or give us a call at
843-793-1122OUR CANCELLATION POLICY Read More >
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.
View this post on Instagram
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
View this post on Instagram
- Circa 1886 Restaurant $$$$ | Contemporary American with a Michelin Star | 149 Wentworth St.
- Hall’s Chophouse $$$$ | Old School Steakhouse | 434 King St.
- Revival $$$$ | Modern Southern Eatery | 162 East Bay St.
- 82 Queen $$$$ | Refined Lowcountry Cuisine | 82 Queen St.
- Charleston Grill $$$$ | Upscale Southern-French Dishes | 224 King St.
Elevated Dining
View this post on Instagram
- Maison $$$$ | Chic French Bistro | 708 King St.
- The Ordinary $$$ | 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 $$$ | Hip outpost offering a rotating menu of inventive, seasonal cuisine | 1085 Morrison Dr.
Casual Dining
View this post on Instagram
- Basic Kitchen $$ | 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
View this post on Instagram
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!
Girls Just Wanna Have Fun (in Charleston)!
When it’s time for you to get away with the girls, there’s no better place to celebrate friendship and sisterhood than in the Holy City. While a girls trip can be anything from an extravagant weekend of shopping at chic boutiques and spa days brimming with luxurious pampering, to adventure filled days exploring the streets of Charleston and experiencing all its delectable cuisine, we know the list of things to do is endless. From planning a shopping spree to Sunday brunch with your tribe, we’ve created the ultimate guide to the best girls’ weekend in Charleston, SC.
Start with the Ultimate Vacation Rental
If you’re only in Charleston for the weekend, you’ll want to stay close to the action. What’s better than walking out your door and stepping onto King Street? Our downtown rentals are centrally located and perfect for ladies who want to explore all that Charleston has to offer. From our stylish apartments on King to our spacious homes just minutes from the action, you can’t go wrong with our Charleston short-term vacation rentals.
Add in world-class amenities and an exceptional concierge team with services like airport transfers, in-suite massages, groceries, and exclusive Charleston experience packages. It’s safe to say there isn’t much our Concierge team can’t help you with during your stay.
Friday – Pampering and Cocktails
Once you’ve arrived in the Holy City, taking your look to glam-ready is first on the agenda. Head to Drybar Charleston for a blowout experience that takes your tresses to the next level. After that, stop at the Nail Place of Charleston for all of your pampering needs. This incredibly chic and pink salon screams luxury from their custom-built pedicure chairs to their complementary wine selection.
Insider tip: The girls from the Bravo hit show “Southern Charm” just might be spotted here.
Now let’s kick off your vacation right! Head to East Bay St. for happy hour at The Gin Joint. This intimate, 1920’s style bar serves innovative and bespoke cocktails with handcrafted syrups, infusions, and funky glassware. The menu is seasonal, so you’re always trying something new. Feeling adventurous? Try their “bartender’s choice,” where you can pick any two words from a list and they’ll create something unique to you!
Now that you’ve enjoyed your happy hour libations, it’s time for dinner! You can’t go to Charleston without eating at FIG. A James Beard Award Nominee for Outstanding Restaurant in 2019 and 2020, FIG dazzles palettes with its elevated low country cuisine and ever-changing menu that fluctuates with the seasons and availability of product. You’re sure to have an unforgettable experience here!
View this post on Instagram
Saturday – Shop ‘til You Drop
It’s time to get fueled up for a day of shopping! One of our favorite cafés in the city is Clerks Coffee Company. Located in the French Quarter at the incredibly chic Hotel Emeline, Clerks offers fresh brewed coffee and tea, gourmet breakfast, and a selection of kombucha. Sip it in the café or venture to their outdoor courtyard and enjoy the Charleston sunshine.
View this post on Instagram
Once you’ve had your morning brew, head to the Historic Charleston City Market, located nearby to the French Quarter and in the heart of everything. Here, local artisans have displayed the fruits of their labor since 1807! It’s the perfect place to grab an authentic souvenir or a little piece of Charleston to take home with you.
