Romantic Getaway at John Rutledge House 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 your escape, we’ve created this five-day romantic Charleston itinerary featuring memorable experiences, intimate dining, historic attractions, and plenty of time to enjoy the city together.
Please note: Many of the restaurants and attractions featured in this itinerary are within walking distance of John Rutledge House Inn®. For destinations farther afield, rideshare services and Bike Taxi are convenient options. We also recommend making dinner and attraction reservations in advance whenever possible.
WEDNESDAY
- Check-in is at 4:00 pm, but you are welcome to drop your bags early to start exploring the ‘Holy City’!
- Explore John Rutledge House Inn and the grounds, then get settled in your beautifully appointed room.
- Savor a romantic dinner at Magnolias. A staple in Charleston for over 30 years, Magnolias remains a forerunner in upscale Southern cuisine and is within walking distance.
- End the night at the Gin Joint, a cozy, intimate bar/eatery serving cocktails and eclectic small plates in a 1920s-inspired setting.
- Return to John Rutledge House Inn® and end the evening with a glass of port, sherry, or brandy before retiring to your room or suite.
Thursday
- Start your day with a complimentary Continental or cooked-to-order breakfast served in your room, ballroom, or courtyard.
- Stroll toward the Battery and White Point Garden, taking in historic homes and views of Charleston Harbor along the way. Continue along East Bay Street to Rainbow Row, the iconic collection of colorful historic homes, before making your way to Waterfront Park for a romantic photo beside the Pineapple Fountain. Pineapple Fountain.
- Stop for lunch at 167 Raw Oyster Bar, a popular King Street spot known for fresh seafood, oysters, and a lively atmosphere.
- Embark on a guided walking tour with Bulldog Tours to discover more about Charleston’s rich history.
- For happy hour, head to Bar Vaute, a romantic speakeasy located beneath French restaurant Brasserie La Banque.
- Enjoy a romantic dinner at Circa 1886 tucked within the original carriage house of our sister property, Wentworth Mansion®.
Friday
- Head to Millers All Day for breakfast, a popular Charleston spot serving Southern favorites in the heart of the Historic District.
- Recreate the Rowboat Scene in The Notebook at Cypress Gardens where you can take a self-guided boat ride through the cypress swamp featured in the film.
- Explore the historic Charleston City Market browsing local art, handcrafted goods, and Charleston-made souvenirs.
- 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 dinner at Chez Nous, an intimate neighborhood restaurant known for its daily changing menu inspired by the cuisine of France and Europe.
Saturday
- Start the day with breakfast at Basic Kitchen, a serene, light-filled restaurant known for fresh, seasonal ingredients..
- Learn about Charleston’s storied past on a horse-drawn carriage ride with Palmetto Carriage Works, exploring the Historic District while hearing stories about the city’s history and architecture.
- Explore the Nathaniel Russell House Museum, an elegant 19th-century home renowned for its spiral staircase and period furnishings.
- Grab lunch at Slightly North of Broad, a longtime Charleston favorite serving refined Lowcountry cuisine in the heart of the Historic District.
- Take a rideshare to Magnolia Plantation & Gardens for a peaceful stroll through its historic romantic-style gardens. If time allows, explore more of the property’s history with a guided house tour.
- End the day with dinner at FIG, a celebrated Charleston restaurant known for seasonal cuisine showcasing locally sourced ingredients.
Sunday
- For your last breakfast, head to Poogan’s Porch, a longtime Charleston favorite serving Southern cuisine in a historic Victorian home on Queen Street.
- Stroll King Street and browse its mix of boutiques, antique shops, art galleries, and local retailers.
- Check out by noon, but feel free to leave your bags with us if you’d like to continue exploring Charleston before your departure.
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 843-723-7999 if you would like our concierge team to assist you in any way.
