The Deep South itinerary — May 2027
For the The Deep South trip (Charleston, Savannah & New Orleans), May 2027 is mixed for weather comfort. Across Charleston, Savannah and New Orleans, daytime highs run from about 29°C / 84°F to 30°C / 86°F. Plan around 7–9 days for the full Charleston, Savannah & New Orleans loop.
In this order — about 7–9 days:
- Charleston2 nights
- Savannah2 nights
- New Orleans3 nights
- Route noteReserve the longest intercity leg first and keep transfer days free of timed sights.
By TripSapien · Updated November 4, 2026
Charleston
Charleston in May
TempTemperature
80°F / 66°F
26.6°C / 19.1°C
RainPrecipitation
14d
2.5in · 64.6mm
LightDaylight
13.5h
Sea
78.6°F
25.9°C
Warm start to beach season with Spoleto Festival USA usually beginning late month.
City overview
Charleston is a low-country port city where church steeples, harbor forts, marsh islands, and preserved 18th- and 19th-century streets sit within a compact peninsula. The visitor rhythm changes sharply by season: spring gardens and Spoleto performances, hot stormy summers, hurricane-aware early fall, and mild winter weekends built around food, history, and beach walks.
Food & drink
Charleston is built around Lowcountry rice, seafood, okra, benne, and Gullah Geechee traditions. Book ahead for the best-known dining rooms, but leave room for she-crab soup, shrimp and grits, oyster roasts in cooler months, and casual seafood around Shem Creek or the islands.
Events & festivals
- Dates unconfirmed
Spoleto Festival USA
Planning lead · dates set closer in · Source: Month Signals
- May 1
- Dates unconfirmed
Piccolo Spoleto Festival
Planning lead · dates set closer in · Source: Month Signals
- May 1
- Dates unconfirmed
Charleston Farmers Market
Planning lead · dates set closer in · Source: Month Signals
- May 2
Show all 17 events for May
- May 4
- May 5
- May 6
- May 7
- May 13
- May 14
- May 15
- May 15
- May 16
- May 20
- May 22
Holidays & observances
- May 31Memorial DayPublic holiday
Top sights
Ranked for May suitability using weather, setting, ratings, and review volume.
- 1Gibbes Museum of Art
- 2Aiken-Rhett House Museum
- 3Fort Sumter National Historical Park
- 4Magnolia Plantation and Gardens
- 5Waterfront Park & Pineapple Fountain
- 6Sullivan's Island & Fort Moultrie
- 7Rainbow Row & The Battery
- 8Historic Charleston City Market
1Gibbes Museum of Art
4.7★ · 941indoorClosed TueCharleston art museum with Southern portraiture, miniature paintings, contemporary work, and a useful indoor anchor during summer storms.
Wikipedia
2Aiken-Rhett House Museum
4.6★ · 1,013indoorOpen dailyPreserved urban plantation complex with original outbuildings and interpretation of the enslaved people who worked there.
3Fort Sumter National Historical Park
4.7★ · 155indoorOpen dailyThe harbor fort where the first shots of the American Civil War were fired, reached by ferry from Liberty Square or Patriots Point.
Show 5 more sights
4Magnolia Plantation and Gardens
Ashley River estate known for romantic-style gardens, camellias, azaleas, swamp walks, and slavery-to-freedom interpretation.
5Waterfront Park & Pineapple Fountain
Harborfront park with shaded paths, pier swings, and the city's best low-effort Cooper River view.
6Sullivan's Island & Fort Moultrie
Barrier-island beach plus a layered harbor-defense fort, useful for pairing beach time with Revolutionary War and Civil War context.
7Rainbow Row & The Battery
Pastel Georgian row houses, oak-lined mansions, and harbor-facing defensive walls at the peninsula's southern edge.
8Historic Charleston City Market
Covered market halls between Meeting and East Bay streets, with sweetgrass basket makers, food stalls, and local crafts.
Neighborhoods
1French Quarter
Gallery-heavy historic core near the market, St. Philip's, and cobbled lanes. Best for first-time walks, architecture, and dinner reservations.
2South of Broad
Quiet mansion streets, gardens, The Battery, and Rainbow Row. Photogenic but residential, so mornings work better than late-night wandering.
3Cannonborough-Elliotborough
Younger restaurant and coffee corridor northwest of King Street, with smaller inns and a less formal feel than the old core.
