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  • Katie & Amanda

Charmed by Charleston

We spent Labor Day weekend in Charleston, South Carolina which not only charmed Katie and Amanda but also Travel + Leisure readers as it won the top spot in the 2023 World's Best Awards' favorite cities in the U.S category for the 11th year in a row! If this isn't your sign to minimize this window and start looking up some flights, we don't know what is! Our weekend was sweeter than southern sweet-tea and we couldn't wait to share all our recommendations and details! Whether you are looking for a girls getaway, couples retreat, or an out of town group gathering, don't miss out on visiting this beautiful city!

First things first, travel is so convenient (for us)! Flights are just a hop skip and a jump away from Chicago. The reason for visiting Charleston was to celebrate one of our favorite couples and their amazing journey ahead, Joe and Serena. There were tons of family and friends flying in for the wedding with a number of options available for an early morning arrival or evening. The airport was easy to navigate through and only a 20 minute Uber ride away from our hotel.

Where to Stay in Charleston

If this is your first weekend in Charleston, we highly recommend staying in the Downtown Historic District. Why? It’s the heart of Charleston, and where you’ll find many of the city’s historic landmarks and attractions. The location is impossible to beat. Located directly on King street, exiting your hotel will put you in the middle of local business, shopping and restaurants. The hotel itself offers 3 restaurants (the food was superb), 4 bars (drinks were top notch), a full service spa for guests (treat yourself - we did) and has several shopping options (like Tommy Bahama, Everything But Water, LV and Gucci to name a few). An indoor/outdoor saltwater pool and fitness center are located on the 4th floor alongside a rooftop clock-tower terrace and bar. We loved how conveniently located in the heart of the historic district our hotel was. The lobby was beautifully decorated with a display between the two spiral staircases and the sitting courtyard with a daily wine hour was well received by us!

An honorable mention would be Hotel Bennett if we didn't stay at The Charleston Place. The hotel is also in a great location on King Street with exceptional walkability and is absolutely stunning. They even have the prettiest pink chandelier room to sip cocktails in, a rooftop pool, and full service spa.

Tourists doing touristy things

It may have been the kid free sleep or the excitement of waking up on vacation but we would find ourselves up early and ready to start the day. While our husbands met for coffee and spa steamers (to get out the booze from the night before) we had the best time walking the streets and seeing all the sights. The best part is you can get around by foot! Many of the attractions are accessible and close by, that's the joy of the small city. Charleston is a great place to go for a long bike ride - its pretty flat, the pace is slow and totally easy to navigate. Luckily our hotel had bikes available for guests to partake in a leisure activity complimentary.

We started the day off with a caffeine pit stop and headed to the Joe Riley Waterfront park to see the famous Pineapple Fountain. The Joe Riley Waterfront Park is a large public park located on the Charleston Harbor, with beautiful views of the water and the city skyline. The pier is relaxing and you can sit and watch the ships come in and out of the waterway. From there we walked along the waterfront known as the Battery which was a civil-war coastal defense landmark. The path stretches along the lower shores of the Charleston peninsula, bordered by the Ashley and Cooper Rivers, which meet here to form Charleston harbor. From there we circled back to Rainbow Row which is known as a row of 13 pastel colored historic homes.

Before heading home we made sure to visit the Charleston City Market which is one of the oldest public markets in the heart of Charleston (conveniently located across the street form our hotel). The market is open daily and is home to more than 300 entrepreneurs. We had the best time walking the stores and seeing all the special items for sale. The store fronts sell everything from food, soaps, clothing, toys and everything in between. No matter what time of day or season you visit, there is always something to find at the market! Katie made sure to find a "purple t-shirt" as requested by Remi and a Christmas ornament for their travel collection.

Dining Recommendations

If you follow the blog you know we are big foodies! We love trying local well-known spots when we are on vacation.

Halls Chophouse has a few locations throughout the country but has been a staple for visitors in Charleston. This spot opened on King Street in 2009 and has been known to have hosted and fed a number of famous people. We were surprised to find out the steaks are actually from Chicago! If you are looking for a night out on the town and to dress to impress, add this to your list of must see eats! Great drinks, entrees and sides, we left full and satisfied.

