We kicked off our trip with a walking tour through one of New Orleans’ charming neighborhoods. The streets were lined with beautiful, historic homes—each with its own story to tell. Our guide brought the neighborhood to life, weaving in vivid details and colorful history as we strolled past porch-lined houses and wrought-iron balconies. Since we visited just after Thanksgiving, many homes were already dressed in Christmas decorations, adding a festive touch to the experience and hinting at the holiday season ahead.
As you admire the homes, don’t forget to look down. Many of the street names are tiled right into the pavement—a charming and distinctly New Orleans detail. Even the utility covers are worth a glance, each one stamped with unique designs that tell their own quiet story. Our guide made sure to point them out along the way, but if you’re exploring on your own, it’s worth pausing for a moment to take it all in. Sometimes, the magic is right under your feet.
The Roosevelt New Orleans, now part of the Waldorf Astoria family, has a storied past. It was originally opened in 1893 by German immigrant Louis Grunewald as The Hotel Grunewald. Today, it’s a landmark—and during the Christmas season, it’s a true spectacle. The decorations alone are worth a visit. While you’re there, don’t miss the conical pendulum clock by Eugène Farcot, paired with a sculpture by Albert-Ernest Carrier-Belleuse, dating back to 1867. It’s a quiet but striking piece of history tucked into the hotel’s grand interior.
We stayed at the Hotel Monteleone, right in the heart of the French Quarter and just a short stroll from Bourbon Street. This historic landmark, a proud member of Historic Hotels of America, blends elegance with old-world charm. One of its most unique features is the Carousel Bar—a slowly rotating bar that’s just as fun to sit at as it is to watch. It’s the perfect place to sip a drink, take in the atmosphere, and enjoy a bit of people-watching as the bar gently spins.
One afternoon, Clare and I set off on a walking tour through the French Quarter and discovered some of the original buildings of New Orleans—along with some of the prettiest homes in the city. There’s no shortage of history in this part of town; nearly every corner has a story to tell.
One of the places that caught our eye was Maison Royale, an exquisite gallery known for its fine art, rare gemstones, and beautifully crafted jewellery. The building itself is a showstopper—the soft pink and grey exterior paired with ornate cast iron balconies makes it stand out even among the architectural gems of Royal Street.
Just down the street, The Historic New Orleans Collection (look for the pink building with the flags) offers a deep dive into the culture and history of the Gulf South. It was founded in 1966 by General and Mrs. L. Kemper Williams and is well worth a visit if you’re curious about the city’s roots.
Roux Royale, also on Royal Street, is a treasure trove for home entertainers. It’s packed with unique and practical items for the kitchen, dining room, or your next dinner party—definitely a spot to pick up something special.
We also passed by The Court of Two Sisters—not just a restaurant, but a New Orleans legend. It’s the kind of place where you can enjoy authentic Creole and Cajun cuisine with live jazz floating through the air. It’s a sensory experience that sticks with you.
One of the more historically rich spots we saw was The Miltenberger House, a picturesque brick townhouse built in 1838 by Amélie Miltenberger for her three sons. The house is steeped in local lore—Amélie’s granddaughter, Alice Heine, later became Princess of Monaco. This is about as close to royalty as you’ll get in the French Quarter.
Then there’s Pat O’Brien’s Bar, which has been a fixture in the French Quarter since 1933. During Prohibition, it operated as the secretive “Mr. O’Brien’s Club Tipperary,” where patrons needed the password “storm’s brewin’” to get inside. Today, it’s home to the famous hurricane cocktail and the original flaming fountain.
One of the most historically significant buildings we came across was Madame John’s Legacy. Built in 1789, it’s the second-oldest structure in the Mississippi Valley and one of the few that survived the fire of 1794. The house features rare West Indian and Creole-Colonial architecture and was named after a character in George Washington Cable’s short story Tite Poulette. It’s a rare survivor—weathering fires, floods, and hurricanes—and was declared a National Historic Landmark in 1970.
We also spotted The Cornstalk Hotel, with its beautifully ornate façade and Victorian charm. It’s rumoured to be haunted and has played host to several celebrities, including Bill and Hillary Clinton. Whether you believe the ghost stories or not, the building is undeniably eye-catching.
Nearby, The Andrew Jackson Hotel stands out with its classic 18th-century European design and wrought iron balconies. It’s listed on the National Register of Historic Places and sits just steps from the French Quarter’s jazz clubs and bustling restaurants.
One of the more intriguing stops was Lafitte’s Blacksmith Shop. Likely built between 1722 and 1732, it’s said to be the oldest bar building still in operation in the United States. It escaped the great fires of the 18th century thanks to its slate roof. Local legend claims it was once used by the Lafitte brothers—infamous privateers and smugglers—as a base for their Barataria operations. Whether fact or folklore, it’s a place soaked in mystery and character.
Another gem was the Avart-Peretti House, built in 1842. This elegant residence was home to several notable figures, including artist Achille Peretti and, briefly, playwright Tennessee Williams—who wrote A Streetcar Named Desire while living there in the 1940s.
We also passed the Beauregard-Keyes House on Chartres Street, originally built in 1826 by Joseph LeCarpentier. Over the years, it’s been home to General P.G.T. Beauregard and author Frances Parkinson Keyes. It’s a striking example of Creole architecture with layers of fascinating history behind it.
