5-Day Itinerary
Romantic Getaway at Kings Courtyard Inn
Charleston consistently ranks as one of the most romantic cities in the country, and it’s easy to see why. From its enchanting gas lanterns and cobblestone streets to the soft clip-clop of horse-drawn carriages and hidden alleyways, the “Holy City” sets the perfect scene for a romantic getaway. Whether you’re strolling hand-in-hand beneath the Spanish moss, savoring candlelit dinners at renowned restaurants, or watching breathtaking sunsets over the harbor, Charleston is a city that captures the heart. To help you plan the perfect escape, we’ve curated a thoughtful itinerary filled with unforgettable experiences and intimate moments.
Day 1— Welcome to Charleston!
WEDNESDAY
- Check-in is at 4:00 pm, but you are welcome to drop your bags early to start exploring the ‘Holy City’!
- Take in the Kings Courtyard Inn’s three charming courtyards and get settled in your beautiful room.
- Head to the Pineapple Courtyard at 5:00 pm to grab a glass of wine and some hors d’oeuvres while you mingle with other guests before heading out to dinner.
- Enjoy a romantic dinner at Magnolias. A staple in Charleston for over 30 years, Magnolias remains a forerunner in upscale Southern cuisine and is just a 10-minute walk from Kings Courtyard Inn.
- Enjoy a nightcap at the Gin Joint, a cozy, intimate bar/eatery serving cocktails and eclectic small plates in a 1920s-inspired setting.
- Head back to Kings Courtyard Inn for a delicious glass of sherry before retiring to your beautifully appointed room.
Day 2
Thursday
- Start your day with a delicious complimentary Continental breakfast in your room, courtyard, or breakfast room.
- Walk down King Street to the Battery and White Point Garden, admiring historic mansions and capturing stunning harbor views. Head up East Bay Street and get an Instagrammable photo to share with your friends in front of Rainbow Row, a series of thirteen colorful historic houses. Then, walk over to Concord Street and continue to Waterfront Park where you can get another romantic photo in front of the famous Pineapple Fountain.
- Rest and refresh with lunch at 167 Raw Oyster Bar, a New England style Oyster Bar just steps from Kings Courtyard Inn. The menu highlights the outstanding seafood mecca that is the East Coast!
- Embark on a guided walking tour with Bulldog Tours to learn about Charleston’s rich history.
- Enjoy a happy hour cocktail at Bar Vaute, a romantic speakeasy located beneath French restaurant Brasserie La Banque.
- Enjoy a romantic dinner at Circa 1886, our sister restaurant, tucked within the original carriage house of Wentworth Mansion®.
Day 3
Friday
- Head to Harken Café to enjoy the carbed comfort of their signature biscuit, delight yourself with the triple-chocolate decadence of the Best Friend cookie, and take it all in over a creamy cappuccino.
- Recreate the Rowboat Scene in The Notebook! Jump in the car and head to Cypress Gardens to take a self-guided boat tour through the cypress trees which goes through the same area that Noah and Allie explored.
- Shop and explore historic Charleston City Market for local crafts, art, and other Charleston products.
- Nothing says romance like a sunset walk on the beach, and Charleston has several great beaches to choose from. Folly Beach, Isle of Palms, and Sullivan’s Island are all a short distance from Downtown Charleston.
- Grab a casual dinner at Edmond’s Oast Brewing Company where you will enjoy a cozy, warm atmosphere and quality-driven, comforting food along with world-class beers, cocktails, and wine.
Day 4
Saturday
- Enjoy a healthy breakfast at Basic Kitchen, a serene, light-filled space featuring local produce and whole grains.
- Enjoy learning about Charleston’s storied past on a horse-drawn carriage ride through the cobblestone streets with Palmetto Carriage Works.
- Explore the Nathaniel Russell House Museum, an elegant 19th-century home renowned for its spiral staircase and period furnishings.
- Enjoy lunch at 167 Raw, a popular seafood spot on King Street, known for its oysters and fresh local catch.
- Take an Uber or drive to Magnolia Plantation & Gardens for a peaceful stroll through one of America’s oldest public gardens. Experience the beauty of the romantic-style garden, and, if you wish, take a guided tour of the historic house.
- End your day of exploration with dinner at FIG, a local favorite specializing in seasonal dishes made from local ingredients.
Day 5
Sunday
- For your last breakfast, head to Poogan’s Porch, a classic Southern restaurant housed in a historic Charleston single house named after Poogan, a beloved Southern porch dog, who made 72 Queen Street his home, becoming the unofficial guardian of the restaurant until he passed in 1979.
- Stroll King Street and indulge in some retail therapy. Explore a variety of boutiques, antique shops, and art galleries.
- Check out by noon but leave your bags if you don’t need to rush to the airport and continue to explore Charleston!
More Tips!
- Sunset sail or Dinner Cruise with Charleston Harbor Tours.
- Couples’ spa day at The Spa at Wentworth Mansion®.
- Romantic drive and selfies at the Angel Oak Tree, a stunning 400-year-old oak tree on Johns Island.
- Scenic drive and wine tasting at Deep Water Vineyard.
- Dinner cruise on the Charleston Princess: Watch the sun set over the water while dining aboard a luxury cruise ship.
- Live Music! Check for live music performances at local venues like the Charleston Music Hall and Firefly Distillery.
To help ensure you capture the full Charleston experience, we highly recommend booking your dinner reservations, carriage tours, and other attractions in advance. Please call 843-723-7000 if you would like our concierge team to assist you in any way.
Please note: All details in this itinerary are accurate at the time of publishing. However, events, schedules, and availability are subject to change without notice. We recommend confirming with venues or organizers for the latest updates before making travel arrangements.