Proper Stays Guest Guide
You are staying in one of our homes, which makes you our guest in the fullest sense. This is the Charleston we know and love: our favorite tables, porches, beaches, and back streets, gathered in one place for you.
Charleston keeps a full social calendar. What’s on right now, then a month-by-month look at the year.
Groceries, pharmacies, and the numbers we hope you never need, all close to our downtown homes.
Charleston mornings are best taken slowly. These are the counters and cafes we send our own families to.
Grits milled in-house, pie for breakfast, and a line that moves fast. A King Street classic.
A Westside market and eatery in the old Harold's Cabin space. Part cafe, part pantry, all neighborhood.
Seasonal New American brunch by Hampton Park. Bright, easy, and worth the short drive up Rutledge.
A neighborhood breakfast counter known for cereal-inspired pancakes, poutine hash, and mimosas on tap.
Big Bad BreakfastJohn Currence's all-day breakfast house. Big plates, house-cured bacon, walk-in only.
The garden-inspired cafe inside The Charleston Place. The city's most civilized breakfast.
Three Little Birds CafeBreakfast and lunch all day: benedicts, pancakes, fresh juices, and handmade smoothies.
American cooking on the Cooper River in Park Circle. Go for the view, stay for the patio.
Hand-rolled Southern biscuits and country ham, sold over the counter. Walk-in only.
“Order the grits wherever you see them. If they are on the menu, someone in that kitchen cares.”
A house rule of ours
Coffee and tea lounge by morning, wine bar by night, tucked down a downtown lane.
Locally roasted, single-origin espresso in a calm room off King. A coffee person's coffee shop.
Sorelle's daytime counter: espresso, Italian pastries, and panini on Broad Street.
The Harbinger Cafe & BakeryA bright upper King bakery and cafe with pastries worth the walk.
Part cafe, part market by Hampton Park, with a big patio for a slow morning.
Lunch counters, oyster shops, and the barbecue that made this city famous. Reserve where you can, walk in where you cannot.
Fried chicken, chargrilled oysters, and soft serve in a converted body shop.
An old-school tavern feel with one of the best burgers in the South.
Neighborhood bar food done thoughtfully, with a lovely brick courtyard.
An artisan Italian deli by day; at night the same room becomes The Italian Boy, a 12-seat tasting counter.
Smash burgers built on short rib, brisket, and chuck. First come, first served.
A downtown neighborhood bistro with elevated comfort food and an inventive cocktail list.
Elevated family-style Filipino cooking built on local ingredients.
“Lunch in Charleston is not a pit stop. Sit down, order the special, stay a while.”
How we do itFried chicken, chargrilled oysters, and soft serve in a converted body shop.
The restaurant that made Southern sourcing a rule. Dinner nightly, weekend brunch.
Lowcountry cooking in a converted Victorian house. Biscuits, she-crab soup, and fried chicken.
The room that started uptown-down South cooking in Charleston. Shellfish over grits, done right.
Velvet-walled Southern fine dining and the twelve-layer coconut cake.
A tiny husband-and-wife room serving some of the city's most personal cooking.
Modern regional Italian and house-made pasta in an airy corner room.
Italian glamour on Broad Street, from morning espresso to late amaro.
Coastal southern Italian over three floors: dining room, old-world bar, and a rooftop for sips and bites.
Elevated Italian from a Roman chef: veal Milanese, handmade pastas, and caviar service.
New York-style pies and square slices with a sharp Italian wine list. Walk-in only.
Coastal Italian on a Navy Yard rooftop: crudos, wood-fired seafood, and sunset views.
Modern Cantonese and Sichuan cooking meant to be shared, with a serious wine list.
Charleston's longest-running family-owned sushi bar. A quiet classic.
Twenty-four seats from the 167 Raw team in their original East Bay room.
Handroll omakase and cocktails: Japanese hand rolls, crudos, and rice bowls on Cannon.
Bold Chinese flavors and dim sum Sundays just off King Street.
