When visitors wander off the Crepe Myrtle clad Cannon Street and into our shop, most of them seem to be visiting Charleston for about 3 nights. Therefore, I often have to try to narrow down all of my most favorite restaurants and sights to try to recommend how said visitors should get the best possible feel for all that Charleston has to offer in just 72 hours or less. I always have quite a time narrowing it down on the spot, so I created this possible weekend itinerary in hopes this helps you have the very best weekend in Charleston! In this neck of the woods, I try to help you make every day feel like the weekend, so I also encourage you locals to come back to this list and give some of these things a try any day of the week!

Before we dive in to this magical itinerary that Instagram feed dreams are made of, let’s cover a couple of bases such as where to stay, how to get around, & what to pack If you’re reading this once you’re already in town, keep scrolling (but save this rec for your next visit). Also go ahead and save this post to Pinterest so you can revisit it, because I’m working on a full hotel round-up so you can have lots of options in many parts of town. I’ll add a link to that in this post, & I’ll also link to my Folly Beach recommendations as soon as that is finished!


-Where to Stay-

I was recently hosted by Hotel Indigo Mount Pleasant, and it was what staycation dreams are made of! If you are coming during the months of June-August, I very highly recommend staying somewhere with a pool. Hotel Indigo by far has the best pool situation in town; it’s plenty big, is surrounded by lush palm trees, and offers a great mix of places to lounge and play. There really isn’t enough space for a hotel pool of this size if you’re on the peninsula, but luckily this one is still super close to downtown Charleston (about a 5 minute Uber ride). Our rooms were really nice since the hotel was recently renovated, and their adjoining suites were perfect for our group so I think it could work well if you’re coming for a bachelorette.

One of our favorite parts of this hotel was the fact that we were at the base of the Ravenel bridge, so we started our day off by walking to the top! What a gorgeous way to take in the Holy City; spotting steeple tops, boats whizzing underneath you, and seeing marshland all around you. You history buffs will also appreciate the mural of Eliza Pinckney that greets you when you’re waiting for an elevator (Eliza is the woman responsible for bringing Indigo to South Carolina!). I also found out the hotel was dog friendly (very difficult to find in Charleston), so next time I’ll have to bring Maddie!

-Packing Like a Boss-

When you come to Charleston, the main thing you want to remember is an umbrella! We are prone to showers throughout the year, so you might also be glad if you have a rain jacket just in case. As far as attire, most restaurants are ok with casual dress; you can go fancy, but a comfy dress or jeans with flip flops are just fine for most places. It can get VERY muggy anytime from May-September, so dress accordingly to stay cool while you walk around. However, you might want some layers or a light jacket for sitting in the cranked up AC. Charleston is a very walkable city, so don’t forget your comfy shoes!

I also wanted to share the source for the outfits we’re wearing throughout this post, because it’s one product I always pack when I go somewhere sunny. The company is a local brand called ZAGS, and all of their products are UPF 50+! I can’t tell you how many sunburned tourists I have seen wander into my store, so you’ll love having one of their colorful party ponchos or shawls on hand in case you need a break from our sweltering rays. The light weight moisture wicking and cooling fabric make the dresses perfect for touring town, and they can also double as a coverup.

-Getting Around Town-

I think you’ll be just fine if you Uber/walk/rent bikes. The airport is only about 15 minutes from downtown, and everything you’d want to see is a pretty quick Uber ride. However, I have heard of some people having trouble getting Ubers back from the beach on peak season Saturdays, so you might need to call a cab for that. Or, If you want to rent a car, you’ll have a little more ease with getting to the beach or exploring the beautiful plantations and gardens in the area. Some of those can be about a 30-40 minute drive from downtown, so I imagine your Uber tab would add up quickly! If you’re driving, don’t let the downtown street signs discourage you from street parking, because there is plenty of free parking pretty much everywhere except right on King Street. Many of the signs read like you have to have a residential permit to park there, but you have free parking for the specified amount of time. Just watch for signs about street sweeping days and such.

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-72 Hour Itinerary (Play By Play)-

If you want to sit back and relax and just follow this guide, be my guest! I’ve tried to group things by location to help you avoid running all over town to try to find each spot. Scroll to the “a la carte” section below if you just want a big list of recommendations divided by category.

Thursday

Many Charleston visitors miss out on the cute local areas of town like Cannonborough-Elliotborough and opt to only eat & shop on King or Market Street- but not you! You’re hip. Plus, you might already be staying in this part of town if you rented an AirBnB.

If the shops are still open when you get to town (most are open until 5), you’ll want to make your first stop our shop, Cannonborough Collective! Actually all of the shops on Cannon Street are pretty adorable; you could start at Candy Shop Vintage, head to CC, then J. Stark, Sugar Bakeshop, Mac & Murphy, and end at Indigo & Cotton. If it’s after hours, just put these back on your list for Friday prior to checking out the King Street shops.

Now you might be ready for cocktail hour dinner, so Wild Common is a great choice for both! It’s one street over from the above shops, located on Spring Street. It’s a smaller size restaurant, and you’ll want to snag a reservation on Resy if you’re coming for dinner. You’ll have the choice of ordering a la carte or enjoying a 4-course meal. You can also just head to their bar if you just need some cocktails and casual small bites.

