Food, Flexibility, & a Jailbreak?! Our Couple's Weekend in New Orleans

One of our favorite travel traditions is turning work trips into weekend escapes. Especially when it is uncharted territory for both of us. So when one of us had to head to New Orleans for a work meeting, the other wasn’t far behind with a suitcase in hand. The plan was simple: meet up Saturday and turn the rest of the weekend into a little getaway. Spoiler alert: flight delays, cancellations, and rebookings tried it—but we made it. If there’s one lesson this trip reinforced, it’s the power of flexibility.

Also, yes—this trip occurred the same weekend that those 10 inmates escaped from that New Orleans jail through a hole behind a toilet. Wild. You can check this News Report, but it didn’t stop us from having a blast, tasting the cuisine, and dancing to live jazz music.

A Bourbon Street Base: Royal Sonesta New Orleans

We stayed at the Royal Sonesta New Orleans, and honestly, it surprised us in the best way. Perfect location right on Bourbon Street, friendly staff, and walking distance to everything we wanted to see, eat, and hear. The pool and pool bar gave resort energy in the middle of the city chaos—yes, please!

The rooms were standard but comfortable. Nothing to rave about, but the vibe of the hotel overall more than made up for it. What did steal the show was Desire Oyster Bar, the restaurant attached to the hotel. The shrimp and grits? So good we went twice. The bartender? Elite. 10/10.

Downstairs at The Jazz Playhouse, we caught a set by Nayo Jones and she blew us away. HER MIC WAS DEFINITELY ON!!!! The vocals were rich, the energy was high, and the band was 🔥. Easily one of our favorite moments.

Now Let’s Talk FOOD

We had big plans for sightseeing and experiences, but food quickly became the center of our trip. From po’boys to red beans & rice, New Orleans cuisine did not play around.

Here’s a bite-by-bite breakdown of where we ate and what we loved:

Kingfish Kitchen & Cocktails

• Duck & Andouille Sausage – 10/10
• Gulf Shrimp Cocktail – 7.5/10
• Overall: 8.5/10
  Classy vibes with bold flavors. Definitely recommend.
  

Deanie’s Seafood

• Chicken & Sausage Gumbo – 10/10
• Crawfish – 7/10
• Overall: 7.5/10
  A solid spot for classic Louisiana comfort food.

Oceana Grill

• Shrimp Po’boy – 10/10
• Cajun Jambalaya Pasta – 8/10
• Fresh Oysters – 8/10
  Overall: 8.3/10
  Casual and cozy, with big flavors and generous portions.

Pier 424 Seafood Market

• Sautéed Crab Claws – 10/10
• Red Beans & Rice – 10/10
• Boiled Crawfish – 9/10
• Blackened Chicken – 7/10
  Overall: 9/10
  Our top pick. This place slapped from start to finish.

Brennan’s

• Turtle Soup – 7.6/10
• Baked Apple – 6/10
• Shrimp & Grits – 7/10
• Beef Tournedos Rossini – 9/10
• Snickers Dessert – 6.5/10
  Vibes and service were A+, but the food was a bit hit or miss for us.

Couple’s Travel Tip: Be Flexible

This trip was a perfect reminder that travel doesn’t always go as planned. Flight delays and cancellations could’ve ruined the vibe—but instead, we stayed flexible, made the most of it, and still created some of our favorite memories. And honestly? Some of the best moments came from just winging it.

Want to see the full vibe? We did a full IG Vlog Review – watch it here to see how it all went down, food pics included!

Planning Your Own NOLA Escape?

We’ve curated some of our favorite New Orleans experiences just for couples—everything from jazz cruises to food tours and so much more. Explore them in our Viator Shop and make your own Crescent City magic.

Until next time, and don't forget your umbrellas!

– Tone & Jess
Umbrella Travels