New Orleans – A Tale of Two Trips

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I have mentioned before that Brooke and I have different perspectives on travel.  These differences can be seen quite clearly in our recent three-day weekend to New Orleans. We both had a great time but experienced two very different sides of the Big Easy.  Brooke’s trip was meticulously planned and involved nice hotels, plantation tours, and fancy restaurants. My trip was completely unplanned, booked at the last minute, included an AirBNB, and plenty of random adventures.

We decided to visit New Orleans when Brooke planned a ladies weekend for her sisters and mom.  I opted to tag along at the last minute, because we have the Southwest Companion Pass, and I simply couldn’t let a free ticket go to waste.  We managed to keep the entire trip cost under $100 (excluding food and entertainment).  Enjoy this tale of two trips told from our own point of view…


Brooke’s Trip

Jesse’s Trip

Total Trip Cost Breakdown

Brooke’s Trip


We rented a car for the first day to drive to two different plantations.  We had a great rental car experience with Alamo. We got to choose our car, which ended up being an awesome Dodge Charger.  Rental and return process were extremely smooth and painless.  If parking in the French Quarter had not been $42/night at the hotel (MORE than the actual rental car price), we would have loved to have had the car for the entire weekend.


  • Fairfield Inn & Suites New Orleans Airport, 1 night – $0 (15,000 Marriott Points)
  • Hyatt French Quarter, 2 nights – $0 (12,000 Hyatt Points + 18,000 Chase UR Points)

We were very impressed with the Hyatt French Quarter.  Every staff member was so welcoming and helpful.  With the hotel being surrounded by Canal, Bourbon, and Iberville Streets, the location cannot be beat.  We walked pretty much everywhere, though the streetcar would have been another close/cheap ($3 unlimited day pass) option to see other areas of the city.  The overall swanky vibe of the hotel and rooms was the best part.  We had a spacious double queen room that included an extra little vanity area, in addition to the bathroom (which you need when you are sharing it among four women!)  Our room overlooked the pool courtyard, which could get a little noisy during the day.  This was not a big deal, as the pool closed at 10PM and was quiet well before we were ready for bed.


What We Did

Plantation tours in New Orleans were on my bucket list. We toured two different plantations on our first day in NOLA: Evergreen and Destrahan.  The tours cost about $20 each and were incredibly interesting.  Evergreen was about 35 minutes from the airport area and was the filming locations for “Django Unchained.”  This plantation uniquely has the home, outbuildings, and 22 slave cabins still standing.  Our 1.5-hour tour only had 12 people, so it was very interactive.

Destrahan was a much smaller grounds area, but we were more impressed with the inside of the house and the costumed tour guides.  This plantation has been used to film movies such as “12 Years A Slave” and “Interview With A Vampire.”  Tour size was comparable to that of the first tour and lasted about an hour.  Both tour guides were natives of the area, so they were overflowing with historical knowledge of the plantations and New Orleans itself.

The second day of our trip included two different tours by Free Tours by Foot.  We booked the Garden District and French Quarter Ghost Tours a couple weeks in advance.  This company uses the unique “pay what you think it’s worth” method.  Booking is free, then at the end of the tour, we decided how much we wanted to pay our guide.  We were lucky enough to get Andrew as our tour guide on both tours (he was AWESOME!)

The 10:30AM Garden District Tour was fantastic (even though it was 100+ degrees)!  We started in Lafayette Cemetery and learned about the unique/shocking burial process in New Orleans.  We then walked through the beautiful Garden District, where we saw the homes of Sandra Bullock, Archie Manning, John Goodman, and Nicholas Cage.

The 7:30PM French Quarter Ghost Tour led us to different spots around the French Quarter, where Andrew told us about history, folklore, and modern ghost stories.  Both tours were a great mix of stories teaching us about New Orleans history, in addition to stories about modern New Orleans.

We used the last day of our trip to go shopping at the Riverwalk Outlets and within the French Quarter…little boutiques and antique shops.  We also stopped back by Jackson Square for pictures and to marvel at the beautiful inside of Saint Louis Cathedral – another free activity within the French Quarter!

