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Where to Eat, Sleep, + Explore for a Weekend in Charleston, SC

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Charleston, South Carolina, Weekend Getaway


Travel & Leisure Magazine announced Charleston, South Carolina as the number one city in the world in 2016. It’s been the leader of the U.S. and Canada for several years, but now it’s claiming the world title, and that’s a big freaking deal. Our weekend in Charleston was spontaneous, thanks to The Gentry Hotel offering a discounted rate to us. With Charleston holding the number one spot, we had high expectations. After three nights and two full days of fun, we pulled together the highlights for a weekend getaway in the charming city of Charleston.

Sleep in Charleston:

The Gentry Hotel:

This hotel (more like a condo), was a highlight for the weekend! It’s a non-traditional hotel in the heart of the French quarter, settled next to Waterfront Park. It didn’t have the typical front desk, lobby, or room keys, but that was never missed. Travelers enter the building and the assigned suite with a code onto a key pad. All information that is needed for entry is emailed prior to arrival. It’s amazing location is a top reason to stay here. We walked almost everywhere during the weekend trip, all thanks to the Gentry Hotel.

Our 2 bedroom suit featured a cozy great room with a full, updated kitchen, complete with a Keurig and coffee. A brick wall led the way to a hallway with two bedrooms, both having their own bathrooms. The beds were very comfortable, the bathrooms were stocked with travel-size toiletries, and there was enough storage space to move in for a month.

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Explore Charleston:

Charleston Museum:

We walked to The Charleston Museum on our first rainy morning in town. We both loved the history that filled the museum, and because I hadn’t researched the city like I normally would, this was the perfect start to discover the stories that made Charleston so special. Like many kids, I have a short attention span in a quiet museum.

Rainbow Row:

This iconic, colorful row of homes is a staple in Charleston. It demands attention in the sweetest southern way. The purple home, recently listed for $2.8 million, stole my heart.

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Waterfront Park:

Just a short walk from Rainbow Row is the prettiest park of Charleston. Stroll along the water under the shade of the old oak trees. The popular Pineapple Fountain is at Waterfront Park and offers a great photo opportunity!


Sullivan’s Island: 

About a 25 minute drive from Charleston is Sullivan’s Island, a sweet little beach town with million dollar homes lining the streets. I felt like I was arriving on a beach set in a Nicholas Sparks novel, and I wasn’t mad about it.

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Oh hey, Marc-André.


Sandlapper Sunset Cruise: 

Cruising the harbor in Charleston is romantic and fun, but going at sunset is the cherry on top. The evening that we went was gorgeous. We got some great photos and even saw some dolphins. Sandlapper sold beer ($4 for a Landshark, but I’ll take it), and had complimentary cheese and crackers.

Horse & Carriage Ride:

This is one of the best ways to see more of Charleston. Our 60 minute tour showed us spots that I’ve added to the list for our next trip to Charleston, like the gorgeous churches that call Charleston home and all the great shopping along King Street.

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King Street:

Ok, believe it or not, we never strolled the sidewalks of King Street during our weekend in Charleston, but I highly recommend it! Whether it’s window shopping or a full-blown southern shopping spree, this is the place to be.


Eat & Drink in Charleston:

Bakehouse Charleston:

This was the perfect spot for a quick breakfast and coffee in the French Quarter. I recommend a caramel latte and their sausage breakfast sandwich. YUM.

167 Raw:

Ohmygosh. BEST MEAL IN CHARLESTON. We arrived a little after noon on a Friday and the host had us wait outside (but brought us rosé and a beer to sip on), because the interior of the restaurant is small. Marc says he counted 24 seats in the restaurant between the bar space and a few high top tables. We loved the vibes of this space and felt like we were truly experiencing a piece of Charleston. Neither of us had ever eaten a raw oyster and this was the place to do it. Sitting at the “bar” space, we had a young guy shucking oyster after oyster in front of us. He gave us an oyster from Prince Edward Island and just squeezed a little lemon on it. It. Was. Amazing.

The guacamole and chips were great, but next time we’d start off with the oyster sampler (now that we’re raw oyster pros and everything). Marc ordered the ahi poké and I got the grilled swordfish taco. Their fresh menu changes every day, but this was the best fish taco of my life. I should’ve ordered ten. The servers matched the way we felt about the food – awesome.

UPDATE: 167 Raw is moving to a new and bigger location! In early 2019, they’ll be located at 193 King Street.

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Poe’s Tavern:

Located near the beach on Sullivan’s Island, I desperately wanted to dig into some of their fish tacos, but the hour long wait didn’t agree with my growling stomach. If you make it to Sullivan’s Island, please eat here for me.

Pearlz Raw Bar:

Less than a 60 second walk from our awesome little hotel, this eclectic restaurant served up fresh seafood and killer tasty drinks. Try the wedge salad or clam chowder for a starter.

Hank’s Seafood:

Anyone I talked to about Charleston recommended Hank’s. We had a 9:30pm reservation, and they got us in right away. The whole experience was DELICIOUS. Being the oyster pros and all, we ordered a sampler and enjoyed tasting the oysters from different regions. I decided to try the roast grouper and Marc settled on the shrimp and grits. I’m still full from this meal.


The Weekend Fox Tips:

  • Take time to walk your way through the city. The history, buildings, homes, and character are worth the steps.
  • Chat with the locals! We met a lot of friendly Charleston locals that gave us great suggestions for our next trip.
  • Parking for Sullivan’s Island was trickier than expected. We drove in circles through the residential streets until we finally found a spot on the side of the road. Some of their laws recently changed and you can only park on one side of the street, now.
  • Like Florida, Charleston can be hot and humid. Stay hydrated and bring bug spray!
  • I’ve heard Charleston is a great place to ride bikes around the city, but we felt it was much more walker-friendly due to the narrow, cobblestone sidewalks and steady traffic on the streets.


I can understand why this southern city has stolen the hearts of so many travelers. I can’t wait to go back and experience more. Have you been to Charleston? What did you love most?!

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Monday 29th of January 2018

What a great post! I love how honest you are with everything.. it would have been so easy for you to say you walked those sidewalks yourselves because we would never know anything different! It makes me really value what you have to say knowing you aren't just saying things to say them. I really enjoy seeing all the pics :)

Bria | Tendril Wild Blog

Thursday 7th of September 2017

I've vacationed in Charleston a couple of times now, and I'm IN LOVE. Like, "move there tomorrow" in love, haha. I agree Rainbow Row and the carriage rides are a must. I also love touring plantations while I'm there and roaming around downtown. There's actually so much stuff to do that you could never take it all in at once. I'm a huge history buff, so Charleston is the ideal destination for me.

Next time I'm there, I'll have to check out some of your recommendations for restaurants...I don't think I hit any of these places the last time I was there. Pinning this post for future reference! :)

Tendril Wild Blog


Friday 1st of September 2017

wow, the pictures do look amazing!! And I'm totally digging how you put together a few of your fav places <3

Stephanie Wheeler Mechtel

Friday 1st of September 2017

Charleston has been on my bucket list for a while. I think I will have to take a weekend trip in 2018!

The Salty Mamas

Friday 1st of September 2017

Definitely one of my top destinations I've never been to!


Friday 1st of September 2017

Agreed! I think it's sitting in my top 5 U.S. cities right now. :)

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