A First Timer’s Guide to 3 Days in Charleston

Updated May 2023 – I originally wrote this post in April 2019 after my first trip to Charleston, but I have since visited a few more times so I thought it would be beneficial to update it! This First Timer’s Guide is one of my most popular posts so I want it to be filled with all the information you need to plan the ultimate first trip! If you’re looking for more Charleston recommendations, check out my 10 Things You Must Do in Charleston post!

If you follow me on Instagram then you know that Megan and I just got back from 3 colorful days in Charleston, South Carolina, and I promised myself that I would get a guide (specifically a first timer’s guide) up ASAP in hopes that I will inspire you to book a spontaneous trip there like we did!

I knew Charleston would be amazing, but honestly it was WAY more beautiful than I could’ve ever imagined! The southern charm oozed from every corner and even though I just returned home I’m itching to go back.

Charleston is a port city in South Carolina known for its cobblestone streets, pastel homes and rich American history. Charleston’s most iconic tourist attractions include Rainbow Row, Fort Sumter, Charleston City Market, South Carolina Aquarium, Pineapple Fountain, Marion Square among many more!

Since we only spent 3 days in Charleston I figured I would do a day-by-day recap of everything we did, so you can see just how much you can actually see (and do and eat) in just 72 hours! *I updated this in 2023 to include options for activities and restaurants for each day*

First Timer’s Guide to 3 Days in Charleston, South Carolina

Day 1

Fly to Charleston & Check into Hotel

Take the first flight out in hopes you’ll land in Charleston in the morning, we were able to land around 9am. We crossed our fingers that our room would be ready at our hotel when we got there (check in wasn’t until 4pm), but luck was on our side and we were able to check in when we arrived at Homewood Suites on Upper King in the Historic District.

This was both mine and Megan’s first time in Charleston so we didn’t really have a preferred area to stay in, but we were really happy with our choice when we got there. First off, it is an all-suite hotel so the room was HUGE – 2 queen beds, living area, kitchen, bathroom, etc.! It was also extremely clean and new, plus they had free breakfast every morning and wine every evening. The location was also perfect right between King St. and Meeting St. around SO many restaurants and stores with just a short walk to everything else.

2023 Update: I’ve since stayed in multiple hotels in Charleston and many more amazing options have opened including The Ryder Hotel, The Francis Marion Hotel, The Pinch Hotel, The Palmetto Hotel, The Dewberry Charleston, The Loutrel, Market Pavilion Hotel, Hotel Bennett and The Spectator Hotel. Scroll to the bottom of this post for more information on all of them so you can make the best decision on where to stay!

Doughnuts or Brunch at Millers All Day

After freshening if you’re looking for a quick bite before exploring grab a snack at Glazed Gourmet Doughnuts on King Street. They’re know for their coffee and doughnuts and they did NOT disappoint. They offer around 12 flavors that change weekly so check their website or stop by for the weekly menu!

If you’re looking for something a little more substantial to eat go to Millers All Day! It’s the ULTIMATE Charleston brunch spot with a menu filled with Southern classics. I highly recommend their Bloody Mary, Banana Bread and Hot Honey Chicken Donut.

Carriage Tour or Two Sisters Walking Tour

Book a Sightseeing Tour for your first day in Charleston to get the lay of the land!

On my first trip to Charleston we booked a Carriage Tour with Palmetto Carriage Works and I can’t recommend it enough. Our tour guide was amazing and we learned so much all while seeing so much of the city. I’m really glad we did this on the first day we were there because we passed so many places we knew we wanted to revisit and really got a feel for the Historic District of the city.

If carriage tours aren’t your thing (and to be honest they aren’t really mine anymore) I HIGHLY recommend booking Two Sisters Walking Tour – it’s hands down the BEST tour in Charleston. Guided by two native Charlestonian sisters, Mary and Therese take you through downtown Charleston’s historic district. The sisters are so entertaining and I learned SO much on my tour! More info here!

Dinner at Church & Union or The Ordinary

Make a dinner reservation at The Ordinary or Church & Union!

