If your love connection could use a little rejuvenation, a romantic weekend in Charleston is potent medicine. Intimate dining, luxurious lodging, vibrant nightlife and outdoor adventure – all offered against the backdrop of one of the most beautiful settings in the nation – have consistently earned the Holy City top national ranking as a romantic destination. Of course, there are plenty of memorable activities that define the Charleston experience; carriage rides, Lowcountry suppers and bed and breakfast inns all make the list. But keep in mind this historic city is rich with a broad variety of options for stoking the fires of love. Here is an itinerary for an unforgettable romantic weekend.
Friday Afternoon – Check-in
A new dynamic in Charleston accommodations has emerged in recent years, and that means exciting choices for lovers. You’ll swoon over The Spectator, located near Charleston Market. With a “Great Gatsby” vibe, this boutique hotel is brimming with style and patrician elegance, while harkening back to the glamour days of Charleston’s French Quarter district. Sip a classic, handcrafted cocktail in the 1920s-themed lounge, explore the city on complimentary retro bicycles and indulge in an artisanal breakfast in bed served to you by your own personal butler. When you book, arrange for an in-room couples’ massage, too. Romance packages offer everything from dinner at renowned local restaurants to a sunset sail for two. Check the website for details.
You’ll also love the retro flair of The Restoration. Five rustic Charleston buildings, adjoining at points between Wentworth and King streets, comprise this hotel, which was meticulously renovated to preserve historical details infused with contemporary touches. There’s an onsite spa as well as a cozy library – complete with a librarian – that houses a small, but eclectic selection of books for guests to enjoy at their leisure. Suites feature all kinds of creature comforts, such as plush bedding and full kitchens.
But hold up – we wouldn’t dare suggest you cook on your romantic vacay! Instead, request a personal chef to prepare an intimate dinner in the privacy of your suite. Otherwise, enjoy dining and drinks at the hotel’s rooftop restaurant and bar, The Watch, and in the morning, a continental breakfast that arrives at your door in a picnic basket. Romance packages for health-conscious couples are a big draw, offering fitness sessions, massages and healthy breakfast baskets for two.
Begin your first evening in Charleston with cocktails and a view atop the Market Pavilion Hotel. Located on the corner of Market and East Bay, it’s an easy walk from The Spectator and just a few blocks from The Restoration. Enter through the revolving doors, board an elevator and take a ride all the way to the top floor. There you’ll find a rooftop bar with some of the most gorgeous views of the city, Ravenel Bridge and Charleston Harbor. Raise your glasses and toast the beginning of your romantic weekend!
Now that you’re feeling warm and fuzzy, it’s time for the pinnacle of any Charleston visit: dinner. Michael’s on the Alley is your destination tonight. (Note: Always reserve dining as far in advance as possible when planning your Charleston weekend.) Tucked away on Hutson Alley, this beautifully appointed steakhouse is upscale but relaxed, blending New York glamour with Charleston charm. Low lighting, dark wood decor, Italian leather banquettes and soft music will put you in the mood for fabulous food and wine you can linger over. Try the Caesar salad prepared table side, the fresh seafood dishes or an expertly prepared wet- or dry-aged steak. Servers are attentive, but never intrusive. Celebrating an anniversary? Let the wait staff know and you'll be treated to a complimentary glass of champagne.
After dinner, take a leisurely stroll back to East Bay, pass the Market Pavilion Hotel and hang a left on Vendue Range, which leads to Riley Waterfront Park. Settle into one of the bench swings beneath the pavilion, snuggle up and drink in the beautiful view of the Cooper River and the illuminated Ravenel Bridge. Walk to the end of the boardwalk and sit a spell. On fine nights, the moonlight shimmers on the water and you might even spot a dolphin or two. Seek out the park’s famous pineapple fountain as a backdrop for a romantic kiss before you head back to your hotel.
After breakfast in bed, put on your walking shoes and make for the Battery, where love is always in the air. Charleston’s famous promenade offers harbor breezes and picturesque water views. Be sure to stroll by the gazebo at adjacent White Point Garden. Surrounded by centuries-old live oaks, it's a popular spot to exchange "I do's."
Follow the Battery walkway down Murray Boulevard and round the bend onto East Battery, which will lead you past some of the historic district’s most stately homes and the colorful, Georgian-style houses of beloved landmark, Rainbow Row.
