Curator’s statement
Charleston is a city steeped in history, where cobblestone streets and centuries-old architecture create a charming, timeless atmosphere. Its blend of Southern hospitality, vibrant culture and world-class cuisine makes it a welcoming and memorable destination. The scenic waterfront and historic landmarks offer an unparalleled sense of place that captivates visitors and locals alike.
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Day 1: Arrive and check in
Check into your hotel and take a moment to relax and settle into your room. Prepare for an unforgettable dinner at one of Charleston’s iconic dining spots, known for its fresh seafood. Head to Leon's Oyster Shop or 167 Raw Oyster Bar. Both are popular and don't take reservations, but you can enjoy a drink at their lively bars while you wait for a table.
Day 2: Explore all Charleston has to offer
Begin your day with complimentary breakfast, courtesy of booking through Pink Palmetto Travel. Afterward, take a stroll to Rainbow Row to admire the iconic, colorful homes and snap a photo at the famous pineapple fountain, all before the midday heat sets in. Stop by Harken Cafe for a refreshing coffee and a light lunch. Then make your way to the historic Charleston City Market, where you can browse a variety of locally-made artisan trinkets — perfect for an authentic souvenir. From there, head up King Street, known for its top-tier shopping, where you'll find everything from boutique shops to designer stores. Return to your hotel for a bit of rest before heading out again to dine at one of Charleston's beloved spots. You can try either Vern's for an upscale, laid-back vibe or Chubby Fish for a fresh seafood experience.
Day 3: Drive to Mount Pleasant
Start your day with another delicious breakfast before making your way to The Works yoga studio, where you can enjoy a rejuvenating stretch to kick off your weekend. Next, take a short drive to Mount Pleasant. Enjoy a leisurely lunch at Saltwater Cowboy's, accompanied by live music and refreshing afternoon drinks along the scenic Shem Creek. Later, return to Charleston for sunset drinks at The Citrus Club. Here you can soak in breathtaking views of the city, before savoring an inventive Asian fusion meal at Pink Bellies.
Day 4: Say goodbye to Charleston
Wrap up your weekend with a final, complimentary breakfast to fuel your day. Then, make your way to Sullivan's Island for a few hours of sun, sand and surf, soaking in the serene beach atmosphere. Afterward, enjoy a laid-back lunch at The Co-Op before heading back to your hotel to check out and make your way home, already dreaming of your next Charleston getaway!
Travel Advisor
Dylan Patterson
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For more inspiration and insider recommendations, visit our Charleston page.