top of page
Swing Street New York City
RetroMan Tours logo

Our Tours

Sinatra performing venues New York City
Chrysler Building 42nd Street New York City

Classic Nightclubs & Speakeasies Walking Tour

Sinatra's New York

The Avenue I'm Taking You To - 42nd Street

Step into the glamour of old New York on a walking tour that celebrates the city's golden age of nightclubs, jazz, saloons and cocktails - from the swanky exclusive nightspots to the jazz halls that launched the careers of legends. 

Take a walk through Frank Sinatra's New York - the city that helped shape his legendary career.  From his earliest performances, to swinging the nights away at the city's storied performance venues, to the classic haunts where he would unwind into the wee small hours of the morning.  Trace the steps of Ol' Blue Eyes and where he left his mark on the town that he never stopped singing about.

On this tour we cross the heart of Manhattan on one of its most storied streets. From iconic buildings to tales of urban decay and revitalization, this tour captures the energy, history and architectural splendor of one of New York's defining thoroughfares.

Let's Start Walking

(c) Retroman Tours 2025

Photo Credits: Library of Congress

bottom of page