Anniversary Adventure: Weekend in Charleston, SC

To celebrate our 5 year anniversary in November 2025, we escaped for a much-needed solo weekend in Charleston, South Carolina. Charleston had been on our list for years, and it’s so cool that we now live only a few hours away. It was filled with history, great food, and beautiful scenery.

LODGING

We stayed at the Best Western Charleston Inn, which provided a comfortable home base for our trip. Its location made it easy to explore downtown but nearby destinations like Johns Island, Mount Pleasant, and Moncks Corner without spending too much time in the car. Best Westerns are one of our favorite hotel chains - they’re usually pretty clean, have a good breakfast, and are reasonably price. We were able to get a pretty decent deal for being rewards members and booking short notice.

ACTIVITIES

🌉 Exploring Downtown

Downtown Charleston is full of charm and easily one of the most walkable and picturesque areas we’ve visited. A few of our favorite stops included:

• Charleston City Market – Free to enter and open daily, this historic market is one of Charleston’s most iconic attractions. They have a “day” and “night” market open with local vendors sell everything from handmade baskets to artwork and souvenirs, making it a great place to browse and soak in the local cultures. This reminded us a lot of a smaller version of Pike’s Place Market in Seattle.

• Charleston Farmers Market – A lively weekend market featuring local produce, artisan products, food vendors, and live music. This is open seasonally in Marion Square. We ended up grabbing lunch and drinks from food trucks here

• Rainbow Row / St. Michael’s Church - Charleston’s famous row of colorful historic homes that has become one of the city’s most photographed landmarks. This really was just as pretty as the pictures! The church is one of Charleston’s most recognizable historic churches and a stunning example of the city’s rich history and architecture

  
  

• Waterfront Park – A beautiful place to stroll along the harbor, enjoy views of the water, and relax near the iconic Pineapple Fountain

🌳 Angel Oak Tree (John’s Island)

Located on Johns Island, the Angel Oak Tree is estimated to be around 400 years old and is one of the oldest living things east of the Mississippi River. It’s a quick stop but absolutely worth the drive to see its massive sprawling limbs stretch in every direction.

While free to visit, the tree is in a gated area and we didn’t know you could only visit during certain hours. Even thought we weren’t able to get up close, the fence is chain link so we were still able to see it and snap photos through the holes.

🍃 Cypress Gardens (Moncks Corner, SC)

No romantic weekend getaway in South Carolina feels complete without a visit to Cypress Gardens: the breathtaking filming location of the iconic boat scene from The Notebook. Whether you’re a fan of the movie or simply looking for a peaceful escape, canoeing through the cypress swamp is the great way to spend an afternoon. It was a perfect detour (~40 minutes from downtown) on our way back home to the upstate.

The self-guided boating tour is included with admission ($10/adult), but are only available on a first come, first served basis. It fill up quickly, especially on weekends and holidays. You’ll need to put your name on the waitlist as soon as you arrive, no reservations beforehand. It’s best to do this before you explore any walking trails or exhibits. We didn’t know this before arriving, but luckily we only had to wait about an hour on a Sunday afternoon.

🌊 Waterfront in Mount Pleasant, SC

Mount Pleasant Memorial Waterfront Park offers beautiful views of Charleston Harbor and the impressive Arthur Ravenel Jr. Bridge. We enjoyed walking along the waterfront, taking in the scenery, and watching boats pass by. The bridge is known as one of the most iconic in the South, and even has a pedestrian path.

FOOD & DRINKS

• The Biscuit Shed - Located at the Charleston Farmers Market, The Biscuit Shed was our brunch stop while exploring the market. Fresh biscuits and local ingredients made it the perfect way to start the day before wandering through the vendor booths.

  
  

• Fratello’s Italian Tavern - This North Charleston restaurant was our choice for an anniversary dinner. The atmosphere was welcoming and less crowded than downtown. Prices were reasonable, and you can never go wrong with Italian food for a romantic evening

• Holy City Brewing - Charleston has a ton of breweries to choose from, but we went with this option since we were going to eat dinner in North Charleston. It’s facility offers a lively atmosphere with plenty of craft beer, a full restaurant, and lots of indoor and outdoor seating.

  
  

• The Watch Rooftop Kitchen & Spirits - I wanted to have a fun parents night out, but since I was pregnant, I wasn’t sure how many options we’d have available. This was the perfect escape from a typical bar scene - a relaxed, yet classy atmosphere with a great selection of both alcoholic and mocktail options. It was a little pricey, but we had fun sitting above the city and enjoying good conversation & beverages.

FINAL THOUGHTS

What we loved most about Charleston was the variety. In a single weekend, we explored historic streets, browsed local markets, stood beneath a centuries-old oak tree, paddled through a cypress swamp, and enjoyed waterfront view.

The city has an energy that’s both vibrant and relaxed - blending history, coastal beauty, and Southern hospitality in a way that feels uniquely Charleston. Despite everything we packed into this trip, we still left with a long list of places we’d like to visit next time. It’s a great destination to explore all year round.