My top pick for dinner on your first night would be The Ordinary, my favorite restaurant in all of Charleston! Order the Crispy Oyster Sliders and ask your waiter for more recommendations since the menu rotates constantly. More info here!

If you can’t get a reservation at The Ordinary check out Church & Union! This restaurant is SO cool, it’s in a former church and so beautiful. I highly suggest the Spicy Local Cauliflower as an appetizer and the Spicy Ahi Tuna Poke Bowl and the Fried Chicken as entrees.

Ice Cream at Jeni’s or Coconut Cake at the Peninsula Grill for Dessert

You deserve a sweet treat on your first night in Charleston so I suggest ending the with ice cream at Jeni’s Splendid Ice Creams on King Street. I was super impressed with how many dairy free ice cream flavors they had and while I wanted them ALL I ended up with Roasted Peanut Butter and Strawberry Jam in a Waffle Cone (because the place smelled like them since they make them fresh) and it was so freaking good. 

If you’re looking to continue the night a little longer I suggest going to the Peninsula Grill for dessert and a nightcap instead! Sit at the Champagne Bar and order their famous Coconut Cake (it’s beyond amazing) and an espresso martini! I highly suggest stopping by the Peninsula Grill at some point during your trip even it’s just for a drink or dessert! It’s a Four-Diamond and Four-Star restaurant and just oozes Southern elegance!

Day 2

Callie’s Hot Little Biscuit for Breakfast

Start your morning with a trip to Callie’s Hot Little Biscuit because it’s not a trip to Charleston without a stop at Callie’s, and after trying the biscuits for the first time I can absolutely confirm. We literally got one of everything, so I can’t give you my favorite, but just make sure a visit to Callie’s is on your list of things to do if you’re headed to Charleston.

Explore the French Quarter, Rainbow Row and South of Broad

After Callie’s plan to spend a majority of the day wandering! I highly recommend taking a few hours just getting lost to find all the hidden gems Charleston has to offer.

The French Quarter neighborhood is part of the original walled city and is home to Chalmers Street (one of the 8 remaining cobblestone streets of Charleston), the Old Slave Mart Museum, the “Pink House”, Dock Street Theater, French Huguenot Church, St. Philip’s Church and much more!

Rainbow Row is a name for the 13 colorful historic houses on East Bay Street along the Battery, it’s one of the most iconic landmarks in Charleston and a MUST see when you’re visiting, especially for the first time! But I’m going to be completely honest, Rainbow Row is picture perfect, BUT I think all the other houses in the French Quarter and South of Broad are just as beautiful (if not more so), so don’t spend too much time actually at Rainbow Row, and don’t be discouraged if you don’t get that picture perfect pastel house photo there because there will be PLENTY of other opportunities for an iconic Instagram photo.

South of Broad is the historic and very exclusive neighborhood sitting on the tip of the Charleston peninsula. Stroll up and down Church Street, Tradd Street, Water Street, King Street and Legare Street and just soak in all the Southern beauty!

Check out my Things You Must Do in Charleston post for some fun facts about Rainbow Row & a list of my favorite streets, houses and landmarks to visit South of Broad and in the French Quarter.

Lunch at 167 Raw or Basic Kitchen

You’re definitely going to work up an appetite walking around so I suggest heading to 167 Raw or Basic Kitchen for lunch!

167 Raw is my 2nd favorite restaurant in Charleston (right behind The Ordinary) and a MUST on your first trip to Charleston! They don’t take reservations, but put your name in at the door and peek into some of the stores along King Street while you’re waiting! We we able to snag 2 seats at the bar after 20 minutes and loved every minute of it! Start with a 167 Dirty Martini, it’s made with house blended tequila and Calabrian Oil and literally life changing! Also your waiter for recommendations and specials because the menu changes seasonally, but we ordered the oysters, Oven Roasted Crab Dip and the Tuna Burger and it was all amazing!

If the wait at 167 Raw is too long head over to Basic Kitchen! It’s just a few blocks away and a great lunch spot. Order the Cauli Wings, Toasted Sesame Soba Bowl and Salmon Bowl, but everything on the menu sounds so fresh and delicious. This is a great place to bookmark if you’re vegetarian or vegan, they offer a ton of veggie options.

