5:00 p.m. Streetcar Ride around St. Charles Avenue
Grab your special one and hope on the St. Charles Line streetcar for a trip into New Orleans’ past. For just $1.25, this 150-year-old trolley will take you for a scenic ride across St. Charles Avenue, a historic, 13.2-mile stretch filled with oak trees, 19th century architecture, antebellum mansions and historic monuments. After cruising through the oldest and most majestic side of NOLA’s Uptown district, hop off at the Pontchartrain Hotel for some rooftop drinks.
6:00 p.m. Rooftop drinks at Hot Tin
Once you arrive at the Pontchartrain Hotel’s lobby, take the right-side elevator to the hotel’s rooftop bar, Hot Tin, for some delicious cocktails featuring breathtaking city views of the Mississippi River and Downtown New Orleans. This intimate lounge, first constructed in 1927, offers many inventive drink specials – however, must-try, house specialties include the ‘menage mule’, the ‘pontch de leon,’ and the ‘champagne safari.’ After your fermented beverage stop, taken an Uber, Lyft, or taxi to Bacchanal Fine Wine and Spirits for a lovely outdoors meal.
Hot Tin, 2031 St Charles Ave, New Orleans, LA, USA +1 504 323 1452
8:00 p.m. Dinner at Bacchanal Fine Wine & Spirits
Now – time for food, wine and live music! At Bacchanal Fine Wine & Spirits, a wine laboratory located in the city’s Bywater district, you’ll be able to choose your grape of choice from over a hundred selections and savor globally-accented small plates at inexpensive prices, all while a live band performs next-generation jazz. When you finish eating, make your way to Frenchmen Street, NOLA’s premier district for music and local art.
10:00 p.m. Frenchmen Art Market Stroll
When in Frenchmen Street, take a stroll through the Frenchmen Art Market, an evening marketplace featuring local and regional artists who sell everything from handmade paintings and drawings to photography and craft goods. Centering Frenchmen’s two-mile strip under an alfresco string-lighted roof, this weekly, free art market will give you and your date a peek into the city’s most authentic and affordable works of art.
Frenchmen Art Market, 619 Frenchmen St, New Orleans, LA, USA +1 504 941 1149
11:00 p.m. Bar/Dance hopping around Frenchmen Street
Once you’re done exploring the art market, head to one of Frenchmen Street’s many bars for live music performances by some of the city’s most talented acts. Even though this musical strip has something playing to satisfy any ear inside every venue, if you’re into, jazz head to The Spotted Cat Music Club, to Dragon’s Den second-floor if you’re wanting to dance salsa, to Cafe Negril if you’re looking to hear authentic roots reggae and to Apple Barrel for some good old blues tunes. And, when your feet are ready to call it a night, be sure to end your date on a sweet note with a late night snack at Café du Monde.
12:30 p.m. Late night snack at Café du Monde
When walking from Frenchmen Street to Café du Monde, you’ll be able to enjoy views of the historic French Quarter, New Orleans’ original settlement ground (1718) and oldest existing neighborhood. And when you reach Café du Monde, pair the restaurant’s world-famous beignets with a side of hot chocolate to share, because nothing says ‘successful-date’ like an order of deep-fried dough covered in powdered sugar.
Café du Monde, 800 Decatur St, New Orleans, LA, USA +1 504 525 4544