trip inspo

5 queer-friendly fall travel destinations to elevate your weekend getaway

A man wearing a flannel shirt sits on a rail overlooking Montreal's skyline.
Photo: Shutterstock

True, summer is over — but there’s nothing like a fall travel weekend getaway to perk up the season. GayCities takes a look at five of our favorite fall destinations with a fresh lens, especially for those looking for splurge-worthy fun.

Whether you’re taking advantage of off-season rates or heading north for an international trip that doesn’t require an ocean crossing, these five LGBTQ+-friendly cities make for the perfect getaway.

Key West

Key West’s motto is “One Human Family,” and hotel rates tend to drop during fall travel, which leaves more spending money for on-the-ground experiences. Discover a drag show, spend a day on the water, and finish the night with a gourmet meal at one of the many restaurants showcasing South Florida’s fresh seafood.


Key West

Southernmost city

Location, Location, Location: Put yourself in the center of it all by staying at La Concha Hotel and Spa, which dates back to 1926 and carries its own haunted history, including the legend of a waiter who allegedly fell down an elevator shaft and continues to roam the halls. Tip: don’t walk backward!

Sole with Soul: Chef-owner Frank Correa’s Cafe Sole offers white tablecloth service but a casual, friendly vibe for which Key West is known. The signature dish, hogfish, stands out for its delicate texture and rich red pepper hollandaise.

Mild to Wild: Looking for a last-minute leather Halloween costume accessory (or for any time of year)? Head to Leather Master of Key West to make your lewk complete.




Provincetown: Cape Cod Gay Summer Getaway

Autumn in Provincetown may be one of the destination’s not-so-best-kept-secrets. The crowds tend to diminish (somewhat) during fall travel, but there’s still plenty to discover during fall travel as a slight chill descends on the northeast, along with flaming foliage that gives the local drag queens a run for their money.

Wine Not?: The Pointe Restaurant & Wine Bar at the historic Crowne Pointe Inn and Spa boasts an extensive wine collection for oenophiles or casual connoisseurs designed to complement the “pier to plate” menu that draws inspiration from New England heritage.

Precious Metal: Stay at the adults-only Brass Key Guesthouse, which offers a range of rooms, suites, and private cottages, along with a complimentary nightly wine and cheese reception, whirlpool, and private grounds to unwind after the night’s adventures.

Picture Perfect: Provincetown’s history as an artist’s colony is still evident by the number of galleries around town. Head to Larkin Gallery on the peninsula’s east end to discover new and established artists who work in a range of mediums.

New York City


New York City

Gay New York: It’s up to you

The City That Never Sleeps rejuvenates once local queens return from their summer shares on Fire Island. Theater lovers anticipate new openings (this season includes Jonathan Groff’s return to Broadway in Merrily We Roll Along and Andrew Rannells in Gutenberg: The Musical!), and Central Park becomes a haven for late-afternoon strolls. Of course, NYC nightlife never disappoints, including The Dickens, a multi-level venue that just opened its Theater District rooftop.

A Room with a View: ModernHaus SoHo is in the heart of New York City’s high-end boutiques and independent retailers, with a serene setting to recharge or unwind. Splurge on a room with city views to feel as if you’re floating above the city that never sleeps, then slumber the night away amid minimalist design details.

Retail Therapy: Prada’s SoHo flagship location is within perilously close distance from ModernHaus SoHo, so make sure you’re aware of your credit limit before doing any damage. The fall 2023 collection includes a fresh take on the puffer jacket, chunky leather shoes that give a Doc Marten vibe, and unconventional kisses of color, including wisteria and alabaster pink cashmere sweaters.

Fierce Fine Dining: Telly Justice and Camille Lindsley’s East Village eatery Hags is everything you want in a high-end dining experience, along with an intentionally queer twist, from the curated playlist and tableside pronoun buttons to a curated wine list focused on small vineyards and seasonal menu for omnivores or vegans.

New Orleans


New Orleans

Southern Decadence and more

Included on nearly every list of the most haunted cities in America, New Orleans doesn’t disappoint when it comes to macabre mischief. Whether you’re traveling for Halloween or want to explore the city’s gay ghostly history another time, you’re bound to discover the city’s complex history around every corner.

Stay in Style: Hotel Saint Vincent was prominently featured in season seven of Queer Eye and with good reason. The Garden District property features unique room layouts, many with vaulted ceilings and a lofty vibe. Head to the Chapel Club for a cocktail that harkens back to the grand salons of the early 20th century.

Take Charge: Commander’s Palace is old-school New Orleans at its best. The landmark restaurant dates back to 1893 and has paved the way for new haute Creole cuisine. Sample classic dishes like turtle soup with sherry, pecan-crusted Gulf fish, and bread pudding soufflé.

Sweet Treats: Skip the candy corn and head to Southern Candymakers for a New Orleans classic: pecan pralines. Handmade on a marble slab, the confections are as quintessential as beignets from Café du Monde.




Gay Montreal

While Europe might be too far for a three-day weekend, consider a smart splurge to our northern neighbor. Montreal offers French flair, late-night eats (poutine, anyone?), and a thriving gayborhood packed with bars and clubs.

Modern Master: Inspired by the French art de vivreSofitel Montreal Golden Mile offers a luxurious setting just steps from the Montreal Museum of Fine Arts. The Prestige Suite’s skyline views are unparalleled, and Le Renoir Restaurant pays tribute to the painter as well as the epitome of French cuisine.

Page Turner: The nonprofit feminist bookstore L’Euguélionne is a terrific find for queer literature where visitors can discover new releases, used books, zines, and other LGBTQ+-themed works.

What’s Old is New: Head to Old Montreal to dine at Maggie Oaks, where you’ll discover a carnivore’s dream. Sure, the menu features obligatory favorites like French onion soup and asparagus harlequin, but the real attraction is the restaurant’s superb cuts of meat, including a sharable t-bone, porterhouse or tomahawk.

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