Ask the team · Bywater, New Orleans
A guest story · April 2025
A triple birthday at The Herald.
How 20 friends used one CastleDay villa for three milestone birthdays.
Editor's note: Liz, Karen, and Jesse celebrated their milestone birthdays together at CastleDay in April 2025 — two of them turning 28, one turning 34. We asked Liz to walk us through how the weekend came together: the activities, the small touches, and the one big party-bus night everyone is still talking about. What follows is her account, in her words.
Three of us had milestone birthdays in the same stretch of April. Two of us turning 28 and me turning 34. We wanted to do it together rather than three separate parties, so we booked The Herald at CastleDay for the weekend and brought 20 of our closest friends in with us.
Here's how we used the space, and what we'd steal again next time.
The weekend at a glance
Step 1
One villa for the whole friend group.
We booked The Herald for the whole group. Twenty of us in one villa for the weekend. The point of a milestone birthday trip is being together, and renting one villa meant nobody had to split off into separate Airbnbs or coordinate breakfast across town. We were all in the same house, the same kitchen, the same pool, the whole weekend.
For a group this size, one villa is the move. The Herald has enough beds, enough common space, and enough outdoor area that 20 people coexist without it ever feeling crowded.
Step 2
Cook everything yourselves.
We cooked every meal of the weekend ourselves and it was honestly the easiest part of the whole thing. The Herald's kitchen has two of every major appliance, plus enough counter space that multiple people could be cooking at once without getting in each other's way. Breakfasts, lunches, dinners, all home-cooked, all doable.
Mornings were the best of it. Someone was on eggs, someone laid out a fruit spread, someone made coffee. By the time the late risers came down, there was a full breakfast already going. Every meal of the weekend ran like that. Total group effort.
We saved a lot of money skipping restaurants for 20 people, and the cooking became part of the hang. People helped, people grazed, people stayed at the kitchen island catching up.
Step 3
A party bus to the monster truck rally.
The headline night of the trip was a party bus to a monster truck rally. We booked through We Live Bus Charters. They picked us up at the villa, ran us to the show, and got us home safely after. It was the highlight of the weekend, and probably the unexpected fan favorite.
Including a monster truck rally as your birthday activity is the kind of thing that sounds chaotic on paper and ends up being unforgettable on the night. Same with the party bus. Instead of coordinating who's driving and parking and being responsible, you all pile in together, you all get there together, you all get home together.
Step 4
Small touches that made it feel like a birthday.
A weekend trip can blur into "just a group hangout" if you don't build in moments that actually mark the birthdays. We did a few small things that did the work:
A few of our friends took it upon themselves to decorate the entire villa for the weekend. Walking into a fully decked-out house set the tone for everything that came after.
We got matching shirts for the birthday girls, which were so fun to show off.
Our friend Lizzie brought her jewelry case over and let each of the three birthday celebrants pick a piece from it. Three of us, three pieces, very meaningful, zero pressure to shop in advance.
The Herald has a pool and a basketball setup, so afternoons were spent just playing around in the private resort-like yard outside.
The best part.
Honestly, the in-between time at The Herald was as good as the planned events. One morning we did a group yoga session on the patio. Afternoons were pool, basketball, and music straight from the TVs in the courtyard. We didn't even need to bring speakers. Evenings rolled into cooking, eating, and hanging in the living room before heading out (or staying in).
When you've got 20 friends in one house for the weekend, the house itself does most of the work. You don't need to overprogram it.
Planning a milestone birthday of your own? Ask the team — we'll point you at the right villa and the right vendors.
Your turn
Throw the one they'll never top.
Each villa sleeps up to 30 — one house, one kitchen, one pool, the whole krewe.
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