Where We Ate

After the plantation tours, Jesse picked us up at the rental car facility and chauffeured us to our hotel in downtown NOLA.  From here, we had our first encounter with Bourbon Street!  Heidi (sister) had previously visited the area, and recommended we try Pat O’Brien’s for dinner and drinks.  Dinner was fantastic – I had the Shrimp Creole.  This is also home to the Hurricane drink, which I had to try for myself.  After dinner, we went into the piano bar section of Pat O’Brien’s, where we spent the rest of the evening being entertained by both the musicians and our new friends (shout out to Ryan and Danielle!)  It was such a fun evening!  At the end of the night, the walk down Bourbon Street was… interesting…to say the least.

Beignets were on our must-try list.  We visited both Café Beignet and Café du Monde in the same day. I think we all agreed that Café du Monde was our favorite.  So much powdered-sugar goodness in one day!

Notable Dishes

  • Shrimp Creole at Pat O’Brien’s
  • Egg Cochon at The Ruby Slipper Café
  • Seafood Platter at The Bourbon House
  • Fried Shrimp Poboy at Port Side Restaurant
  • Beignets at Café du Monde and Café Beignet
  • Shrimp Roumalade Salad at Ignatius (Magazine Street)
  • Jasmine Iced Tea at Addiction Coffee House
  • Pralines and Key Lime Pecans at Leah’s Pralines

Overall, we planned this trip over the course of a few weeks. This ensured all four of us ladies got to see and do what was most important to us during a short trip. We set up an itinerary, but allowed flexibility in our plans. We definitely felt that after three full days, we had gotten a good taste of New Orleans!  Here is our full 3-day itinerary:

Day 1:

  • Rented Car
  • Evergreen Plantation
  • Destrahan Plantation
  • Lunch at Port Side Restaurant
  • Checked into hotel in French Quarter
  • Bourbon Street
  • Dinner and Piano Bar at Pat O’Brien’s

Day 2:

  • Café Beignet
  • Street Car to Garden District
  • Free Tours by Foot – Garden District Tour
  • Magazine Street
  • Lunch at Ignatius
  • Back to French Quarter
  • Addiction Coffee House
  • Dinner at The Bourbon House
  • Free Tours by Foot – French Quarter Ghost Tour
  • Café du Monde

Day 3

  • Brunch at The Ruby Slipper Café
  • Browse shops on Canal Street
  • Riverwalk Outlets
  • Jackson Square
  • Saint Louis Cathedral
  • Browse shops on Royal Street
  • Late lunch at Hard Rock Café on Bourbon Street
  • Drove through the 9th Ward to see the Hurricane Katrina damage/rebuilding efforts before heading to airport

Jesse’s Trip


This option was much less expensive than multiple Uber/Taxi rides. Also, I chauffeured the ladies from the airport to their French Quarter hotel after they returned their rental car.


  • AirBNB, 2 nights- $0 ($49, redeemed 4,900 Barclay Arrival Plus Miles)

This was my first experience with AirBNB. Since I was planning not to interfere with the ladies’ trip, I would be traveling solo. I looked for a shared room, so I could hopefully meet fellow travelers and join them on adventures. I found a listing that looked promising: 8 minute walk to Bourbon Street, two shared rooms with bunk beds. The pictures made the property look clean and bright. Man, was I tricked…

I arrived late on Friday evening to a locked door on an old house in a shady part of town. I knocked and called the host for 20 minutes with no success. She finally called me back, but had “completely forgotten” about my reservation. I found out that I was her final guest, because she had “stopped paying rent and was supposed to vacate the property yesterday!” The place was a complete dump with disheveled bunk beds and one tiny A/C unit for the entire house. (New Orleans is HOT in August!) I ended up sleeping with a fan pointed at my face to keep from sweating too much.

The bathroom was also a complete mess. Plumbing issues prevented the toilet from flushing correctly, and the “shower” was simply an old bathtub with a hand-shower tethered to a faucet! I tried to tough it out, but after two nights, I’d had enough. The final straw was jolting awake around 5AM to angry shouting on the street outside my bedroom window. I contacted AirBNB and received a full refund for this mess.

