The 2021 Charleston City Guide – Couples Trip Edition

Charleston, South Carolina is a city in its own league. No matter how many times you visit The Holy City, you can’t help but fall more in love with all its charm, good eats, and hospitality. When I moved to Charleston, one of the first things friends and family constantly asked me were “what do you suggest as a local?!” This blog post has been a long time coming, but I wanted to make sure I was able to truly give you a locals perspective, so I waited until I felt like Charleston was truly home – and well, it definitely is!

I also noticed that a lot of the city guides were mostly geared towards general vacations, but there are so many sides to Charleston, so I figured I would actually make a series of guides geared toward the audience and what their primary reason is for visiting the city.

The first part of this city guide is geared towards couples visiting Charleston for a quick weekend trip. There’s so much to try to fit in, but I really curated this list towards what I would want to do if I were visiting just for the weekend, and sharing all my favorite places with you.

Don’t worry, the next few guides will be launching over the next few weeks so you won’t have to wait long if a couple’s trip isn’t your thing, and as always, feel free to reach out to me @saciamatthews on Instagram if you’re making a trip and you need more suggestions – trust me, I have plenty of opinions on the best of the best in Charleston!

Where To Stay

I. Emeline – This chic and sexy hotel is located in Downtown Charleston, near East Bay Street and the City Market, making it a prime location for a romantic weekend in Charleston. Recently opening, it brings a very West Coast meets East Coast vibe to the city, and the rooms are perfectly dark and romantic, making it a cozy choice for a weekend stay. Best of all? You can begin your day at their coffee shop – Clerks Coffee Company, my favorite coffee shop in the city!

II. The Dewberry – If you love a good mid-century modern vibe, upscale accommodations, and gorgeous Charleston views, look no further than The Dewberry. Since you’re coming to Charleston for a romantic weekend, I highly recommend going for the Charleston Flat, which is basically like your own apartment in the middle of downtown Charleston. We love the soaking tub feature, floor-to-ceiling windows, and gorgeous furnishings that give you all the good feels of a luxury vacation.

III. Zero George – Charleston is all things classic, charming, and romantic, which is what you’ll find if you choose to stay at Zero George. This luxury boutique hotel is known for not only exceptional accommodations but exquisite culinary experiences if you choose to take part in their on-site dining. These rooms are designed to feel very uniquely downtown Charleston, and reminiscent of staying in one of the historic homes we all love, with modern updates and amenities.

Where To Eat


I. Miller’s All Day – This has to be my all-time favorite breakfast restaurant, and I am not a huge breakfast person. Miller’s boasts a robust menu in one of the most ‘instagrammable’ restaurants in the city. Make sure to try their country ham or breakfast potatoes and prepare to never want to leave!

II. Virginia’s On King – This is my husband and my go-to brunch restaurant, especially on Sundays post-travel or weddings. Virginia’s is located on King Street amidst the hustle and bustle making it not only an easily accessible place for brunch but right in the thick of some epic people watching amongst a historic Charleston street. We love everything on their menu, but especially the fried green tomatoes, crab cake benedict, and fried chicken and waffles.

III. Hall’s – Gospel Brunch Sundays – Make your reservations early for an experience like non-other! Hall’s is known for its upscale and one-of-a-kind dining experience, but an insider’s secret is that the best day to go is none other than Sunday Morning! Every Sunday a different gospel choir graces Hall’s with their presence and sings soulful songs and hymns to patrons as they dine on upscale, yet delicious brunch favorites with a Charleston twist. My personal brunch favorite? Shrimp and Grits, of course!


I. Rodney Scott’s BBQ – There are so many places in Charleston to get delicious BBQ, but our personal favorite is Rodney Scott’s. I love the vibe of the restaurant overall, it’s a really cute place located just off historic King Street, and you can ALWAYS hear some smooth music while dining over BBQ classics such as Brisket, smoky pork ribs, or even southern favorites like catfish! This is our go-to lunch when we’re moving around downtown, and sometimes we even make a special drive downtown just to get our fix! Want to get excited before you go? You can check out Rodney’s story on Netflix’s Chef’s Table: BBQ, and see how special this place and Rodney’s story truly is.

