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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 Fifth Avenue New York Gray Fedora Hat Size 7 1/4
VINTAGE Knox Fifth Avenue New York Gray Fedora Hat Size 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.

Vintage Stephen L. Stetson “Manhattan” Fedora 7 3/8 Shark Gill Ribbon 1963
Vintage Stephen L. Stetson “Manhattan” Fedora 7 3/8 Shark Gill Ribbon 1963

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.

Vintage 1950s Cavanagh Edge Fedora Rare Size 7 5/8 Charcoal w/ Original Box
Vintage 1950s Cavanagh Edge Fedora Rare Size 7 5/8 Charcoal w/ Original Box

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