Charleston · Charleston & Savannah
Charleston and Savannah in 5 Days: A Grown-Up Itinerary
Charleston and Savannah are about two hours apart by car, and they make a perfect pair: Charleston for the dining and the harbour, Savannah for the squares and the moss. Here's how we'd split five days.
- Days 1-3
- Charleston: history, harbour, gardens, jazz
- Days 4-5
- Savannah: squares, riverfront, Bonaventure, a piano bar
- Between
- About two hours by car
Some links on this page go to booking partners. If we join their affiliate programmes we may earn a commission when you book, at no extra cost to you. It never decides what we recommend. How we make money.
Day 1: Charleston's historic district
Carriage ride, rooftop and a Southern dinner.
Afternoon
Old South Carriage Company
14 Anson St
An easy first hour in town.
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.
Sunset
The Rooftop at The Vendue
19 Vendue Range, by Waterfront Park
A drink by the harbour.
An art hotel's rooftop bar a block from the harbour, with steeple and water views; open from 11:30 a.m. daily and until midnight on Friday and Saturday.
Dinner
Husk (and the Bar at Husk)
76 Queen St
Finish in the bourbon bar.
Southern cooking in a restored mansion since 2011, Michelin Recommended. The separate bar in an 1890s kitchen house next door is one of the South's great bourbon bars, and a fine stop even without dinner.
Day 2: The harbour
Fort Sumter, then a sail.
Morning
Fort Sumter (ferry from Liberty Square)
Liberty Square, 340 Concord St
First boat from Liberty Square.
A 30-minute boat ride out to the fort where the Civil War began, with a National Park Service ranger talk and museum. The whole trip takes about 2 hours 15 minutes.
Sunset
Schooner Pride sunset sail
Floating dock by the SC Aquarium, 360 Concord St
Two hours under sail.
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.
Dinner and jazz
Charleston Grill
Belmond Charleston Place, Meeting St
Jazz every night.
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.
Day 3: Gardens, then the road
A garden morning, then drive south (about two hours).
Morning
Middleton Place
4300 Ashley River Rd, about 25 minutes
Leave by early afternoon for Savannah.
Landscaped gardens, a house museum and stableyards on the Ashley River, with free garden tours on the hour from 10 a.m. to 3 p.m. Open 9 to 5 daily; adults $29.
Dinner in Savannah
The Olde Pink House & Planters Tavern
23 Abercorn St, Reynolds Square
Then a nightcap with the pianist downstairs.
Southern dining in an 18th-century mansion. Downstairs, the Planters Tavern cellar bar has fireplaces, the same menu and a pianist from 7:30 p.m.
Day 4: Savannah's squares
A walking tour, a museum and a proper dinner.
Morning
Genteel & Bard walking tours
Historic District squares
The 10 a.m. history walk.
Audio-enhanced walking tours (you hear the guide through a headset) covering the squares, Jones Street and the Mercer Williams House, with history tours at 10 a.m. and 1:30 p.m. and ghost walks after dark.
Afternoon
Telfair Museums (Telfair Academy, Jepson Center, Owens-Thomas House)
Telfair Square and Oglethorpe Square
One ticket, three sites.
Three sites on one ticket, valid for a week: a classic art museum, a contemporary gallery and the Owens-Thomas House & Slave Quarters, toured every 15 minutes.
Sunset
Peregrin at Perry Lane Hotel
Perry Lane Hotel, 256 E Perry St
The rooftop conservatory.
A rooftop conservatory bar, redesigned with SCAD in 2024, with skyline views, cocktails and street-food-style bites; open 11 a.m. to 11 p.m.
Dinner
The Grey
109 Martin Luther King Jr Blvd
Book well ahead.
Chef Mashama Bailey's restaurant in a restored 1930s Greyhound bus terminal, cooking Southern food with real depth. Bailey was named North America's Best Female Chef for 2026 by The World's 50 Best.
Day 5: Live oaks and the river
Bonaventure in the morning, the river at night.
Morning
Bonaventure Cemetery
330 Bonaventure Rd, Thunderbolt
Open 8 to 5; free to enter.
A hauntingly beautiful riverside cemetery under live oaks and Spanish moss. Free to enter, 8 a.m. to 5 p.m. daily; the historical society leads free tours at 2 p.m. on the second Saturday and Sunday of each month.
Lunch
The Wyld Dock Bar
2740 Livingston Ave, on the marsh
Seafood on the marsh.
A casual waterside seafood spot on the Turner Creek marsh: order at the counter, then settle in with local shrimp, oysters and a cocktail by the fire pit and bocce court. Boats tie up at the dock.
Dinner
Vic's on the River
Old cotton warehouse between Bay St and River St
River views and the piano bar from 7.
Southern cooking and local seafood in an old cotton warehouse with tall windows over the Savannah River, and a piano bar nightly from 7 p.m.
For more time in either city, see the 3-day Charleston itinerary and the 3-day Savannah itinerary.
Everything here was checked in September 2026. Seasons, show dates and reservation rules change, so confirm before you go.
Questions people ask
How far is Savannah from Charleston?
About two hours by car. Most people drive; it's easy to do on the morning or afternoon of a travel day.
Should you visit Charleston or Savannah first?
Either works. We start in Charleston for the bigger dining scene and end in Savannah, which is slower and a lovely place to wind down.
How many days do you need for Charleston and Savannah?
Five days is the sweet spot: three in Charleston and two in Savannah. With a week, give each city three full days and add a beach day.