Weekend Trip in Charleston, South Carolina: 3–Day Itinerary in May

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Charleston, South Carolina is one of the cities we have been dying to visit in the U.S. as we’ve heard so many great things about this charming, historic city. Candy was visiting me in Tampa during May, so we decided to make a road trip up to Charleston together with my corgi, Kuma.

GETTING TO CHARLESTON

The nearest airport to Charleston is Charleston (CHS) Airport which is 9.7 miles away. Other nearby airports include Myrtle Beach (MYR) (86 miles), Savannah (SAV) (87.2 miles) and Columbia (CAE) (106.8 miles).

Since we were on a road trip, we drove from Tampa, Florida, which was 430 miles and it took us 6.5 hours to get to Charleston with minimal traffic. It was a pretty easy drive and we passed through small towns. We stopped by one of the small towns’ gas stations and had some yummy ice cream too.

Walking with a corgi

Candy & Kuma strolling the French Quarter in Charleston, SC

WHERE TO STAY IN CHARLESTON

We stayed at the Palmetto Hotel, which is located in the heart of French Quarter, Charleston’s historic district where many of the famous attractions are located. We were within walking distance to almost everything we had on our itinerary. They were also a pet-friendly hotel so Kuma was able to stay with us here. Hotel Emeline was another hotel we were looking to stay at with similar prices and amenities.

Expect to pay premium prices if you want to stay in the French Quarter. If you have a car, you will most likely have to pay hefty valet fees as well. We were shocked that we had to pay $70 per night.

Downtown Charleston is located about a mile up north and you can probably save a little more money in that area for accommodations. Hotel Bennett has excellent reviews.

Hotel room at Palmetto in Charleston

Palmetto Hotel

CHARLESTON 3–4 DAY ITINERARY

We mainly wanted to stay in the French Quarter area so that we did not have to take our car out to drive somewhere. The only time we drove our car was to visit one of the plantations and to see the Angel Oak Tree.

Since we were traveling with Kuma, this itinerary is partly dog-friendly. Some museums and tours were dog-friendly so Kuma was able to explore these places with us.

Corgi in a dog stroller

SOmetimes Kuma needs a little break from all the walking

DAY 1

9 AM Breakfast

Poogan’s Porch was highly recommended as one of the top spots for a delicious breakfast, and given its dog-friendly ambiance, we were thrilled to give it a try. The iconic building, originally a home built in 1891, was adorable and the inviting porches evoke a sense of Southern hospitality and warmth. The staff were all extra friendly with Kuma and made sure she had a bowl of water by the table.

We chose to have breakfast here on the first day since we were doing a tour right afterwards and the meeting point was right around the corner from Poogan’s.

Walking down a porch

Poogan's Porch Entrance

Sitting outdorrs drinking coffee

Outdoor dining area

Southern Bisbuit and Gravy

Biscuit and Gracy with Scrambled Eggs

10 AM Historic Walking Tour

We booked the Historic Walking Tour with Bulldog Tours ahead of time online and what attracted us to this tour was that it was dog-friendly. I took Kuma in her stroller because the walking tour was two hours and my little fur baby cannot handle that much walking since she is a senior dog now.

Charleston SC Historic Walking Tour

Historic Walking Tour

White Historic Building Charleston

Historic Building in Charleston, SC

Make sure to take water with you as it can get hot. The tour guide tried her best to stay in shaded areas, but there are some spots where the sun is beaming down on you. To be honest, we did not enjoy this tour too much. We usually love tours but we just could not get engaged on this one. Maybe we had an off day because their reviews at Bull Dog were all excellent.

If you want to try another tour or avoid walking, there are carriage tours as well which is the top-rated tour to do in Charleston. There are also bus tours if you want to avoid the heat and stay in a nice air-conditioned vehicle.

1 PM Lunch

There are so many eateries to choose from in the French Quarter of Charleston. Originally, we were going to have lunch at The Peacock because it was right next to our hotel and the decor inside looked gorgeous, but after looking at the limited menu, we decided to try another spot.