After the City Market, shop your way back to King Street, known as the mecca of shopping in downtown Charleston! Some of our favorite boutiques and brands include:
- Beckett*
- Hampden*
- Maris DeHart*
- Julep*
- House of Sage*
- House of Nomad*
- Worthwhile*
- Magnifique*
- Anthropologie
- Louis Vuitton
- Gucci
*local businesses
Sunday – Ladies Who Brunch
For your last day in Charleston, we recommend a delicious brunch and some sightseeing! Some of our favorite brunch spots include Park & Grove, Butcher and Bee, Daps Breakfast and Imbibe, Millers All Day, and 5Church. If you’re looking for a rooftop brunch, we recommend The Watch Rooftop Kitchen and Spirits on Wentworth St. This rooftop restaurant serves great views and even better food. It’s the perfect inspiration to kickstart a day of exploration.
If sightseeing is also on your Charleston bucket list, you’ll want to check out these iconic stops throughout your day:
And, if you’re looking for ideas for something a little less traveled, why not try something new?
View this post on Instagram
Don’t forget to browse our luxury rentals when you’re ready to book. With our dedicated Concierge team, we can help with the planning and ensure that your girls weekend is all kinds of fantastic fun! And, because there is so much to see and do with your girl tribe in tow, we know you’re sure to have an unforgettable girls’ weekend in Charleston.
Browse Rentals
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
View this post on Instagram
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
View this post on Instagram
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
View this post on Instagram
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
View this post on Instagram
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
View this post on Instagram
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.
Charleston is an exciting city that provides the culture, history, and entertainment it takes to make your trip unforgettable. However, it may just be the water surrounding this coastal city that creates an undeniable thrill. Those with a passion for watersports will find Charleston to be a place of seemingly endless opportunities. Whether you’re in it for the adrenaline rush, views of the coastline, or looking to catch a wave, there’s something on the water for you. Enjoy this three-day Charleston watersports itinerary and allow it to inspire your next Charleston adventure.
There’s so much more to Charleston just waiting to be discovered! Explore our Charleston Insider’s Guide to get acquainted with the best restaurants, shops, and activities in the Holy City. Request your complimentary guide today.
The Only Itinerary You Need to Enjoy Charleston Watersports
Day 1: Hydrofly Watersports
When you’re visiting Charleston and looking for a new adventure on the water, you’ll want to book a full-day or half-day session with Hydrofly Watersports. Make those childhood superhero dreams come to life as certified instructors teach you how to maneuver up to 20 feet above the waves with the assistance of a water jet pack attached to your feet. It only takes a few minutes to get the hang of it, and once you do, it’s sure to be a day of flying fun you’ll never forget. After you’ve mastered flyboarding, you could even book a follow-up wakeboarding or tubing session if you just can’t get enough.
185 Lockwood Drive, Charleston, SC 29403, (843) 990-0707
Day 2: Charleston Sailing Adventures
Departing daily from the Charleston Maritime Center, Charleston Sailing Adventures provides guests with extraordinary opportunities to make the most of their time on the water. Book a sunset cruise with a certified captain to enjoy the Charleston skyline. There’s truly nothing like watching the sun burns away over the Holy City horizon. If you’re looking for an in-depth look at marine life, book a dolphin eco-tour and make waves alongside the beautiful creatures that call these waters home. Guests enjoy tours from the comfort of a 27-foot stiletto catamaran providing a safe and stable environment with opportunities for magnificent views.
10 Wharfside Street, Charleston, SC, 29401 (843) 277-9019
Day 3: Session Sports
Dedicated to helping kiteboarders take their skills to the next level, Session Sports is Charleston’s premier destination for kiteboarding rentals and lessons. Come in and browse the vast selection of kites, boards, and accessories and feel free to ask questions of the knowledgeable staff on-hand. If you’re just stepping into the sport or looking to improve on technique, lessons are available for beginners through advanced kiteboarders. A passionate team of instructors is ready to provide the instruction on safety, skills, and equipment care you need to make the most of your time on the waves.
62 Brigade Street, Charleston, SC 29403, (844) 347-5852
Unwind in Style
After a thrilling day out on the water, make sure you have a place to unwind that makes you feel like you’re resting up in the comfort of your own home. Booking a vacation rental with the team at Luxury Simplified Retreats means you’ll have a place to land at the end of each fun-filled day that brings the comfort, convenience, and luxury you deserve. With an extensive portfolio of Charleston properties available, we’re here to help you customize your stay. Contact us to get started planning!
Book one of our luxury rentals today and start planning your personalized getaway. And, with our Concierge team, we can coordinate all the details for your water-centric getaway so that you can start enjoying fun on the water from the moment you arrive. We look forward to hosting your stay!