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5 Great LGBT-Friendly Destinations for Fall

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All summers have to end, but don’t dismay — the influx of fleece and leaf-peeping has its perks. TPG Contributor Kelsy Chauvin takes a peek at some of the top LGBT-friendly destinations to book this fall, with either swimsuit or sweater in hand. (All photos by the author unless otherwise specified.)

The Vieux Carre, New Orleans. Photo by Kelsy Chauvin.
The elegant Vieux Carre in New Orleans.

1. New Orleans, Louisiana

With its oppressive summer humidity finally fading, the Big Easy in fall makes for a fabulous last hurrah for gays on vacay. The 44th-annual Southern Decadence, aka “Gay Mardi Gras,” has already marched through the French Quarter, but New Orleans has long been a proud LGBT destination, so even a weekend later in the season will bring some glitter. Gay Halloween is the next big thing, with a weekend full of French Quarter festivities and the Lazarus Ball, all benefitting AIDS-support charity, Project Lazarus (October 29-November 1).

Fly into Louis Armstrong International Airport (MSY) and grab a cab to the Quarter, where you can get by on foot, streetcar or taxi. Hunger won’t be an issue in the Crescent City, but settling on an eatery will. Start simple with a po-boy and ice-cold beer at the no-frills Fiorella’s Café on Decatur Street. For dinner, go upscale-delicious at Kingfish on Chartres Street for classics and newfangled dishes (smoked rabbit, anyone?). To hear what’s new in the local music scene, hop in another cab and head to Frenchmen Street.

Even with so much real-deal character, New Orleans is still a tourist town, so hotels big or small are easy to find. The recently renovated Sheraton New Orleans on Canal Street is a good choice for its central location, upper-floor views and competitive rates. At this Starwood Category 4 property, rooms start at $219 or 10,000 Starpoints per night. The Starwood Preferred Guest Credit Card from Amex and the SPG Business Amex each offer two stays and five nights of elite credit annually across Starwood’s 1,200 hotels and resorts. Bonus: Holders of MasterCard credit cards like the Barclaycard Arrival Plus currently get 20 percent off a two-night weekend stay.

Note that there are many more points hotels in and around the Vieux Carre — on Canal alone you’ll find the Marriott New Orleans, DoubleTree by Hilton, the Ritz-Carlton and many more.

Commercial Street, Provincetown. Photo by Kelsy Chauvin.
Don a sweater and stroll down Commercial Street in Provincetown.

2. Provincetown, Massachusetts

Autumn in Cape Cod makes for a perfect transition to cooler temperatures, because it’s almost always sweater weather along the North Atlantic. At its northern tip, Provincetown is a famous LGBT destination and hosts the popular Women’s Week, Men’s Weekend and other LGBT events through November.

To get there, fly into Boston Logan Airport (BOS) and rent a car for the scenic drive down the coast and up the cape, though you won’t need a car much once you get there. P-town is dotted with cafés and cute restaurants, and the Mayflower is one of the oldest. It has been serving Portuguese, seafood and other dishes since 1929 — don’t miss the classic kale and sausage soup. Joon Bar + Kitchen, further up Commercial Street, is a sweet spot for fine dining and excellent wines.

With a population of about 3,000, compact Provincetown is more of a bed-and-breakfast and independent hotel zone than a points-property mecca, but you can still maximize your stay by booking with a credit card that earns you category bonuses for travel and/or hotel spending, such as the Chase Sapphire Preferred, Citi ThankYou Premier or Citi Prestige. The Crown & Anchor Inn is one of the larger hotels with a restaurant and versatile theater space, with fall rates starting at $165. On the water is the Surfside Hotel & Suites, a larger gay-welcoming spot with rates from $220 during fall months.

Hyatt Key West Resort & Spa. Photo by Kelsy Chauvin.
It always feels like summer at the Hyatt Key West Resort & Spa.

3. Key West, Florida

Key West is the year-round LGBT hotspot of the East Coast for good reason: No matter when you visit, it feels like summer. That breezy vibe pairs well with this city’s quirky side — it celebrates its pirate past with open-air bars and booze cruises aplenty. You’ll catch the local drift instantly upon arrival at wee Key West International Airport (EYW), which is served largely by Southwest and American. There you can rent a car or hop a shuttle into town.

