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Frank Sinatra Walking Tour of Hoboken, New Jersey

The story of Frank Sinatra is a story of the 20th-century American dream.

The Hoboken Historical Museum has put together a 23-stop self-guided walking tour of sites significant to the life of the New Jersey city’s favorite son.  I recently followed the tour with the fabulous D.C. History and Culture group.

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As a Sinatra fan since college, I found the tour a great way to get a feel for the unique meld of style and grit that made Ol’ Blue Eyes the singular star he was.


Here are the tour’s top 10 spots to imagine yourself strolling through Hoboken with Frank Sinatra at your side:

Frank Sinatra’s Birthplace

Frank Sinatra was born in Hoboken on December 12, 1915, in what was called a “cold-water flat” — an apartment with no running hot water.

His father had immigrated from Sicily in 1903 and become a boxer.  His name was Saverio Antonino Martino Sinatra, but he boxed under the pseudonym Marty O’Brien, because of anti-Italian bigotry in the Irish-dominated sport.

In 1914, he eloped with Natalie Garaventa, called Dolly.  Her family didn’t approve, because he was illiterate and Sicilian.

Sixty years later, performing across the Hudson River at Madison Square Garden in 1974, Frank Sinatra said:

My country is personal to me because my father, who wasn’t born here, God rest his soul, he made sure that I was born here.  And he used to tell me when I was a kid that America was a land of dreams and a dream land.

The building at 415 Monroe Street burned in 1967, but a Hollywood-style star marks the place where Ol’ Blue Eyes was born.

St. Francis Church

Francis Albert Sinatra was baptized at this Church at 308 Jefferson Street on April 2, 1916.

St. Ann Church

Local legend claims that Frank Sinatra made his public singing debut at this Church at 704 Jefferson Street.  In 1984, he introduced President Ronald Reagan at the parish’s St. Ann’s Feast.

Firehouse Engine Co. No. 5

Dolly Sinatra became a power player in the Hoboken political scene.  After her husband broke his wrists boxing, she helped him secure a slot as a fireman.  He would rise to become a Captain at the firehouse at 412 Grand Street.  Today it’s an apartment building (with hot water).

Leo’s Grandevous

Frank Sinatra used to drop by this Italian restaurant at 200 Grand Street after a performance.  They still hold a spot for him at the bar, and keep his barstool on display above.  The walls are covered with Sinatra-bilia.

The restaurant also maintains an outdoor seating area marked by a Sinatra mural.

The staff were welcoming and enthusiastic and even gave our small group complimentary magnets.

2nd Sinatra Family Home

The Sinatras opened up a bar, and called it Marty O’Brien’s.  They began to make a comfortable living.  And they didn’t stay in the cold-water flat.  They moved to 703 Park Avenue, in a more prestigious area of Hoboken, in 1927, when Frank was 11.

3rd Sinatra Family Home

In 1932, when Frank was 16, the Sinatras moved a block closer to the waterfront to 841 Garden Street.

Dolly and Marty Sinatra Final Home

Frank Sinatra bought the imposing house at 909 Hudson Street for his parents.

Lepore’s Chocolates

Complimentary samples are available at the Sinatra family’s candy shop of choice at 105 4th Street.

Frank Sinatra Memorial Park

Frank Sinatra Memorial Park on Frank Sinatra Drive boasts a statue of the star and a view of New York, New York, across the Hudson River.

The tour is more than a walk around Hoboken through Frank Sinatra’s blue eyes.  It’s a journey through the American dream.  It’s a stroll through the story of a father who had to hide his name to support his family, and of a mother who saw something in him that her own parents didn’t, and of their son, who made that name one of the most loved and revered in American culture.

bonus:  Luca Brasi’s Italian Deli

Not a Sinatra haunt, but it’s worth mentioning this spot at 100 Park Avenue, which covers its walls with photographs of mobsters real and fictitious and offers “Sandwiches You Can’t Refuse!

What to Know before You Follow the Hoboken Historical Museum’s
Frank Sinatra Walking Tour

The self-guided Frank Sinatra Walking Tour begins at the star’s birthplace at 415 Monroe Street and ends at his statue in Frank Sinatra Memorial Park on Frank Sinatra Drive.  You can start or stop at any point and skip or linger at stops along the way.

Wear street clothes and comfortable shoes.

Allow one to two hours, depending on whether you want to stop for a drink at Leo’s Grandevous, a sample at Lepore’s Chocolates, or a sandwich you can’t refuse at Luca Brasi’s Italian Deli.


To book a room at the W Hoboken, click here.

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