Charleston, South Carolina, is one of the most beautiful and historic cities in the USA, and a perfect destination for travellers looking for a unique American travel destination. This itinerary for 3 days in Charleston is designed for first time visitors & book lovers!

I’ve visited Charleston three times, and it remains one of my favourite cities in the US, so I love to share some of my favourite reasons to visit the Holy City.

As a big fan of the city, and a massive bookworm, I’m so delighted to partner with Charleston Literary Festival to bring you this itinerary for 3 days in Charleston for booklovers, designed specially for those attending Charleston Literary Festival this November.

This Charleston itinerary includes many of the best things to do in Charleston for first time visitors, highlight events from Charleston Literary Festival, some of Charleston’s best bars & restaurants, and a few exclusive events and tours which are available during the festival for ticket holders of the VIP Premium Weekend Experience.

This post is sponsored by Charleston Literary Festival, which is coming to Charleston from November 1-10, 2024. Find out more about the festival & secure your tickets here!

What is Charleston Literary Festival?

Charleston Literary Festival is one of the longest and most ambitious literary festivals in the USA, offering an epic ten days of literary talks & events in Charleston, South Carolina. Charleston Literary Festival is returning this November, from November 1-10, with events hosted in the Dock Street Theatre.

More than 50 world class authors will be in talks at Charleston Literary Festival this year, and the line up is truly incredible – from Booker Prize nominees such as Claire Messud and Paul Murray, to leading scientists and health experts like Dr Sharon Malone and Charan Ranganath to award-winning journalists and Pulitzer-Prize winning historians, this will be a festival full of life-changing ideas and discussion.

You can buy Early Bird All Session Passes, purchase tickets to individual events, or for the ultimate literary experience, purchase a VIP Premium Weekend Experience Pass to unlock access to exclusive parties, tours and events.

Friday

Charleston Literary Festival: Dr Sharon Malone, Grown Women Talk

Kick off your weekend with Charleston Literary Festival’s opening literary event, with leading women’s health expert and advisor to Michelle Obama, Dr Sharon Malone. Dr Malone is the author of Grown Women Talk, which is part memoir, part guide to getting & staying healthy, healthy aging and getting heard in an increasingly complex medical system.

Event Details: Dr. Sharon Malone, Grown Women Talk, with Michele Norris at 11am on Friday 1st November.

Lunch at Leon’s Oyster Shop

Leon’s Oyster Shop is one of my favourite restaurants in Charleston, and absolutely oozes Southern charm! Nothing says low country like fried chicken & oysters, and Leon’s is a local favourite. It has so much character, a lovely relaxed atmosphere and the MOST delicious food! Feast on hush puppies with honey butter, crispy catfish sandwiches, fried chicken and of course, oysters!

Charleston Literary Festival: André Aciman, My Roman Year: A Memoir, with Edoardo Ballerini

Fellow fans of the book (& film) Call Me By Your Name won’t want to miss catching award-winning author André Aciman at Charleston Literary Festival, in conversation with world-class audiobook narrator Edoardo Ballerini. Aciman will discuss his new memoir, Roman Year, which is a romantic reflection of his time in Rome while on the cusp of adulthood. Roman Year is out this September, giving you just enough time to read it before the festival!

Event Details: André Aciman, Roman Year: A Memoir with Edoardo Ballerini at 1pm, Friday 1st November

Charleston Literary Festival: Emily Wilson, The Iliad

Modern retellings of the classics are taking the literary world by storm, so there is no better time to join the conversation with Emily Wilson, author of The Iliad, a sparkling translation and retelling of Homer’s timeless epic. I’ve loved the revival of ancient Greek classics in recent years, fans of Madeline Miller’s Circe and The Song of Achilles won’t want to miss this one!

Event Details: Emily Wilson, The Iliad at 3pm on Friday 1st November.

Delaney Oyster House

Take a brief break & let the day’s big ideas sink in, while relaxing over champagne, oysters and Southern cuisine at Delaney Oyster House. This is one of my favourite spots in Charleston, it has a lovely intimate atmosphere, warm hospitality and of course, amazing low country seafood!

Charleston Literary Festival: Paul Murray, The Bee Sting

Catch Irish novelist Paul Murray in conversation with Bill Goldstein, as they discuss his epic family drama, The Bee Sting. Paul Murray has been lauded as one of Ireland’s most exciting young novelists right now, and has captured the literary world’s attention with his latest novel which charts the rise and fall of the Barnes family, and the secrets that they keep as they face their own reckoning. The Bee Sting was shortlisted for the 2023 Booker Prize, and was one of my favourite books that I read last year – I still haven’t got over that it didn’t win! 