Check out Duval Street for a slew of dining options, or head off the beaten path for zesty Mediterranean at Azur Restaurant, which has great weekday lunch and wine specials. The Historic Seaport is an appropriately laid-back spot to imbibe and try some fresh-catch conch on the open-air deck of the Conch Republic Seafood Company.

While Key West is home to many B&Bs and indie inns, you can still use your points at a number of hotels. Top among them are the Hyatt Key West Resort & Spa, whose spacious rooms start at $229 or 25,000 Hyatt Gold Passport points per night; be sure to see The Award Traveler’s Guide to Hyatt Gold Passport to best maximize your stay. The Westin Key West Resort & Marina is one of the top Old Town accommodations, and rooms at this Starwood Category 6 property start at 20,000 Starpoints or $269 a night.

Fall looks good on Tornoto, especially in its High Park. Photo courtesy of Shutterstock.
Fall is a good look for Toronto, especially in leafy High Park. Image courtesy of Shutterstock.

4. Toronto, Ontario, Canada

In case Canada’s biggest city wasn’t already gay enough, hosting 2014 World Pride put it on the global LGBT map but good. In fall, the city’s humidity has finally receded and Toronto becomes an autumnal playland, easily accessible from Toronto Pearson Airport (YYZ) thanks to the Union Pearson Express train and abundant in-city transit.

It’s easy to find an impressive meal in Toronto’s famous dining scene. In the “Gay Village” known as Church Wellesley, consider sampling authentic Japanese fare at local-favorite Guu Izakaya. A bit south of the village, innovative cuisine awaits at Richmond Station, a top-rated restaurant run by Top Chef Canada winner Carl Heinrich. 

Check into the central Ritz-Carlton Toronto, and a posh option with high-rise vistas; rates for this Tier 5 property start at $429 or 50,000 Ritz-Carlton Rewards points per night, and you should check out The Award Traveler’s Guide to Marriott Rewards (which partners with Ritz-Carlton Rewards) to make the most of your stay. Conveniently located in the heart of the Village, the Holiday Inn Toronto Downtown Centre is a solid choice if you’re on more of a budget, as its sleek rooms start at $154 or 30,000 IHG Rewards Club points per night (and less if you’re using Points + Cash).

Escape to Le Parker Meridien Palm Springs, where summer never ends. Photo courtesy of the hotel
Escape to Le Parker Meridien Palm Springs, where summer never really ends. Photo courtesy of the hotel.

5. Palm Springs, California

It’s always a good time to escape to Palm Springs, but this oasis of Mid-Century Modern architecture (on special display during Modernism Week, October 9-12, 2015) is an especially ideal spot to cling to the last vestiges of summer. Cinema Diverse, the city’s LGBT film festival, has wrapped for the season, but Palm Springs Pride is still ahead (November 6-8, 2015).

From compact, partially open-air Palm Springs International Airport (PSP) — served by Alaska, Delta, Virgin America and American — pick up a rental car and zip into town. Foodies delight in the culinary options that span Asian, Mexican and everything in between, but a new staple on the scene is Serious Eats, with its filling favorites and excellent bar, open for dinner and weekend brunch. Lesbian-owned Dish Creative Cuisine is a high-end fave with big-city flair — as well as great vegetarian and seafood dishes, and craft cocktails perfect for enjoying on the street-side patio.

Hotels dot the local landscape, and smart points travelers will appreciate the spotless, sleek Renaissance Palm Springs, a Marriott Rewards Category 7 property that starts at $129 or 35,000 points. Get closer to the city center at the Hilton Palm Springs, with its giant courtyard and pool; at this Category 6 hotel, rooms start at $210 or 30,000 HHonors Points. (See The Award Traveler’s Guide to Hilton Honors to make the most of your stay.)

Looking to splash out in the desert? Escape to the artsy Le Parker Méridien Palm Springs, which features sprawling grounds and a croquet lawn, a spa with carpeted tents rimming an indoor pool and the West Coast sister of Midtown Manhattan’s popular Norma’s restaurant; rooms here start at $439 or 20,000 Starpoints per night — and be sure to check out the talent at the piano bar, Mister Parker’s.

For more information on LGBT points-and-miles-savvy travel, be sure to check these posts:

Best Gay Neighborhoods in America
The Gay-Friendliest Airlines in the Skies
5 Great Gay Beaches in the USA

What’s your favorite destination for early fall?

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