As the vibrant hues of autumn take over the landscape, Charleston, South Carolina, emerges as an enchanting destination for a fall weekend getaway in 2023. With its historic allure, captivating architecture, and a delightful blend of culture and relaxation, Charleston offers a splendid escape that promises a memorable experience. From exploring the cobblestone streets of historic downtown to basking in the mild October weather and indulging in beachside activities, this charming city has it all.
One of the highlights of visiting Charleston in the fall is the delightful weather. By October, there’s a good chance that the stifling summer heat has subsided, giving way to milder temperatures that are perfect for exploring the city on foot. With highs ranging from the mid-70s to low 80s°F (24-28°C) and pleasantly cool evenings, you can comfortably enjoy outdoor activities without worrying about the sweltering heat. Pack a light jacket or sweater for the evenings, and you’ll be all set to enjoy Charleston’s fall ambiance.
Lace up your shoes and head out for a stroll
Stepping foot in historic downtown Charleston is like entering a living history book. As you wander through cobblestone streets lined with colorful antebellum houses, you’ll be transported back in time to an era of Southern elegance and charm. The historic district is brimming with well-preserved architecture, quaint shops, and an abundance of. Take a guided walking tour to learn about the city’s rich history, from its role in the American Revolution to the Civil War and beyond.
Step inside a hidden garden
A celebration of architecture, history and gardens, this beloved event takes you inside some of Charleston’s most iconic historic homes and intricate gardens. Each year, for one month only, the Preservation Society of Charleston invites you to get up close and personal with some of Charleston’s oldest and most exquisite homes. During “The Fall Tours: Architecture, History and Gardens” you can step inside private homes and gardens, ordinarily closed to the public, and walk through history.
Take a step back in time
Aside from the taking in the sights and sounds of historic downtown Charleston by foot, Charleston is also a hub for cultural experiences from incredible art galleries to world-class museums. The Charleston Museum is notable as the oldest museum in the United States. The Gibbes Museum of Art showcases Southern art and Lowcountry history, offering a unique perspective on the region’s artistic heritage.
In early 2023, Charleston, celebrated the opening the International African American Museum as a fitting addition to its historic landscape. Situated at the Gadsden Wharf, where countless enslaved Africans disembarked, the museum stands as a powerful testament to resilience and history. The museum’s compelling exhibits narrate the African American journey, from the depths of the Middle Passage to the heights of cultural contributions. Through immersive displays, interactive installations, and personal stories, visitors gain profound insights into the rich tapestry and enduring legacy of the African American experience.
Slip on your flip flops and head to the beach
No trip to Charleston would be complete without spending time at its pristine beaches. Head to Folly Beach or Isle of Palms, where you can sink your toes into the soft sand, soak up the sun, and listen to the soothing sound of the waves. Cast a line from one of the popular fishing piers, or even try your hand at paddleboarding or kayaking. As the sun sets over the ocean, you’ll be treated to a breathtaking display of colors that paints the sky. You’ll find great dining options offering up coastal fare at both of these oceanfront communities.
Located on the iconic fishing pier of Folly Beach, Pier 101 serves up family friendly plates for the whole group. Sit inside or outside on the pier, enjoy ocean views, sea breezes, and watch the sky dance in vibrant colors as the sun sets over the Atlantic Ocean. You’ll find some of Folly Beach’s top restaurant’s located along Center Street, including Taco Boy, Jack of Cups, Rita’s Seaside Grill or Lost Dog Cafe. Head over to Dolce Banana Cafe for ice cream and frozen treats and for the cherry on top of a fun night on Folly, take a cone of your favorite flavor for a stroll on the beach.
This island paradise just a short drive from downtown Charleston is a favorite among kiteboarders who flock to Breach Inlet where the winds are reliably brisk year round. In addition to six miles of beaches, Isle of Palms includes a quaint downtown retail and dining district along Ocean Boulevard. Popular restaurants and cafes along this stretch of the island offer a wide variety of delicious seafood and other local specialties, including Coda del Pesce, Coconut Joes Beach Grill, Acme Lowcountry Kitchen and the locally loved Sea Biscuit Cafe, that serves up only breakfast, but is well worth the wait!
Nothing says fall in the South like a coastal fair
The October weather makes this the perfect time to celebrate fall at the fair, and there’s plenty for everybody to do at this favorite, family-friendly fair. Held in nearby Ladson, SC, just an easy 25 minute drive from the downtown Charleston peninsula, this is a fun-filled, small town fair filled with food, rides and entertainment. From the recognizable ferris wheel, to fiddler competitions, 4-H events, arcade games and cotton candy, The Coastal Carolina Fair is a fun-filled destination for kids – big and small alike.
