A city rich with history, music, and creole flavors, the birthplace of jazz should be on every traveler’s bucket list. I grew up one state away in Dallas, Texas, and I’ve visited New Orleans at least once every few years for the last two decades.

Here’s my perfect 5-day New Orleans itinerary for luxury solo travelers like myself. The best time to visit is from December (when the hurricane season has solidly ended) through April (before it gets too hot).

You can time your trip to participate in (or avoid) Mardi Gras in late February/early March or Jazz Fest in late April/early May.

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Cheat Sheet
  • Fly: Book flights into Louis Armstrong New Orleans International Airport (MSY), unless you have time for the pre- and/or post-trips outlined below. Then you’ll need flights into Jackson (JAN) and/or back from Destin (VPS) or Pensacola (PNS)
  • Drive: Rent a car from Discover Cars or prebook your airport transfers from Holiday Taxis
  • Read: A Confederacy of Dunces; A Streetcar Named Desire; New Orleans, Mon Amour
Cypress forests and plantation houses
Oak Alley Plantation in Vacherie, Louisiana

If you have time, I recommend flying into Jackson, Mississippi (JAN) and renting a car two days before you want to arrive in New Orleans. Stay the night at one of the grand old houses in Vicksburg, like the Duff Green Mansion, Baer House, or Bazsinsky House. Have a sunset dinner at 10 South Rooftop Bar & Grill for gorgeous views of the Mississippi River and Yazoo Canal. “That Famous Fried Chicken Sandwich” is famous for a reason—it comes on a brioche bun with candied bacon, pepper jack cheese, and a maple-chili glaze.

Natchez Trace Cypress Swamp

The next morning, visit Natchez Trace Cypress Swamp (a 90-minute drive). It’s an aquatic forest that’s heady with the fragrance of blooming honeysuckle in the spring. Also, you’ll see technicolor lizards, iridescent blue-green beetles, and dragonflies darting about. 

Natchez Trace Cypress Swamp

Don’t fret when Google Maps announces you’ve arrived and there’s no turnoff! The small parking area is less than a mile ahead, marked with a small brown sign that says “nature trail.” You can continue past it on Natchez Trace Parkway another 1/2 mile northeast to reach bathrooms (with sinks and flush toilets) and a picnic area.

From the Cypress Swamp, head south for 3.5 hours to Darrow, Louisiana. If you’re hungry, stop for fried green tomato & bacon tacos at The Pig & Pint in Jackson.

Inn at Houmas House

In Darrow, stay at The Inn at Houmas House for a night on the lush, manicured grounds of a historic plantation. The rooms are located in luxurious cottages near the 1840 Greek Revival mansion, not inside of it. However, each comes equipped with beautiful antique furniture and unique artwork.

Have dinner at one of the on-site restaurants, Carriage House or Latil’s Landing. Afterward, don’t miss the chance to wander through the lantern-lit gardens on foot after dark. The ancient live oak trees, fountains, and whimsical sculptures make for a magical walk back to your room.

The gardens at Houmas House
Oak Alley Plantation

In the morning, tour the nearby Oak Alley Plantation ($27.79/adult) to see the famous oak trees and the mansion that was used as Louis’s house in Interview with the Vampire. You can also learn about the history of the enslaved people who lived and worked on the sugarcane plantation.

From Oak Alley, you’re one hour’s drive into New Orleans.

Day One

To kick off your perfect five-day New Orleans itinerary, check into Hotel Peter & Paul, a former 19th century church and Catholic school. Whether you choose to stay in the schoolhouse, the rectory, or the convent, all of the rooms are dripping with character and romance.

Hotel Peter & Paul in Faubourg Marigny

One of the city’s most unique zip codes, Faubourg Marigny is the perfect home base for five days in New Orleans. It has quiet residential streets lined with historic houses painted in every color of the rainbow. It also has the lively Frenchmen Street, full of jazz joints, artsy bars, and Cajun bistros. And it’s all within easy staggering distance of The French Quarter, which is just a few blocks to the west.

Have dinner at Charlie’s, the oldest steakhouse in New Orleans, and don’t be put off by its appearance. It’s a first rate establishment that just happens to look like a dive, but its doors have been open since 1932 for good reason. There are no frills and no menu. You pick a cut of steak and a few sides and—trust me on this one—you say hell yes to the onion strings.

Day Two

Kick off the second day of your perfect five-day New Orleans itinerary with Sunday Jazz Brunch at Muriel’s Jackson Square (801 Chartres Street). They serve delicious creole-inspired plates with traditional jazz accompaniment in a 19th century building with exposed brick and a lantern-lit courtyard.