4Upper King Street
Dining, bars, hotels, and nightlife north of Calhoun Street. Lively after dark and easy to pair with the visitor center.
5Mount Pleasant
Suburban harbor base for Shem Creek seafood, Patriots Point, and easy bridge access to Sullivan's Island.
6Sullivan's Island
Residential barrier island with broad beaches, lighthouse views, seafood restaurants, and Fort Moultrie history.
Getting around
The historic peninsula is walkable, and the free DASH shuttle helps with short hops between the visitor center, market, aquarium, and waterfront. Beaches, plantations, and most day trips require a car or rideshare; summer parking at island beaches fills early.
Savannah
Savannah in May
TempTemperature
83°F / 65°F
28.6°C / 18.2°C
RainPrecipitation
15d
2.8in · 71.2mm
LightDaylight
13.5h
Beach season begins, but afternoons already feel hot in the squares.
City overview
Savannah is a planned colonial city of shaded squares, live oaks, river warehouses, and a strong preservation layer around the Historic District and Victorian District. The calendar swings from spring garden weather to heavy summer heat, fall ghost-tour and festival demand, and mild winter weekends.
Food & drink
Savannah food leans coastal Southern: shrimp and grits, crab stew, fried green tomatoes, biscuits, pralines, and seafood near the river or marsh. The strongest dining mix is split between polished Historic District restaurants, Starland casual spots, and beach seafood on Tybee.
Events & festivals
- Dates unconfirmed
This annual spring event offers self-guided walking tours through private homes and gardens in Savannah's National Landmark Historic District.
Planning lead · dates set closer in · Source: Month Signals
- Dates unconfirmed
Held in the spring.
Planning lead · dates set closer in · Source: Month Signals
- May 16
- May 16
- May 22
- May 22
Holidays & observances
- May 31Memorial DayPublic holiday
Top sights
Ranked for May suitability using weather, setting, ratings, and review volume.
- 1Cathedral Basilica of St. John the Baptist
- 2Telfair Museums
- 3SCAD Museum of Art
- 4River Street
- 5Tybee Island
- 6Forsyth Park
- 7Bonaventure Cemetery
- 8Savannah Historic District Squares
1Cathedral Basilica of St. John the Baptist
4.8★ · 7,521indoorOpen dailyTwin-spired Gothic Revival church with stained glass and murals, a major visual anchor near Lafayette Square.
Wikipedia
2Telfair Museums
4.5★ · 797indoorClosed MonThree-site museum group including the Telfair Academy, Owens-Thomas House & Slave Quarters, and the contemporary Jepson Center.
Wikipedia
3SCAD Museum of Art
4.5★ · 356indoorClosed TueContemporary museum run by Savannah College of Art and Design, giving the historic city a strong student and design layer.
Wikipedia
Show 5 more sights
4River Street
Former cotton warehouses along the Savannah River, now restaurants, bars, shops, and cobblestone ramps down from Bay Street.
5Tybee Island
Beach town and lighthouse island 30 minutes from the Historic District, useful when heat makes inland sightseeing harder.
Wikipedia6Forsyth Park
Thirty-acre park south of the historic core, anchored by the 1858 fountain, shaded walks, lawns, and a Saturday farmers market.
Wikipedia7Bonaventure Cemetery
Large Victorian cemetery east of town known for live oaks, funerary sculpture, and bluff views over the Wilmington River.
Wikipedia8Savannah Historic District Squares
A grid of pocket squares framed by churches, houses, museums, and inns; walking square-to-square is the core Savannah experience.
Neighborhoods
1Historic District
Squares, inns, museums, churches, and restaurants in the walkable core north of Forsyth Park.
2Victorian District
Colorful 19th-century houses, quieter blocks, and the south edge of Forsyth Park.
3Starland District
Creative corridor with SCAD influence, murals, small galleries, coffee, vintage shops, and casual restaurants.
4River Street
Touristy riverfront nightlife and warehouse restaurants, best for a short evening walk rather than an all-day base.
5Ardsley Park
Residential early-20th-century streets with broad medians, useful for architecture walks away from the visitor crowds.
6Tybee Island
Beach-and-pier escape with lighthouse history, seafood shacks, and a completely different pace from the squares.
