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There’s something about the sun-filled days in Charleston and the surrounding lowcountry that can entice anyone to lace up their shoes and embark on a little outdoor exploration. It’s not often that one city can deliver all the elements layered perfectly to make for an unforgettable vacation experience – mild weather, year round sunshine, miles of beaches, ocean views, lined with cobblestone streets, steeped in history, and mouth watering culinary experiences that are some of the best in the world.  Add in skyline views dotted with historic church steeples and topped by a breathtaking, walkable suspension bridge, and there simply is no where in the world like the Holy City. With so much rich history, vibrant architectural styles, intricate ironwork, lush gardens and hidden cemeteries it’s easy to spend days exploring the cobblestone streets of this unforgettable city.  If you’re planning a visit to Charleston, pack comfortable shoes and plan to include these five of the most unique outdoor Charleston activities in your itinerary. 

Be sure to grab our Insider’s Guide to help you discover the very best of Charleston before you even arrive! Packed full of the best restaurants, bars, activities, and hidden gems, you’ll know just how to enjoy every second of your experience.  

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Insider's Guide to Charleston

5 Unique Outdoor Charleston Activities for Your Itinerary 

Gateway Walk 

The Charleston Gateway Walk allows you to step back in time and explore the network of charming alleyways and gardens throughout the city. While Charleston is known for its array of beautiful gardens that you can occasionally catch a glimpse of behind a wrought iron gate or tucked behind a historic home. Enjoy the Gateway Walk as it winds you through a variety of these gardens and even a few graveyards open to the public. This is one of our favorite ways to discover the unique nooks and crannies of this fascinating city! 

Walk the Ravenel Bridge 

It’s worth taking the time to walk one of Charleston’s most iconic structures. Whether you’re seeking a little exercise after too much seafood, or you’re in search of a scenic, leisurely stroll, the Ravenel Bridge will definitely deliver. As you walk over the bridge connecting Downtown Charleston with Mount Pleasant, you’ll witness the bustle of a busy seaside port, spot Fort Sumter where the first shots of the Civil War were fired, and marvel at the breathtaking, sweeping views of the Charleston Harbor, and the Atlantic Ocean beyond.

Pitt Street Bridge 

The Pitt Street Bridge is a true hidden gem in the area, even for many locals! Cross the Ravenel Bridge into Mount Pleasant to find a former trolley bridge that was a vital connection to Sullivan’s Island. Today, lined with palmetto trees and park benches, it’s used as a hangout for all things outdoor recreation. Relax with a picnic on the grass, enjoy fishing, or kayak through the surrounding marsh and tidal creeks that lead out to Charleston Harbor. 

Charleston Tea Garden 

Pay a visit to the Charleston Tea Garden to cool off and enjoy a refreshing treat! You’re free to tour the factory, browse specialty items at the gift shop, and relax around the grounds as you take in the expansive views of tea bushes reaching towards the horizon. Of course, there is plenty of delicious teas to taste as well! 

Angel Oak 

Many may say you haven’t really been to Charleston without witnessing this iconic landmark in person or even snapping a photo with it. The Angel Oak remains a beloved sight in Charleston, and a top destination with visitors traveling to see it each year. Though there’s debate over the age of the tree, estimated to be 400-500 years old, it’s certain by the sheer size and complexity of the branches that it existed long before anyone knew the name “Charleston.” 

Luxury Simplified Retreats Offers the Best Stays in Charleston 

Book your stay in the heart of Charleston, SC while enjoying the highest quality concierge services, impeccable luxurious homes, and more! Luxury Simplified Retreats offers some of the best vacation rentals in the city within walking distance of King Street, Broad Street, and even Rainbow Row. Browse our Experience Packages to consider making your trip especially unique, then select your favorite vacation rental from our distinctive portfolio. We’re confident you’ll experience a memorable vacation when you book your stay with Luxury Simplified Retreats. 