Japanese-Filipino fusion: hand-folded dumplings and kakigori shaved ice.
Jackrabbit FillyChinese-American plates served family style. A destination in its own right.
Pink BelliesVietnamese-inspired plates and the garlic noodles everyone talks about.
Chubby FishDayboat seafood, chalkboard menu, small room. Arrive when the doors open.
A bright King Street fish house with a 14-seat raw bar and easy Sunday brunch.
Pristine oysters and sustainable seafood in a historic Charleston single house.
Counter-serve seafood market and kitchen. The freshest catch on the way to Folly.
A bright, updated take on the classic island fish house.
Wood-fired French seafood and raw oysters from chef Nico Romo on Shem Creek.
Southern seafood on the water in a 1940s naval building. Ask for a harbor-side table.
A tiny hidden house with a two-dish, daily-changing menu from southern France and northern Italy.
A King Street corner bistro: steak frites, plateau de fruits de mer, and a proper bar.
A European bistro in an 1820s townhouse with seasonal small plates and an all-French wine list.
Parisian-styled cocktails and bistro plates on upper King. Reservations by phone only.
Known to locals as Fast & French: communal counters, escargot, and pate plates since 1984.
French, Italian, and Spanish small plates in a luminous blue room off Market.
Live-fire cooking under the oaks on Johns Island. An open-air night to remember.
Farm and sea to table cooking in a small, seasonal room near upper King.
Feel-good bowls, tempura cauliflower wings, and natural wine in a sunny room.
Kevin Johnson's ingredient-driven Cannon Street room, complete with the pickle wall.
Live-fire cooking, dry-aged meats, and uncommon wines on Cannon.
Seasonal New American brunch by Hampton Park. Bright, easy, and worth the short drive up Rutledge.
A multi-course tasting menu from James Beard semifinalist Orlando Pagan. Books 30 days out.
Inventive coastal cooking upstairs; gelato downstairs at Beardcat's.
The restaurant that made Southern sourcing a rule. Dinner nightly, weekend brunch.
Greek cooking with a Charleston accent: spreads, grilled fish, and a lively counter.
Coastal Mediterranean inside The Cooper hotel, with harbor views from the terrace.
A Greek taverna in Mount Pleasant with saganaki, souvlaki, and a big patio.
Feel-good bowls, tempura cauliflower wings, and natural wine in a sunny room.
For anniversaries, closings, and nights that deserve a tablecloth. Book these as early as you can, especially in spring.
A tiny hidden house with a two-dish, daily-changing menu from southern France and northern Italy.
A tiny husband-and-wife room serving some of the city's most personal cooking.
MalagonAn authentic Spanish taperia and market. Come hungry, order broadly, share everything.
Seasonal Lowcountry cooking that earns its national reputation. Reservations open 28 days out.
Live-fire cooking, dry-aged meats, and uncommon wines on Cannon.
A European bistro in an 1820s townhouse with seasonal small plates and an all-French wine list.
A multi-course tasting menu inside an 1800s carriage house. Charleston at its most romantic.
Lowcountry classics, live jazz, and a long bar under slow-turning fans.
Eleven dining rooms around a courtyard garden, serving she-crab soup since 1982.
The maverick kitchen behind Charleston's most famous shrimp and grits.
“The best tables in town book out weeks ahead. Text us before you give up on one.”
Your hosts
The city's celebration steakhouse. Sunday gospel brunch is a Charleston rite.
Marbled & FinA modern steakhouse with a serious raw bar. Steak and seafood done with style.
Stone-fire grilling at the table, prime steaks, and a lively Market Street room.
Live-fire cooking, dry-aged meats, and uncommon wines on Cannon.
Wet-aged prime beef and tableside service inside the Market Pavilion Hotel.
From rooftop sunsets to natural wine in a shoebox. Charleston pours well at every altitude.