Muriel’s Jackson Square

Walk off your brunch on a tour of the Garden District. Strolling through this New Orleans neighborhood feels like wandering in a time warp. Your guide will explain the variety of architectural styles showcased by the most jaw-dropping of the mansions, as well as their most significant historical residents. After your walk, you can have a drink and/or check out the shops on Magazine Street.

Novelist Ann Rice lived in this house in the Garden District from 1989-2004

Have dinner at Paladar 511, a stylish neighborhood restaurant in the Marigny. It’s a six-minute walk toward the river from the hotel and the New York times calls it “the most consistently excellent Italian food in town.” I swooned over their zhoug-roasted carrot starter (zhoug is a bit like Yemeni chimichurri—it’s a spicy, garlicky cilantro sauce). Likewise, I was blown away by their cheese-filled mezze luna (half-moon shaped ravioli) in a light lemon butter sauce.

After dinner, catch a show at the historic Preservation Hall or Tipitina’s.

Day Three
Laundry Hack

Now that it’s day three of your perfect five-day New Orleans itinerary, you might be running low on clean clothes. If that’s the case, you can save by scheduling a pickup and delivery from Bolt Laundry. They’re fast, professional, and much more reasonably priced than any hotel laundry service. I had two large bags of dirty clothes returned to me smelling fresh and neatly folded within three hours. Meanwhile, the total bill was less than $45. By comparison, it costs $15.60 to have one pair of slacks washed at Virgin Hotels New Orleans.  

Hidden gem for lunch

After you send off your dirties, drive across the Mississippi to Gretna for an early soul food lunch at Chicken’s Kitchen (629 Derbigny St, Gretna). It’s a takeout-only restaurant with a devoted local following. The joint is named after the owner, Marlon Chukumerije, who goes by Chicken. Chicken credits his cooking chops to watching his matriarchs and the Food Network.

They open Monday-Friday from 10:30am until they sell out, which I hear happens by 3pm every day. You’ll have to circle the block a few times to find a parking spot and then join a line that wraps around the building. Note that the menu changes daily. I would recommend coming on Monday or Wednesday so you can try the fried chicken or catfish and the delightful honey-soaked cornbread.

2-piece fried chicken with five star mac, honeyed cornbread, and potato salad from Chicken’s Kitchen
Fontaineblue state park

After lunch, make the 70-minute drive across Lake Pontchartrain Causeway to Fontainebleu State Park. At over 23 miles long, the Causeway is the longest continuous bridge over water in the world. Voted the best state park in Louisiana by Southern Living readers, Fontainebleu is located on land that was formerly a 19th-century sugar plantation. You can kayak through the cypress groves of Cane Bayou (keep an eye out for turtles) or walk some of the 27-mile Rails-to-Trails path.

Dinner & Evening Diversions

Have dinner at the seven-time James Beard Award winning Commander’s Palace, a Garden District legend since 1893. Since the 1970’s, revered restaurateur Ella Brennan has joined forces with a list of chefs that reads like a who’s who of culinary greatness. For instance, Emeril Lagasse and Paul Prudhomme. Now helmed by Meg Bickford, its first female executive chef, the Palace is still turning out its famously creative haute Creole cuisine.

After dinner, check out the local artists’ creations at Frenchmen Art Bazaar (619 Frenchmen Street). It’s open nightly from 7pm until midnight and it’s only an 8-minute walk from the hotel. You’ll find original artwork, unusual jewellery, and other crafts on offer. When I visited in April, the goods included strangely bedazzled toilet seats for your bathroom and a vintage photo booth complete with all the trappings of a bygone era.

Day Four
Brunch & Philanthropy

To start the fourth day of your perfect five-day New Orleans itinerary, have brunch at Cafe Reconcile (1631 Oretha Castle Haley Blvd., open Tuesday-Friday from 11am-2:30pm). It’s a non-profit training centre that prepares young locals who are considered to be “at risk” for careers in the culinary arts. They take their craft seriously and the food is off the hook. There was a line out the door on a Tuesday afternoon when I went in April. Furthermore, the BL(fried green)T on jalapeño cornbread toast was as dreamy as it sounds.

The BLFGT at Cafe Reconcile

After brunch, visit the New Orleans Museum of Art ($20 per out-of-state visitor, closed Mondays). As befits the French heritage of the city, NOMA is known for its comprehensive collection of French art, including Portrait of Estelle Musson Degas (1872) by the renowned impressionist Degas. Before you leave, take a stroll in the (free) Sydney and Walda Besthoff Sculpture Garden at New Orleans City Park, directly adjacent to the museum. The ponds and ancient oak groves are dotted with massive sculptures, including a Louise Bourgeois spider and a Rodin.

