Charleston · Weekend itinerary
A Weekend in Charleston: 2 Days for Grown-Ups
Two days is enough for a very good Charleston weekend if you stay in the historic district and don't try to do everything. This plan keeps the pace gentle and gives you two memorable nights.
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Saturday: The historic district
Everything today is on foot.
Morning
Old South Carriage Company
14 Anson St
An hour of history from a carriage seat.
A one-hour, 2.5-mile carriage ride through about 30 blocks of the historic district, pulled by Percherons or Belgians with a Palmetto Guild-certified guide. The easiest way to get your bearings.
Lunch
Slightly North of Broad (S.N.O.B.)
192 E Bay St, French Quarter
Lowcountry lunch in an 18th-century warehouse.
Lowcountry cooking with a contemporary edge in an 18th-century warehouse with exposed brick and an open kitchen. The menu changes daily; open for lunch and dinner.
Sunset
Citrus Club at The Dewberry
The Dewberry, 334 Meeting St
The city's highest rooftop, adults only.
Charleston's highest rooftop, an eighth-floor terrace with olive trees and 360-degree river-to-river views, pouring citrus-driven cocktails. Adults 21+ only.
Dinner and jazz
Charleston Grill
Belmond Charleston Place, Meeting St
Dinner with a live jazz set.
Half refined dining room, half jazz club: Executive Chef Michelle Weaver's kitchen, with live jazz, soul and Brazilian sets seven nights a week. Open 5:30 to 10 p.m. daily.
Sunday: Brunch and gardens
Gospel at brunch, then a slow afternoon among the live oaks.
Brunch
Halls Chophouse
434 King St
Gospel brunch runs 10 a.m. to 2 p.m.; book.
A family-run steakhouse on King Street, famous for its Sunday gospel brunch (10 a.m. to 2 p.m.), when a local choir sings through the dining rooms.
Afternoon
Magnolia Plantation and Gardens
3550 Ashley River Rd
Last admission is 4 p.m.
Romantic, informal gardens and swamp walks on the Ashley River, a few minutes from Middleton Place. Open 9 to 5 daily (last admission 4 p.m.).
Evening
The Gin Joint
182 E Bay St
A quiet classic cocktail to end the weekend.
One of Charleston's first craft cocktail bars (2010): a dim, pre-Prohibition-style room and a shaded courtyard, classic drinks and good bar snacks.
Arriving on a Friday? Add a set at Forte Jazz Lounge (two shows a night, Thursday to Saturday) or a sunset sail on the Schooner Pride. With a third day, follow the 3-day Charleston itinerary. For more ideas for two, see Charleston for couples.
Forte Jazz Lounge
475 King St
Charleston's only strictly jazz venue, patterned on New York listening rooms: candlelit tables and two sets a night Thursday to Saturday (7 and 9:30 p.m.). Open Wednesday to Saturday.
Schooner Pride sunset sail
Floating dock by the SC Aquarium, 360 Concord St
Two hours under sail on an 84-foot, three-masted schooner as the sun drops behind the steeples, past Fort Sumter and the Battery, often with dolphins. Not narrated; the crew answers questions.
Tip: Sails run March to early November.
Everything here was checked in September 2026. Seasons, show dates and reservation rules change, so confirm before you go.
Questions people ask
What should you do with a weekend in Charleston?
Take a carriage tour, walk South of Broad and the Battery, have a rooftop drink at sunset, eat one great dinner (Charleston Grill with jazz, FIG or Husk), and on Sunday book the gospel brunch at Halls Chophouse.
Is Charleston good for a 2-day trip?
Yes. The historic district is compact, so two days covers the highlights without a car, and one of the Ashley River gardens fits into a morning.