Experience · Lexington-Fayette

Date Night Downtown Performance & Dinner

Begin your evening with a light appetizer and cocktail at a stylish downtown eatery before immersing yourselves in a captivating performance at the Otis A. Singletary Center for the Arts. Conclude your date with a refined Italian dinner, offering a perfect end to a cultural and romantic night out.

A 4.5-hour Lexington-Fayette evening plan for couples — Bourbon on Rye, Otis A. Singletary Center for the Arts, ItalX.

Duration: 4h 30m
Cost: $100–$250
Stops: 3 stops
Walking: Moderate walking · Total 1.4-mile driving route
Best time: 5:00 – 10:00 PM
Ideal for: Couples · Solo · Friends

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The plan

1Bourbon on Rye(45 min)→
2Otis A. Singletary Center for the Arts(2 hrs)→
3ItalX(1 hr 30 min)

Why this plan works

The 3 stops cover about 1.4 miles total, which keeps you in one pocket of Lexington-Fayette instead of crossing town between them. Otis A. Singletary Center for the Arts is the main event and takes the biggest block of time; the other stops are built around it. It finishes at ItalX — a short, low-effort stop you can skip if you're ready to call it. Best suited to couples, solo, and friends who want a planned Lexington-Fayette outing without improvising between stops.

The story

The itinerary

3 stops, one great day

1
45 min
Bourbon on Rye
Nightlife
Warm, mellow eatery serving pub grub classics & bites alongside craft cocktails, beers & wine.
What to do — Arrive for an early drink and a shared appetizer to kick off your evening. Review the evening's performance program.
0.7 mi · 14 min walk or 5 min drive
Then A short walk will take you to the arts center for the main event.
2
2 hrs
Otis A. Singletary Center for the Arts
Arts & Culture
Sizable theater at the University of Kentucky featuring plays, concerts & educational events.
What to do — Take your seats for an engaging live performance. Check their schedule in advance for specific showtimes and tickets.
Scout Side Quest
Before the show starts, each make one wildly specific prediction about the performance. See who comes closer.
0.7 mi · 14 min walk or 5 min drive
Then Head to ItalX for a sophisticated Italian dinner, just a short distance away.
3
Optional 1h 30m
ItalX
Food & Drink
Elevated contemporary Italian cuisine & a robust wine list served in an elegant restaurant.
What to do — Enjoy a post-show dinner with delicious Italian dishes and perhaps a glass of wine to discuss the performance.
Scout Side Quest
Deliver your official review of tonight's show over dinner, but you each only get three adjectives to do it.

Scout Stories

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The route

On the map

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Common questions

Planning this outing

Is this a good Lexington-Fayette itinerary for couples?: Yes. It's built for couples, solo, and friends and runs about 4 hr 30 min across 3 stops, starting at Bourbon on Rye.
How long does this outing take?: Plan on 4 hr 30 min door to door, including time between stops.
How much does this Lexington-Fayette itinerary cost?: Roughly $100–$250 per person, before parking and tips. Free and low-cost stops are marked on each card.
Is this itinerary walkable?: Yes — every hop is under a mile, about 1.4 miles of walking in total.
Do I need reservations?: No. Every stop on this plan takes walk-ins, though weekends move faster if you arrive early.

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