Charleston was on my list for years drawing me in with its southern charm, rich history, and of course delicious seafood. I poured my heart into planning this perfect weekend with my boyfriend of seven years. From amazing food to hanging out at the beach, paddle boarding with dolphins, and seeing all the main tourist attractions, I thought I had every detail of the trip planned. Little did I know that my boyfriend was also planning to finally propose on this trip! Charleston will always hold a special place in my heart and I highly recommend it for a romantic weekend with the one you love.

Day 1:

Sweet welcome from our Airbnb Host!

We chose to make the trip a three day weekend since we had a longer drive. We found the perfect Airbnb that was halfway between downtown and Folly Beach. It was a small quirky place with a shared bathroom. Thankfully we were the only guests and it worked out great for us! Halfway through the weekend, I discovered the owner spoke French and enjoyed talking about Charleston in my favorite language! We talked about where she grew up in France and my history with the French language as well.

Orange Theory:

At this time my now fiancé and I were both members of Orange Theory. Working out at a 9 am class while on vacation shows you the sort of travelers we are. I love that I can sign up for any class across the country at Orange Theory. Minus the big cities, you don’t have to pay any extra money!

Folly Beach:

After our workout and some very necessary showers, we decided to head out for a beach day. All the street parking is free at Folly Beach, but it is first come first serve. We got really lucky and only had to drive around for about 5-10 minutes before we found street parking on East Arctic Avenue. If you can’t find any street parking, there are some lots you can pay $7 for the day.

Our delicious appetizers at Pier 101

We were starved so our first stop was at Pier 101 right on the beach. A mid-morning sun shower came pouring down, so we got inside just in time. We ordered the Folly Beach Crab Dip and Fried Shrimp Seafood Basket as appetizers. Did I mention we were super hungry? Then for my entree, I ordered the grilled fish of the day with a side of delicious cheese grits.

After we wrapped up our late lunch, the sun came out and we were ready to soak it in! If you read my St. Simons blog post, you’ll remember we aren’t super big beach people so we only hung out on the beach for 2 hours. It wasn’t very crowded on a Friday which was a nice treat! With our chairs all packed up, we decided to explore downtown Folly before heading to our next activity. They had many typical touristy shops that were fun to walk in and see the items, but nothing fancy.

Sunset Dolphin Safari

Sunset views near Charleston Sup Safari!

We were very excited about our evening activity since a friend recommended this company when she visited a few months prior. Charleston SUP Safaris is located right on the edge of Folly Island and offers paddleboarding tours every day and also has rentals. The best part is that this excursion involves dolphins, my favorite animal. Even though we signed up for a group tour, we received a private one since no one else signed up! They do a great job explaining all the protocols and helping you on the board for beginners like myself. While paddling our instructor taught us about the importance of the marsh in this area as well as giving us a ton of Charleston recommendations. Sealing the deal on this experience was having a dolphin swim right by my board!

Bowens Island Restaurant

By the time the tour finished, it was 8:30 pm and the large lunch we ate earlier in the day wore off. Our tour guide gave us the best seafood recommendation in the area so we drove over as fast as we could before they closed. Bowens Island Restaurant is far down a country road behind lots of beautiful houses and nestled behind gorgeous oak trees. We ordered the Big Ole Seafood Platter which was perfect for two very hungry people. It was very dark by the time we ate, but I can see the views being stunning here for a sunset dinner. It is very popular so do expect a wait if you go at peak hours!

Day 2:

McLeod Plantation Historic Site

Stunning southern home at McLeod Plantation!

I knew I wanted to visit one of the many plantation homes in Charleston to really immerse myself in the history of this city. At McLeod Plantation, the land was beautiful to look at but what was more captivating were the stories of the people who lived in the house. It was not a traditional plantation by any means with a variety of organizations and soldiers of all races who lived there. They have a guided tour at the top of every hour which we did. The person doing the tour was in full character which is great for families and kids, but I know we personally just wanted the facts so we left about halfway through it.

Angel Oak Tree

Gorgeous tree limbs at Angel Oak Tree!

