Planning a weekend in Charleston is all about balancing its historic charm with its fun, modern energy. Here’s a sample itinerary perfect for a group, like a bachelorette party, looking to experience the best of the city.
Reservations are a MUST: For dinner and brunch with a group, make reservations weeks or even months in advance. Charleston's best spots fill up fast.
Book Your Stay Early: Especially for a group, the best Airbnbs and hotels get booked far ahead of time.
Wear Comfortable Shoes: You'll be doing a lot of walking on beautiful but uneven cobblestone and brick streets.
Afternoon (3:00 PM - 5:00 PM): Settle In & Explore
Arrive, check into your hotel or Airbnb (Cannonborough/Elliotborough is great for being near the action).
Once settled, take a stroll South of Broad. This is your time for the quintessential Charleston photo ops. Walk along the Battery, see the grand historic homes, and get your group shot in front of the iconic Rainbow Row.
Evening (6:00 PM - 11:00 PM): Welcome Dinner & First Night Out
7:00 PM: Head to a lively dinner spot. A restaurant in the Upper King or Cannonborough area is perfect for kicking off the weekend. Think trendy but fun.
9:00 PM: After dinner, explore the bars on Upper King Street. It’s the heart of Charleston's nightlife. Start at one of the many chic rooftop bars for a cocktail with a view, then see where the night takes you.
This is your main day, so choose your own adventure!
Option A: Beach & Boat Day
10:00 AM - 3:00 PM: Head to the beach! For a funky, laid-back vibe with casual bars, go to Folly Beach. For a more pristine, upscale beach experience, head to Sullivan's Island (and grab lunch at a spot like The Obstinate Daughter).
Alternative: Charter a boat for a few hours! This is a classic Charleston bachelorette move. You can cruise the harbor, spot dolphins, and anchor at a sandbar for a swim.
Option B: City Exploration & Shopping
10:00 AM - 3:00 PM: Dive into the city. Start with some retail therapy along King Street, which has everything from high-end boutiques to unique local shops.
Explore the historic Charleston City Market to pick up souvenirs and see local artisans, including the famous sweetgrass basket weavers. Grab a casual lunch from one of the many great spots nearby.
Late Afternoon (4:00 PM - 6:00 PM): Sunset Drinks
Head to Shem Creek in Mount Pleasant. It's a 10-minute Uber ride and offers a fantastic, casual waterfront scene. Grab a drink at Tavern & Table or Red's Ice House and watch the shrimp boats and dolphins come in as the sun sets. It’s a perfect, relaxed pre-dinner activity.
Evening (8:00 PM onwards): The Big Night
8:00 PM: This is your big night out dinner. Head to one of Charleston's acclaimed restaurants for an unforgettable meal.
10:00 PM: Time to celebrate! Hit the lively bars and dance spots on Upper King. This is your night to go all out.
Morning (10:30 AM - 1:00 PM): The Farewell Brunch
You can't leave Charleston without experiencing its brunch culture. This is a non-negotiable! Head to your reserved spot for mimosas, bloody marys, and fantastic Southern brunch fare. It's the perfect way to recap the weekend's memories.
Afternoon (1:00 PM onwards): Last Look & Departure
Depending on your flight or departure time, take one last stroll, grab a coffee from a local cafe, or pick up any last-minute souvenirs before heading to the airport.