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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.

Vintage Knox Fedora Hat Brown Fur Felt 7 1/8 With Original Box 1950s
Vintage Knox Fedora Hat Brown Fur Felt 7 1/8 With Original Box 1950s

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.

Vintage Royal Stetson Fur Felt Fedora Hat Size 7 1/2 with Original Box
Vintage Royal Stetson Fur Felt Fedora Hat Size 7 1/2 with Original Box

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 7 3/8
1950s Champ fedora 7 3/8

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