I love seeing anything related to nature on a trip. When I heard about this Angel Oak Tree I knew it had to be on our list to visit. It took us about 25-30 minutes to get to the tree from the plantation. The Angel Oak Tree site is in the opposite direction of many of the other touristy attractions but it was worth the trip over. The tree is over 300 years old with many limbs and branches touching the ground and some as tall as 65 feet. Since many of the branches are low you can weave in and out of the tree feeling like you are in a jungle. Even though the parking is free, expect the crowds on a weekend. We walked around the tree for about 20-30 minutes and that was plenty of time to take pictures and soak in the beauty.

King Street

Exploring the beautiful and historical streets of downtown Charleston was next on our list. Finding parking downtown is the only challenging part of this city. We found a metered spot on Society Street. The metered spots have time limits so choose a garage if you know you will be gone for a while.

Mead Tasting Bar at Savannah Bee Company!

King Street is full of tons of shops from affordable to designer. My favorite part of walking down this road was taking some of the side streets and seeing all the quaint local houses/apartments in the area! As we were walking we stopped at Savannah Bee Company to smell all the delicious products they had. This store had a mead bar at this location and it was a fun thing to try! Continuing down King Street, we stumbled upon the Belmond Hotel. Since it was stunning on the outside, we decided to walk into the beautiful hotel and sit at the bar and enjoy a drink since we had some time to kill before dinner.

Dinner at FIG

Delicious wine and cuisine at FIG!

This restaurant was our top choice for dinner. Since we planned our trip a little last minute, there were no reservations available. Book at least 2-3 months in advance if you want to eat here! They do have a bar area that is first come first serve with about 10 seats at it. We chose to get to the restaurant around 4:45 pm hoping to snag one of those 10 seats and we did! My now fiancé had a backup reservation at 82 Queen just in case, but as soon as we sat down he called them to cancel (brilliant game plan!)

Dining at FIG was such an amazing experience. I think I actually prefer sitting at the bar at local places like this because you learn so much more about the food and the restaurant. Based on what local catch is available at the pier, the chef creates a new menu every day. We had a delicious rice appetizer, paired with a pasta dish and a seafood stew for our entrees. They even had my favorite Austrian wine to sip on while dining. It is a very expensive restaurant but it was worth the splurge for the food and the experience.

Pineapple Fountain and Waterfront Park

My sweet man right before he proposed!

After dinner, we wanted to walk down by the water to see the pineapple fountain and other sites. Little did I know this was the plan all along. My fiancé proposed down by the public pier and hired a professional photographer to sneakily take pictures and have a photoshoot with us afterward. It was so perfect and so fun! He hired King Street Studios if anyone is interested! By the time everything happened, it was only 8 pm. We were so excited and overjoyed we decided to go back to our Airbnb to call our friends and family and unwind.

If you are wanting to go grab a post-dinner drink (which is what I thought we were doing!) go to The Gin Joint, 82 Queen,  5 Church, or Bin 152. These are all places I still have saved to try when I head back and come from friend recommendations and great online reviews!

Day 3:

I thought we were done celebrating but my sweet man had another trick up his sleeve! He knows how much I love breakfast food and brunch and he made another reservation!

Breakfast at High Cotton:

Mouthwatering cinnamon roll at High Cotton!

Near where we had dinner before is this charming breakfast/brunch spot right in the heart of downtown. High Cotton is very southern and very traditional, and it was probably one of the fanciest brunches I’ve ever had! With your meal comes this delicious breadbasket. We ordered a cinnamon roll to share but that was a mistake since we didn’t know about the bread originally. I ordered the eggs benedict with a side of cheese grits and my southern self was very happy and delighted.

Rainbow Row:

Charming houses on Rainbow Row!

We couldn’t leave this stunning city without seeing one of the most popular tourist attractions. It was a hot humid day for a stroll but this area is so charming. It is a residential area so there are lots of cars and people around but worth the quick easy walk from downtown. I love that they have some markers about the history outside these historic homes.

Even though we went to Charleston for a 3-day weekend, I felt like we barely skimmed the surface of this city. Charleston has activities for any person whether you like the outdoors, shopping, history, or are a foodie. The opportunities are endless! I can’t wait to come back again in the future to explore it more!

Charleston Budget: