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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.

Fedora - Dynafelt - size 7 3/8" lined vintage brown
Fedora - Dynafelt - size 7 3/8" lined vintage brown

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 Dark Brown Fur Felt Fedora Hat - Size 7 3/8
Vintage Dark Brown Fur Felt Fedora Hat - Size 7 3/8

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 Borsalino Bruma Fedora Punti 6 7 3/8 Heathered Felt Italy
Vintage 1950s Borsalino Bruma Fedora Punti 6 7 3/8 Heathered Felt Italy

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