We ended up at Rudy Royale where they are known for their chicken dishes and cocktails. Candy ordered the pulled chicken sandwich and I ordered a Bloody Mary cocktail and a burger.

I enjoyed my meal but Candy’s dish was terrible. The pulled chicken wasn’t even pulled. It was big chunks of chicken and it was really dry. It almost tasted like microwave chicken. Needless to say, we were disappointed with the food here especially since they are known for chicken dishes.

If you want another option for lunch, try Slightly North of Broad. They serve local cuisine and customers recommend the shrimp and grits, pork chops, and scallops,

Slightly north of broad entrance

SNOB - Slightly North of Broad

3 PM Old Slave Mart Museum

We personally did not step inside this museum during our visit, but the Old Slave Mart Museum tells the poignant story of Charleston's role in the domestic inter-state slave trade from the years 1856 to 1863.

There are mixed reviews of this museum, but from what I gather, it’s a relatively small museum where the efforts to preserve the history and bring attention to the atrocities that occurred in that location are genuinely appreciated. However, many visitors feel there are also better museums available that delve deeper into this complex and sensitive topic.

Old Slave Mart Museum

Old Slave Mart Museum

5 PM Pink House

The Pink House definitely stands out prominently on the charming and picturesque streets of Charleston’s historic French Quarter, offering numerous great photo opportunities for visitors and photographers.

Historic Pink House Charleston SC

Having a casual conversation with Kuma in front of the Pink House

It was built in the early 1700s and holds the distinction of being the oldest house in the entire historic district of Charleston. Throughout the years, this house has been used for various purposes, including as a tavern and brothel, a law office, a private residence, and even an art gallery. We were told by our tour guide that the lantern located next to the door is indeed the original one, adding to its historical value and charm.

In front of a pink house

Such a cute entryway into the Pink HOuse

7 PM Joe Riley Waterfront Park

Charleston’s Waterfront Park is a beautifully serene place to take a leisurely stroll and enjoy the breathtaking views as you catch the sunset. Their iconic pineapple fountain, a symbol of hospitality, is prominently located here as well.

Charleston thoughtfully developed this charming area, including inviting covered bench swings on the pier, making it a perfect spot to relax and soak in the picturesque surroundings.

Sunset hour at pineapple fountain

The famous Pineapple Fountain

8:30 PM Dinner and Cocktails

Frannie & the Fox is the perfect place for dinner and a nightcap to pleasantly conclude the evening. The restaurant has a lively and inviting atmosphere that immediately draws you in, complemented by a fantastic selection of a variety of food on the menu, along with an impressive list of classic cocktails.

Two women at a bar

Enjoying our drinks at the bar

Espresso Martini Cocktail

Crystal's favorite Espresso Martini cocktail

DAY 2

8 AM Breakfast

If you are staying at the Palmetto Hotel, we recommend taking advantage of their complimentary breakfast. They have a simple breakfast buffet that is elegantly laid out with some of the best tasting food including pastries, grits, fruits, and more.

Plate of morning fixings

We grabbed a little bit of everything

A corgi waiting to eat

Kuma wanting for some of our breakfast

Calli’s Hot Little Biscuits is another great option for quick on-the-go food, conveniently located at the Charleston City Market. This eatery is well-known for having some of the best biscuits in town, and guests can choose from a delightful variety of flavors to suit their palate.

10 AM Powder Magazine

The Powder Magazine museum is truly a cultural gem that is not to be missed during your visit. While it may be considered a small museum, it is undeniably packed with a wealth of insightful and fascinating information about the rich history of Charleston.

Holding a vintage rifle

This rifle was super heavy

The staff members are not only very friendly but also exceptionally knowledgeable, making it a delight to engage with them as they generously share some captivating stories about Charleston’s past with visitors.

Inside Powder Magazine

Powder Magazine

1 PM Lunch

For lunch, Church and Union offers a lovely ambience that is reminiscent of its history as a former church, which adds a unique charm to the dining experience. We had the opportunity to enjoy lunch here ourselves, and while the service was attentive and the hand-crafted cocktails were truly excellent, we were somewhat disappointed by the food presentation, which we found to be lacking in appeal.