  • Hilton River Walk – $0 (36,114 HHonors Points)

After the AirBNB experience, I badly wanted a nice bed and a warm shower. I browsed all hotel listings near the French Quarter and found a reduced point rate at the Hilton River Walk. I booked a King Bed room and was upgraded at check in to an executive level city/river view room. The view was fantastic, but I mostly enjoyed NOT being in that terrible house!

While I solved the lodging issue, I still had to deal with parking fees. The Hilton charges $38/night for self-parking, which is absolute robbery!  Street parking can be a big risk overnight, and most public garages nearby were $30 or more.  Tripadvisor pointed me to the Harrah’s Casino parking garage.  The normal fee of $30/day is waived if you log 30 minutes of play in the casino, including the penny slots! So, for FREE PARKING, you only need to sit at a slot machine for 30 minutes playing 1 penny at a time while sipping your FREE DRINKS!


Despite my lodging woes, the trip was absolutely fantastic! I met some really great people, ate delicious food, and had some random adventures.  Since I made absolutely no plans in advance, I relied heavily on Yelp recommendations and suggestions from people I met along the way.

Café Amelie

I arrived for brunch on Saturday at opening time to find a line. We entered into a tree-covered courtyard, and I opted to sit in the air conditioning at the bar. My shrimp & grits were phenomenal, and the bartender, Aaron, whipped up an awesome bourbon & rhubarb cocktail! Aaron also provided a list of activities, restaurants, and bars, which proved to be great suggestions.

Satchmo Summerfest

IMG_7777New Orleans is well known as a hub for great jazz music. Satchmo Summerfest brings talented jazz bands, food trucks, and craft beer together on the edge of the French Quarter. There were two performance stages, and bands rotated every hour. I sat under a shaded tent, sipped an Abita IPA, and enjoyed the smooth tunes.

Café du Monde

No trip to Nawluns is complete without a trip to the world-famous Café du Monde for beignets and café au lait! I arrived to the café to find a long line for patio seating. I opted to walk to the smaller indoor seating area and wait for a table to open. I ended up chatting in line with some ladies from the Golden Age Club, Biloxi, MS. We agreed to sit together if a table opened up, so we could all get into the A/C and enjoy our beignets. Two of the ladies were sisters who grew up in New Orleans. They told me stories of when the coffee and pastries cost only 25 cents! ($2.42/ea today!) I made a total mess with the powdered sugar, but the beignets were delicious!

Cochon Butcher

This butcher shop in the warehouse district was a very nice surprise.  Some locals recommended it, so I popped in for a buckboard bacon melt.  This sandwich includes bacon (butchered & cured on site), cheese, and homemade collard greens!  Incredible!  I loved the sandwich and local IPA so much that I came back to try the Gambino sandwich… also delicious.  Say hi to Chris, the bartender, if you stop in.  He knows the city very well!

While at the Cochon Butcher, I met a wonderful Australian couple (Hey Paul & Kate!!) on a trip around the world!  They had amazing stories – visiting Cuba, camping in Antarctica, etc.  After sharing one of their native cocktails, I convinced them to join me for a beer flight at NOLA Brewing.

NOLA Brewing

The brewery is set right along the river with a great deck.  You can sit up top and sip your beer while watching riverboats and barges float by.  We hung out in the tasting room and enjoyed a few beer flights.  Our favorites were the Buffalo Stout (Bourbon Barrel Aged), Girl Scout Cookie, Pineapple Habanero IPA, and the Lowline Sour.  Overall, the selection was huge, with 22 beers on tap!  Highly recommended.

White Linen Art Walk

Returning to the city, we stumbled onto a street festival.  Everyone was wearing white clothing, and milling through art galleries.  We grabbed some free drinks and joined the adventure.  In general, art is mostly lost on me… particularly when the “art” is a $12,000 charcoal drawing of a toilet & $4,000 toilet paper!

Hurricanes and Pizza

Who needs some AC??
Who needs some AC??

We grabbed a couple hurricanes to go, because you have to drink at least one hurricane while in New Orleans.  Then we walked to Wood Pizza Bistro & Taphouse for a late night snack.  We sat at the pizza bar and chatted with Simeon, the head chef.  They definitely make a great pie here, and the tap list is impressive.  Also, if you sit at the end of the pizza bar, you get to control the AC vents in the restaurant.  I enjoyed pointing them at random people to see if they noticed… yeah, this was post-hurricane!