The Supreme Court Building is, in my opinion, the finest example of Beaux-Arts architecture in all of New Orleans. Having spent half my federal career working within the Federal Judiciary, I’ve always had a special appreciation for courthouse buildings—and this one didn’t disappoint. Constructed from granite and marble, it has a truly grand façade, partially veiled by palm trees that add a distinctly Southern touch. The Royal Street entrance is especially striking, with round-arched windows framed by towering Ionic pilasters. Just outside stands a monument to Edward Douglas White—former U.S. Senator and Chief Justice of the United States Supreme Court from 1910 to 1921. It’s a dignified tribute in front of a building that commands quiet respect.
Jackson Square—originally known as Place d’Armes or Plaza de Armas—is one of the most iconic cultural landmarks in New Orleans. Its location near the Mississippi River, the grand Saint Louis Cathedral, and the Cabildo has made it a natural gathering spot for centuries. Designed in 1721 by architect and landscape architect Louis H. Pilié, the square was renamed in 1850 in honour of President Andrew Jackson, hero of the Battle of New Orleans. Today, a dramatic statue of Jackson on horseback stands at the square’s centre, casting a proud silhouette against the cathedral’s spires.
St. Louis Cathedral, with its Renaissance and Spanish Colonial design, is the oldest cathedral in the United States. It’s impossible to miss—the structure towers over the square and draws the eye from every direction. Just next door, the Cabildo now serves as a museum, tracing Louisiana’s history from its Native American roots through the Reconstruction era. The stories held within those walls are deep and layered, echoing the complex identity of the region.
In colonial times, Jackson Square was a hub of daily life. It was a space for everything—from military drills and open-air markets to public executions. That contrast between beauty and brutality is part of what makes the history of New Orleans so compelling—it’s layered, raw, and deeply human.
Not far from Jackson Square, you’ll also find the Joan of Arc statue, standing proud in a small triangular park where Decatur, North Peters, and Saint Philip Streets intersect in the French Market District. Installed in 1999, this gilded equestrian statue of the Maid of Orleans is a striking tribute—and a reminder of the French heritage that pulses through the city’s veins.
What trip to New Orleans would be complete without a visit to one of its famous cemeteries? We made our way to St. Louis Cemetery No. 2, one of the city’s historic above-ground burial sites. With its maze of crumbling tombs, narrow walkways, and moss-draped statuary, it feels like stepping into another time.
And in case you’re wondering—yes, Easy Rider was filmed in St. Louis Cemetery No. 1, the more famous neighbour just a few blocks away. While that one draws the most attention, Cemetery No. 2 has its own quiet, haunting charm and is just as rich in stories.
One of the highlights of our trip was visiting the New Orleans Museum of Art and exploring the Sydney and Walda Besthoff Sculpture Garden, which stretches across eleven serene acres in City Park, right next to the museum. I found the sculptures personally inspiring—there’s something powerful about seeing art so thoughtfully placed in nature.
I snapped a few photos while the sun was out, but it was after a rain that the pieces truly came alive for me. With beads of water clinging to the surfaces, the sculptures took on new textures and moods—more mysterious, more moving. It’s amazing how a little rain can shift your entire perspective. See what you think.
And really, what would New Orleans be without its old cars rumbling down narrow streets, the odd and wonderful characters that give the city its soul, the ever-present street musicians pouring jazz into the air, and the hidden alleyways and quirky little shops that surprise you at every turn? It’s a city that doesn’t just welcome you—it draws you in, charms you, and leaves a little piece of itself with you long after you’ve gone.
One of our must-see stops was the Old Ursuline Convent, one of the oldest surviving buildings in the Mississippi River Valley. Also known as the Archbishop Antoine Blanc Memorial Complex, it’s considered a true treasure of the New Orleans Archdiocese. You’ll find it tucked away on Chartres Street—and for us, it was more than just a historical site. Clare attended Ursuline in Bethesda, Maryland, so this was a personal pilgrimage of sorts. We just had to find it.
The convent is named for the Sisters of the Ursula Order, who arrived in Louisiana in 1727 to open a school and orphanage for girls. Construction of the original building began in 1733 and wrapped up a year later. It was designed by Ignace François Broutin and built by Michael Seringue—names that are woven into the architectural history of colonial New Orleans.
A second building was added in 1745 and completed in 1751. When the sisters moved to a larger facility in 1824, the original convent became a residence for the archdiocese. A gatehouse and portico followed in 1825. Over the years, the convent has served many roles—a school, a home, a makeshift hospital, and an orphanage. Its thick walls have quietly witnessed nearly three centuries of New Orleans’ history.
And of course, no trip to New Orleans would be complete without an evening stroll down Bourbon Street. The sights, the sounds, the smells—the sheer decadence of it all—it’s a full-on sensory experience, and one you won’t soon forget. Music pours from nearly every doorway, neon lights flicker overhead, and the energy is infectious.
At one point, we nearly lost one of our female companions to a smooth-talking local who seemed convinced he’d found his match. Don’t worry—we swooped in and rescued her just in time. I’m sure it made for a great story once the laughter settled down.