Shopping on King Street

Since you’ll already be on King Street I suggest taking a walk along Charleston’s most famous street and doing a little bit of shopping! There are so many cute boutiques it’ll be hard for you not to do a little bit of window (and real) shopping! There are clothing stores, antique stores, art galleries and great souvenir shops so it won’t be hard to spend a few hours here.

Dinner at La Farfelle or Lenoir

Make a reservation for dinner at either La Farfelle or Lenoir for your second night in Charleston.

La Farfelle is an amazing modern Italian restaurant in Harleston Village that should not be missed when visiting! Order a classic Italian cocktail like a Spritz, Negroni or Sbagliato and for dinner split the Whipped Ricotta, Squid Ink Spaghetti, Agnolotti and Braised Broccoli Rabe. If you have room for dessert order Christal’s 24-Karat Cake!

Lenior is a modern Southern bistro that is another amazing dinner option! Their menu is seasonal, but I suggest asking your waiter for suggestions that’s what we did and loved everything we had!

Day 3

Head to the Spa & Treat Yourself to a Massage

You’re going to be walking a LOT so if you can swing it I suggest booking a massage for the morning of your third day! Charleston is home to so many amazing spas so treat yourself if you can! I’ve gone to the Amethyst Spa at The Restoration Hotel, but here are a bunch of other hotels that offer spa treatments:

• Francis Marion Hotel
• The Pinch
• The Dewberry
• Hotel Bennett
• The Spectator
• The Charleston Place

Lunch at The Citrus Club at The Dewberry Hotel or Poogan’s Porch

Depending on the weather either head over to The Citrus Club at The Dewberry or Poogan’s Porch for lunch!

My top pick would be The Citrus Club, it’s my absolutely favorite rooftop in Charleston and a MUST visit on your first trip. It’s modern chic rooftop cocktail lounge with amazing views of all of Charleston and the harbor! It’s first come, first serve and opens at noon! The drinks are fruity and delicious and the food is equally as amazing. I highly suggest the Citrus Salad, Dewberry Smash Burger and Loaded Fries!

If the weather isn’t ideal (it’s either too hot or raining) head over to Poogan’s Porch for lunch! Located in a restored Victorian house on Queen Street, Poogan’s Porch is a traditional Southern restaurant and Charleston’s oldest independent culinary establishment making it VERY popular! They’re known for their Bloody Mary, Fried Green Tomatoes, Pimento Cheese Fritters and Fried Chicken.

Check out the John Rutledge House, Pineapple Fountain and Waterfront Park

After lunch walk along Broad Street to see the John Rutledge House! It’s a National Historic Landmark and not to be missed on your first trip. It was built in 1763 for John Rutledge, the first governor of South Carolina, and has since been restored into a boutique hotel.

From there stroll further down Broad Street towards the harbor to the Four Corners of Law, located at the intersection of Meeting and Broad Streets. The crossroads feature 4 historic buildings used by federal, state, local and religious institutions – US District Court, County of Charleston Historic Courthouse, Charleston City Hall and Saint Michael’s Church.

Continue further down Broad Street past Washington Square and the Old Exchange and Provost Dungeon and finally to Waterfront Park to see the Famous Pineapple Fountain.

Sunset Sail with Schooner Pride

Go back to your hotel to grab a few extra layers (you’ll need them for this next activity), then head to Liberty Square next to the South Carolina Aquarium for a sunset sail with Schooner Pride. It is Charleston’s only 3 mast tall sailboat and one of my favorite Charleston activities! I’ve actually taken this sunset sail every single time I’ve visited Charleston and it never gets old!

If you’re looking for a narrated sail, the Schooner Pride offers lots of other options during the day.

Dinner at The Darling Oyster Bar or Husk

End you night with dinner at either The Darling Oyster Bar or Husk!

The Darling Oyster Bar is a seafood restaurant on Upper King Street with a raw bar and great cocktails. Order oysters (obviously), Creole Shrimp and Key Lime Pie!

