Did you know Charleston is considered one of the most romantic city in the US! From cozy sidewalk cafes perfect for mornings filled with coffees and pastries, to strolling hand-in-hand through gardens overflowing with camellias, jasmine and magnolias, and incredible restaurants for those whose “one & only” is also a foodie at heart, no other southern city offers such an endless array of activities filled with romantic possibilities.
You can discover all of Charleston’s best-kept secrets by downloading the Insider’s Guide to Charleston. This curated guide is bursting with restaurants, activities, and top destinations, and it includes some of our Top 5 favorite things to see and DO in Charleston, for any kind of vacation you can dream of.
Here are some of our favorite ways to experience Charleston when love is in the air.
Indulge in The Best Brunch
Voted the Second-Best Brunch Restaurant in the US, Charleston’s High Cotton serves up classy southern brunch in a soft, romantic atmosphere. Located in the French Quarter of Charleston, this elegant spot surprises and delights brunch go-ers daily. Our favorite offerings are the Chicken and Waffles and the Crabcake Benedict. Keep the celebration going by ordering a bottle of bubbly and the Mimosa Trio.
(Sight) See the Romance!
Spend your days exploring the historic city of Charleston! Book a private horse-drawn carriage tour and learn about the rich history of Charleston from a local. You’ll be an expert in no time. Fans of The Notebook will enjoy a trip to Cypress Gardens. The Gardens are the backdrop of the famous rowboat scene. Take one of the rowboats for a spin yourself while you’re there – it’s the perfect romantic photo op.
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A Day Trip for Two
After you’ve made the most of your time in the city, take a day trip to Sullivan’s Island for a beach day! This 2.5 mile beach sits along a charming coastal town with trendy eateries and fun boutique shops. Complete your day trip with cocktails at a new local favorite, The Longboard. At this beautiful escape, you’ll find unique cocktail creations with exotic flavors, and the freshest oysters in town. We recommend cooling down with the Passion Fruit Frosé, the Wadma-Law-Breaker, or the Sullivan’s 1040.
Date Night Every Night
A week away means a week of date nights! Charleston is known for its incredible food scene, and these places do not disappoint. We’ve hand-selected the most romantic and memorable Charleston dining to end every night on a high note. Looking for more? Browse our Insider’s Guide to Charleston to see more of our favorite restaurants in the Holy City.
Fine Dining
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- Circa 1886 Restaurant $$$$ | Contemporary American with a Michelin Star | 149 Wentworth St.
- Hall’s Chophouse $$$$ | Old School Steakhouse | 434 King St.
- Revival $$$$ | Modern Southern Eatery | 162 East Bay St.
- 82 Queen $$$$ | Refined Lowcountry Cuisine | 82 Queen St.
- Charleston Grill $$$$ | Upscale Southern-French Dishes | 224 King St.
Elevated Dining
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- Maison $$$$ | Chic French Bistro | 708 King St.
- The Ordinary $$$ | 1920s Bank Turned Upscale Seafood Restaurant | 544 King St.
- FIG $$$ | Neighborhood American Bistro | 232 Meeting St.
- The Grocery $$$ | New American Neighborhood Spot | 4 Cannon St.
- Butcher & Bee $$$ | Hip outpost offering a rotating menu of inventive, seasonal cuisine | 1085 Morrison Dr.
Casual Dining
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- Basic Kitchen $$ | Bright, Local Ingredients with Vegetarian and Vegan Options | 82 Wentworth St.
- Fuel $$ | Repurposed 1950s Gas Station with Refined Caribbean Eats | 211 Rutledge Ave
- Rodney Scott’s BBQ $$ | James Beard Award-Winning Lowcountry-style BBQ | 1011 King St.
- R Kitchen $$ | Snug Spot with an Open Kitchen Offering a Seasonal 5-Course Menu | 212 Rutledge Ave
- Tavern & Table $$ | Casual, Rustic-Chic Restaurant in Shem Creek | 100 Church St.
Nightlife
Rooftop Bars
What’s more romantic than seeing the twinkling lights of the city from above at one of Charleston’s famous rooftop bars? Delight in handcrafted cocktails, live entertainment, and beautiful views of Charleston skyline.
Dessert Bar
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After a delicious dinner in the city, stop by Carmella’s, a trendy dessert bar on East Bay Street —just a short walk from Waterfront Park. A local favorite, this spot is known for its cakes and cannolis, as well as its cocktail offerings. Our favorite pairings are the Espresso Martini and the Cannoli Cake or the Frosé and Lemon Blueberry Cake.
Natural Wine Tasting
If you haven’t tried natural wine yet, we highly recommend that you try Monarch Wine Merchants. Taste, sample, and shop at this neighborhood natural wine shop located King street, Charleston’s popular downtown shopping destination. From Orange Wine to Rosato, you’re sure to find a new favorite at Monarch.