Additionally, the dishes were decidedly average at best, which was unexpected for such a posh establishment. We had been hoping for a more elevated culinary experience.

Alternatively, you might consider trying Magnolias. They are well-known for offering a delightful variety of classic and innovative southern dishes, which many satisfied customers consistently rave about.

3:30 PM Charleston Harbor Cruise

After lunch, take a relaxing harbor cruise aboard a replica 1920s-Bay-Steamer and enjoy live narration from the captain about Charleston’s historic and iconic sites including The Battery, Fort Sumter National Monument, and more.

5 PM Rainbow Row

A couple of hours before the sunset, head to the iconic row of pastel-colored historic homes on East Bay Street known as Rainbow Row. This is probably the most photographed spot by influencers and photographers because the colorful 18th-century homes are charming as ever and makes for great photos.

Walking down rainbow row

Walking down Rainbow Row

If you’re interested in having your photos taken here but need a photographer, we recommend booking a private professional vacation photoshoot. We’ve done this several times in various cities around the world and it’s a great way to capture your memories.

The photographer will not only take beautiful pictures of you at the iconic Rainbow Row but also at several other remarkable and scenic locations throughout Charleston. Additionally, they will most likely share some intriguing fun facts and fascinating history tidbits about Charleston, enriching your experience even further.

A corgi at Rainbow Row

Crystal and Kuma taking a break at Rainbow Row

7:30 PM Dinner

If you’re looking for a dog-friendly restaurant where you can comfortably dine with your furry friend, Eli's Table offers delightful seating options both in the front and back of the establishment. We sat in the front of the restaurant and it was a nice, quiet experience. The service was great and we enjoyed our food. The fried green tomatoes are highly recommended.

If you’re in a mood for seafood, 167 Raw Oyster Bar boasts a great vibe with high-quality, flavorful meals like lobster rolls and oysters.

DAY 3

6:30 AM Sunrise at the Waterfront Park Pier

If you’re an early bird, don’t miss the sunrise at the Waterfront Park Pier. I just happened to be walking my dog early in the morning and noticed the beautiful pink skies towards the harbor. I started walking in that direction and I’m so glad I did because the sunrise was absolutely gorgeous over the water.

Sunrise at waterfront park pier

Sunrise at the Waterfront Park Pier

8 AM Breakfast

Harken Cafe & Bakery is a charming little spot nestled on Queen Street, known for its exceptional coffee and a delightful selection of homemade pastries and signature biscuits. Both locals and visitors alike rave about this cozy establishment, making it a popular destination for anyone seeking a warm atmosphere and tasty treats.

9 AM Boone Hall Plantation and Gardens

There are several beautiful plantations to visit around the charming city of Charleston, and one of the more popular and well-known ones is Boone Hall Plantation. Here, you will find the world-famous Avenue of Oaks, an impressive and majestic row of ancient trees that you can drive through, leaving you in awe of their grandeur.

Walking down Avenue of Oaks

Walking down Avenue of Oaks

Additionally, there are several engaging tours and insightful history talks available that are truly fascinating and essential to learn as part of America’s rich and complex history.

If you plan to spend the majority of the day at Boone Hall, they do have a cafe called Butterfly Cafe on-site that sells snacks, drinks, and pre-made sandwiches.

Boone-Hall-Plantation

Boone Hall Plantation

House at Boone Hall Plantation

Gorgeous House on the Plantation

1 PM Angel Oak Tree

If you decide to leave Boone Hall in the afternoon, since you’re already out driving, it might be a good idea to also stop by and take the time to see the magnificent Angel Oak Tree. This impressive live oak tree, which is estimated to be more than 400 to 500 years old, is widely regarded as the largest Live Oak Tree located east of the Mississippi River.

