Our Trip to Charleston

This past weekend my new-ish boyfriend and I completed our first ever trip together to Charleston, SC. While it is quickly becoming known as the bachelorette capitol of the world (along side Nashville, Austin and Las Vegas), it was insanely cheap to fly from Chicago to Charleston for a 5 day trip. Due to the new BF’s affinity for all things cheap, this is how we picked our first destination spot together.

Even though we did see about 4-5 bachelorette parties on the trip, the city of Charleston provided a true escape from the overwhelming busyness of Chicago. While Charleston was amazing, I think we would have been happy with any destination given the affordable price range and the promised 5 days of no work.

Overall, the entire trip went smoothly. Dating someone is one thing, traveling with them is another. I have had terrible experiences traveling with really good friends, just because they weren’t on the same page as I was when it came to dealing with stress, figuring things out, packing in site-seeing, etc.

Luckily, Jack and I both like doing the same dumb touristy things, eating as much as we can, and getting an ample amount of sleep on vaca. We did have one mishap, when I happened to drink too many oyster shooters and dragged him into a bar with a night club atmosphere. After squatting down to twerk in my floor length dress, Jack ran out from embarrassment (seeing as it was only 9 pm and there were a handful of sober people staring). Other than that, I kept the booty shaking to a minimum and we got along just fine. Unfortunately, due to splitting the vacation 50/50, I did work myself into about a grand of credit card debt due to the lavish restaurants we picked. Considering this was the only true get away I’ve done all summer, I think it was worth it.

A tip if you’re going to Charleston, make sure to decide what kind of trip you want it to be before hand. Jack and I chose the foodie/history route, doing carriage tours and making sure to hit all the top restaurants. We managed to also fit in one beach day, but it was a trek to get out to the islands and took a bit of coordinating. I’ve had friends make Charleston a spa and golf trip, while others focused on the party aspect by renting boats on the ocean and going out to the bars on King Street.

If you’re looking for the foodie experience we had, here are some top suggestions:

  1. Husk Restaurant – voted top restaurant in Charleston
    • Pro tip – if you go for lunch, it’s easier to get reservations and much cheaper!
    • 12
  2. Cru Cafe
    • Upscale restaurant in an intimate old house setting. The shrimp bisque was some of the best I had in all of Charleston
  3. Fleet Street
    • Only restaurant in Charleston on the water. Had the best she-crab soup of the entire trip and fantastic views of Fort Sumter
    • .IMG-2262IMG-2256
  4. Henry’s Bar
    • Such a fun bar with different themes to each room. You can listen to live jazz in the Whisky parlor or relax in rocking chairs while watching an outdoor movie at the back bar. There is also a club portion (yes, this is where the twerking incident happened)
    • IMG-2066
  5. 5Church
    • Think of an old huge abandoned church turned into a trendy restaurant. Highly suggested for brunch.
    • IMG-2081.JPG
  6. Pearlz Oyster Bar
    • Oyster shooter after oyster shooter, after oyster shooter – great happy hour on M-F
    • IMG-2145
  7. Blind Tiger Cafe
      • Amazing bar in a building from 1803 with beautiful old crumbling courtyard. Make sure to ask to eat outside here.


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