Last July, my friend Caitlyn and I were busy planning our next adventure together when she suggested we invite a few other people along. We debated between a few different cities but ultimately decided on Charleston. Both of us invited three friends to tag along and thus our first annual girls getaway was born. We had SO MUCH FUN and are already brainstorming our next destination... where should we go?!?
Nicknamed the Holy City for all the churches that dot the skyline, Charleston is the perfect mixture of Southern hospitality and Coastal living. There is no shortage of delicious food and I could have spent days exploring the quaint streets of this peninsula city. Charleston is a great option for a long (or regular) weekend trip. Most of our group arrived on Wednesday evening and left Monday afternoon - which gave us plenty of time to see the main highlights and explore more of the city's hidden gems.
When to go: The Atlantic hurricane season runs from June 1 to November 30, with the peak period being from early August through the end of October. While few hurricanes make landfall each year and there is statistically a very low risk that a storm could impact your vacation, I suggest visiting Charleston during the other half of the year. We found awesome flights at the end of February and had pretty good weather (low 70s) but I do think it'd be lovely to go later in the spring, when all the flowers have bloomed!
How to get there: Each of us flew into Charleston's two-terminal airport on United. From Minneapolis, I had a layover in O'hare - which worked out well because a few of the girls were flying direct from Chicago, so I met up with them at the airport! When you land in Charleston, you'll have no problem calling an Uber to pick you up and bring you back to your hotel. It was relatively cheap; I think the 25 minute ride was around $20 total. Getting around: The two best ways to explore Charleston are to walking and Uber/Lyft. Most of the historic sites are relatively close to one another, so walking is the easiest way not to miss anything. For bigger distances, we used Uber/Lyft. I think each ride was close to $8, which we then split up between us so it was super inexpensive! To get to the Magnolia Plantation, we used Uber - and just made sure we allowed enough time for an Uber to come out and pick us back up. I had done a lot of research about day-trips from Charleston and was set on exploring Wadmalaw Island - so we hired David from Holy City Transportation to share an entire day with us, which I'll share more on below.
Stay | Hotels For group trips, I tend to lean towards Airbnb/VRBO properties - and this was no exception. We ended up using a local company, called Walk Away Stays, to book a beautiful four bedroom house for our time in Charleston. It was super well-located for exploring and there was so much space for our group. We spent a lot of time in the common spaces hanging out and loved having a kitchen, where we could cooked dinner one night and made breakfast one morning to cut down on costs. The biggest downside to this property was the garbage truck that came by the nearby restaurant every morning to dump bottles. If I came back to Charleston with a large group, I'd definitely try to stay here again. They have smaller options for different sized groups, but if it were just Mike and I, I'd love to stay at one of the following boutique hotels in town:
King Charles Inn | What I'd call an "affordable splurge" - their prices are reasonable for the location and amenities provided... including their outdoor pool, free parking, and evening reception with artisan cheese boards!
The Mills House| This bright pink hotel is absolutely gorgeous. My friend Dana stayed here the night before the rest of our group arrived and she loved it!
The Vendue | Charleston's first and only hotel dedicated to the arts - with over 300 pieces of original art for guests to enjoy. It is also home to one of the best rooftop bars in the city.
The Dewberry | A posh hotel in a former federal building that offers complimentary bicycles for you to explore the city!
Hotel Bennett| One of the newest hotels in Charleston... this is the spot to stay if you're seeking luxury.
Where to Eat and Drink: Charleston is foodie haven and there is no possible way you can go hungry here. There are so many restaurants with a range of specialties - you'll have a hard time deciding on where to go. With our group's large size and a variety of dietary preferences, we narrowed down our list of restaurants that could accommodate us. They're listed alphabetically below. A few restaurants on my list to check out when I return are Poogan's Porch, Butcher & Bee, The Macintosh, and Edmund's Oast. Beech| 315 King Street
After a night out, all of us were looking to indulge in something healthy and Beech perked us all back up. They've got unbeatable açaí bowls and it was here that I tried my first poke bowl! This is a fabulous place to stop for a quick snack or light lunch as you shop your way down King Street.
You may be familiar with this spot, as it's been nationally featured numerous times for their inclusive mission. Run by employees with intellectual and developmental disabilities, Bitty and Beau's offers all of your traditional coffee drinks in addition to sweets and smoothies.
A trip to Charleston would not be complete without a stop (or two) at Callie's. They have a variety of fresh biscuits, but the biscuit sandwiches are totally worth writing home about. Be prepared for a wait. I returned home and researched how to ship their pimento cheese because there's nothing like it anywhere else... hint: it's not easy or cheap.
** Side note: Callie's Upper King location re-opens on Friday and Saturday nights from 10pm-2am for all your post-bar snack needs. Darling Oyster Bar | 513 King Street
Honestly, I was a little underwhelmed by our visit here. The food wasn't bad and they've got some excellent happy hour deals if oysters are your thing, but I had really high expectations after so many people recommended this spot and I don't think it necessarily lived up to the hype. That being said and if you decide to stop in, be sure to try the Creole Shrimp - they reminded me of my mom's and the serving size is perfect for sharing, or for your main entree.
We walked past this adorable, re-purposed 1950's era gas station when we were looking for a spot to grab lunch before we had to head to the airport for our flights home. We could have spent all afternoon on their back patio.
I must confess that I didn't personally come here, but my friend Dana was making cheeseboards for the night we stayed in and she came here to get some cheese/accompaniments and now I want one of these stores in my backyard. Their second location (804 Meeting Street) has a cafe and wine bar where you can enjoy a sandwich or one of their cheese & charcuterie boards. This is definitely a must-visit for when I'm back in town.
The Charleston area has some pretty popular bbq joints, but a few people had recommended Lewis and it did not disappoint. Their meats were smoked to perfection and so flavorful - I didn't even need sauce! As a bonus their sides paired perfectly and I could have eaten an entire bowl of their mac&cheese.
This casual Mexican eatery was full of energy and ended up being one of my favorite places we ate in Charleston. We didn't know it was National Tequila Day until we showed up, but we took full advantage of their happy hour. Their homemade tortilla chips were some of the best I've ever tasted. I tried three of their tacos - the Taco El Pastor (grilled pork) being my favorite. This is truly a hidden gem and I highly, highly suggest you get here if you're in the area.
We stopped into Prohibition for drinks twice because they were so tasty - they've got a quieter back bar area, as well as a nice patio if the weather is nice. Some popular choices by the group included the Queen of Siam, Aperol Spritz, and the Bacon Maple Old Fashioned.
Our group originally came into Stars for drinks on their rooftop. Later that night, as we were heading out, we realized there was a DJ on the first floor - so we ended up staying for another hour to dance the night away!
A chic bar on King Street where we sat back and reminisced on our amazing time in Charleston as a group. The drink menu is creative, but our server was quick to offer suggestions based on each of our preferences. Pro tip: arrive early to secure yourself a table, especially if you've got a large group. They don't take reservations.
The Park Cafe | 730 Rutledge Avenue
I absolutely loved my dish at the Park Cafe and could totally see myself eating here regularly if I was local. The service was speedy and friendly, the food was fresh and delicious, and the airy atmosphere was refreshingly welcoming. It's perfectly located for breakfast before you head out to explore Magnolia Plantation or head back to the airport.
Play | Things to Do One of my favorite things to do in Charleston was just walk around the neighborhoods and admire the gorgeous houses. I wouldn't be exaggerating if I told you that everything here is extremely photogenic. We explored Tradd Street, Church Street, meandered down Stolls Alley, and found ourselves doing this Gateway Walk that a fellow reader suggested. We also took (a few too many) pictures along Rainbow Row, a row of bright, colorful homes on Bay Street and then spent time at Waterfront Park, which overlooks the Cooper River and Charleston Harbor and is home to the famous Pineapple Fountain.
Magnolia Plantation is one of the most popular plantation and gardens in Charleston. Located about 20 minutes north of downtown, it definitely is worth visiting on your visit to the area. We opted to do the house tour and then explore the gardens on our own. After, we had the chance to meet some of the animals at the zoo & nature center on property - We spent around 3 hours, which was the perfect amount of time to get the full experience. The tour of the house was really interesting and then we opted to explore the gardens on our own.
Lastly, but certainly not least, I have got to share more about our island tour with Holy City Transportation because this might have been the biggest highlight of my entire trip. When we first started planning this trip we had thought about renting cars because I really wanted to escape the city for the day. Further research had me swooning over Deep Water Vineyard and I knew the everyone else would love it too. I actually coordinated everything through Fran at the vineyard and she was incredibly helpful- but you can book directly through David, our driver, as well.
David picked us up after brunch and we spent the whole day with him. It was so nice to be able to kick back, relax, and not have to worry about anything for the day. We first stopped at the Charleston Tea Plantation - the only tea plantation in North America - for a trolley tour and some sampling. Then it was onto Deep Water Vineyard for a tasting and a delicious cheese plate. Make sure you try some of their muscadine grape juice! On the same property and just across the way is Firefly Distillery. We did a tasting here, which included our choice of six of their spirits. They're known for making amazing Sweet Tea Vodka, but I was a huge fan of their Lemonade Vodka. Their moonshine was pretty tasty too. After, each of us ordered drinks/wine to enjoy outside. They have a bunch of picnic tables and lawn games and they do live music on Saturdays. David had to practically beg us to get back on the bus because none of us wanted the day to be over. On the way back we stopped to see the 400+ year old Angel Oak Tree. I cannot say enough good things about our time with David andHoly City Transportation. It was the perfect way to escape the city for the day and not go to the beach (it was too chilly) -