If you’re looking for more southern food head over to Husk. The restaurant itself is located in a STUNNING Victorian-era home and the ever changing menu won’t disappoint!

Best Restaurants/Bars in Charleston SC

Below are some of the best restaurants and bars in Charleston! Some of these are included in this post and the rest come HIGHLY recommended by myself and friends and should definitely be on your radar!

• The Ordinary (location) – Upscale seafood restaurant and literally the best meal I’ve ever had! Make a reservation as soon as you book your trip!
• Prohibition (location) – Jazz age theme restaurant
• Sugar Bake Shop (location) – Small batch bakery with super Instagrammable front
• La Farfalle (location) – Amazing Italian food! Highly recommend!
• FIG (location)
• Callie’s Hot Little Biscuit (King Street location & City Market location) – Iconic Charleston biscuit shop, a MUST if you’re visiting, especially on your first trip!
• Leon’s Oyster Shop (location) – Amazing fried chicken!
• Chubby Fish (location) – Extremely popular seafood restaurant! It’s walk in only and the line usually begins are 4:30pm
• Miller’s All Day (location) – A MUST for brunch!
• SNOB (location)
• 167 Raw (location) – My second favorite Charleston restaurant! Order the 167 Dirty Martini, it’s made with house blended tequila and Calabrian Oil (more about my menu favorites here!)
• Basic Kitchen (location) – They have a large variety of vegetarian and vegan menu items!
• The Darling Oyster Bar (location)
• Uptown Social (location) – Upscale pub fare with a rooftop deck
• Church and Union Charleston (location) – Located inside a repurposed church
• Hank’s Seafood (location)
• 82 Queen (location) – Southern restaurant!
• Lenior (location)
• Peninsula Grill (location) – Go for dessert at the Champagne Bar and order their famous coconut cake
• Husk (location) – Rotating menu of Southern dishes (I think the Savannah location is better though)

Best Places to Stay in Charleston SC

Homewood Suites by Hilton Charleston Historic District

• 415 Meeting Street, Charleston, SC 29403 – Upper King St Area
• Part of the Hilton Collection
• All suites hotel!
• Amenities include:
  • Free hot buffet breakfast everyday
  • Free WiFi
  • Outdoor pool
  • Fitness center
  • Valet parking
• Pet friendly!
• This is where we stayed on my first trip to Charleston and really enjoyed it! The rooms are very spacious, clean and updated!
• Suites are great for families and include 2 beds, full-sized sofa bed, and fully equipped kitchen!
• BOOK HERE

The Ryder Hotel

• 237 Meeting Street, Charleston, SC 29401
• Art deco boutique hotel in the heart of Historic Charleston!
• Named in Condé Nast Traveler’s “Hot List 2022: The Best New Hotels & Industry Openings in the World,” and voted “Top 5 Hotels in Charleston” on the Condé Nast Traveler Readers’ Choice Awards.
• Restaurant, bar/lounge, poolside bar and coffee shop on premises!
• Amenities include:
  • Outdoor Pool
  • 24 hour fitness center
  • Free WiFi
  • Parking available
  • Free bicycle rentals
  • Beach towels, loungers & umbrellas available!
• I’ve stayed here before and I can’t recommend enough!
• BOOK HERE

The Francis Marion Hotel

• 387 King Street, Charleston, SC 29403
• 4 Star hotel with spa near Marion Square
• The only high rise hotel in Charleston’s historic district which gives it amazing views of the historic harbor
• Member of Historic Hotels of America
• The Swamp Fox Restaurant and Bar serves breakfast, lunch and dinner
• Amenities include:
  • Free WiFi
  • Fitness center
  • Full service spa
• BOOK HERE

The Pinch Hotel

• 40 George Street, Charleston, SC 29401
• Brand new luxury boutique hotel right in the heart of King Street’s shopping district
• Named one of Condé Nast Traveler’s top 20 hotels in Charleston
• Amenities include:
  • Complimentary daily breakfast with coffee, tea and pastry service
  • Free WiFi
  • Valet parking
  • Bike share
  • Spa
  • Welcome cocktail
• BOOK HERE

