Skip to main content

Charleston Itineraries

Cozy Retreat

stow away to charleston this winter

Watch Video

Cozy Retreat

Day One

Check into The Dewberry, your inspired residence for the next 72 hours. The former federal building transformed to sophisticated boutique hotel boasts five-star service and luxe accommodations throughout. The mid-century modern decor and gracious staff give the entire property a welcomed nostalgic feel. From the moment you enter the revolving door and step foot in the lobby, you are made to feel perfectly at home.

View Details

Check in & Settle in

Say hello to the concierge to hear some of the best kept secrets in the Lowcountry and to learn how to take advantage of the property's complimentary bicycles and house cars. Make your way up the elevator and to your room. Peruse your private library, pour yourself a drink from your in-room bar and be sure to peer into your armoire featuring hand-painted wallpaper by local artist Becca Barnet. No detail has been overlooked in your cozy quarters.

View Details

Living Room Libations

Much like its namesake suggests, The Living Room is known for serving up gracious hospitality with its creative hand-crafted libations. Ryan Casey, the head mixologist, has a knack for shaking (or stirring if that's your fancy) sublime classic cocktails or crafting new favorites behind the iconic brass bar. Once you pick your poison, ask for it on the rocks and inspect your ice cube - each is custom cut to fit its matching glassware and hand stamped with The Dewberry logo.

View Details

Steakhouse Dinner

Take advantage of The Dewberry's chauffeur service or complementary bicycles and head to dinner at Oak Steakhouse. Located on Charleston's historic Broad Street, Oak boasts celebrated steaks and seafood and an expansive wine menu. Sit on the first two floors and marvel at the wine rack that spans two stories or make your way upstairs to a cozy dining room modeled after a private dining room - complete with a fireplace.

View Details

Raise the Curtain

A show at The Gaillard is not to be missed. This world-class performance hall houses some of the most exciting and inspiring acts in Charleston ranging from contemporary comedy to classical music. Set amidst a grand lawn and complete with neoclassical columns and a grand staircase that leads to the performance hall, the venue is an inspired setting for a show.

View Details

Cozy Retreat

Day Two

Begin your day at a Hemingway-esque brasserie for brunch, treat yourself to an enchanting spa visit, explore Charleston's largest art gallery and embark on a dining experience with delightfully nonconformist dishes and drink offerings.

View Details

Peaceful Pause

Make your way to the spa. Inspired by John Dewberry's own carriage house, the space exudes a cozy charm throughout. Its five homey treatment rooms are each adorned with hand crafted wallpaper, local artwork and the ability to control everything from the music to the climate ensuring a blissful experience.

View Details

Afternoon at the Gallery

Discover the world of Southern art at the Gibbes Museum. Affectionately known as the aesthetic heart of the Lowcountry, the museum that first opened its doors in 1905 recently overwent a major renovation and today is lauded as one of the city's most beautiful buildings. Home to more than 10,000 works of Southern art, it's easy to spend an entire afternoon wandering the museum's corridors.

View Details

Dinner & Drinks

Cozy up at old-school American tavern Little Jack's for classic craft cocktails and mouth-watering comfort food. INSIDER TIP: Try the Tavern Burger, with a side of garlic & herb fries, and you might just find yourself returning every evening during your trip.

View Details

Cozy Retreat

Day Three

For the next 24 hours, take it slow and savor your last day here in Charleston. Wander through a curious and charming gallery, discover just what a candle library looks like - it's as dreamy as it sounds - and savor a meal that you won't soon forget.

Fuel for the Day

Make your way down to the familiar brass bar where, in addition to a great cocktail, you can also find a mean morning latte or freshly steeped tea as the bar transforms into a coffee and tea station during the morning hours. Take your drink of choice to go or retreat to a cozy book corner and sip slowly - you're in no hurry today.

View Details

Another Day, Another Gallery

Make your way to the Meyer Vogl Gallery, one of Charleston's contemporary galleries in the French Quarter District. This unassuming Meeting Street gallery houses beautiful works of art from artists near and far adorning the space with vibrant colors and beautiful brushstrokes.

View Details

A New Kind of Library

Earn your rank as a chandler and make candles with scents of your choosing with a class at Candlefish. Or, if you aren't looking to try your hand at candle making, pop into their store to shop their candle library boasting 100 scents or, as they say, 100 reasons to strike a match. Whatever your style - you're sure to find your perfect scent here.

View Details

Stay a While

Close out your day and your Charleston getaway with a memorable meal at Indaco. Ask for a seat at one of the community tables with a view of the restaurant's open kitchen. Choose between a tantalizing spread of house-made pastas or crispy wood-fired pizza. Sample cured sausages, gourmet salumi and take advantage of the on tap Negroni cocktail. Ciao for now.

View Details

Request a Visitors Guide

Where should we send your visitor guide?

*We will not sell or give away your personal information. Your privacy matters to us.

Would you like to receive e-mail updates about deals and events in Charleston?
May we send you offers from our partners?

Request a Digital Visitors Guide