Planning The Perfect Girl's Trip to Charleston, SC

I’ve written about Charleston before, and it still stands as one of my favorite places in the United States. I’m sure you’ve heard the buzz about Charleston by now, and everything everyone says about this little city matches its growing popularity. I was so excited when my girlfriends and I decided that Charleston was the perfect place to meet for our annual reunion. It’s such an easy flight from anywhere on the east coast, and although not easy for the west coast gals, I didn’t care at all since, well, we were heading to Charleston!

The Planning:

Our group texts all day everyday in a group chat, which is the perfect way to stay in touch on the regular. These girls are the best of friends a girl could ask for. We could go years without seeing each other and pick up right where we left of the next time we’re together. To me, that’s true friendship. I adore and cherish each and every one of them so much! That said, we all lead insanely busy lives and live all over the US, so planning a destination trip isn’t a walk in the park. Every time we plan something, we always use Doodle to take a poll and find out the best date that works for everyone. Once we set a date, everyone schedules their own flights, then lets the group know the time they land and depart. For this trip, we knew we wanted to stay in an Airbnb or VRBO since there was six of us, so we created an Excel file of all of our options:

Where we stayed:

Luckily, we researched this trip months before since it was the weekend before the fourth of July and knew it would be super busy. We ended up staying at this Airbnb, and it was a perfect, fun place to stay. The home was located three blocks from King St., where there was a Drybar and great restaurants. The only things we truly need on a girls trip anyways 🙂 The Airbnb was three stories, with plenty of room to sleep, huge kitchen, and two decks where we hung out and drank wine together. Highly recommend! If you’re looking into hotels, check out my past post about the absolute best hotel in Charleston, Zero George. I also stayed at The Hyatt Place the first night, since I arrived the night before at 2am before all of my girls flew in. I wanted to make sure I had a safe, brand name hotel that was close to our Airbnb, and this hotel was the perfect place to rest my head for a few hours.

Where we ate & drank:

Husk: I’m sure you’ve read about Husk 100x’s if you’re planning a trip to Charleston. Husk is a very well known, farm to table restaurant serving low country, farm fresh food. I came here for lunch with my grandparents before the girls flew in. I personally did not think that Husk was beyond amazing like most people say, but the food was certainly fresh and delicious. I came here during my last trip to CHS and think the restaurant has a better vibe at night compared to lunch. Husk reminds me a lot of San Francisco’s Nopa restaurant. The burger was divine!

The Watch Rooftop & Kitchen: We wanted a fun rooftop to dine at the first night in the Holy City, and The Watch delivered. We started the night off fun with tequila shots at the bar (hello girls trip!) and followed them by ordering way too many bites and a bottle of rosé while enjoying the view.

Leon’s Oyster Shop: We rode bikes here during the day for an early lunch. We came in sweaty and hungry. Although their colorful outdoor tables were compelling and colorful, we opted for a cool table inside the eclectic restaurant. The food was fun and yummy! I devoured my cold shrimp cocktail, and fresh avocado toast. I’d highly recommend this spot for a large group. They don’t take reservations, but we went on a Friday afternoon and had no problem getting a table. PS: They have frosé and frozen gin & tonics!!

Fleet Landing: We came right from Leon’s to Fleet Landing for drinks on the water. Fleet is definitely a bit of a tourist stop, but I think it’s a gorgeous place to enjoy a cocktail or beer on their large deck overlooking the water. We spent the rest of our first afternoon here, laughing, soaking up the sun and indulging in spinach artichoke dip!

The Darling Oyster Bar: If you’ve made it this far down my list, you probably can tell that the food scene in Charleston is incredible. I didn’t have one bad meal while there, but The Darling Oyster Bar was my absolute favorite. For starters, it was three blocks from the house we rented, and the decor was fun and girly. I wanted to snap pictures of everything! Our table started with tequila cocktails followed by all kinds of seafood – fresh oysters, cold shrimp, asian fried oysters, and hush puppies. Everything was SO good. This would be my first stop the next time I visit. A must!

The Obstinate Daughter: We came here for a leisurely lunch on our last day. The menu is so good that we decided to order a little bit of everything, pizza, cheese plates, chicken & brussel sprouts, and a salad. The food was to die for (a theme in Charleston) and the ambiance inside and outside on the patio was welcoming and cozy – we spent hours chatting away. We liked this eatery even more when we found out our waiter was also from Vermont, where we all grew up! Such a fun afternoon on Sullivans Island.

Indaco: The perfect spot to finish up an amazing trip. Indaco is a rustic Italian restaurant right across from The Darling Oyster Bar. We spent our night filling our bellies with seafood pasta a great wine.

Jeni’s Ice Cream: Fun flavors and staff with major southern charm. I think I tasted 7 flavors before I chose the winner 🙂

Where to sip:

Stars Rooftop: A huge rooftop bar with, of course, frosé! It’s a thing here, ya’ll!

Mynt: Definitely for the younger crowd. Mynt is more of a nightclub with loud music and cheap drinks. It’s cons are outweighed by a huge patio in the back with the biggest swing I’ve ever seen.

The Gin Joint: Incredible cocktails!

The Co-op on Sullivans Island: Our waiter at The Obstinate Daughter gave us the best tip ever – this place right next door to the restaurant sells…..frosé *TO-GO* and cold brew. Best place ever? A lot of frosé was consumed on this trip!

Activities:

For such a small city, Charleston packs a big punch. There is so much to do, I already can’t wait to go back.

Bike Rentals: Most hotels offer complimentary bikes, there are two different rental bike shops, and they also have city bikes like most cities where you pay by the hour and can drop the bike at any station near your location once you’re finished using it. Charleston’s city bikes are called Holy Spokes, and these worked out perfectly for our crew. No wasting time signing papers, setting up the bikes, and dragging them back to a shop. You just download the app, grab, and go! Biking around the city is easily the best way to see everything and stay cool in the humid temps while doing so. Trust me, I’m not usually one to jump on a bike, but Charleston is the perfect place for this. That said, us crazy bikers definitely upset a few cars along the way 🙂

Eating and Drinking your way through the city is a fun way to get to know the locals and the flavors of low country. Make a list of your must stops, grab your bike (to outweigh those calories!) and make your rounds to the most popular eateries and watering holes.

The Farmers Market on Saturday mornings is the perfect spot to grab a smoothie and have a leisurely morning.

Sullivan’s Island is a quick $15, 20 minute Uber over the bridge. Have the Uber drop you at Obstinate Daughter, enjoy lunch, grab some frosé next door, and walk to the beach to spend the day soaking up the sun. We were going to skip this, but I’m so glad we went! Sullivan’s is such a cute area and the beach is beautiful.

Sip at local coffee shops! Being on a girls trip, we were running off of lots of wine and very little sleep. I loved popping in the local coffee shops to enjoy a few minutes in the air conditioning and sipping on a cold brew. Our favorite was Relevator, which received 5 stars from my coffee snob friend 🙂 We came here everyday!

Rent a private catamaran and sail along the bay for 2 hours. We used Charleston Sailing Charters and sailed with Captain Brian. This was SUCH a fun activity and very fairly priced. Since we were out on the bay, we got to escape the heat a bit, and enjoy seeing the city from the water. We brought a cooler of wine, snacks, and music and had the best afternoon.