Kentucky is known for its rural charm and big city lights, as well as a combination of favorite things: bourbon, horse racing, and great Southern food. If you stay at a Kentucky vacation rental near the Daniel Boone National Forest, your Valentine’s Day can include hand-in-hand hikes and horseback rides through the countryside. Head to Louisville and enjoy a variety of activities, as well as awesome Southern food restaurants and plenty of shopping. Take a look at the top places to stay in Kentucky for Valentine’s Day.

natural bridge kentucky
Source: Flickr/Kentucky Photo File

1. Louisville

Louisville might not be the obvious choice for lovers, but it has a surprisingly wide variety of Valentine’s Day activities from balloon rides to river cruises. If you want to go traditional – dinner, chocolate, and a show – begin at LouVino, a restaurant that does fine wine and a four-course meal, or the Portage House. The latter offers a Valentine’s Day special with diver scallops and Southern-style food: pulled pork and grits. Opt for something more light-hearted at Wick’s Pizza. The heart-shaped pizza and made to order toppings makes both the heart and the stomach smile. Up the romance factor, and check an item off your bucket list, with a hot-air balloon ride at twilight via SkyCab Ballon, Balloon Odyssey, or Aero Force Balloon. If being high in the sky doesn’t appeal to you, try a moonlight cruise on the River Queen or take a carriage ride down historic Louisville; just don’t forget a cozy blanket and thermos of coffee. Love is about family, too, so take your significant other and kids out to the Louisville Zoo.

Find vacation rentals in Louisville

2. Frankfort

Halfway between the two biggest cities of the state, the capital of Kentucky, Frankfort has offerings of its own such as the Woodford Reserve Distillery. Take a lantern tour to set the mood, and then enjoy good bourbon, food, and dessert. The Buffalo Trace Distillery features as annual Buffalo Love event with a bourbon tasting. Tour the distillery, start with cocktails, and then finish with a six-course meal. As long as you’re in a loving mood, try Aphrodite’s Delight at the Wallace Station Deli. This meal begins with a salad topped with strawberry’s, pomegranate seeds, avocados, and goat cheese, and it culminates with chicken in honey chili glaze. Alternatively, Hudson Hollow boasts as special Valentine’s Day menu topped off with chocolate-dipped strawberries and red velvet cake.

Find vacation rentals near Frankfort

3. Lexington

Start your Valentine’s Day celebration early in Lexington at the Joseph-Beth Booksellers. The entire family is invited to a special breakfast with every kid’s favorite big red dog: Clifford. Drop off the kids at your vacation rental, and continue on to Good Foods Co-op chocolate sampling. Think chocolate-dipped bacon, Kentucky Proud Bourbon Chocolatier Sauce, and organic vanilla ice cream. There’s also the Equus Run Vineyard’s Kisses & Calories chocolate festival if you haven’t gotten enough of the good stuff yet. Stop at Holly Hill Inn for a seven-course meal or Winchell’s Restaurant for a plethora of seafood topped off with tiramisu.

Find vacation rentals in Lexington

Find the perfect Kentucky vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

4. Owensboro

Owensboro doesn’t do boring, so you and your valentine have a choice of many interesting dates from a St. Valentine’s Candelite Dinner at the Western Kentucky Botanical Garden to a murder mystery dinner. At the St. Valentine’s Candelite Dinner, stroll hand-in-hand through the orchids, and then enjoy drinks and dinner. Add a little mystery to your night with the “Til Death Do Us Part” dinner performance with a dance party following it. Work off those calories with ice skating at the Edge Ice Arena for the annual SweetHeart Skate event.

Find vacation rentals in Owensboro

5. Bowling Green

If you want to know where to go in Bowling Green for Valentine’s Day, head to the restaurants. Reserve your spot early at one of these top restaurants: 643 Sports Bar, Home Cafe and Market Place, and White Castle. Get your southern on at the Home Cafe and Market Place that specializes in Southern homestyle food – five courses of it – for Valentine’s Day. Opt for something more casual at 643 Sports Bar that offers good food and a comedy show or live music while you eat.

Find vacation rentals in Bowling Green

6. Elizabethtown

Celebrate your time together – whether it’s been months or years – with a tandem skydiving. This event by Skydive Kentucky has a special Valentine’s Day offer. After your adrenaline rush, head over to the Saber and Quill for a Valentine’s Day dinner and dance. It offers a buffet dinner, dessert station, live music, and all the dancing your feet can handle.

Find vacation rentals in Elizabethtown

7. Huntington

Huntington might be one of the smaller towns of the group, but it has plenty of options such as live music from the Keith-Albee Performing Arts Center. The center has a history of pairing lovers with sultry music, so check our its listings. Skip dinner and go right to dessert at Friends of the Market’s ice cream tasting. There’s dark, dark chocolate, salty caramel, and other succulent flavors. Finish with a moonlit walk through Blackwater Falls State Park along the luminary-lit paths.

Find vacation rentals near Huntington

 
Ready to go?  Check out these amazing Kentucky vacation rentals on Tripping.com.