Weekender’s Guide to Charleston

Charleston is by far one of my favorite cities. I tend to get spoiled with how much I love it and how amazing of a destination it is, because the drive from Chattanooga is so easy. 

It’s one of those trips that in my head seem so casual, like a weekend pop over, but in reality is such an amazing and diverse destination. 

One of the absolute best things about Charleston is the fact that it’s perfect for any type of vacation you’re looking for — Girl’s weekend, family trip or a romantic getaway, you cannot go wrong. After traveling there for all three reasons, I finally decided it was time for the Weekender’s Guide to Charleston! 

One part of traveling for a weekend is building out your itinerary. I always have a small plan mapped out in my agenda and make a list of *Must See’s*. Our schedule always, always changes but having a tentative guide helps us to ensure we don’t miss anything we want to do. 

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Where to Stay

Traveling to Charleston, there are three main places to stay. In Charleston, in Sullivan’s Island and in Folly Beach. I’ve never stayed in Sullivan’s Island, but it’s definitely next on my list. Each spot has different perks. First, parking in Charleston can get hectic, if you’re want to pop out of your hotel and explore historic and gorgeous downtown, I would suggest staying in the city. If you’re looking to relax on the beach some or stay in a ‘beach town’ area, I would suggest one of the islands and ubering into the city to explore. We love Folly Beach because of how dog friendly it is. We like to stay at The Tides or at an Airbnb on Folly. I highly, highly suggest grabbing an Airbnb no matter which part you stay in!  If you want a mix of water and city, we loved the Waterfront Courtyard Marriott.

Where to Eat

Eating in Charleston is one of Babe and I’s favorite activities. We’re undercover foodies, we don’t necessarily travel anywhere just for the cuisine but it is definitely one of our favorite parts of a new city. Finding hidden gems and local spots gets us so excited. In Charleston, you could travel there multiple times a year and never run out of places to eat! 


Hominy Grill. One of our all time favorite spots, ever. You must get the ‘Big Nasty’, a chicken biscuit smothered in cheese and sausage gravy. One of our favorite things we’ve ever eaten. 

Toast. Beware this place can garnish a line out the door pretty quickly. The food is phenomenal and the bottomless mimosas are only $10. Yes, Plz


Rita’s (Folly Beach). Not only is this place the cutest and right across from the beach. Their drinks and food are delicious. 

Fuel. We’ve been here multiple times and love it more and more with every visit. You really can’t go wrong with anything on the menu but a few of our favorites are the Jerk Chicken Sandwich, Kale Salad Veggie Burger and Fried Goat Cheese Balls. Request to sit out back, it’s one of my favorite porches ever! 

Poe’s Tavern (Sullivan’s Island). I’ve never been to this spot, but it’s next on my to eat list. Everyone raves about their menu.

*If you’re staying on Folly or just want to pop in for the day, their little beach strip is adorable and perfect for grabbing a seafood lunch. You can’t go wrong with any of the spots! 


The Watch. I was a little hesitant about this spot because yelp reviews claimed the food was average but the rooftop view was great. I have to disagree because both the view and food were incredible for us. I had the burger and ate every bite. Great cocktails too! 

Fleet’s Landing. The only spot on the water in Charleston, this seafood restaurant is fun, great views, great drinks and great food. 

A few other restaurants we love — Paw Paw’s, Magnolia’s, Poogan’s Porch, Amen Street and Coast. If you’re looking for a reservation, be sure to call ahead of time (even two-three weeks before). Restaurants book up fast here! 


The Gin Joint. This low key bar is perfect for pre dinner cocktails or end of a date drinks. 

Market Pavilion. Adorable rooftop pool bar, great for grabbing drinks day or night. 

Republic. This ‘Vegas-y’ type bar is perfect for a girl’s weekend or Bachelorette party. The atmosphere is fun and upbeat, with a great dj! 

-The strip around public is really great if you’re looking for a night on the town, lots of fun bars and restaurants and late night pizza joints for that third meal. 😉

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What to do. 

-Explore. Walking off all that food you’ve inhaled over your trip is easy. I could spend a full day walking around Charleston, dreaming of the day I can convince Hubs to move there. A few of our favorite sites: Rainbow Row, the Pineapple Fountain, Waterfront and King St (#ShopaholicsHeaven).

-Carriage Tour. This is one of my must do’s for anyone who asks me about Charleston. I had to drag RJ to do it and he was so obsessed as soon as it started. It’s a fun and relaxing way to see a lot of the city and hear about historic events. I would suggest this for any trip you’re on (girl’s weekend, family vacay or romantic getaway)

-The Market. The open air market is something I remember about my early childhood visits to Charleston and something I still love to do. Seeing local vendors and handmade pieces is so great. 

-The Beach. Folly Island is dog friendly during the off season, so we love to take the pups out for a visit and a swim! 

Visit Boone Plantation. Ladies, this is where the Notebook was filmed AND where Blake Lively + Ryan Renoylds got married #Swoon. Don’t worry if you think your significant other will be bored, he won’t! It’s full of history and fun facts. Plus, it’s absolutely stunning. 

A few more photos from this past trip. xo

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Click Here to Pin this Guide for Future Adventures! 

Have y’all ever travelled to Charleston?! If not it definitely should be at the top of your list, it’s perfect any time of year. I’m writing you from 38,000 ft in the air, somewhere above Denver. Excited to land in sunny, San Diego. Be sure to follow along on the adventure over on Instagram @YesPleaseDaily.

I hope you enjoy the rest of your weekend, happy Sunday! 
xo, Riley 

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