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Travel story · New york

Sinatra's New York

From the Village's candlelit bistros to the jazz clubs of Midtown, follow Frank Sinatra's New York — the city that never sleeps, where the night only really begins after midnight and the martinis stay dry.

Sinatra's New York
Wikimedia Commons · Public domain

Day 1: Hoboken roots

Start in Hoboken, across the Hudson, where Frank was born. The ferry back to Manhattan is the same crossing he made thousands of times.

Vtg 50s Penney's Marathon Gray Wide Brim Stratoliner Fedora 7 1/4
Vtg 50s Penney's Marathon Gray Wide Brim Stratoliner Fedora 7 1/4

Day 2: The Village and the joints

The clubs of Greenwich Village were his proving ground. Walk along MacDougal Street and find a place where live jazz still plays. Order a dry martini, no discussion.

Royal Stetson Fedora Hat Mens Size 7 1/8 Gray White Black Feather w/ Box Vintage
Royal Stetson Fedora Hat Mens Size 7 1/8 Gray White Black Feather w/ Box Vintage

Day 3: Midtown, after dark

Finish in Midtown, where the Rat Pack ruled. A late dinner and a walk beneath the lights of Times Square. Do it your way.

1950s Champ fedora
1950s Champ fedora

Along the way

  1. 01

    Hoboken

  2. 02

    MacDougal Street

  3. 03

    The Waldorf Astoria

  4. 04

    P.J. Clarke's

  5. 05

    Times Square

  6. 06

    Carnegie Hall