The Ultimate Charleston Weekend: Three Days Exploring the Holy City

Planning a weekend getaway to Charleston? Get ready to immerse yourself in the historic charm, coastal beauty, and vibrant culture of the Holy City. We’ll guide you through a curated list of must-do activities for a memorable weekend in Charleston, including an unforgettable sailing charter experience on Esprit de Joy! From exploring historic sites to indulging in delicious cuisine, this itinerary has something for everyone.

Day 1: Honor A Rich 300-Year History 

Day one is steeped in history – from the market complex that was first established in the 1790s, to the ground of one of the oldest plantations in the South, this day is perfect for history buffs looking to observe our past and present.

1. Charleston City Market:

Start your day by strolling through the Historic City Market, a 4-block open air market filled with local artisans, craftsmen, and unique vendors. Explore the stalls, shop for local souvenirs, and soak in the vibrant atmosphere of this iconic landmark.

2.The Battery and Waterfront Park:

Head towards The Battery, a historic seawall and promenade located at the southern tip of the Charleston Peninsula. Take a leisurely walk along the waterfront, enjoy the shade of majestic oak trees, and admire the stately antebellum mansions. Visit Waterfront Park nearby for its iconic Pineapple Fountain and stunning views of the Charleston Harbor.

3. Magnolia Plantation and Gardens:

Take a 30 minute drive to spend the afternoon immersing yourself in the beauty of Magnolia Plantation and Gardens. This historic plantation is the Low country’s oldest public attraction and offers guests breathtaking gardens to stroll, a plantation house tour, and over 400 acres of protected wetlands and scenic nature trails. Explore the picturesque grounds and learn about Charleston’s plantation era.

The Battery Charleston South Carolina

Day 2: Experience the Charleston Waterways as a Local 

1. Sailing Charter:

Embark on a sailing charter adventure to explore Charleston’s coastal beauty. Book a sailing charter and set sail across the Charleston Harbor, taking in the panoramic views of the city skyline, the Arthur Ravenel Jr. Bridge, and historic landmarks like Fort Sumter. Enjoy the soothing sound of the water, the refreshing breeze, and the chance to spot dolphins along the way.

2. Sullivan’s Island:

After your sailing charter, head to Sullivan’s Island, a charming barrier island just a short drive from downtown Charleston. Relax on the pristine beaches, take a dip in the Atlantic Ocean, and enjoy a seaside lunch at one of the local eateries. Captain Kyle recommends the Tell Tale Heart burger from Poe’s or the dozen wings from HomeTeam BBQ.

3. Rainbow Row and French Quarter:

Return to downtown Charleston and explore the colorful Rainbow Row, a row of pastel-hued historic houses (no. 79 to no. 107)  on East Bay Street. Wander through the quaint streets of the French Quarter, known for its art galleries, boutique shops, and historic churches. Be careful when selecting your footwear, this area of town is home to the eight remaining cobblestone streets dating back to the 17th century.

Day 3: Delight in Award-Winning Food & Beverage 

1. Brunch in Charleston:

Indulge in a quintessential Charleston brunch experience at one of the city’s renowned restaurants. Sample delicious Lowcountry specialties like shrimp and grits, she-crab soup, or Charleston’s famous biscuits. Fuel up for the day ahead. If you can manage to snap a reservation, our team loves the Gospel Brunch at Hall’s Chophouse.

2. Rooftop Views

Some of the best views in Charleston are from above. Take to Meeting or Broad Street and ascend onto the rooftops of The Vendue, The Watch or The Dewberry’s Citrus Club for panoramic views of the skyline and steeples. 

3. Plantation Tour:

Take a plantation tour to delve deeper into Charleston’s history. Boone Hall Plantation, Middleton Place, or Drayton Hall offer captivating glimpses into the region’s antebellum past and showcase beautifully preserved architecture and stunning gardens. Don’t forget to stop at the Boone Hall Farms Roadside Market located just outside the plantation gates for fresh produce and plants. If you find yourself here in August and September, the ‘U-Pick’ sunflower fields are a fun activity!

A weekend in Charleston offers a perfect blend of history, coastal beauty, and delectable cuisine. From exploring historic landmarks and strolling along the waterfront to embarking on a memorable sailing charter, this itinerary will help you make the most of your time in the Holy City. Immerse yourself in Charleston’s rich culture, relax in its natural beauty, and savor the flavors that make this city a true gem of the South.

1 thought on “The Ultimate Charleston Weekend: Three Days Exploring the Holy City”

  1. Jill,
    Congratulation to Kat and you on this venture, well done! I’m happy to be hearing such wonderful things about it. The boat, your presentation, everything looks absolutely fabulous. Wishing you continued luck with it. Hope one day to get back to Charleston and board the Esprit de Joy with you. Take care and have a wonderful year.

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