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A famously vibrant and cohesive community, The Castro is San Francisco’s hippest neighbourhood.

Its thriving gay and lesbian population enjoys an open and celebratory identity – a situation that belies the tumultuous struggle for gay rights of the past and present.

Heroic activism in the 60s and 70s led by personalities like Harvey Milk made The Castro’s distinct Victorian streets the front line in one the civil rights movement’s most hard-fought, and bloody, battles.

And while the deeply entrenched gay community is identifiable today more for its rainbow flags than political placards, having become a tourist attraction in itself, The Castro’s unique queer identity endures – thanks in no small part to the stylish shops, bars and old-school eateries that saturate its five blocks.

Discover and shop The Castro with this full-day itinerary.

  • Start the day by exploring Mission Dolores (3321 16th St) and the relatively ancient cemetery just outside. Founded in 1776, it is the city’s oldest building.
  • Continue three blocks to pick up picnic supplies at Bi-Rite Market (3639 18th St), one of the best local, organic, premium food stores in the city.
  • Pick a vantage spot in nearby Dolores Park where you can enjoy the views of the city and of its eccentric residents while leisurely chowing down your picnic.
  • Dust the grass from your clothes and head down 19th Street to Paxton Gate (824 Valencia Street, between 19th and 20th streets). At this creepy and charming gift shop you’ll find taxidermy animals and other strange, beautiful curios that make fun and unusual presents for people back home.
  • Take a short walk up Valencia to Candy Store (3153 16th St), an imaginatively curated shop with on-trend clothes, quirky books and arty objects.
  • Reward yourself for all that exploration with a conscientiously mixed cocktail at Elixir (3200 16th St), a certified organic saloon which, as luck would have it, is a just two-minute walk farther along 16th Street.

Written by insider city guide series Hg2 | A Hedonist’s guide to…

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(Image: Thomas Hawk)

About the author

Brett AckroydBrett hopes to one day reach the shores of far-flung Tristan da Cunha, the most remote of all the inhabited archipelagos on Earth…as to what he’ll do when he gets there, he hasn’t a clue. Over the last 10 years, London, New York, Cape Town and Pondicherry have all proudly been referred to as home. Now it’s Copenhagen’s turn, where he lends his travel expertise to momondo.com.

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