Ask the team · Bywater, New Orleans
A guest story · September 2025
Our wedding weekend playbook.
How we used all three CastleDay villas — from a 45-person family dinner to a 150-person pool party.
Editor's note: Sam and Gigi rented all three CastleDay villas for their New Orleans wedding weekend in September 2025. We asked Sam to walk us through how they used the property — the events, the vendors, the small decisions that ended up mattering. What follows is his account, in his words.
We had our wedding weekend from Wednesday, September 17 through Sunday, September 21, 2025. The ceremony and reception themselves were held elsewhere in the city on Friday the 19th, but CastleDay was our base of operations for the rest of it — where everyone slept, where our families had dinner the night before the wedding, where we threw a pool party the day after, and where most of the in-between hours unfolded.
We rented all three villas (The Herald, The Cocodrie, and The Florentine) for the long weekend. It ended up being one of the most fun stretches of our lives, and our guests are still talking about it.
The weekend at a glance
Step 1
One villa per side of the family.
The single best logistical decision we made was giving each side of the family its own villa. Mine in one, Gigi's in another, our friends and overflow in the third.
The practical reason is capacity: one villa simply isn't enough to house both families comfortably. Spreading across three solves that, and once you do, you find it also solves a lot of softer problems you didn't know you had. Each side has its own kitchen, its own living room, its own pool. When the families wanted to be together, they walked next door. When they didn't, they had somewhere to go. If there's a single argument for renting all three villas at once, this is probably it.
Step 2
Let the families have their own night.
A number of relatives on both sides flew in a day or two before the wedding. Once my mom realized how many people would be in town early, she decided to organize a Thursday night family dinner. My family (her included) was staying at The Cocodrie, so it really felt like she was hosting everyone at her place — Gigi's family walked over from The Herald, where they were staying. She planned it a few weeks ahead, hired a private chef, and that was essentially the whole production: no rented tables, no rented chairs, no real decor. About 45 family members came.
Like all three villas, The Cocodrie's indoor dining area opens directly onto a covered outdoor patio through full sliders, so she opened them up and let the dinner spread across both spaces.
Gigi and I stopped by to say hello to both families, but we ducked out fairly early to meet our college friends at Parleaux, an outdoor brewery a few minutes away. That evening ended up being one of our favorites of the entire weekend — just the two of us with the people we don't see often enough.
None of that would have worked in a hotel-block-plus-restaurant arrangement. Because the dinner was at the villa and on our families' terms, our parents got to host their own night, the cousins got to catch up properly, and we got to slip away without being rude about it. This is one of the underrated benefits of renting all three villas: more than one thing can happen at once. Nobody is waiting on the bride and groom to make an entrance.
Step 3
A 150-person pool party.
Saturday afternoon, from two to six, we threw a pool party at The Florentine. There were about 150 people on property — our 65 overnight guests, plus friends and family staying at hotels nearby, plus locals joining for the day. Because the three villas sit next to each other and Ubers drop right at the gate, the logistics were close to nothing: no shuttle coordination, no hotel block to wrangle.
For setup, we rented a few circular tables and chairs from the local True Value and bought a couple of 10×10 tents from Walmart — the whole thing worked surprisingly well. A reasonable reminder that you don't need a full event-rental package to host 150 people.
The formal event wrapped at six and the vendors broke down, but a contingent of guests stayed on, and the party rolled organically into informal hangouts across all three villas.
How we ran it
Three small vendors instead of one large caterer. Southerns, a popular local food truck known for its award-winning fried chicken, served fried chicken sandwiches and hamburgers. Mr. Snowball Catering set up a tent outside with a full snowball cart. And because it was really hot, we had someone inside cutting fresh fruit for guests all afternoon. People grazed across all three. No seated meal, no buffet line, no formal service moment to schedule around.
One full open bar — beer, wine, cocktails — staffed by Movers and Shakers, a local woman-owned mobile bartending company that handles a lot of New Orleans weddings.
We ran our own playlist through two large Bluetooth speakers linked together — plenty loud for 150 people. Then, halfway through, Big Fun Brass Band marched in and played a one-hour set. It became the moment of the day. When they finished, the playlist picked back up as if nothing had happened.
Cornhole on the lawn, plus two cold plunge tubs we bought just for the party. The cold plunges were the sleeper hit of the weekend — guests kept circling back to them all afternoon.
Pool floats and a few props. No florals. The Florentine's own design carries most of the weight.
We rented portapotties as a precaution. A few guys used them, but they were barely touched — the villa's bathrooms handled 150 people without issue.
All in, the whole event came to a little under $11,000. Roughly: food (the truck, snowballs, and fruit station) was about $4,500. Bartenders, including mixers, were about $2,000. Big Fun Brass Band was another $2,000. And everything else — furniture rentals, cold plunges, alcohol, ice — was another $2,000 or so. For 150 people, that comes to under $75 a head, dramatically less than a traditional wedding caterer’s plated dinner would have run us.
Step 4
Stack the day.
Gigi's family organized a swamp tour for the out-of-town guests on Saturday morning, before the pool party. On paper that should have been logistically tight — a swamp tour ending around one, a pool party starting at two. But the tour dropped people back at their own villa, which is of course next door to The Florentine, so guests could walk inside, change, and stroll over to the pool party with time to spare.
That ease is the underrated thing about hosting events on-site. When the day's next event is a hundred feet away, you can program more into a single day without anyone feeling rushed. A swamp tour and a pool party on the same Saturday is unthinkable if your base is a hotel downtown. From CastleDay, it's just two things in a row.
If you have out-of-town guests, organizing one local activity — swamp tour, food tour, cemetery tour; the specifics matter less than you'd think — is worth the small effort.
Don't overlook the time in between.
Some of my favorite moments of the weekend weren't on the calendar at all. Each family had its own slow mornings on its own patio. Kids were in the pools by nine. Afternoons between events meant naps, swims, and wandering between the houses. Late nights after going out, we ended up back at the villas rather than paying for an after-party somewhere else.
Because everyone was within a block of each other, the weekend never lost momentum. No one disappeared back to a hotel at ten and stayed gone. Something was always happening at one of the three villas.
Why this setup worked.
Privacy
No strangers in shared hallways. No noise complaints from the neighbors. Just our people.
Three pools, three outdoor spaces
One villa served as the party hub, but having three full compounds meant nobody felt crowded.
Everyone in one spot
Family and friends within a block of each other. No shuttles, no group texts about where to meet.
No venue rentals for events
The 45-person family dinner and the 150-person pool party both happened on property. Two events, zero venue fees.
Cost
Once you add up 65 hotel rooms for four nights plus venue rentals for two events, the comparison stops being close.
Planning a wedding weekend of your own? Ask the team — we've hosted this weekend before.
Your turn
Put the whole guest list on one block.
Each villa sleeps up to 30. Book one, two, or all three — the way Sam and Gigi did.
Check availabilityMore on wedding weekends →Ask the team · 1319 Japonica Street · Bywater · New Orleans