Getting around
The Historic District is best on foot, with DOT fare-free shuttles and ferries covering some visitor routes. A car helps for Tybee, Wormsloe, Bonaventure, and late-night returns from outlying districts.
New Orleans
New Orleans in May
TempTemperature
85°F / 69°F
29.6°C / 20.6°C
RainPrecipitation
8d
5.7in · 145mm
LightDaylight
13.5h
May is hot and humid, with Jazz Fest spillover and evening Frenchmen Street plans easier than midday cemetery walks.
City overview
New Orleans sits on a bend of the Mississippi River, where the French Quarter, Tremé, Marigny, Bywater, Garden District, and Uptown turn Creole architecture, brass-band music, Catholic parade calendars, and river commerce into one city. The French and Spanish colonial grid, St. Charles Avenue streetcar, above-ground cemeteries, and festival schedule make the visitor map unlike any other U.S. city.
Food & drink
New Orleans food is specific: gumbo, jambalaya, red beans and rice, crawfish etouffee, po'boys, muffulettas from the Central Grocery orbit, oysters, pralines, and beignets at Cafe du Monde. Use the French Quarter for old Creole dining, Magazine Street for neighborhood restaurants, and the Tremé-Marigny-Bywater corridor for music plus late meals.
Events & festivals
- Apr 22 – May 2
New Orleans Jazz Festival 2027
When you have a festival that stretches over two weekends, it's going to have a massive lineup, and the New Orleans Jazz Festival is no exception.
Source: TripSapien festival dataset
- May 1
- May 1
- Dates unconfirmed
Big free music festival at locations all around the French Quarter each Spring, usually the week before the start of JazzFest.
Planning lead · dates set closer in · Source: Month Signals
- May 2
- May 3 – May 13
New Orleans Jazz & Heritage Festival
Planning lead · projected date · Source: TripSapien festival dataset
Show all 30 events for May
- May 5
- May 5
- May 6
Meshuggah: The Forty-Year Anomaly w/ Testament & Blood Incantation
Music · Metal.
Source: Ticketmaster
- May 6
- May 7
- May 8
- May 8
- May 9
- May 11
- May 12
- May 13
- May 14
- May 14
- May 15
- May 15
- May 15
- May 15
- May 16
- May 16
- May 16
- May 16
- May 21
- May 22
- May 23
Holidays & observances
- May 31Memorial DayPublic holiday
Top sights
Ranked for May suitability using weather, setting, ratings, and review volume.
- 1St. Louis Cathedral
- 2National WWII Museum
- 3New Orleans Museum of Art and City Park
- 4Steamboat Natchez and Mississippi riverfront
- 5Mardi Gras World
- 6Frenchmen Street
- 7St. Charles Avenue Streetcar
- 8French Quarter and Jackson Square
- 9Audubon Park
- 10Garden District and Lafayette Cemetery No. 1
1St. Louis Cathedral
4.8★ · 5,222indoorOpen dailyThe cathedral on Jackson Square traces its parish to 1720, with the present triple-spired building completed in the 1850s after earlier fires and rebuilds. It anchors Chartres Street beside the Cabildo and Presbytere.
2National WWII Museum
4.8★ · 30,542indoorOpen dailyThe museum opened in 2000 in the Warehouse District and grew from the Higgins Boats built in New Orleans for Allied landings. Exhibits cover the European and Pacific theaters, aircraft, oral histories, and the U.S. Freedom Pavilion.
Wikipedia
3New Orleans Museum of Art and City Park
4.7★ · 5,429indoorClosed MonNOMA opened in City Park in 1911 and holds French, American, African, Japanese, and decorative arts collections. The Sydney and Walda Besthoff Sculpture Garden sits beside bayous and live oaks in the same park.
Show 7 more sights
4Steamboat Natchez and Mississippi riverfront
The Natchez paddlewheeler docks near the Toulouse Street wharf and runs jazz cruises on the Mississippi River. The Moonwalk and Woldenberg Riverfront Park give free views of ships, bridges, and the French Quarter levee edge.
5Mardi Gras World
Blaine Kern's warehouse on the riverfront shows parade floats, sculpted props, costumes, and workshop processes used by Carnival krewes. It is near the Convention Center and Warehouse District.
