There is no other way to say it: Charleston to truly a dream. The historic, the kind locals, the incredible food, and oh my goodness, the coast – it just does not get any better. I couldn’t have loved my past few trips to Charleston any more, and I cannot wait to share my adventures with you!
Back in 2018, Ilir and I planned a week-long Carolina trip this summer where we went from Charlotte to Spartanburg, Raleigh, Durham, Wilmington, Southport, Charleston and finally Greenville. We spent the longest amount of time in Charleston and I am SO glad we did. Charleston is magic. You all know my love for my sweet Chicago, but Charleston gives it a run for its money. Ha! Truly, I fell in love with this gorgeous city. So, this summer, we decided we just had to go back!
Our love for Charleston began when Ilir and I took a short trip to Savannah, Georgia, and on our way home, he surprised me with a day trip to Charleston, since I had been dying to go (he’s the best). You can read all about it here. This little taste of southern beauty definitely got us hooked. Last summer, we gave ourselves three and a half days to explore this magical city even more and this summer we spent another two and a half ways. Having visited three times now, I am way too excited to share what we did, where we ate and where we cheers-ed with you all. I mean it when I say we truly planned these past two trip for months. I love researching cities, making plans and creating itineraries, and we pulled together pretty stacked schedules through all that hard work. Time to share our favorites!
What to Do in Charleston
Explore Rainbow Row and the Beautiful Town
No trip to Charleston is complete without gawking over some of the most stunning streets in America! It will absolutely take your breath away. Every turn you make, there are just more and and more beautiful homes. Give yourself some time to just walk around and explore. You won’t regret it.
Pop in and Out of Restaurants and Shops Downtown
The Charleston downtown is such a special place! I’ve never been anywhere else with such a beautiful, historic, colorful downtown and it truly has my heart! Ilir and I spent quite a bit of time exploring downtown, popping in and out of restaurants, grabbing cocktails and moving on to shops. Definitely recommend!
Go on a Charleston Harbor Tour
We loved seeing even more of the gorgeous city in a different way, via boat! The Charleston Harbor Tour takes you along the coast and then out to islands surrounding the pretty city. Ilir, my little history buff, was so excited that we cruised over to Fort Sumter, as well. The captain was hilarious and we learned so much about the history of Charleston. Couldn’t recommend this more! Plus, being out on the ocean is just too much fun.
Set Sail on the Schooner Pride for a Charleston Sunset Sail
Speaking of being out of the ocean, there is no better time to set sail than during sunset. The Schooner Pride is well-known throughout Charleston as such a spectacular experience. We loved pairing our sunset sail with the harbor tour since the harbor tour was much more educational and the sunset sail was much more relaxing and experiential. We’ve done this sail twice now and both times it’s been incredible.
I told Ilir that all I wanted out of our first sail was to see a dolphin. As we boarded the ship, there was an entire family of dolphins playing around in the harbor and my heart truly exploded. Absolute trip highlight! Second time around, my expectations were pretty high, and I was pretty pleased to again see dolphins playing around our boat!
The crew was incredible, the views were stunning, and the experience was amazing. Absolutely recommend!
Tour the Town on a Charleston Carriage Ride
While the harbor and sunset sails were such a great way to see the city from the water, you definitely need to incorporate a tour of the gorgeous streets as well. We booked a carriage ride through Palmetto Carriage Works, as I loved their stance on the treatment of these beautiful animals. The horses and mules are not overworked, given six months a year to roam around a nearby farm, they are kept incredibly healthy and they develop wonderful relationships with their caretakers.
The tour around Charleston was stunning. Each time you take a carriage ride, your route will be different, which is so fun! Our guide was incredibly knowledgable, very fun, and we learned so much! The history of Charleston architecture and design is astonishing.
Visit a Charleston Beach
I’m such a sucker for the coast, and Charleston certainly isn’t short of beautiful shores. Over the past two years, we’ve spent time on both Isle of the Palms and Folly Beach, and Isle of the Palms has definitely been our favorite! It is STUNNING. The area around it also has the most beautiful homes and is worth a little walk around.
