Is Key West LGBTQ-friendly?

Your guesthouse will shape a couples trip more than any bar will. Island House and Equator Resort are both men-only, with clothing-optional pools, so decide where you stand before you book, because some couples love that and some would be mortified. Mixed couples, women, and anyone who wants a quieter room should look at Alexander's Guesthouse on Fleming Street or Cypress House at 601 Caroline Street, where breakfast is served on a deck under rustling breadfruit leaves. Ask any Old Town guesthouse for the room's square footage rather than reading the adjectives, because several converted conch-house rooms barely fit a queen bed and two suitcases. One timing warning for late October: Fantasy Fest, the 10-day costume and body-paint street party, usually ends on Halloween weekend. Room rates rise steeply that week and Duval gets loud until 3am. It's great fun if that's what you came for. If you came for anniversary quiet, book the first week of November.

The island handles a split-interest couple easily, because nearly everything in Old Town is within a 20-minute walk. The history buff can spend the morning at the African Cemetery at Higgs Beach, where 294 Africans freed from slave ships in 1860 are buried, then walk past Tennessee Williams's house at 1431 Duncan Street, which is still privately owned, so it's a pavement visit. Meanwhile the foodie heads to Blue Heaven on Thomas Street in Bahama Village, where roosters scratch under the tables and the Key lime pie comes with a meringue piled four inches high. Meet back on Duval and look for the photos of the 2003 Sea to Sea rainbow flag: Gilbert Baker made it 1.25 miles long, enough to stretch from the Gulf of Mexico to the Atlantic. Higgs Beach is the easiest place on the island for a relaxed queer afternoon, with coarse sand, warm shallow water, and the White Street Pier a short walk east.

Skip sunset at Mallory Square unless you enjoy elbowing past cruise passengers while a juggler narrates the whole thing. A sunset sail is quieter, and both Viator and GetYourGuide list them, so compare the two prices before you book. Fort Zachary Taylor is another option: pine shade and the sound of the Atlantic, though the park closes at sundown. For the big dinner, book the Afterdeck at Louie's Backyard, 700 Waddell Avenue, and ask for a table on the lowest deck, where the waves slap the pilings right under your feet. Café Marquesa on Fleming Street is the indoor option, with candlelight and a set of quieter two-tops along the wall. Dress lighter than you'd expect: on October 19 it was still 27.7°C at 7pm with 70% humidity, so linen will serve you better than a blazer. Finish on upper Duval for the 11pm drag set, which ends in time to get home before the street turns rowdy.