Wikipedia6Frenchmen Street
Frenchmen Street in the Marigny has music clubs such as The Spotted Cat, Blue Nile, d.b.a., and Snug Harbor within a few blocks. It is a short walk downriver from the French Quarter, beyond Esplanade Avenue.
Wikipedia7St. Charles Avenue Streetcar
The streetcar line began in 1835 and now runs from Canal Street through the Garden District, Uptown, and Carrollton. It passes oak canopies, universities, mansions, and restaurants on one of the city's easiest low-cost rides.
Wikipedia8French Quarter and Jackson Square
The French Quarter is the 18th-century colonial core, and Jackson Square sits where the Place d'Armes faced the Mississippi River. St. Louis Cathedral, the Cabildo, the Presbytere, Pontalba Buildings, artists, and carriage stands cluster around the square.
9Audubon Park
The Uptown park sits beside the Mississippi River and Tulane University, with live oaks, lagoons, walking paths, golf, and the Audubon Zoo. The St. Charles streetcar stops nearby at Audubon Place and Tulane.
10Garden District and Lafayette Cemetery No. 1
The Garden District developed in the 19th century with Greek Revival, Italianate, and Victorian mansions along Prytania and Coliseum streets. Lafayette Cemetery No. 1 sits opposite Commander's Palace, though access can change during preservation work.
Neighborhoods
1French Quarter (Vieux Carré)
The Quarter is dense and old, with Jackson Square, Royal Street galleries, Bourbon Street bars, hidden courtyards, Creole townhouses, and the riverfront within a tight grid.
2Marigny and Bywater
Marigny and Bywater are downriver and music-heavy, with Frenchmen Street clubs, Crescent Park, colorful cottages, St. Claude Avenue venues, and neighborhood restaurants.
3Tremé
Tremé is tied to Black New Orleans culture, with Congo Square, Backstreet Cultural Museum, brass-band history, Creole cottages, and second-line routes near North Rampart Street.
4Garden District and Lower Garden District
The Garden District is mansion-lined and leafy, with St. Charles Avenue, Magazine Street shops, Lafayette Cemetery No. 1, Commander's Palace, and streetcar stops.
5Uptown and Carrollton
Uptown stretches along St. Charles and Magazine, with Tulane, Loyola, Audubon Park, Maple Street bars, old oaks, and po'boy counters.
6Warehouse District and CBD
The Warehouse District and CBD feel more modern, with the National WWII Museum, Ogden Museum, Julia Street galleries, hotels, Superdome access, and convention crowds.
Getting around
RTA streetcars and buses cover the French Quarter edge, St. Charles Avenue, Canal Street, Rampart Street, cemeteries, City Park, and parts of Uptown using Le Pass fares. Walking works in the Quarter and Marigny, the St. Charles streetcar works for Garden District days, and rideshare is practical for late-night Bywater or airport trips.
Planning the The Deep South route?
Add your dates and we'll pace all 3 cities — every place checked for closures, limited hours, and booking needs in May.
Weather by month for the The Deep South trip
In May, climate averages for Charleston, Savannah and New Orleans show daytime highs from 29°C / 84°F to 30°C / 86°F, with nights down to about 19°C / 66°F in the coolest of those cities. The rainiest of those cities averages about 8 rainy days. Based on climate averages for Charleston, Savannah and New Orleans, May is mixed for weather comfort.
The most comfortable months for this route are November, April and October, based on average daytime temperatures and rainfall in Charleston, Savannah and New Orleans. May 2027 is mixed for weather comfort.
Common questions about the The Deep South trip
- When is the best time to do the The Deep South trip?
- The most comfortable months across Charleston, Savannah and New Orleans are November, April and October, based on average daytime temperatures and rainfall for those cities. May is mixed for weather comfort — see the city climate sections below for the averages in May 2027.
- How many days do you need for the The Deep South trip?
- A comfortable The Deep South trip runs about 7–9 days, allowing roughly Charleston 2, Savannah 2, New Orleans 3 nights plus travel between stops. Add a day if you want a slower pace or extra day trips.
- What's the route for the The Deep South trip?
- The classic order is Charleston, Savannah & New Orleans. The detailed month sections below cover Charleston, Savannah and New Orleans.
Ready to plan the The Deep South trip?
Turn this route into a day-by-day plan for May 2027, every stop checked for closures and booking needs on your exact dates.