Explore the Town’s History with a Charleston Heritage Passport
Like I’ve said, the history behind the city of Charleston is incredible. The Charleston’s Visitor’s Bureau offers a Heritage Passport that gives you access to nine historical sites. I wish we would have had time to visit them all, but the ones we did see were just incredible. For any history lovers, Charleston is the town for you and the Heritage Passport is such a perfect way to explore the history.
Where to Eat in Charleston
Magnolia’s is a classic Charleston restaurant that definitely lives up to its reputation, blending traditional ingredients and cooking techniques with a modern flair for beautiful presentations. If you’re looking for a classic, must-visit Charleston destination, this is definitely one of them.
We stopped at Paw Paw’s for their happy hour and had the most incredible crab dip and drinks. We were so impressed and see why Paw Paw’s gets such great reviews. Their food has a modern flair on traditional Southern dishes that feels like the epitome of Charleston.
The Darling Oyster Bar
As such an Instagrammable destination and topped off with the cutest name, I of course had to make sure we made a stop at The Darling Oyster Bar! While neither Ilir or I are oyster people (and this is an oyster bar… ha!) we loved our meal and had some of the best fried halibut we’ve ever had! If you’re making a girls trip to Charleston, you definitely have to add this adorable place to your list.
I had read amazing reviews about Eli’s Table, but we ran out of space in our schedule to make dinner reservations. BUT, we were lucky enough to still get a chance to try them out when we were walking around downtown and popped in for their happy hour. The staff was so kind and I have never in my life had better fried green tomatoes. If you go, you cannot walk back out those doors without them. A Charleston MUST, in my opinion.
Obstinate Daughter gets such incredible reviews, so we had to go! It was our first stop as we traveled into Charleston for our first trip and it was absolutely delicious. It is over on Sullivan’s Island about 15 minutes outside of Charleston, which is another adorable spot to explore. The design both inside and outside is just perfect, as well, with its beachy, Southern style. The food is American flare tapas style and has so many interesting choices. Ilir and I grabbed delicious drinks and shared the Gnocchi alla Romana and Miss Carolina pizza.
Hominy Grill was one of my absolute favorite stops in Charleston. The James Beard Award winning chef/owner Robert Stehling created such a delicious, southern menu. Ilir and I went for brunch and were just blown away. I had the shrimp and grits and it was the best shrimp and grits I have ever had. Ilir got the bread pudding french toast and said it was the best french toast he has ever had. He’s still talking about it to this day! II’d say that’s a brunch win.
Came to Taco Boy for the Instagrammable exterior, stayed for the delicious tacos. Ilir and I loved the appetizer trio to start, and split the daily special crunchy tacos plus got the carne asada taco (his favorite) and the baja fish taco (my favorite). Such a fun, casual stop!
Vintage Coffee Cafe
Vintage Coffee Cafe was the perfect start to our beach day! Located in Mount Pleasant (Charleston’s neighboring town), on the way to Isle of the Palms, this adorable cafe stole my heart. The inside is just as beautiful as the outside. Ilir got the mushroom melt breakfast sandwich which was so fresh and phenomenal. I, of course, got the avocado toast, which had such a delicious tomato-onion marmalade that gave the toast such a yummy, sweet touch. They have such an interesting menu of toasts; I’d definitely go back to try them all! Ilir was eyeing the acai bowl and wants to go back for that, too – ha! We also got a delicious latte and fresh lemonade. It was truly the perfect start to a beach day.
During our Isle of the Palms beach day, we took a quick break from the waves to hop over to Sullivan’s Island and pop into Poe’s Tavern. They had such delicious burgers with interesting twists, which is always my favorite. Ilir, my burger man, said it broke his top 5 (which is hard to do). It was also nice to have a place nearby where we could grab food, even with coverups on and sand on our feet.
We had such a lovely evening our last night in Charleston, which began at Poogan’s Porch. Ilir and I had an early dinner for before our sunset sail, so we ended up not being too hungry (burgers and beaches will do that to you) so we ordered drinks and appetizers and left so full and satisfied.
We had to make a stop at this iconic, Charleston favorite, and we are so glad we did. It was stunning inside and out and the food was incredible. I started off with a delicious muddled blueberry and gin cocktail and Ilir got a Charleston brew. We split the pimento cheese fritters and the fried green tomatoes and they looked like pieces of art. I wish we had more room so I could have tried the sweet tea glazed salmon – next time!