Stay with the Best
Whether you’re planning a weekend getaway or a month-long visit to the Holy City, you’ll find that our team at Luxury Simplified Retreats goes above and beyond to provide an unforgettable experience. Choose your dream vacation home from an impressive portfolio of high-end properties tucked alongside grand historic homes and some of the top historic sites located on the Charleston peninsula. Each property boasts its own unique character and features stylish furnishings and contemporary décor.
Browse our high-end accommodations and start start planning your romantic getaway today!
Are you ready to elevate your happy hour? Look no further than our curated list of the best rooftop bars in Charleston, SC. From mimosas at brunch to late-night fun, we know the best spots to add to your itinerary for any group.
Ready to plan the rest of your trip? Use our Charleston “Insider’s Guide” to unlock the vacation of your dreams in Charleston, South Carolina!
The Best Rooftop Brunch – The Watch Rooftop Kitchen & Spirits
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The Watch Rooftop Kitchen & Spirits is the perfect place to start your day before shopping and sightseeing. With its central location right off King St., you’ll be ready to jump into action after a delectable brunch. The Watch sits atop the Restoration Hotel and boasts a “breathtaking panorama of Charleston’s architectural history, from its iconic 350–year–old church steeples to the Greek Revival-period buildings that inspired Edgar Allan Poe.” Thirsty? Their brunch carafes serve four to six people and can be filled with Mimosas, Bloody Mary’s, or Margaritas. From “Vanilla Bean Brioche French Toast” to a “Fried Chicken Biscuit,” The Watch serves up a tasty Southern brunch for sweet and savory palates alike.
The Best Rooftop Brews – Pour Taproom
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For a unique rooftop experience, try Pour Taproom! Beer, wine, and cider fans will rejoice in sampling from over 70 rotating taps while taking in the scenic Charleston horizon. To utilize the self-serve tap system, patrons hook their credit or debit card up to a QR code. Looking to sample the selections? The taps are pay-by-the-ounce, so you can sip away without paying for a full glass. Once you’ve settled on a beer that you like (or two!), order up some bar bites and unwind with live music. This rooftop bar is great for a large group with varying tastes or a fun date night for two!
The Best Rooftop Bar Nightlife – Uptown Social
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Are you the life of the party? So is Uptown Social. This trendy, youthful bar offers nightly live music, late–night hours, and refreshing cocktails. Located on King Street in the Historic District, this #instagrammable bar is, without a doubt, THE place to have a good time. We recommend trying one of their Brooklyn pizza pies (like the famous “Wake N Bacon” or the “Falco Classic”) and pairing it with an order of the “Truffle Fries.” Ready to get the party started? Try a “Gone with The Gin,” an “Uptown Old Fashion,” or create–your–own pitcher to share!
The Best Luxury Rooftop Bar – Fiat Lux at Hotel Bennett
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For those who indulge in a bougie lifestyle or simply enjoy the art of the cocktail, Fiat Lux is a must-visit on your trip to Charleston. Overlooking Marion Square and located inside the stunning Hotel Bennett, Fiat Lux serves elegant glamour and delicious drinks. This indoor/outdoor bar concept is perfect for panoramic views of the city, with cover for questionable weather days. Fiat Lux boasts an expansive spirit selection and specialty seasonal cocktails. With ingredients like Boba Pearls, House-Made Wasabi Infusion, Strawberry Jam, and more, you’re likely to experience a flavor explosion unique to any other cocktail expedition.
BONUS: While you’re here, stop by Charleston’s premier Champagne Lounge, Camellias, located on the first floor. This breathtaking lounge was named the “Most Instragrammable Restaurant in South Carolina” by Food Network Magazine. Be sure to ask your server about a Champagne Flight!
The Best Rooftop View – Citrus Club at the Dewberry
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Cocktail aficionados will appreciate the craft and presentation of the cocktails at Citrus Club. Located on the 8th floor of the Dewberry Hotel, this James Beard Award–Nominated bar offers citrus–inspired drinks and the highest rooftop in Charleston. Adjacent to Wragg Square and Marian Square, its sweeping views encompass the lush landscapes of the gardens below. With a rum-forward drink menu, it‘s safe to say the libations have an elevated Tiki vibe. Be sure to order one of their signature daiquiris for the complete experience!
Now that you’ve made your plans, it’s time to book your accommodations. Luxury Simplified Retreats offers a portfolio of Charleston’s most exclusive vacation rental homes, condos, and villas. You receive upscale amenities, personal services, attention to detail, hand-selected vacation experiences, and premier locations when you book with us.