It’s just a short walk from this point to the corner of East Bay and Cumberland, where you’ll find Carmella’s, an airy Italian cafe serving beautiful pastries, authentic Italian coffee drinks and some of the best people-watching in the city. Pause here to rest your feet and sip a cappuccino. Periodically, customers are treated to the surprise of a live, pop-up opera from the Small Opera Company.
Once you’ve gotten that shot of espresso to fuel your day, your next destination is Goat. Sheep. Cow. on Church Street. You’re on a mission to create the perfect romantic picnic. Choose from an amazing array of fine European cheeses, charcuterie, condiments, salads, wines and more. Don’t forget a baguette to complement it all. Take your luscious loot back to the hotel for a little quiet time before your al fresco dining adventure.
Feeling refreshed? Good. Pack up that picnic and pick up the keys to your chariot for the day – a classic convertible. Mercedes 280 SL? Or is a ’66 Ford Mustang more your style? Dream Classic Rentals has the perfect ride for you and will deliver it to the location of your choice. (The Restoration offers a package with classic car rental; inquire before you reserve your accommodations.)
Hop in and take your dream car for an exhilarating ride to Sullivan’s Island, home to one of the area’s most beautiful beaches. (Note: Parking is often at a premium here. Try driving farther down from the main public access and you’ll have better luck.) Soak in some South Carolina sun and watch the waves as you eat your picnic, then take a walk along the shoreline where writer Edgar Allen Poe once strolled as a young soldier in the 1800s.
If you’d rather not venture that far for your picnic, secure a pair of vintage bicycles from the front desk of your hotel and bike to one of Charleston’s best-kept secrets: Chapel Street Fountain Park. Though it’s located downtown, you’ll feel like you’ve traveled a whole lot farther as the high energy of the city falls away. Picnic beneath the live oaks, crepe myrtles and blooming foliage. And, as the name implies, a serene fountain serves as the park’s focal point. It’s simply gorgeous and typically uncrowded. Go ahead and cozy up with that baguette, bottle of wine and, naturally, each other.
After your picnic, enjoy a little spontaneity. There are so many things happening in historic downtown – from art exhibits to festivals at Marion Square to shopping at the novelty shops of King Street. Find information about local tours and select a cherished memento of your visit to the Holy City at the Preservation Society of Charleston Shop on King Street.
Other points of interest to consider: Calhoun Mansion, where you can tour the Italianate home and gardens and be awed by the owner’s eclectic collection of furnishings and art; Gibbes Museum of Art, which houses special installations and a permanent collection spanning four centuries; and the Gateway Walk, a self-guided tour that will take you past some of the city’s most intricate wrought iron gates and ethereal churchyards. Just make sure to leave a little time for a couples’ snooze back at the hotel – there’s still plenty of romance to experience in Charleston.
It’s your final night in Charleston and you’re dining in one of the most romantic settings in town: Peninsula Grill’s courtyard. When you reserve (again, well in advance of your trip!), request a table amid the palms and flickering gas lanterns. Indulge in inventive Lowcountry cuisine and seasonal dishes in this unparalleled outdoor dining room. And don’t dare skip dessert. Peninsula Grill is home to a six-layer Ultimate Coconut Cake that has won accolades across the country. Share a piece and pair it with a sparkling rosé for a sweet ending to a perfect meal.
Now it’s time to immerse yourself in some nightlife. Hail a bicycle rickshaw and tell your driver to head to The Cocktail Club on King Street. This second-floor, upscale lounge, housed in an 1881 building, is known for its craft cocktails, many of which are “farm-to-shaker.” The reclaimed wood, leather accents and fireplaces create a warm ambiance. There’s a rooftop terrace, too. Live music and dancing rev up and last until the wee hours, so go ahead and let loose. Relieve your dancing feet with a rickshaw ride back to your hotel.
While nobody is happy to leave Charleston, you can end your romantic weekend on a high note. Because you made reservations in advance, there’s a table for two awaiting you at Hall’s Chophouse for their Gospel Sunday Brunch. Breaking your fast with She Crab Soup, shrimp and grits and mimosas to the soulful sounds of live gospel music makes a grand finale to a weekend filled with Charleston romance.