The magnificent Angel Oak Tree

The magnificent Angel Oak Tree

Currently, the tree boasts a remarkable circumference of 25 feet, a diameter spread of approximately 160 feet, and covers an expansive area of about 17,100 square feet of ground. The tree trunks themselves are so heavy and substantial that some of them have grown so large they drop down to the ground, a phenomenon that is only commonly found among the oldest live oaks in existence.

3 PM Old Exchange & Provost Dungeon or The Charleston Museum

If it starts to get a little hot outside, we recommend checking out one of Charleston’s museums to cool down indoors and learn more about Charleston.

The Old Exchange & Provost Dungeon was built in 1771 and is the site of some of the most important events in South Carolina history. You can enjoy a guided underground tour that allows you to explore the eerie yet intriguing dungeon, where prisoners were once held captive.

Inside a provost dungeon

The Old Exchange & Provost Dungeon

The remainder of the museum provides an insightful look into the building's varied past, showcasing its roles as a commercial exchange, custom house, post office, city hall, military headquarters, and museum.

The Charleston Museum calls itself America’s First Museum as it was founded in 1773, making it the oldest museum in the United States. Its mission is to preserve and interpret the cultural and natural history of Charleston and the South Carolina Lowcountry.

In addition to the museum, you can also tour the two National Historic Landmark houses, The Joseph Manigault House and the Heyward Washington Historic House. Many visitors seem to thoroughly enjoy this museum.

signing-the-declaration-of-independence

Crystal signing the Declaration of Independence

5:30 PM Dinner

For dinner, here are some suggestions:

Pearlz Oyster Bar: Their seafood menu features an assorted mix of raw shellfish, freshly caught local seafood, classic Lowcountry recipes, and beloved regional favorites. Visitors often rave enthusiastically about how delicious and incredibly fresh their seafood offerings are.

Poogans Smokehouse: If you’re in a mood for a hearty BBQ meal, this is the place to go. The restaurant seems to have some mixed reviews recently but we actually ate here and enjoyed our meal. Our BBQ plate had lots of flavor and there was plenty to share between the two of us. Our only complaint during our visit was that the service was extremely slow and terrible.

Tempest Charleston: This restaurant has a lovely ambience with excellent food but we felt that it was a bit expensive for the small portions. Regardless, this place was given the Travelers’ Choice award by TripAdvisor in 2023 so we thought it was worth a mention.

FIG: For a more upscale dining experience, many visitors rave about this restaurant. They are committed to sourcing products with a focus on integrity, flavor, and a sense of soul, and they artfully incorporate these seasonal offerings into their thoughtfully curated menu. One of their consistently popular dishes, which many diners highly recommend, is the delightful and well-crafted Ricotta Gnocchi.

Tempest Charleston

Tempest Charleston

Poogans Smokehouse

Poogans Smokehouse

8 PM Nightcap

Enjoy a lovely nightcap at the popular and lively Carmella’s Cafe & Dessert Bar, a favorite spot among locals and visitors alike. This bustling place is always packed and offers an impressive selection of the best drinks and delectable desserts, all set against a backdrop of a fun and vibrant crowd.

Overall Thoughts on Charleston

This was one of the most expensive trips we have taken in quite some time; in fact, it ended up being even more costly than some of our trips to Europe and Japan. The French Quarter is an extremely pricey area for both accommodations and dining, making it a significant consideration for budget-conscious travelers. To save a bit of money, we recommend staying in the outskirts of the French Quarter and also dining at restaurants located in those surrounding areas.

Sunset in Charleston SC

Gorgeous sunset in the French Quarter

We heard from many locals later on that some of the better and more authentic restaurants are actually situated outside of the increasingly touristy French Quarter neighborhood. With that being said, the French Quarter is a truly charming and historic town, brimming with culture, and we highly recommend taking the time to visit this vibrant area during your travels.

If you’re interested in the outfits we wore during our visit to Charleston, be sure to check out our detailed outfit post. We put a great deal of thought into our wardrobe choices to ensure that we could truly embody and match the southern charm vibe that Charleston is so famously known for.


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