II. Leon’s – Leon’s is a classic Charleston staple if you’re looking for great food, a wonderful atmosphere, and a bit of a reprieve from the buzzing downtown scene. While Leon’s is conveniently located downtown, it’s away from the hustle and bustle of the inner downtown streets, and a great location to take in a change of pace. My personal recommendations are the fried chicken or the shrimp roll, and please, thank me later!

III. Amen Street Fish + Raw Bar – If you want a fresh lunch with seafood delicacies that truly give you the vacation feels, then this is the place for you. Located right in the thick of downtown on East Bay Street, Amen Street Fish + Raw Bar is a fab lunch choice. Known for their fish and oysters, I really love to get their fried oysters (maybe some fresh oysters as well!), and their blackened Mahi sandwich for an unforgettable lunch experience. Depending on the time of year you come to Charleston (Summer-Fall), it might be best to make a reservation so you can beat the crowd.


A note about dinners in Charleston – no matter the time of year, you will likely want to make a reservation at any Downtown Charleston location. Walk-in slots fill SO fast, and you don’t want to scramble with trying to find a bite to eat (although you can hardly go wrong with any restaurant you choose here!).

I. 167 Raw – If you want to be transported to a hip, modern Massechutes style restaurant, look no further than 167 Raw. Arguably some of the freshest seafood in the city, this restaurant stays incredibly busy at its charming location on King St. We love ordering the lobster roll that’s brought in fresh, and we also love the swordfish pastrami sandwich – trust me, you have not had anything like it and you’ll be incredibly addicted. The crispy oysters are also some of the best in the city. Trust me, a date night dinner here is an absolute must!

II. Felix – Felix is probably my favorite date night restaurant in downtown Charleston. Talk about a gorgeous, romantic restaurant full of french inspiration and details, with even an incredible bar (we’re talking aesthetic and drink options, totally unique to downtown!). My favorite thing to order here is the steak frites, which are perfectly portioned, and so succulent. The crab croquettes are also the perfect starter, with a Vieux Carre is the ultimate beginning to a romantic evening.

III. Penisula Grill – If you want to go extreme on the romantic side, Penisula Grill has you covered. Peninsula Grill is a reservation must, as it was recently named one of the Top Ten Fine Dining Restaurants in America by TripAdvisor, people are knocking down the doors to get in. Their menu is extensive and exquisite, with each item being better than the last. Personal standouts are the Oyster Rockefeller, Lobster Three Ways, Lamb Loin, and of course any of their incredible steak options. This is a can’t miss dinner reservation on your couples trip to Charleston if you’re looking to add all the romance to the trip! By the way, do NOT end your meal without a slice of coconut cake. Remember, calories don’t count when you’re on vacation!

Rooftop Bar Experiences

If you’re looking for the best city views, Charleston has amazing rooftop bars that you can check out!

I. The Vendue – We adore the food and drinks at The Vendue, and the rooftop bar just adds to the ambiance. Usually buzzing with crowds of people, get here early and grab a seat as it’s first-come, first-serve. We held our intimate rehearsal dinner here, and everyone was so in love with the breeze, the views, and the great quick bites they serve! This is a great place to start your walk around downtown or just next door to the Waterfront Park, where you’ll find the pineapple fountain!

II. The Watch Rooftop – This stunning rooftop is connected to The Restoration Hotel, and hosts a gorgeous rooftop bar where you can see epic Downtown Charleston views. Something that makes The Watch unique is that they have indoor options for seating as well, just in case the weather is cooperating. The food is exceptional, and you cannot go here without trying the truffle fries, Watch Burger, or the honey buffalo shrimp! I’d recommend going here to cap off a night of fun exploring the city, or around sunset for the best views.