Stay in Luxury
A fall weekend trip to Charleston, SC promises a blend of historic charm, cultural richness, and coastal beauty. With its historic downtown, captivating museums, mild October weather, and inviting beaches, Charleston beckons travelers to experience the very best of the Lowcountry. Whether you’re a history enthusiast, an art lover, or simply seeking relaxation by the sea, Charleston is the ideal destination to create lasting memories against the backdrop of a picturesque Southern fall. Book a stay at any of our luxury vacation homes in the heart of Downtown Charleston or on Folly Beach, Isle of Palms or Sullivan’s Island and be that much closer to having your toes in the sand. The team at Luxury Simplified Retreats goes above and beyond to offer guests an outstanding experience with beautiful beach rentals and unparalleled concierge services. Browse our Experience Packages to consider making your trip especially unique, then sit back, relax, and leave all of the planning to us.
While Charleston, SC is known for its hospitality, it’s incredibly dog-friendly too! Whether you live locally or simply like to bring Rover along when you travel, the walkability and mild climate in Charleston make it a popular destination for spending time outdoors with your pooch. Charleston has a strict leash law in place, and good dog-manners are a “must have,” but if there’s a restaurant with a patio or porch, your dog is more than likely welcome — though it’s always a good idea to call ahead. But if you’re planning on bringing your dog to one of our beautiful beaches and giving your pup the full sun, sand and surf experience there are a few rules to know, and it starts with being a responsible pet owner and always cleaning up after your pet.
Folly Beach loves its pups! Many restaurants have outdoor spaces for you to dine al fresco with your dog by your side. However, if you’re looking for a fun walk on the beach, know that dogs are not allowed on the beach from 10am to 6pm from May 1st to September 30th. At all other times, dogs are welcome but must remain on the leash or under voice control.
If you’re looking for alternatives when the beach is too packed, there’s a dog park located on the island at 512 E Erie Ave!
Known as the widest beach in the Charleston area, Sullivan’s Island is a dog’s playground with tidal pools and expansive beach! However, all dogs, including those of both residents and visitors, must have a dog permit from the Town of Sullivan’s Island. Non-resident permits are $50 per dog annually and resident permits are $25 annually. Permits are issued at Town Hall at 1610 Middle Street. Make sure you have proof of your rabies vaccine as well!
Summer hours for dogs on the beach run from May 1st to September 30th. During that time dogs can be off leash from 5:00 a.m. to 10:00 a.m., on leash from 6:00 p.m. to 5 a.m. No dogs are permitted on the beach between the hours of 10:00 a.m and 6:00 pm. Winter hours for dogs on the beach run from October 1st to April 30th. During that time dogs can be off leash from 5:00 a.m. to noon and on leash from Noon to 5:00 a.m.
Isle of Palms
The City of Isle of Palms recommends you obtain a dog permit if you plan to have your dog on the beach. Permits are free of charge, and you must have proof of up-to-date rabies inoculation signed by a licensed veterinarian.
Dogs are allowed to be off-leash during summer hours, from 5am to 9am from April 1st through September 14th and then for winter hours, 4pm to 10am beginning September 15th to March 31st. If you’re on the beach during other hours, just make sure your dog is on the leash!
You can also visit the spacious dog park on Isle of Palms located behind the Recreation Department at 24 28th Avenue.
Pet Safety Beach Tips
Remember, if it’s hot at the beach for you, your dog will be extra toasty underneath all their fur! Limit the time your dog has on the beach and make sure you provide plenty of water throughout the day. Additionally, never leave your dog in the car. Within minutes, a car can reach dangerous temperatures.
If you’re planning a Charleston vacation and wonder if you should bring your dog, we’ve put together some tips to help you and your furry friends have the best vacation possible. Whether they’re sniffing their way through charming and historic downtown Charleston SC or splashing in the waves and digging in the sand on Folly Beach, your dog will be happy that you brought them along – after all, their favorite place in the world is wherever you are! So grab their leash and book one of our pup-friendly luxury vacation rentals today.
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.
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- Circa 1886 Restaurant $$$$ | Contemporary American with a Michelin Star | 149 Wentworth St.
- Hall’s Chophouse $$$$ | Old School Steakhouse | 434 King St.
- Revival $$$$ | Modern Southern Eatery | 162 East Bay St.
- 82 Queen $$$$ | Refined Lowcountry Cuisine | 82 Queen St.
- Charleston Grill $$$$ | Upscale Southern-French Dishes | 224 King St.
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- Maison $$$$ | Chic French Bistro | 708 King St.
- The Ordinary $$$ | 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 $$$ | Hip outpost offering a rotating menu of inventive, seasonal cuisine | 1085 Morrison Dr.
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- Basic Kitchen $$ | 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.
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.
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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!
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
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
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.