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!
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!
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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.
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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?
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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
Fall is a fantastic time of year to make your way to Charleston, South Carolina. While it makes for a pretty exceptional destination year-round, there’s something about the crisp temperatures and vibrant fall colors that add a certain seasonal magic just before winter rolls into the city. Whether you’re looking for that perfect city tour, simply strolling the cobblestoned streets through Charleston’s historic neighborhoods, or hoping to spend a day at the pumpkin patch, fall is a great time to make the most of this captivating city. And, while there is so much to see and do in Charleston every day of the year, we’re sharing a few must-try destinations to experience fall in Charleston.
And while you’re here, don’t forget to explore everything the Holy City offers! Our Charleston Insider’s Guide will point you towards the best places to eat, drink, and play from a local’s perspective!
Here’s our “Ultimate Itinerary to Enjoy Fall in Charleston, SC”
Day 1: Hibben United Methodist Pumpkin Patch
There’s something about a visit to the pumpkin patch that makes everyone feel like a kid again. Still, a visit to Hibben United Methodist Pumpkin Patch from October 1 through late October comes with the added benefit of purchasing a seasonal pumpkin for a great cause. The Hibben United Methodist Pumpkin Patch allows you to browse an array of pumpkins right in the heart of Mt. Pleasant’s historic corridor, plus all proceeds go to select local charities. There are other great pumpkin patches dotted all around the Charleston area, so you’ll more than likely be close to one no matter where you’re staying. The incredible fall weather in Charleston makes pumpkin picking the perfect fall outing and adults and families alike can enjoy the hunt for getting the perfect pumpkin.
Hibben United Methodist Pumpkin Patch
690 Coleman Ave.
Mt. Pleasant, SC
Day 2: USS Yorktown Ghost Tours
Charleston’s fall season is bound to be scenic, but it’s made all the more intriguing with a side of spooky. Booking a USS Yorktown Ghost Tour is a sure way to add a kick of intrigue to an already captivating trip to the Holy City. Docked in the Charleston Harbor, the USS Yorktown is a renowned source of mystery linked to a violent past. This aircraft carrier has hosted many service members over its lifetime, and some believe spirits remain onboard today. This 90-minute tour is sure to be unforgettable and potentially, other-worldly.
USS Yorktown Ghost Tours
40 Patriots Point Road
Mt. Pleasant, South Carolina 29464
(843) 277-0587
Day 3: Kudu Coffee and Craft Beer
Fall in Charleston is best experienced alongside friends and family. What better way to enjoy an afternoon together than finding a comfortable seat at a local coffee shop? When you’re in town as the weather changes from warm to cool, make your way towards Kudu Coffee and Craft Beer, where there’s a little something for everyone to sip. This local establishment encourages great flavors alongside great conversation. The menu hosts everything from single-origin coffees to a carefully selected listing of craft beers and a recently expanded wine menu. A variety of pastries and sandwiches make the perfect beverage pairing while you’re here. This comfortable coffee house is a true representation of local Charleston culture at its best. This little nook is always worth a visit so start your day here before you head out exploring!
Kudu Coffee and Craft Beer
4 Vanderhorst Street
Charleston, South Carolina 29403
(843) 853-7186
And, if it’s a Saturday morning in the fall, you’ll want to head to the nearby Charleston Farmers Market at Marion Square. Locals and tourists alike enjoy strolling through this one of a kind farmers market which has been voted “Best Outdoor Event” and “Best Attraction” in Charleston for multiple years in a row. Market goers will find a large selection of produce, plants, herbs, flowers, prepared foods, as well as breakfast and lunch vendors, live entertainment and an assortment of arts and crafts from local artisans. On Saturday mornings from spring through late fall, the Farmers Market is truly the hub of activity in Charleston’s downtown historic district.
“Fall” in Love with Your Charleston Stay
Charleston is a city that captures the imagination all year long, but when you’re here in the fall, make sure to cozy up in a vacation home that keeps you falling in love with this incredible destination. The team at Luxury Simplified Retreats is here to help you select a location that keeps you close to the exciting entertainment and comfortable enough to feel like you’re right at home.
Let’s start planning your fall retreat to the Lowcountry today. Whether your fall travel has you dreaming of a downtown getaway tucked among historic homes or days of book-reading and touch football on the beach, booking with us offers every kind of autumn stay. Contact us today to start planning your next Charleston vacation.
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!