III. Little Palm at Ryder – Little Palm recently opened downtown Charleston, and it has the cutest new bar in town! This bar is gorgeous with a very west coast meets Charleston vibe, and really reminds you of spending an afternoon in Palm Springs. While you may not get the same exact views as the other two bars, the ambiance here is hip, great, and gives you a break from the historic vibes of Charleston by bringing in something very modern, which I adore! You can make reservations, which is amazing for a rooftop bar downtown to beat the crowd. Finally, make sure you try out the Easy Breezy cocktail, and share a snack or small plate with your partner so you can get nice and cozy!

What To Do

Since you’re coming for a romantic couples vacation, I picked out some locations/places where you can have a really fun date-day/night experience (especially outside of food, although eating dates are always a good time).

I. Spa Day at Hotel Bennett – If you’re looking for the ultimate relaxation, then your first stop needs to be to the spa at Hotel Bennett. Located on King Street (and attached to the CUTEST coffee/dessert shop, La Patisserie), you can’t go wrong with a treatment from the staff at Hotel Bennett. You’ll definitely want to make an appointment for the treatments of your choice, but you’ll have plenty to choose from including massages, facials, body wraps, and more.

II. Walking Around The Battery – Walking The Battery is a can’t miss thing to do, especially if this is your first time in Charleston. Prepare to fall in love walking the historic streets of The Battery, with homes dating back to pre-civil war. I highly encourage you to do some kind of tour (either on your own or with a guide) to find out the (real) history of The Battery, secret stories about the homes. Start your walk at White Point Gardens, where you’ll find free parking and gorgeous water views of the harbor, and begin your journey through these historic homes.

III. Gibbes Museum of Art – The Gibbes Museum of Art is truly a hidden gem downtown. This gorgeous museum hosts ongoing exhibitions of classic and modern arts, and you’ll find yourself in a dream as you walk around the historic museum and into the outdoor gardens. I highly recommend grabbing a light lunch and working it off with a walk around this gorgeous museum. Make sure you take a photo on the steps out front – a perfect Charleston photo-op!

IV. Charleston City Market – Finally, a trip to the Charleston City Market is a must on your couple’s trip to bring home any goodies that make you reminiscent of your time in the Holy City. Walking through the market with your partner in tow is the best because you’ll see all kinds of items, shops, food/snacks, and people, making it a great experience to take in the culture of Charleston. Personally, I’d grab a bag of Benne wafers to snack on the way home, grab a lovely sweetgrass basket to add to your home decor, and perhaps some cigars to take you back to your trip to Charleston once you settle back into your normal routine.

The Best Locations For Photos

I’ve been asked what the best streets are for photos in Charleston, and there are truly SO many iconic places, but I’m going to share your best bet for getting a great shot that gives you the edge!

I. Church Street and Chalmers – You can set your GPS for Dock Street Theatre, and stumble upon an iconic Charleston landmark, but if you step out into the middle of the street you’ll see a historic church in the background – St. Phillips. This view is everything, and a nod to “The Holy City,” Charleston’s sweet nickname due to the number of steeples you’ll find all over the peninsula.

II. Rainbow Row / East Bay St. – A classic Charleston shot is against Rainbow Row, where you’ll find many colorful homes on East Bay Street. The street is so iconic and if you do a general search of Charleston, you are sure to see tons of Rainbow Row photos, making it perfect to remember your time here.

III. Meeting Street and Queen / The Mills House – The pink wall flanked by two palm trees is the modern take on classic Charleston vibes. This clean wall makes it perfect to show off a fun outfit, and strike a pose in front of it, with historic details like pre-civil war doors, and gas lanterns making your location easily identifiable – you’re in Charleston and you’re in love!

Remember, if you’re traveling here and would like to book a couples session, we’d be more than happy to try to accommodate you as our schedule allows! Feel free to e-mail for investment information and details.

I hope you have the very best time on your couple’s trip to Charleston, South Carolina. There’s truly no other city like Charleston, and make sure to explore all you can, but have some rest mixed in too. If you end up using any of these recommendations, I’d love to hear your thoughts. Feel free to message me or tag me in your adventures on IG – @saciamatthews!

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