Killer PoBoys

The next day for lunch, I visited Killer PoBoys, a random sandwich shop in the back of an old bar.  They offer eclectic poboy sandwiches, including the Glazed Pork Belly Poboy with rum & ginger cane syrup, lime slaw, and garlic aioli.  Sweet, savory, tender meat with tangy slaw and chewy, crisp bread… mmm mmm good!

Addiction Coffeehouse

IMG_7846A nice cold coffee is the perfect cure for a hot day!  I popped into the relatively new Addiction Coffeehouse to try their now-famous Mrs. Tracy’s Addiction.  This drink blends cold-brewed New Orleans-style coffee (coffee + chicory) with honey, thai coconut milk, and a dusting of cayenne pepper.  Drink it hot, or pour it over ice, and enjoy!

Avenue Pub

This dive bar on the outskirts of downtown would be easily missed, if not for the frequent recommendations from locals.  I am definitely glad that I listened.  The bar features 45 beer taps crammed onto a tiny wall, with beers from all over the world.  They also have a very impressive whiskey/bourbon list.  I sat at the bar and sipped some Flemish sour beers and heavy Russian imperial stouts and chatted with the (very drunk) bartender.

I also met the legendary “Captain Dave” at the bar.  He was already hammered and asked the bartender for three glasses of their best whiskey.  She returned with three $58 glasses of 23-yr Pappy van Winkle!  Captain Dave casually slid a glass to me and the gentleman sitting on his left.  He slurred something that sounded like, “a good captain never drinks alone.”  While we enjoyed our drinks, he regaled us with tales of his time as a “quarterback for LSU” and the “three times he played Augusta National golf course.”  Thanks for the drink and the laughs, Captain Dave!

French Quarter/Cathedral/Ragtime Jazz

Most of the other time during my trip was spent roaming around the French Quarter.  I popped in and out of random shops, walked by the river, marveled at the cathedral in Jackson Square, and enjoyed some street music.  The ragtime jazz band outside of Jackson Square was particularly fun, as random people would wander up with brass instruments and join the jam!


Overall, I had a great time exploring New Orleans with no real plan or agenda.  This allowed me to meet some great people and share adventures with them.  I love new experiences, but I especially enjoy hearing people’s stories.  Their stories inspire me to continue to travel and see the world.  If I had a strict schedule to adhere to, I would likely have skipped right past some of the experiences or people who made my trip special.

So, what do you think?  Which sort of trip would you prefer – the well-planned luxury trip, or the free-wheeling adventure?  Tell us in the comments!

Item Points/Miles/Loophole Actual Cost
Roundtrip Airfare x 2 from MCI to MSY 18,317 Southwest Miles from the Chase SW Premier Card & Companion Pass (fees covered by gift cards from Amex Platinum $200 Airline Credit) $0
Fairfield Inn & Suites – 1 night 15,000 Marriott Points $0
Hyatt French Quarter – 2 nights 12,000 Hyatt Points + 18,000 Chase Ultimate Rewards Points $0
AirBNB – 2 nights 4,900 Barclay Arrival Plus Miles for $49 statement credit $0
Hilton River Walk – 1 night 36,114 Hilton Honors Points $0
Brooke’s Rental Car – 1 day $32, with free insurance from the Chase Sapphire Card $32
Jesse’s Rental Car – 3 days $22/day, with free insurance from the Chase Sapphire Card $66
French Quarter Parking Overnight Free with 30 minutes of play at Harrah’s (including penny slots & free drinks) $0

7 thoughts on “New Orleans – A Tale of Two Trips

  1. This post was very timely… I will be traveling to New Orleans next month with my girlfriend and two other friends.

    I am a mixture of the luxury and free-wheeling adventure. We’re staying 4 nights at the Hyatt French Quarter (thanks for the tip on free parking!), but other than that do not have any solid plans. We know we want to go to Cafe du Monde, drink some Hurricanes, and a couple of the other usual New Orleans must-dos, but other than that we’re leaving it open for adventure.


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