Lots of Love in Lexington – A Valentine’s Day Itinerary

Spend Valentine’s Day in Lexington! Skip the bourbon and horses, and go for the romance.

Sipping Chocolates at Chocolate Holler, Lexington, Kentucky
Sipping Chocolates at Chocolate Holler


What is more romantic than a couples massage? Massages at The Massage Center are the perfect way to relax together and kick off a date with your special someone. Luckily, one of our favorite coffee shops in Lexington is in the same building. So after you are nice and refreshed from your massage, get a beverage from Old School Coffee. They always have creative seasonal drinks, and Valentine’s Day is no exception. 

With your cups of love, make your way to the University of Kentucky’s Arboretum where you can take a walk or find a bench to profess your love for each other on. 

After you have worked up an appetite, we suggest Joe Bologna’s for dinner. Here you will get extremely fresh Italian food served to you inside what used to be a church. Much of the original elements of the church have remained, including the stained glass. Maybe order spaghetti and reenact the iconic Lady and the Tramp scene?

For dessert, head to the Distillery District where you will find Crank & Boom ice cream. You could attempt to romantically feed each other the Gooey Butter Cake, but if that isn’t your style you can just sit and enjoy the ice cream of your choice while chatting. But seriously, the Gooey Butter Cake is so good. There are plenty of things to do in the Distillery District so this is a great place to be in case you don’t want the night to end and choose to continue your date. 

The Manchester Hotel, Lexington, Kentucky
The Manchester

If you are looking for somewhere to stay the night, we recommend The Manchester and the 21c Museum Hotel. They each have a restaurant and bar on-site as well.


If you are more interested in creating your own date itinerary, here are a few more places that we love in Lexington:

Happy Romancing!