Dinner at Saffron

For dinner, try Indian-Creole fusion at Saffron (4128 Magazine Street). The menu includes standouts like truffle naan and herb- and spice-crusted Bombay Shrimp with tomato-ginger remoulade. The cocktails are also sensational—if it’s on the menu, don’t miss the Girl From Ipanema (chevre-infused cachaça, melon cordial, mint, lime, and salt).

The Girl From Ipanema cocktail at Saffron

After dinner, catch a burlesque show at The AllWays Lounge & Cabaret or Fleur de Tease.

Day Five

Your perfect five-day New Orleans itinerary continues with a muffuletta for lunch from Central Grocery & Deli (923 Decatur Street, open 9am-5pm daily). The famous New Orleans sandwich is made of Sicilian bread heaped with cured meats like mortadella and salami, provolone cheese, and olive salad. Thanks to the massive size of the signature sesame seed bread, 1/4 of a sandwich is plenty of lunch for one.

French Quarter

Now that you’re properly fuelled, do what no proper trip to New Orleans would be complete without doing: go drinking in the French Quarter. Some of the best establishments, in terms of both beverages and atmosphere, are:

  • The Carousel Bar at Hotel Monteleone (214 Royal Street, 11am-12am daily). The historic bar first opened in 1949 and it’s situated around an actual rotating carousel.
  • Lafitte’s Blacksmith Shop Bar is the oldest bar in the city (it was established in 1772).
  • Black Penny (700 N Rampart Street) is the farthest you can get from the tourist traps that line the French Quarter. It’s a charming dive with a welcoming atmosphere and a loyal following of locals.
  • Erin Rose Bar (811 Conti Street) is an artsy Irish pub with a jukebox and a secret Bloody Mary recipe that everyone wishes they could get their hands on. They also have delicious frozen Irish coffee.

Walk off your buzz on a tour of St. Louis Cemetery No. 1, the oldest public cemetery in New Orleans. It was established in 1789 and can only be visited on an official tour. Your guide will tell you the fascinating history of many of the residents, who are buried in above-ground graves. Much of the city sits below sea level, so traditional underground graves would flood.

Casual dinner and a jazz show

For dinner, continue your iconic New Orleans sandwich day with a po’boy from Liuzza’s by the Track (1518 N Lopez Street, open Mondays-Saturdays 11am-8pm). The Breathtaking Beef & Horseradish po’boy has a serious kick and a devoted local fanbase, but they also have more traditional options like shrimp and oyster po’boys.

Celebrate your last night in NOLA with a jazz show at Happyland Theater (3126 Burgundy Street) or The Broadside (600 N Broad Street), which has both indoor and outdoor stages.

Beach recovery

If you have more time after your perfect five-day New Orleans itinerary, you can drive about four hours east and spend some time in recovery from all that NOLA-style drinking and carousing on the beach in Destin.

Photo by Aaron Burden on Unsplash

This tastefully appointed, 873-square-foot beachfront condo at Pelican Beach Resort has unobstructed ocean views and access to two heated pools.

The best way to enjoy Destin’s crystal clear waters and Maldivian-caliber shallows is to charter a pontoon for yourself and up to five of your favourite people. This one comes with a water slide and includes four hours from $480.

best places to eat in the Destin area
  • Stewby’s Seafood Shanty (235 Santa Rosa Blvd in Fort Walton Beach, open from 11am-8:30pm Sun-Thu, -9pm Fri-Sat) 
  • McGuire’s Irish Pub (33 East Highway 98 in Destin, open 11am-2am daily)
  • East Pass Seafood & Oyster House (56 Harbor Blvd. in Destin, open 11am-8pm Sun-Thu, -9pm Fri-Sat)
  • The Shack (104 Miracle Strip Pkwy SW in Fort Walton Beach, open 11am-9pm daily)

You have beach access directly in front of your condo, of course, but the pristine waters of Henderson Beach State Park are worth a visit as well. It’s less than a 10-minute drive and it’s open from 8am until sundown daily ($4 per single-entrant vehicle; $6 per vehicle with 2-8 people; $2 for pedestrians, bicyclists, and extra passengers).

Drop off your rental car and fly home from VPS (Destin–Fort Walton Beach Airport) or PNS (Pensacola International Airport), 90 minutes west.

Need more of the Deep South? Here’s your 4-day luxury Savannah itinerary!

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Everyone’s different, but for me, luxury happens at a leisurely pace. I don’t like rushing around and I prefer to leave room to happen upon unexpected adventures as well. Hence, my perfect itineraries tend to include two dining suggestions and 1-2 activities per full day. They should be used as backbones to flesh out with your own ideas and discoveries.

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