There’s always plenty of love in the air in Lexington, Kentucky. So if you’re looking for a Valentine’s Day (or any day) getaway to get those sparks flying, the Bluegrass has a host of things to do, see, and savor.
Wine & Dine
Pictured: Millstone
Lexington’s culinary scene is an always-evolving feast for the senses, and Valentine’s Day is the perfect time to indulge. The V at The Vine offers a thoughtfully curated multi-course dinner for an elevated night out, while Mileta's handmade pastas and craft cocktails set the tone for cozy romance. For a relaxed yet refined experience, Millstone pairs good conversations with unforgettable meals.
Keep the night going at Ona, a softly lit cocktail bar ideal for snuggling up with someone special for hours of conversation. Or take a short drive out of the city for a romantic evening at Talon Winery and Vineyards, where more than 20 award-winning wines and free live music every weekend make for a dreamy date night.
Pictured: The Kentucky Castle
Want to really feel like you're living in a fairytale? Make dinner reservations at the Kentucky Castle. Yes, it’s actually a castle. Yes, the food is amazing. And, yes, you have to see it to believe it.
Check out all of Lexington’s enticing bars and restaurants in our searchable Restaurant Guide.
A Little Horseplay
Pictured: Lane's End Farm Tour
Nothing evokes the romance of Kentucky like a drive through the picturesque Bluegrass hills of Lexington’s Horse Country.
From famous nurseries like Mill Ridge to breeding farms, racetracks, and feed mills, a Horse Country excursion will leave you entranced, alive with Bluegrass traditions and in the mood for love. Just be sure to schedule your visit in advance.
Couples (Retail) Therapy
Pictured: Relic in the Distillery District
Go the vintage route at The Domestic and Street Scene. Check out Relic in the Distillery District, or explore some of Lexington’s retail hotspots found in the Chevy Chase neighborhood.
Whether you’re just window shopping for the fun of it or searching for something special, our Lexington Districts and Neighborhood page will put you on the right track.
Our Sweeter Side
Pictured: Martine's Pastries
If you think your visit to Lexington can’t get any sweeter, think again. Treat your sugar to something sugary from the pastry case at Martine’s, sample an ice cream flight for two at Crank & Boom, or tour the candy kitchen at Old Kentucky Chocolates before taking home a box of your own.
We recommend anything with bourbon in it.
An Exhilarating Performance
Pictured: Live Music at Tee Dee's Lounge
Live music, theater, standup comedy—we’ve got it all. The beautiful and historic Lexington Opera House makes for an elegant date night, while Rupp Arena attracts some of entertainment’s biggest stars.
For a more intimate experience, try Tee Dees Lounge, The Burl in the Distillery District, and Comedy Off Broadway is the spot for laughs.
Can’t fit everything you want to do into one trip? Don’t worry. You can always come back for an encore.
Get a Room
Pictured: The Manchester Hotel
Lexington has hundreds of luxurious hotel rooms waiting to be enjoyed. Whatever your style or budget, we’ve got the perfect little love nest to match. As a matter of fact, our newest boutique hotel, The Manchester, is perfect for your dining and luxury stay needs.
Browse all of Lexington’s fine hotels below, find the best deals, and book the trip of your fantasies today.
