• This field is for validation purposes and should be left unchanged.

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! 



The Holy City draws visitors from around the country for its rich history, delicious cuisine, and stunning sights. While our historic town is a year-round destination, summer is when it truly comes to life. Energetic, vibrant, and brimming with potential, those who love to get out and explore will want to experience our Lowcountry jewel. Keep reading to discover how to make the most of your three-day summer itinerary in Charleston.

Searching for more things to do and places to see on your vacation? Our Charleston Insider’s Guide is full of the top shops, restaurants, historical sites, and much more!

The Perfect 3-Day Charleston Summer Itinerary

Day 1: Take a Culinary Tour of the Holy City

You’ll want to dedicate one day of your Charleston trip to savoring the renowned cuisine that calls our city home. Fresh seafood, inventive Southern dishes, and locally brewed beer are all staples to the popular Holy City foodie scene. Whether you want to sip a local brew as you watch the sunset from Shem Creek or dig into a plate of locally sourced gourmet fried chicken in a downtown restaurant, the opportunities are endless here! With so many incredible places to eat, it can be a difficult decision. Here are a few favorite breweries and restaurants to choose from during your three-day summer itinerary in Charleston.



Day 2: Enjoy Scenic Views and Rich History in Downtown

Summer in Charleston is the perfect time to enjoy Charleston’s landmark destinations that encompass a rich, historical past. The Battery  is a must-see on an afternoon stroll around the city. This fortified seawall at the tip of the downtown peninsula overlooks Charleston Harbor where the Ashley River and Cooper River converge. With roots dating back to the early 18th century, it’s a location that holds some of the city’s most fascinating stories. From here you can look out to Fort Sumter, often regarded as the location where the first shots were fired during the Civil War, when the Confederacy fired on the US garrison of Fort Sumter on April 12, 1861. And, while you’re walking around the Battery, be sure to take a break under the shade in White Point Garden. It is one of the most beloved areas of the city and the location of some of Charleston’s most magnificent mansions. Other historic sites to put on your list include The Charleston City Market, St. Philip’s Church, Marion Square and The Nathaniel Russel House.

Day 3: Hit the Beach

During the summer, you definitely should plan to spend at least one day of your extended weekend in Charleston at the beach. While the Lowcountry is home to some of the best stretches of sand along the South Carolina coast, we recommend checking out Folly Beach for the ultimate day under the sun. This is a quintessential beach town with plenty of shops, restaurants, and miles of shoreline. Whether you sunbathe, build sandcastles, or try your luck at surfing, you’ll find many incredible ways to spend an amazing day at the beach.

Plan Your Long Weekend in the Holy City

Luxury Simplified Retreats has the perfect property for your Charleston summer vacation! Our collection of rentals features an array of locations in the area, including downtown and Folly Beach. The best of the Holy City is right outside of your door! We love our city, and we know that you’ll love it too. Don’t forget to check out our concierge services and our experience packages for ways to enhance your stay!

Start planning your trip today by booking one of our properties! We look forward to welcoming you to the Holy City.