167 Raw (Oyster Bar) is a Charleston dining essential. We were fortunate enough to pop in for lunch on Thursday when we arrived and it was one of the best meals we had. They have several restaurants in SC and we wish we had more time to try them all. The menu highlights the outstanding seafood mecca that is the East Coast and serves the freshest seafood.

Church and Union had one of the coolest, most unique dining ambiances we've ever experienced! The restaurant and bar were converted from an old church. This gothic establishment exceeded our expectations when it came to aesthetic, food and service. Our server had the best recommendations and we dinned on several appetizers and dishes that were delicious for dinner. Church and Union isn't just a dinner spot! They are known for their lively brunches too. We highly recommend grabbing a reservation in advance.

Henry's has been the place to be since 1932! It is the oldest continuous restaurant in Charleston and the state of South Carolina. Henry’s offers the best of Charleston: a historic, eclectic restaurant and bar featuring live music, a beautiful southern porch and rooftop deck, an exclusive dance lounge, and a classic speakeasy bar. We sipped on (too many) cocktails and danced late into the night while enjoying live music at Henry's on the Market!

We genuinely enjoyed all the places we dinned at in Charleston, but there were a few spots on our list we simply didn't have time to try that that we've notated for next time! The south is know for BBQ so on our next visit we plan to check out the brisket at Lewis Barbecue and famous pulled pork from Rodney Scott's. We're bummed we never got around to checking out Leon's Oyster Shop that specializes in fried chicken and oyster or Husk Restaurant that highlights Southern cooking and localized ingredients.

Weekend Wedding Details

This wedding brought so many family members and friends together, it was the perfect weekend to make lasting memories.

Friday evening we attended an intimate rehearsal dinner followed by an inviting welcome party hosted at the Cannon Green. Walking into the event we were greeted by "his" and "her" drinks. The tablescape was a showstopper draped in lace and lined with stunning floral arrangements and candles. After a delicious meal everyone moved outside to the terrace where the welcome party was held. You couldn't have asked for a better evening, the weather was perfect, the company was inviting and the drinks were flowing! We ended the evening with a 1 a.m. pit stop for pizza and a rickshaw ride back to our hotel.

Saturday was the most magical evening filled with love, laughter and the best company. The wedding was hosted at The Cedar Room. The building was previously a cigar factory and boasts rustic brick, hardwood flooring, historic wood columns and floor to ceiling windows. The space was airy and perfectly laid out for a wedding ceremony and reception. As most people know the ceremony was officiated by Wells Adams and he absolutely crushed it. It was a perfect mix of humor and sentiment that kept everyone in attendance engaged. Joe and Serena also exchanged personal heartfelt vows that brought tears to our eyes (some from laughter too). While the rooms was transformed guest enjoyed cocktail hour outside on a beautiful patio while munching on delicious hors d'oeuvres. We had the best time from start to finish and only left the dance floor to refill our drinks and grab desserts/late night snacks.

You can get all the in-depth information and details about the Welcome Party & Rehearsal Dinner and the Wedding Celebration in People's exclusive article or on Joe and Serena's Bachelor Happy Hour podcast where they share behind the scenes content (like the hurricane fiasco that gave everyone travel anxiety).

Looking the part

The most important aspect in planning our trips were looking the part. For this vacation we channeled our inner southern belle and summoned all the southern charm we could muster! It was time to trade in our modern black urban chic attire for brightly colored hues, linens, crochet and floral outfits. Everything we wore in Charleston is linked on our LTK for easy outfit inspo. It was fun to branch out from our comfort zone and try new looks that fit the vibe of our destination.


Charleston exceeded all our expectations and there's so much more we'd love to explore if we have the opportunity to go back. On our next adventure we'd love venture out and see Sullivan's Island, Island of Palms and Kiawah Island. When Joe and Serena announced their wedding location we were both thrilled with the prospect of traveling to new destination. Never did we ever think we'd fall in love with the city as much as we did. So much that Katie extended her trip an additional day. We are not exaggerating when we say everyone had an amazing experience in South Carolina!

X0 - Katie & Amanda



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