Event Details: Paul Murray, The Bee Sting, with Bill Goldstein at 5pm, Friday 1st November.

The Black & White Masked Literary Feast

Kick off your weekend in Charleston in style with an exclusive, invite-only literary event. VIP Premium Weekend Experience ticket holders for Charleston Literary Festival are invited to the Black & White Masquerade, inspired by Truman Capote’s legendary 1966 Black & White Ball. Charleston is renowned for its society events, so this is an exclusive opportunity to experience one first-hand!

The Black & White Masquerade is held on Friday, 1st November, but if you’re a VIP Premium Experience ticket holder attending the second week of the festival, you’ll be invited to an exclusive party at a historic home on Legare Street, which is rarely open to the public.

Saturday

Callie’s Hot Little Biscuit

Biscuits are a staple of southern cuisine, and nowhere does them better in Charleston than the Callie’s Hot Little Biscuit. Callie’s is recognised as serving the best biscuits in the South, and is keeping this traditional southern recipe alive with its eatery on King Street, where you can eat in or take biscuits to go. The biscuit with pimento cheese is such a classic (and so delicious!) but you can also order biscuit sandwiches like Sausage, Egg & Pimento Cheese Biscuit, a classic Bacon, Egg & Cheese Biscuit or even Goats Cheese Biscuits! Callie’s is gluten-free friendly too, offering buttermilk or gluten free biscuit options. Yum!

Private Garden Tour

Discover the gardens, flowers and landscaping of Low Country on an exclusive, private garden tour with Charleston Literary Festival. This Garden Tour is only available to those who have booked the VIP Premium Weekend Experience for Charleston Literary Festival, so make sure you reserve your pass in advance – spots are limited!

Historic Downtown Charleston 

Spend the rest of the morning exploring Charleston’s stunning, historic downtown district. Downtown Charleston is the largest historic downtown in the USA, and every street seems to be prettier than the last! This is the perfect place just to wander, although you’ll want to make sure you check out Meeting Street, King Street, Market Street and Broad Street which are some of the main streets in downtown Charleston.

Rainbow Row

Make your way towards E Bay Street to find Rainbow Row, one of the most Instagrammable spots in Charleston. Rainbow Row is a string of pastel-coloured, Georgian townhouses that date back to the 18th century. Today, the historic homes of Rainbow Row are a popular backdrop for wedding & engagement photoshoots.

Waterfront Park & The Pineapple Fountain

Just past Rainbow Row, you’ll find the lovely Waterfront Park. Stroll along the Cooper River & find the iconic Pineapple Fountain, which is a symbol of Charleston. You’ll find pineapples all over Charleston, as it’s considered a symbol of the city’s hospitality, but the grandest pineapple photo moment is definitely the Pineapple Fountain!

Charleston Literary Festival: Charan Ranganath, Why We Remember

Start your second day at Charleston Literary Festival with a groundbreaking discussion that will totally change the way you think about memory, and the impact it has on your life. Neuroscientist & psychologist Charan Ranganath is the author of Why We Remember, and is one of the world’s leading memory experts. In this discussion, he’ll share the latest research which is radically reframing our understanding of memory, and explains the role memory plays in learning, decision-making, trauma and healing. 

Event Details: Charan Ranganath, Why We Remember, with David Adams at 12pm, Saturday November 2nd.

Toast

Toast is an iconic and unmissable Charleston brunch spot, hailed as a “must-eat” by the New York Times. Toast has two locations in Charleston, on my first trip to Charleston I had brunch at the Meeting Street location, which I think is super charming. At Toast, indulge in more delicious Southern cuisine, like peach-stuffed french toast, biscuit eggs benedict, fried green tomatoes, shrimp & grits or chicken & waffles. Toast is also famous for their bottomless mimosas – and you are on vacation, after all!

Charleston Literary Festival: Katherine Bucknell, Christopher Isherwood: Inside Out

Join biographer Katherine Bucknell as she discusses her discoveries about author & icon of gay liberation, Christopher Isherwood. Isherwood was the author of Goodbye to Berlin, which inspired the musical Cabaret, and lived a remarkable life, beginning as the heir to a crumbling estate in England, living in Berlin in the 1930s, and ending his life as an icon in Hollywood. 

Charleston Literary Festival: Claire Messud, This Strange Eventful History

This Strange Eventful History is one of the biggest books of the summer, and longlisted for the Booker Prize 2024. Catch author Claire Messud in conversation with Georgina Godwin, as she discusses her novel that traces three generations of an itinerant French family with roots in colonial Algeria. I love a sweeping family saga, this one is literally next on my TBR pile!