The Palmetto Hotel

• 194 East Bay Street, Charleston, SC 29401
• Upscale 4 star boutique hotel located in the French Quarter of Charleston just steps from the Pineapple Fountain and Port of Charleston
• Amenities include:
  • Free English breakfast each morning
  • Coffee/tea in common area
  • Free bike rentals
  • Free WiFi
  • Lobby Bar
• BOOK HERE

The Dewberry Charleston

• 334 Meeting Street, Charleston, SC 294403
• Luxury hotel with spa and rooftop bar near Marion Square
• The Citrus Club is a whimsical rooftop cocktail bar located on the 8th floor terrace (I love it so much, it made it on my 10 Things You Must Do in Charleston list)
• The Living Room serves breakfast, lunch, aperitif and dinner
• The Dewberry Spa offers facials, massages, body treatments and more!
• Amenities include:
  • Parking
  • Free WiFi
  • Gym
  • Full service spa
  • Library
  • Terrace
• BOOK HERE

The Loutrel

• 61 State Street, Charleston, SC 29401
• 4 star luxury boutique hotel with 50 guest rooms and suites at the northern edge of Charleston’s French Quarter
• Named #1 Charleston Hotel in Travel + Leisure’s World’s Best Awards
• Lush rooftop terrace ornamented with greenery and open air seating
• Veranda Lounge, the garden inspired lounge located in the lobby, serves small plates and cocktails
• Amenities include:
  • Free breakfast
  • Complimentary mini bar snacks and beverages
  • All inclusive clubroom, an exclusive social club on the Mezzanine level serving complimentary sips and small plates for guests
  • Free WiFi
  • Fitness Studio
  • Parking
• BOOK HERE

Market Pavilion Hotel

• 225 East Bay Street, Charleston, SC 29401
• Luxury hotel next door to the Charleston City Market and one block from the Charleston Harbor
• Features 3 restaurants and 2 bars/lounges, a poolside bar and coffee shop
• Amenities include:
  • Pool
  • Free WiFi
  • Parking
• BOOK HERE

Hotel Bennett

• 404 King Street, Charleston, SC 29403
• 5 star, luxury hotel that overlooks iconic Marion Square
• 3 restaurants and 3 bars/lounges on site plus a coffee shop
• Amenities include:
  • Heated outdoor rooftop pool open year round
  • Free WiFi
  • Pool cabanas, loungers and umbrellas
  • Full service spa
  • Fitness center
• Optional King’s Club access and amenities include customized itineraries, private lounge with veranda overlooking King Street, open bar, private concierge, spa upgrades and culinary offerings throughout the day
• BOOK HERE

The Spectator Hotel

• 67 State Street, Charleston, SC 29401
• 1920s inspired luxury boutique hotel in Charleston’s French Quarter
• Every guest receives a personal butler for the duration of your stay! The Spectator is the only hotel in Charleston that offers personal butler services.
• Prohibition style speakeasy bar, “The Bar”, was named one of the country’s top five bars by USA TODAY
• Amenities include:
  • In room complimentary gourmet continental breakfast
  • Free WiFi
  • Parking
  • Free bicycle rentals
  • Full service spa
  • Free daily reception
  • Free minibar
  • Welcome cocktail
• BOOK HERE

Other things to keep in mind when visiting Charleston for the first time:

• You’re going to walk A LOT! We walked between 6 and 10 miles everyday so definitely bring your walking shoes! Uber and Lyft is available in Charleston, but everything is pretty close together so we only took a car once.
• Bring a hat and sunscreen!
• If you’re doing any boat activities bring warm clothes because it’s definitely much cooler on the water.
• Make sure to leave plenty of time to just walk around, like I mentioned above the best parts of Charleston are found by just wandering around.

PIN my First Timer’s Guide to 3 Days in Charleston Post for LATER:

Location: Charleston, South Carolina | Photos: Tracy Davis, Megan Zietz & Myself