While it’s well-known that Charleston is one of the top destinations in the South for mouth watering cuisine it’s a common misconception for visitors to assume they need to travel to downtown Charleston for a top notch culinary experience. For vacationers who’ve chosen to vacation on the slower-paced, small town island of Folly Beach, this couldn’t be further from the truth. While the dining scene on Folly may cater to a “flip flop and shorts” kind of clientele, that doesn’t mean that they are serving up only corndogs and baskets of burgers & fries – delicious food can be found pretty much everywhere on Folly. From shrimp & grits at breakfast, to Spam sliders (yes! that’s even on a Folly Beach menu) and Kimchi Beef tacos, you’ll find the local dining spots on Folly Beach serving up some taste-bud-pleasing, delectable fare. You’ll definitely enjoy the casual, laid-back atmosphere of the area plus the diversity of food offerings awaiting you at each amazing restaurant. We’re sharing our guide for where to eat on Folly Beach 

And, before you plan your next trip to Charleston, don’t forget to request access to our Charleston Insider’s Guide. We’ve pulled together a guide to “where the locals go” for the best in dining, spas, parks, golf – you name it! Local recommendations can be invaluable when planning your itinerary and trying to make the most of your time in the Lowcountry. 

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Insider's Guide to Charleston

Your Guide for Where to Eat on Folly Beach


Lost Dog Café 

Indulge in traditional Southern cuisine with a twist! Lost Dog Café is one of the most delicious stops if you’re searching for breakfast to power up for a long day on the beach, or if you need a go-to eatery for a family brunch. With a diverse menu full of both classic favorites and innovative creations, there is something for everyone to enjoy. The Folly Benedict is a real crowd-pleaser, and you’ll be blown away by the Graham Cracker Peanut Butter French Toast.  

Jack of Cups Saloon 

Get an authentic taste of Folly’s food scene at Jack of Cups Saloon. As a long-standing local favorite, there’s a reason visitors and locals alike flock to this unique café in the heart of Folly. Here you can enjoy Asian Fusion, Indian cuisine, and Italian plates all in one seaside joint. Each plate offers a unique taste, so much so that it may even turn into a highlight of your trip.   

The Crab Shack 

Calling all seafood lovers! Experience some of Charleston’s freshest seafood at The Crab Shack on Folly Beach. After all, what’s a beach trip without a dozen oysters and a Lowcountry boil? That’s not all! You can often find live music at this Folly favorite while enjoying creative frozen cocktails and great times with family.  

Taco Boy

With more than one location in Charleston, Taco Boy is considered a local legend for margaritas and tacos.  The team at Taco Boy elevates the street taco of West Coast, beachside food trucks and adds a lowcountry twist.  And with an all new location on Folly Beach Taco Boy now features an updated taco menu, frozen drink bar, festive décor, and a roof top mezcal and tequila bar with ocean views.

Wiki Wiki Sandbar

You might not even know that you were looking for a Hawaiian-inspired fusion restaurant until you actually came across one, but Wiki Wiki Sandbar offers a one-of-a-kind taste of Polynesia. This newcomer to the Edge of America, features a menu inspired by the Hawaiian Islands and melds flavors that reflect both exotic island travel and its lowcountry Southern roots.

Loggerhead’s Beach Grill 

Loggerhead’s Beach Grill offers a classic beachy atmosphere with plenty of outdoor seating, so you don’t have to say goodbye to the sunshine, even on a lunch break! The atmosphere is only made complete by the old bright blue Volkswagen bus parked outside and the frequent live music found here. Don’t forget to try the conch fritters for a true taste of Charleston’s seafood offerings. 