Event details: Claire Messud, This Strange Eventful History, with Georgina Godwin at 4pm on Saturday November 2nd.

Buxton Books

Booklovers won’t want to miss Buxton Books, which is the perfect spot to pick  up a literary souvenir or to take home one of the books featured in Charleston Literary Festival. Buxton Books is a gorgeous, independent bookstore, which opened in 2016 and has become a pillar of Charleston’s literary community. I personally love buying books when I travel, there’s always something special about a book that came home with you from a trip – leave some room in your suitcase!

The Darling Oyster Bar

The Darling Oyster Bar is one of the prettiest bars in Charleston, and the perfect spot to stop for champagne, cocktails & oysters while you de-brief the day’s discussions with your book club or travel buddy. 

Maison Charleston

For dinner, make a reservation at Maison, which was named one of the top restaurant openings in America by Thrillist, when it opened. I visited Maison shortly after it opened, on a work trip with my colleagues (when I worked for a fine dining restaurant group in New York City), and it was one of our team’s favourite restaurants of the trip! Maison has a strong Parisian flair, and serves high end spins on French comfort food. 

Sunday

Brunch in a historic home

The VIP Premium Weekend Experience Package for Charleston Literary Festival includes an intimate and exclusive Sunday Brunch in one of Charleston’s loveliest historic homes, which is the perfect way to begin your final day in Charleston. Make some new, like-minded friends over a relaxed Sunday brunch, in an unforgettable location.

Literary Walking Tour

Get an insider’s guide to the literary history of downtown Charleston, with a literary tour guided by a historian/author. This tour is exclusive to ticketholders of the VIP Premium Weekend Experience of Charleston Literary Festival, which has limited spots – get in quick!

Second Sundays

This is a bonus activity if you’re in Charleston for the second week of Charleston Literary Festival, on Sunday 9th November. Second Sundays is a street party held on the second Sunday of the month, on King Street in Charleston. I stumbled upon Charleston’s Second Sundays on my first trip to the city, and it made me fall in love with Charleston even more! It’s a lovely, welcoming community event with a relaxed vibe, and is a great way to feel like you’re part of the Charleston community for an hour or two.

The Battery

The Battery is one of Charleston’s most jaw-dropping neighbourhoods, lined with some of Charleston’s most impressive historic homes. Stroll along the waterfront of East Battery and South Battery to admire some of Charleston’s most magnificent architecture.

White Point Garden

From The Battery, you’re very close to the lovely White Point Garden, which truly make you feel like you’re in the heart of the South – or in The Notebook! The small garden is lined with romantic live oaks, and on our first trip to Charleston we were part of a proposal! A man walked up to us and asked us to take a picture of him and his girlfriend, but his hands were really shaking when he handed us his phone. He then whispered “I’m about to propose!”. Such a lovely moment, this garden will always have a special spot in my heart as one of the most romantic spots in Charleston!

Charleston Literary Festival: Michele Norris, Our Hidden Conversations

One of the wonderful things about Charleston Literary Festival is the blend of fiction and non fiction events throughout the program, which is sure to leave you inspired, better informed and with plenty of food for thought. On Sunday morning, join award-winning journalist Michele Norris as she discusses her transformative national project on race & identity, which provides a window into real-life experiences of race in the United States through personal stories, essays and photographs. 

Event details: Michele Norris, Our Hidden Conversations, with Kerri Forrest at 2pm on Sunday 3 November

Charleston Literary Festival: David W. Blight, Yale and Slavery

History buffs won’t want to miss this discussion between Pulitzer-Prize winning historian David W. Blight and Richard Brodhead, former Dean of Yale College and former President of Duke University, as they discuss Blight’s investigation into Yale University’s historical involvement with slavery, the slave trade and abolition. The pair will discuss Blight’s findings, and its future implications in what is sure to be a thought-provoking conversation.

Event details: David W. Blight, Yale & Slavery, with Richard Brodhead at 2pm on Sunday 3 November

The Living Room at The Dewberry

The Living Room at The Dewberry Hotel is one of the most stylish hotel restaurants in town, and a perfect all-day spot. Sink into an plush, mid-century armchair and enjoy a light bite and a drink before the late afternoon activities. Bookworms won’t be able to resist a peek at The Living Room’s curated reading library, over a glass of wine.

Magnolias Restaurant

For your final evening in Charleston, dine at a classic Charleston institution: Magnolias. This is a beautiful, old fashioned restaurant that is all class, with warm hospitality, elegant Southern cuisine and a romantic atmosphere. We dined at Magnolias on our first trip to Charleston, and it was an unforgettable evening, and is a perfect way to round out a weekend in Charleston.

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