Rosemary RoseA French Riviera-inspired lounge above The Nickel hotel: olive trees, fire-pit tables, and Mediterranean small plates.
“A porch, a cold drink, and nowhere to be: that is the whole recipe.”
Charleston evenings
Lively up front, intimate reservation-only bar in back. A neighborhood favorite.
A speakeasy-styled hideaway with handcrafted cocktails and Caribbean notes.
Madison MaisonMaximalist, flower-filled, and fun: cocktails, champagne, and caviar bites.
Modern, creative cocktails and shareable plates from a decorated bar team.
SeahorseFrom the Chubby Fish team: Japanese-style highballs and inventive drinks.
Classic cocktails and live jazz in the lobby of The Charleston Place.
A cozy neighborhood spot for classic cocktails, martinis, and zero-proof drinks.
Wine & CompanyNeighborhood bottle shop and bar with rare finds and Tuesday tastings.
A James Beard-nominated natural wine program with Mediterranean snacks in Park Circle.
Old Village's living-room wine shop. Locals, corks, and conversation.
Blind Tiger PubA onetime speakeasy from 1893 with a courtyard that feels like old Charleston.
A vinyl-driven listening bar: craft cocktails, deep cuts, and groovy nostalgia.
Come by land or boat: a waterfront marina bar with local beer and easy eats.
A big waterfront taproom with a full kitchen and room to spread out.
Organic-minded pioneers brewing on the old Navy base since the beginning.
The WhaleA craft beer collective pouring rare finds from around the world.
Johns Island's community brewery with a big patio and easygoing crowd.
Charleston's biggest stage: stadium shows and touring headliners on Daniel Island.
A Navy-base warehouse turned event space hosting concerts, markets, and festivals.
Open-air concerts and festivals on the Cooper River at the old Navy base.
A restored 1849 train depot theater with impeccable sound. Something on almost nightly.
An industrial-chic venue on the upper peninsula for live music and special events.
The downtown institution for touring bands, packed floors, and late nights.
James Island's beloved listening room: two stages, a deck, and music every night.
Live music with your toes in the sand. A beachfront rite of passage since 1972.
A restored art deco movie palace hosting intimate shows on King Street.
Charleston's grand performance hall: symphony, Broadway tours, and jazz festivals.
Two centuries of history, a working harbor, and water in every direction. Here is how we would spend the week.
A rolling tour of the city's breweries. Leave the driving to them.
“Walk the side streets. The best of this city hides between the landmarks.”
Local advice
Kayaks, paddleboards, and captained charters from the marina.
Private sailing charters near Kiawah and Seabrook.
A full wellness club: serious gym floor, sauna, steam room, and an on-site cafe. Day passes available.
Every island has its own personality. Pick your day trip, and we will tell you where to eat when you get there.
Quiet, residential, and 15 minutes from downtown. Wide beach, no hotels, and a short strip of very good restaurants.
Inventive coastal cooking upstairs; gelato downstairs at Beardcat's.
Burgers and beers in honor of the island's most famous soldier, Edgar Allan Poe.
“Salt water first, then lunch. Everything tastes better after a morning in the ocean.”
Beach day rulesA classic family beach town with a livelier boardwalk. About 25 minutes from downtown.
The bohemian one. Surf shops, food trucks, and a fishing pier, 20 minutes south of downtown.
Across the Ravenel Bridge. Shem Creek shrimp boats, waterfront decks, and easy parking.
A charming Old Village inn with a New American menu.
Rustic-chic plates on the creek. Watch the dolphins at dusk.
North Charleston's most walkable neighborhood, built around a mile-wide 1912 circle. Breweries and front porches.
Forty-five minutes south: golf, tennis, bike paths under the oaks, and ten miles of protected beach.
Resort dining, spa days, and ocean-view cocktails open to visitors.
Waterfront seafood at Bohicket Marina on the way home.
