The Classic Italian Restaurant Frank Sinatra Always Dined At In His Hometown

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The impact Frank Sinatra has had on the music world can’t be replicated, and those who want to be closer to Ol’ Blue Eyes can do so by experiencing some of the establishments he frequented throughout his life. One of these is Leo’s Grandevous Italian restaurant in Sinatra’s hometown of Hoboken, New Jersey. Before Sinatra moved west, reached large-scale fame, and favored dining at a vintage Las Vegas steakhouse, the young lad and his bandmates would frequent Leo’s Grandevous after local gigs for a drink and a bite to eat. While Sinatra didn’t return for dining at Leo’s after his move west, the “My Way” singer is still honored in the establishment with dozens of his photographs adorning the walls. 

Leo’s has been in business since 1939, serving up delicious, authentic Italian food. In the 1930s, Leo DeTerlizzi purchased the bar he was working at and transformed it into a restaurant where his wife, Tessie, cooked. Now, the restaurant is still a family business, but operated by DeTerlizzi ‘s grandchildren, Grace and Nick Sciancalepore. Over the years, Leo’s has received some modernizations, like a replacement bar, but that’s to be expected for a business that’s been around for over 85 years. Even with updates, much of the charm and history is still seen and felt by regulars and the Hoboken community.

Connecting with Frank Sinatra in Hoboken

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It’s unclear what Frank Sinatra ordered from Leo’s Grandevous Italian restaurant, though much of the original recipes that Tessie curated decades ago remain untouched. This means that whatever you order, you may be enjoying the same dish Sinatra once did. If all else fails, you can always opt for ordering a martini made how Sinatra preferred them. Hopefully, Leo’s will be around for decades more thanks to more than just its celebrity history. The family atmosphere and deliciously well-made food keep the Italian dining spot a welcoming place to sit and enjoy a meal.

Visiting Leo’s is just one of the ways fans can catch a glimpse into the life of the Chairman of the Board on a visit to Hoboken, New Jersey. The city of Hoboken celebrates Sinatra’s legacy in a multitude of locations, and visitors (and locals) can embark on walking tours that include some of the singer’s old stomping grounds from before he was famous. Of course, if visiting Leo’s and Hoboken aren’t in the cards, you can always enjoy a meal that will make you feel closer to the singer by whipping up Sinatra’s surprisingly humble breakfast favorite, a classic egg sandwich.