5-Day Itinerary

Romantic Getaway at Wentworth Mansion

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.

Please note: many restaurants and attractions are walkable from Wentworth Mansion®. If you do not have a car, we recommend Uber, Lyft, or rickshaw.

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’!
  • Explore Wentworth Mansion’s beautiful grounds and common areas, then get settled in your luxurious room. Be sure to rehydrate with a complimentary bottle of water or soft drink.
  • Head to the Sunporch at 5:00 pm to enjoy a glass of wine and some hors d’oeuvres from Circa 1886 Restaurant while you mingle with other guests before heading out to dinner. 
  • Enjoy a romantic dinner at Peninsula Grill. Peninsula Grill offers a range of dishes inspired by the local Lowcountry cuisine, which combines modern Southern cooking techniques with fresh seafood, prime cut steaks and local produce
  • 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 Wentworth Mansion for a delicious cordial before retiring to your beautifully room where a house-made chocolate awaits.
Day 2

Thursday

  • Start your day with a great early morning workout with complimentary passes to a local health club, then return for delicious full breakfast at Circa 1886, our on-site restaurant.
  • Take a stroll around the Battery and White Point Garden, to admire historic mansions and capture 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 on iconic King Street. 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 craft cocktail at Doar Bros, a popular cocktail specializing in modern creative cocktails, classic cocktails, and shareable small plates.
  • Enjoy a romantic dinner at Circa 1886, our award-winning, fine dining establishment, tucked within the original carriage house.
Day 3

Friday

  • Enjoy a quick pastry and coffee in the Harleston Parlor, enjoy breakfast at Circa 1886, or head out to grab a coffee at one of many notable cafés— Harken Café is one of our favorites!
  • Recreate the Rowboat Scene from “The Notebook” at Cypress Gardens or explore one of the many nearby plantations. Middleton Place and Magnolia Plantation & Gardens are two of our favorites. 
  • Shop and explore historic Charleston City Market for local crafts, art, and other Charleston products or iconic King Street—famous for the perfect local and regional shops and boutiques, art galleries, and antiques.
  • 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.
  • Enjoy another romantic dinner at Marbled & Fin, a new fine dining establishment in Charleston featuring the finest beef and seafood.
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 Church & Union, a posh New American dining destination and cocktail bar in a former church with dramatic decor.
  • Get on the water for a romantic sunset sail on the Schooner Pride. Beer, wine, and soft drinks are also available for purchase. Cheers!
  • End your day of exploration with a final romantic dinner at Lowland, a cozy Southern Tavern serving timeless classics and luxurious comfort food. If you would like something on the more casual side, we suggest The Grocery, a neighborhood gathering place featuring an innovative seasonal men plus signature cocktails, wine & craft beers.
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!

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.

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