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Louisville, KY - Churchill Downs & Bourbon Trail

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I’m trying to plan an anniversary trip for my boyfriend and I to Louisville, KY either in early May or early June and need thoughts on itinerary. We’re both in late 30’s (but don’t feel like it!). Would love some thoughts & suggestions on my itinerary. Food wise I’m open to anything but he likes “regular” food, so no 610 Magnolia, etc. I’m afraid. Would love to try some regional food (hot brown is on the list of course), as well.

So far thinking:
Thursday – drive in. Should arrive 5:00 or 6:00, staying at Brown Hotel. Ideas for early afternoon or evening activity? Dinner?

Friday: Breakfast?
Churchill downs for racing (anyone know when tickets go on sale?) Where should we sit? Would like private seats or box, is that possible?
Dinner:

Saturday: Want to do some of the Bourbon Trail. For sure want to visit Makers and Old Rip Van Winkle, but totally open to suggestions on the others. I really do not want to do a group tour, but I’m worried it’s going to be too far to drive in one day? Should we plan on spending Saturday night in Bardstown (not loving that idea but I’ll do it)? I’m not opposed to hiring a driver, I’m just worried we’ll spend so much time driving and not hit many distilleries. Is it like wine tasting where you can get pretty buzzed, or are they spaced out enough one of us where only one of us could do the tasting so we could still drive?

Thank you in advance!

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