view of what we did and where we stayed. Here are the trip’s activity highlights, with accommodation links.

Accommodations & Dining

Itinerary Photo Highlights

Scroll through for highlighted photos from each day of the itinerary.

Day 1 – Millers All Day
Day 1 – Rainbow Row
Day 1 – The Ordinary
Day 2 – Fort Sumter
Day 2 – FIG
Day 3 – Kiawah Island
Day 3 – Lenoir
Day 4 – Fort Moultrie
Day 4 – Sullivans Island
Day 4 – Obstinate Daughter

Itinerary Details

Day 0 – Arrive to Charleston

  • Pick up a 4-day rental car from the airport
  • Check into The Iris Charleston

Day 1 – Explore Downtown Charleston

  • Brunch at Miller’s All Day
  • Explore downtown Charleston
  • Shop along King Street
  • Wander the streets of the French Quarter
  • See the pretty houses along Rainbow Row
  • Dinner at The Ordinary

Day 2 – Mount Pleasant and Fort Sumter

  • Coffee at Brown Fox Coffee
  • Pick up take-out lunch from 167 Raw Oyster Bar
  • Sign up for a Historic Fort Sumter Tour
  • Eat the take-out lunch on the boat cruise to Fort Sumter
  • Learn the important history of the Fort from the 1800’s
  • Dinner at FIG

Day 3 – Kiawah Island Beach Day

  • Breakfast at babas on cannon (and buy lunch sandwiches & snacks there)
  • Drive to Beachwalker Park on Kiawah Island
  • Take a walk along the Kiawah beach and relax on the beach
  • Dinner at Lenoir

Day 4 – Sullivan’s Island & Fly Home

  • Bagel breakfast from Holey City Bagels
  • Check out of hotel
  • Explore Fort Moultrie on Sullivan’s Island
  • Lunch at The Obstinate Daughter
  • Stroll along the beach at Sullivan’s Island
  • Head back to Charleston Airport to fly home

Itinerary Tips

  • The Iris was a fantastic luxury apartment off of Upper King Street – we loved having more space, and it would be great for longer stays with the kitchenette and laundry machine. It was a decent price for downtown Charleston; however, it was a ~1.5 mile walk to the French Quarter.
  • Make reservations well in advance for the famous restaurants – The Ordinary and FIG both open up for booking 28 days in advance on Resy.
  • It is possible to get a walk-in seat at the bar at FIG if you go early – we were # 7 & 8 in line at 4:40pm (restaurant opens at 5:00pm).
  • Everything at FIG was AMAZING! This might be our favorite meal ever.
  • If you only have 3 dinners in Charleston, swap out Lenoir for Husk. We had eaten at Husk on a previous trip and loved it.
  • 167 Raw Oyster Bar does not take reservations and is quite small, so it works great for take-out.
  • We met friends for coffee in Mount Pleasant one morning – but otherwise would recommend just staying in Charleston for all of your breakfasts. Poogan’s Porch is known for a delicious Southern brunch.
  • Notable dishes:
  • Biscuits & Gravy at Miller’s All Day
  • Crispy Oyster Sliders, Raw Oysters, Ember Roasted Okra at The Ordinary
  • Lobster Roll and Local Farm Salad with Scallops for 167 Raw Oyster Bar take-out
  • Burnt Eggplant & Housemade Cottage Cheese, Ricotta Gnocchi, Vine Ripe Tomato Tarte Tatin, Bouillabaisse, and Sticky Sorghum Pudding at FIG
  • Blueberry BBQ Chicken Wings at Lenoir
  • Frogmore Chowder at The Obstinate Daughter

if I Had More Time…

Other restaurants that were recommended to us include Edmund’s Oast, Leon’s Oyster Shop, and The Darling Oyster Bar.

If we spent more time in Charleston proper, there are many museums we could have visited.

Itinerary Photos

Additional photos capturing favorite memories from the Long Weekend in Charleston trip…

Traveling internationally for 25+ years. Technology executive by day. Guitarist by night.

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