Other restaurants I like in Cannonborough-Elliotborough are listed below in the a la carte itinerary section. If you want a night cap, I’d check out Elliotborough Mini Bar or Warehouse for a more casual vibe. Opt for Bourbon N’ Bubbles or Vintage Lounge on Upper King if you’re in the mood for something swanky. If you want a bar for dancing and such, I really wouldn’t know because I never stay out past 10!

Friday

Start the day with a neighborhood spot that serves breakfast on the weekdays; I love Daps or The Park Cafe. Huriyali or Five Loaves Juice Bar are also a good options if you want something on the lighter side like an acai bowl or smoothie.

I’m personally not a fan of fighting the crowds because your girl is kind of a speed walker, so I prefer to head down the narrow King Street sidewalks to shop on Fridays over weekend days. Here are some of my favorite stores on King, starting near Marion Square and working your way south: Simply J, Goorin Brothers, The Skinny Dip, Shoes on King, Jude Connally, White’s Mercantile, & V2V. If you want to shop the chain stores like Anthropologie & J. Crew, those are in the couple of blocks around Wentworth & King. Keep walking south for some other local favorites of mine like Charleston Shoe Company, Ibu, Vieuxtemps, Julep, & E. Blackhurst.

Keep making your way down King & try Miller’s All Day for a great lunch! You could also head left on Broad Street if you wanted to try the Fast & French or One Broad.

Miller's All Day Charleston SC

Spend the afternoon crossing off your sightseeing list; first you’ll definitely need to visit Rainbow Row! I like to head down Tradd Street from there to peruse the lovely window boxes and colorful front doors. I wrote this post about a good door tour route to see at Christmastime, but they are also some of my favorite doors to see year-round! Next you’ll want to make sure you go to the Pineapple Fountain and perhaps have a stroll along the battery or sit & swing at Waterfront Park. A couple of cute shops in the area are Indigo Home & Maris DeHart (both on Vendue Range).

pink door in Charleston on Tradd Street

When it’s time for dinner, you’ll already be near East Bay if you ended your visit at the pineapple fountain, so I would try one of these spots: SNOB, Minero, or The Establishment. Afterwards, I highly recommend the Gin Joint for cocktails! Most locals swear by Pearlz Oyster bar for oyster shooters, but I love the ones at Darling Oyster Bar a tad better. Or, if you prefer to eat your calories instead of drink them, try: Carmella’s, Kaminskys, or walk up Market Street if you want a free sample of homemade pecan pralines.

Saturday

Enjoy pool time if you’re staying somewhere like Hotel Indigo, or it could be a good day to head to the beach. Each beach has it’s own special vibe, but I would have to say my favorite is Sullivan’s Island. While there I would check out Obstinate Daughter, Poe’s Tavern, or Home Team BBQ. Insider tip- the frosé pouches at the Co-Op are all the rage right now!

If you didn’t bring a suit, you could also use the day to sightsee around some of our beautiful plantations and gardens! Cypress Gardens and Boone Hall are in their own necks of the woods, but west of the Ashley you’ll find some that would allow for visiting multiple sites in one day; Middleton Place, Magnolia Plantation, Drayton Hall, & Legare Waring House.

Get cleaned up then head out to dinner & drinks downtown: lately I have been on a kick of recommending Camelia’s at Hotel Bennett for drinks and Basic Kitchen or Parcel 32 for dinner.

Sunday

It could be a good day to just brunch and chill. Or, if you like to visit other churches when you’re traveling, you’ll enjoy the beauty of the building (and the short service) at the pink French Huguenot Church. Ok now back to brunch. Some of my favorites lately are: Felix, Parcel 32, Harold’s Cabin, & The Darling Oyster Bar. I also swear Moe’s Crosstown Tavern has the best shrimp and grits in town, it’s just not the place you go if you’re looking for cute-sy ambiance.

If you haven’t sat atop one of our rooftops and enjoyed the steeple-clad views yet, check out The Watch or Citrus Club.

72 Hour Itinerary (A la carte)

If you prefer to fly by the seat of your pants, peruse the categories below and choose your own adventure!

Fancy-ish Restaurants

Zero George // SNOB // Hank’s Seafood // Charleston Grill // Parcel 32

Casual-ish Restaurants

Basic Kitchen // Minero // Fleet Landing // The Darling Oyster Bar

Off-Peninsula Restaurants that are worth the drive

Wild Olive // Obstinate Daughter // Vicious Biscuit // Fat Hen

Cannonborough-Elliotborough Restuarants

Xiao Bao Biscuit // Josephine’s // Felix // Babas // Malagon

Favorite Coffee Shops & Cafes

Huriyali // The Harbinger // Five Loaves Cafe & Five Loaves Juice Bar // Vintage Coffee // Second State Coffee // Upstairs at The Skinny Dip (coffee & wine only)

Saturday/Sunday Downtown Breakfast & Brunch

Daps // Felix // Parcel 32 // The Park Cafe (temporarily closed)

My Favorite Shops & Sights

Browse my recent post about the most Instagram Worthy Spots in Charleston & I think you’ll find what you’re looking for!


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