A Long December Weekend for Two

Experience the magic of Charleston during the holidays with a thoughtfully curated three-night getaway. From charming historic streets and festive lights to beautiful hotels and memorable dining, this itinerary brings together the best of Charleston for a cozy December escape.

Three nights in Charleston with historic streets, excellent restaurants, holiday markets, and a few local experiences.

Where to stay

The Dewberry Charleston

A stylish, upscale hotel overlooking Marion Square. Mid-century interiors, a rooftop cocktail bar, and an excellent downtown location.

Best for: A luxury couples’ weekend

Hotel website

Emeline

A boutique hotel in the historic district, close to the City Market, shopping, and restaurants. Relaxed, modern interiors.

Best for: Walkability and boutique charm

Hotel website

The itinerary

FRIDAY

Arrive & Explore

• Check in and walk King Street.
• Browse the shops and holiday decorations.
• Dinner at FIG for seasonal Lowcountry cooking.
• Finish with cocktails at The Dewberry’s Citrus Club rooftop.

SATURDAY

Historic Charleston & Holiday Lights

• Breakfast at a local café.
• Explore Rainbow Row, the Battery, and Waterfront Park.
• Visit the Charleston City Market.
• Dinner at Leon’s Oyster Shop for oysters and fried chicken.
• Evening at the Holiday Festival of Lights on James Island.

SUNDAY

A Charleston Christmas

• Browse the Marion Square Holiday Market.
• Lunch and shopping downtown.
• Watch the Charleston Holiday Parade at 3 p.m.
• Attend the downtown tree lighting festivities.
• Dinner at a restaurant near your hotel.

MONDAY

One Last Charleston Morning

• Coffee and breakfast downtown.
• Walk the French Quarter and visit a few galleries.
• Check out and head home.

A little off the beaten path

Bowens Island Restaurant

A casual local seafood spot known for steamed oysters and marsh views. A good alternative to a downtown dinner. Must-Visit Seafood in Folly Beach.

Pitt Street Bridge

A quiet waterfront walking path in Mount Pleasant. Great for a sunset walk and photos. Experience Mount Pleasant

McLeod Plantation Historic Site

A guided history experience focused on Gullah Geechee heritage, enslavement, and the Lowcountry’s past.

Before you go

• Reserve early: FIG and popular downtown hotels can book up.
• Transportation: Downtown is walkable. You’ll need a car or rideshare for James Island and Mount Pleasant.
• Weather: Pack layers and a light jacket for cooler evenings.
• Holiday events: Confirm start times and ticket requirements before traveling.

Travel tip: For a December couples’ getaway, choose The Dewberry if the budget allows. Its location beside Marion Square makes the holiday weekend especially convenient.