Kentucky Derby

On my bucket list!

As said above, don’t do infield if you can swing that. I still think you can/would have a blast, but assuming you are ~33ish with the 1989 username, I’d try and go the non-infield ticket route. Infield is more debauchery geared towards younger adults/college IMO

I’ve never been to Friday Kentucky Oaks but know many people who have and they have all said it’s a blast. Everyone wears pink for breast cancer awareness and the fillies race. I’m hoping to attend next year

Actual Derby race, break out your best fun suit and bring cash ha. Covered seating is great but if it’s a good day weather wise, uncovered is great too, maybe better depending on your ticket site line

The Seelbach downtown is an old school hotel with cool history and great location. The Omni is a similar location but really nice with a cool bar/bowling alley

Jeff Ruby’s is amazing but I’d imagine that week/weekend booked up already. I also really enjoy Pat’s steakhouse. Old school vibe place

You can do the bourbon trail closer towards Lexington, KY and even some distilleries closer in Louisville

I’m not a veteran by any means but happy to try and answer/comment on anything else you might have. Regardless, it’s an awesome experience and y’all will have a blast

I’ve only done the infield (probably 20 years ago). Had a blast. That was more of a Mardi Gras vibe

Been a few times and have only done the infield. Only worth doing if you know what you're in for, which is getting sloshed with thousands of idiots + inevitably leaving soaked by alcohol and rain.

My friends and I have never really done any Derby events (i.e. Oaks). Usually just head to Bardstown on Friday and bar hop then get to Churchill ~9am on Saturday.

Might be too late but see if Jack Frye’s has any dinner reservations available. Great restaurant awesome atmosphere especially during the derby.

There are a ton of things to do in Louisville. Sadly, I think you are probably late to the game at this point. Bourbon tours, restaurants, hotels are mostly booked by now

look into the Kentucky Derby Experience. It is kind of an all inclusive deal. Free food and drinks and good tickets.
The Oaks is great and be sure the wife has a hat.
Hot upper crust babes everywhere, and of course they have a few that look like hookers.

I've done Derby and Preakness a bunch of times. I've only done the infield but it was a large group of baws in their 20's and 30's. Completely different agenda than a married couple. I agree with the sentiments that Oak Race is an underrated event. Completely worth doing. I also find that first weekend in May can have some really crappy weather. Either too cold or too hot, or just too wet.