No pool at your home? Two boutique hotels downtown welcome Proper Stays guests at theirs: just tell the front desk you are staying with us. They are also a lovely first stop if you arrive before check-in. Drop your bags, order a cocktail and a bite, and enjoy a little hotel scene before settling into your own private home.
A polished boutique hotel in the French Quarter with a stylish courtyard pool, coffee from Clerks, and dinner at Frannie & The Fox.
Charleston will come to you. Private chefs, in-home spa days, bartenders, babysitters, and stocked kitchens: every one of these teams works inside our homes, so ask us to help you book any of them.
A private chef in your rental's kitchen, for one showstopper dinner or every night of your stay. Share any dietary needs when you book.
Chef Tadd and his team cook refined Lowcountry dinners in your home, from intimate date nights to corporate gatherings.
“Some of the best nights of a Charleston trip happen at your own dining table.”
Why we love a chef night in
Premium wagyu steaks and meats delivered straight to your door. Perfect for a group grill night or a chef-cooked dinner in.
The city's oldest caterer, serving timeless and inventive Southern spreads since 1979. Ideal for bigger groups and celebrations.
Spa days, cocktail hours, and cooking classes without leaving your living room. Every one of these comes to you.
In-home massage and spa services by appointment: Swedish, deep tissue, hot stone, couples massage, facials, and more.
A traveling esthetician offering facials, waxing, eyelash tinting, and organic airbrush spray tans, with her own handmade organic skincare line.
Skilled bartenders who set up in your home and keep the drinks flowing for your gathering.
Southern gentlemen bartenders, butlers, and party hosts, ready to serve, pamper, and entertain.
A hands-on cooking party in your kitchen: pasta lovers of all ages learn to make authentic Italian pasta and sauces from scratch.
Full-service party planning for bachelorettes and celebrations, from over-the-top decor to stocking the fridge before you land.
Mobile spray tans that come to your rental, so the whole group is glowing before the first night out.
Downtown's go-to salon for blowouts, color, and waxing. Perfect for girls' days and bachelorette parties.
Send them your shopping list and arrive to a fully stocked kitchen, loaded into the home before you walk in.
Beach chairs, umbrellas, water sports, and lawn games delivered to your home before you arrive.
Clean, up-to-date baby gear rentals: cribs, car seats, high chairs, and everything else you did not want to fly with.
In-home babysitting from a dedicated agency of experienced, carefully matched nannies.
Park the car once. Uber and Lyft are everywhere downtown, a peninsula ride often costs less than valet, and Turo covers longer rentals. For everything more fun than a sedan, start here.
Bike rentals with baskets, locks, and route maps included. An affordable, scenic way to explore.
Street-legal golf carts for cruising the city day or night. 4, 6, and 8 passenger carts, delivered year round.
Scooter rentals delivered to your door. A stylish, Southern-charm way to see the city.
The classic downtown pedicab: flag one down or call ahead for short hops across the peninsula.
“Park the car once. Between bikes, carts, and pedicabs, downtown is best explored without it.”
How locals moveParty buses and limousines for weddings, bachelorettes, and big nights out.
A one-of-a-kind painted party bus for a night your group will not forget.
Private cars and Sprinter vans for airport transfers, golf trips, and group outings, including Kiawah and Seabrook.
Booking with Proper Stays means a Charleston team in your corner, not just a key code. Here is what every guest gets.
Text (843) 640-0897 during your stay. A real person on our Charleston team answers - directions, recommendations, a forgotten door code, anything.
Celebrating something? Traveling with kids, grandparents, or a group? Text us your dates and who’s coming and we’ll sketch a day-by-day plan from the places in this guide.
Three ready-made days built entirely from places in this guide. Follow them to the minute or treat them as a sketch. Want one tailored to your group? Text us.
Charleston in the rain is porches, oysters, and low light. Lean into it.
Two days, two beaches, and exactly zero arguments about where to eat.
Golden hour to last call, all within a short walk or ride.
All 166 of our recommendations on one map. Filter by section, tap a pin for the details, and get directions in one tap.