Leon’s Oyster Shop
We wanted one last, true southern meal on our way out of town and by popular recommendation and raving reviews, we stopped at Leon’s Oyster Shop. The fried chicken was delicious and the environment was so fun and old-school.
Carmella’s Dessert Cafe
I cannot say enough amazing things about Carmella’s Dessert Cafe. We’ve now gone three times in a row, across every trip we’ve ever made to Charleston. I can’t imagine you’d find a better dessert in here. Our favorites are the Boozy Tiramisu Shake and the Canolli Cake. They were both so beautifully made and just delicious. I am still dreaming of these.
Not only does Carmella’s have delicious desserts and shakes, but they also have gourmet sandwiches and a fun bar. It is such a cute little spot with chandeliers and rustic wood and just the most friendly staff. We absolutely will be back (over and over again).
Where to Drink in Charleston
Coffeeshops & Cocktails
Vintage Coffee Cafe
I mentioned Vintage Coffee Cafe above for food too, but if you are just on the search for a coffee, they also have a delicious menu. I got their Iced Honey Latte and it was unbelievably good.
Husk is ranked as one of the best restaurants in Charleston and the reviews are just incredible. If you don’t have time to head to dinner there or can’t get a reservation (it can definitely be tricky!), I definitely recommend stopping in for cocktails. They have a delicious menu and their bar is actually in an restored stable, which is so fun! We grabbed cocktails here before our sunset sail and it was so perfect.
On our first trip, we were in Charleston three days and somehow found ourselves at Rarebit twice. Second trip around, you already know we of course made another stop in – we love it that much! They have delicious cocktails, and my favorite part is that they have Moscow mules ON TAP. So fun! The design of the restaurant and bar is gorgeous and it is right on King Street, making it the perfect place to stop before or after dinner (or for dinner – the food looked great too).
The Gin Joint
As a gin lover, I had my eye on The Gin Joint! It is consistently ranked one of the best cocktail bars in Charleston and it did not disappoint. They also have a great happy hour I definitely recommend checking out.
There were so many incredible places we wanted to go, but of course couldn’t go everywhere, even after multiple trips. Here are a few other places we researched or that were recommended to us where we will definitely have to go to on future visits:
- Hall’s Chophouse
- The Ordinary
- Butcher & The Bee
- SNOB (Slightly North of Broad)
- Cannon Green
- FIG (Food is Good)
- 167 Raw
- Sugar Bake Shop
- Black Tap Coffee
WHERE TO STAY IN CHARLESTON
Hotel Indigo in Mount Pleasant
We had such an incredible stay over at Hotel Indigo in Mount Pleasant! If you’re not familiar with the area, Mount Pleasant is just next door to Charleston. Staying in Mount Pleasant can be a much more affordable option while still sticking close to the downtown – the drive from our hotel was just over the bridge and less than 10 minutes away! Mount Pleasant is also close to our favorite beach, Isle of the Palms, which makes it an ideal staying spot.
Hotel Indigo is a brand-new, uniquely designed boutique hotel, backed by one of the largest hotels in the world, IHG. This hotel brings together locally inspired design concepts with top tier hospitality and professionalism. I loved walking around the hotel and seeing touches of coastal life and Charleston charm incorporated into the space. The hotel also has culinary creations inspired by local flavor you won’t see at many other hotels. While we definitely loved our room, our absolute favorite part of the stay was just outside the back doors.
Standing apart from other hotels in the Charleston area, Hotel Indigo opens up to a resort-style beach area that feels so luxurious. Ilir and I loved hopping in the pool or laying out for a little bit in between adventuring downtown. We also had such a fun time night swimming after a long, hot day of running around Charleston.
We would definitely recommend Hotel Indigo if you are looking for dependable, more affordable option with lots of local flair!
And that’s a wrap! I hope this travel guide was helpful for you. If you’re daydreaming about making a trip to Charleston, I can’t recommend enough booking that flight. And if you’ve already got your ticket, ENJOY!
Have you been to Charleston? Where are your favorites? Drop them below! XO