Explore Old Louisville with a writer

Explore historic Old Louisville with an immersive walking tour with a local writer

Join the most popular Airbnb Experience in Louisville a walking tour of intriguing Old Louisville. Explore the Olmsted-designed Central Park and fairytale Saint James Court then discover one of historic Old Louisville’s secret terraces – all with big, exuberantly loving dog Cassius Thunderpaws (and his person) in a very small group.  Featured in Style Blueprint Nashville!

We’ll be in a historic, and overlooked but up-and-coming neighborhood – my home! Cash & I stroll the park, the mansion-lined streets, and the hidden courtyards and green spaces of Old Louisville daily and love to share its secrets with visitors.

You might never notice Floral Terrace or the Witch’s Tree if you drove past. I’ll share insights as a local resident and writer about our neighborhood’s history, challenges, and potential. Also, there will be doughnuts!

Old Lou high/low burger+bourbon crawl

Historic Old Louisville is an enigma. Victorian mansions are interspersed with gritty corners and people love it – or avoid it. Without investment from big national brands, local old school places have thrived, and we’ll visit three such gems. Ollie’s Trolley is a cult favorite, carry-out diner; Dizzy Whizz is a greasy spoon open since 1947; and Buck’s is a faded movie star version of a fine dining restaurant (we’re just there for the bar).

Featured in Louisville Courier Journal!

We’ll start with one of Louisville’s best kept secrets, the zesty, spiced Ollieburger. Here at Ollie’s Trolley you’ll learn the secret history of the tiny diner that could’ve been the next KFC but is now one of only three Ollies left in the country. You’ll see why crowds from all walks of life line up for their greasy bags of goodness. Ollieburger + fries are included in the experience. Next up we’ll hit a classic example of Americana, Old Louisville’s beloved Dizzy Whizz. Here at this family-owned old school drive-up/eat-in diner you’ll pick a treat from the old fashioned dairy bar, on me. Then we’ll take a short walk through a corner of this historic preservation district with a Cliff’s Notes history of its fascinating past and its current challenges and potential.