Find Your Charleston Getaway with Luxury Simplified Retreats 

When you’re looking for a vacation that delivers all the rest and relaxation mixed with once-in-a-lifetime experiences Luxury Simplified Retreats is here to help craft your unique Charleston vacation. Whether you’re staying on Folly Beach, Downtown, or even a luxury destination like Palmetto Bluff in Bluffton, SC, you can rest knowing that you’ll be in good hands. From a friendly, professional concierge service team to assist you every step of the way, to exquisite rental homes in Charleston’s most desirable areas, you’ll find everything you need when staying with Luxury Simplified Retreats. Contact us to begin planning your uniquely tailored getaway and book your stay in one of our luxury Charleston rentals homes. 


While its true, bringing a championship golf tournament to Charleston SC during a global pandemic will certainly present many challenges, come May 2021, all eyes will be on The Ocean Course at Kiawah Island Resort for the highly anticipated PGA Championshipan event that any golfer looks forward to. While no one can predict what lies ahead for travel during the COVID-19 pandemic, whether you’re traveling to the tournament as a couple or with a small group, or attending the event with the hopes of entertaining a large group, Luxury Simplified Retreats has a wide variety of options available for your visit. Browse our 2021 PGA Championship accommodations below to help you select where to book your stay. 

World-class golfing isn’t the only thing you can expect to find when traveling to Charleston. From mouth watering cuisine to a colorful, West Indies inspired cityscape, you’ll soon discover why Charleston ranks as a top vacation destination year after year. Request a copy of our complimentary Insider’s Guide to be sure you’re making the most of every moment.  

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We Have the Best 2021 PGA Championship Accommodations for You 

Although you’ll find the sweeping dunes of the 2021 PGA Championship course along the Atlantic beachfront on Kiawah Island, the sights and sounds of downtown Charleston shouldn’t be overlooked! You’ll discover the history and charm that reflect Charleston’s role in both the Revolutionary and Civil wars, plus attractions around Downtown, Folly Beach and Charleston’s many barrier islands that will truly make this trip unforgettable. 

Downtown Charleston 

Luxury Simplified Retreats The Royal Fern

Why not turn this trip into a true vacation? Stay in Downtown Charleston to experience the absolute best dining and shopping scene the city has to offer. Between dishing up the best southern cuisine in the country and a myriad of boutiques and shops lined up and down King Street, you’ll be taken by the abundance of character found in the Holy City. This part of town is one you don’t want to miss!  

Our Downtown Charleston rentals are best suited for couples traveling together or small groups of friends and family. With so much to do nearby, you’ll have no trouble walking to dinner, bars, and other activities.  

Folly Beach 

Folly Beach is another corner of the Charleston community that you can’t miss and truly feels like a destination of its own! With a beautiful coastline and even more remarkable cuisine to indulge in, this eclectic beach town is home to some of Charleston’s best surfing spots and with it’s laid back vibe, Folly Beach is the perfect environment to host your family and friends. 

Our Folly Beach homes are typically larger, and effortlessly deliver the wow factor, tailor made to host groups for wonderful entertaining opportunities. You’ll find homes with comfortable coastal interiors, appointed with luxury details, many with ocean views or their own private pool.

Interior View of Seaclusion Luxury Vacation Rental

Turn to Luxury Simplified Retreats for 2021 PGA Championship Accommodations 

With days packed full of walking the course and watching the world’s greatest golfers battle it out, you won’t want to worry about the details of planning your days away from the course. Allow our Concierge team to take care of that for you. At Luxury Simplified Retreats, we provide rental accommodations  that meet only the highest of standards to ensure your trip is worry-free and relaxing from start to finish. With a vast portfolio of Charleston properties, we know you’ll be able to find the perfect place for a once-in-a-lifetime tournament experience. Book one of our luxury vacation rentals and let us help you start planning today …  we can’t wait to host your stay in the Lowcountry.  

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. 

Hydrofly Watersports 

185 Lockwood Drive, Charleston, SC 29403,  (843) 990-0707  

Day 2: Charleston Sailing Adventures 

Sailboat named Prevailing Wind

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. 

Charleston Sailing Adventures 

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. 

Session Sports 

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!