Blue Life Charters |33 Lockwood Drive Charleston SC 29401 |  (843) 743-4915

Welcome to the enchanting city of Charleston, where Southern charm meets rich history, creating an irresistible allure for travelers. Nestled in the heart of South Carolina, Charleston boasts pastel-hued homes, cobblestone streets, and a culinary scene that promises to tantalize your taste buds. This comprehensive guide is your key to unlocking the best experiences during your perfect 3 day Charleston itinerary.

As locals in the tourism industry my wife and I have dedicated our professional lives to ensuring guests have the best possible experience while visiting. Therefore, we crafted our personal favorites into a 3-day tour of the city so that you can truly enjoy every moment while visiting Charleston.

Day 1: Immerse in Charleston’s Charm

Your Charleston adventure begins with an immersive experience in the city’s unique charm. Start your day at the iconic Joe Riley Waterfront Park, where the serenity of the waterfront sets a tranquil tone for your journey. Here you can enjoy the views of the Harbor watching a variety of boats pass by. Also, don’t forget to visit the Pineapple Fountain, a symbol of hospitality.

Take a leisurely stroll down the historic King Street, a bustling thoroughfare offering a mix of boutiques, charming cafes, and significant landmarks. Here you can spend some time shopping to your hearts content with the finest fashion southern hospitality has to offer. If you’re not much of a shopper then rent a bicycle and explore the city at your own pace. There are so many vibrant streets and alleys tucked away in the local neighborhoods beckoning for you to explore.

For a delightful dinner, venture to the Elliotborough neighborhood and savor artfully crafted cuisine at Chubby Fish. The daily-changing menu ensures a fresh culinary delight, and the lack of reservations allows for a spontaneous dining experience. Another favorite is Chasing Sage and completely worth the experience with a pre-booked reservation. Be sure to order the chef’s menu for a delightful 5-course meal you will never forget!

Waterfront Park Pineapple Fountain

Day 2: Explore Charleston’s Rich History

Dedicate your second day to unraveling the rich history that permeates Charleston’s streets. Begin your morning at the historic City Market, a vibrant hub showcasing the talents of local artisans. Make sure to stop by Miller’s All Day Cafe nearby for a great breakfast to start your day!

Meander along The Battery, a historic seawall adorned with antebellum mansions and picturesque gardens. Capture the vibrant pastel hues of Rainbow Row and delve into the city’s history in the neighborhoods South of Broad.

Conclude your day with a private sunset cruise on a sailboat overlooking the city from the water with Blue Life Charters and truly capturing why Charleston earned it’s nickname: the Holy City. This will most likely end up being your trip’s highlight so don’t forget your camera and a bottle of bubbly to savor each moment.

Charleston viewpoint from a private sailboat tour with Blue Life Charters

After a beautiful sunset on the water make your way to Wild Common for cocktails and delicious bites to eat. They offer a rotating menu so there is always a surprise there, no matter if you’ve been before or not. Like most restaurants in Charleston, don’t forget to make your reservation ahead of time. The strategic timing and reservation tip ensure you make the most of Charleston’s culinary treasures. Another dinner option to choose from is Sourghum & Salt. A small restaurant tucked away in one of the many downtown neighborhoods. This hidden gem is sure to put a smile on anyone’s face.

Day 3: Coffee, Culture, and Culinary Delights

Embark on your final day in our 3 day Charleston itinerary with a visit to the enchanting Harken Cafe, where the magical ambiance and delightful pastries set the perfect tone to start your final day in Charleston. Explore Queen Street and the French Quarter, home to architectural gems like the pastel pink French Huguenot Church. Indulge in brunch at Husk, a quintessential Southern restaurant.

Now it’s time to venture beyond the city to Sullivan’s Island or Folly Beach for a refreshing coastal experience. Both are beautiful beaches with very different environments.

Folly Beach offers a very eclectic atmosphere similar to going to the Keys. A surfer beach town that is both inviting and entertaining, no matter your age. If your spending your day here make sure you end up at Bowens Island Restaurant for dinner. While this restaurant isn’t “technically” on Folly Beach, we think it’s close enough. Located at the tip of a 13-acre island, 5-minutes from Folly Beach, Bowens Island is famous for its locally harvested oysters, fried shrimp, hushpuppies, cold beer, and its undisturbed view of the marshes, rivers, and wildlife that surround the property.

Folly Beach Morris Island Lighthouse

Sullivans Island offers a more sleepy beach town atmosphere with a small strip of restaurants and bars and the perfect place for a quiet day with your book and some sunshine. After a day at Sullivans you will need to stop by Shem’s Creek for an amazing seafood dinner extravaganza. Shem’s Creek is lined with places to eat and drink, offering award-winning coastal cuisines combined with stunning waterfront views. Get a table next to the water and watch as Dolphins swim by while you sip on your favorite cocktail and indulge in our local seafood cuisine. No matter the route you take for your final day in Charleston, this will be sure to place the cherry on top for a magical weekend in the lowcountry.

Where to Stay While Visiting

Selecting the right accommodation is crucial for a memorable stay in Charleston. Opt for areas like South of Broad, French Quarter, or King Street, where Southern hospitality and luxury intertwine. The Spectator Hotel, nestled near the City Market, provides a voyage and adventure-inspired experience. Experience a touch of royalty at The Dewberry, renowned for its marble interiors and signature scents. You can revel in luxury with Southern comfort at the Bennett Hotel, nestled right next to Marion Square, the heart of our city. These strategic choices ensure proximity to key attractions and an indulgent stay.

Getting Around

While Charleston is often deemed walkable, the city’s attractions can be dispersed. Many of the hotels offer bicycle services in order to scoot around the city at a relaxing pace. If you prefer someone else to peddle the are bicycle taxis at almost every busy corner of the tourism areas. Consider renting a car to navigate the city seamlessly, providing flexibility for exploration. Alternatively, rideshare options like Uber and Lyft are easily available, though peak times may incur higher costs. Strategic accommodation choices can also facilitate convenient exploration on foot, enhancing your overall experience.

Staying Longer than 3 Days

Charleston’s allure might tempt you to extend your stay. Consider additional excursions to nearby attractions like Magnolia Plantations and Middleton Place, Boone Hall, or Isle of Palms. Explore Cypress Gardens for a serene boat ride in the swamp or take a short drive to Savannah, GA, for another taste of Southern charm. These extended adventures promise a deeper understanding of the region’s diverse offerings, turning your 3-day Charleston itinerary into an immersive Southern exploration.

Magnolia Plantations Charleston SC

When is the Best Time to Visit

Charleston welcomes visitors throughout the year, with each season offering a unique charm. Spring (March to May) and fall (September to November) provide pleasant weather and fewer crowds, creating an ideal atmosphere for exploration. However, the city’s Southern charm shines in every season, allowing you to choose based on your weather preferences. Whether you prefer blooming gardens or festive holiday lights, Charleston has something to offer year-round.


Charleston, with its cobblestone streets, historic homes, and delectable cuisine, promises an unforgettable experience. Whether you follow our meticulously crafted 3 day Charleston itinerary or extend your stay to explore more, Charleston is sure to leave an indelible mark on your heart. Embrace the Southern hospitality, savor every culinary delight, and relish the rich history that makes Charleston a true gem of the South. Your journey awaits in this enchanting city where time seems to slow down, allowing you to immerse yourself in its beauty and charm.