Your guide to summery getaways that are—secretly, blissfully—even better in autumn. Let the season begin again.

Words: Andrew Sessa


1. Channel Islands, California

Unadulterated natural beauty and nearly year-round warm weather just three hours from L.A.

Why Now: Despite having some 145 plant and animal species found nowhere else in the world, this five-island archipelago just off the Southern California coast has stayed oddly under-the-radar (Channel Islands National Park ranks 41st out of the 59 designated national parks for visitation). It’s especially great in fall, when water temperatures can reach a comfortable 70 degrees for snorkeling, diving, kayaking, and even swimming. Nature also gets into full swing in autumn as birds migrate and elephant seals arrive to mate.

What’s New: The National Park Service has big plans for low-impact expansion of trails, transport, and lodging thanks to $62 million in funding. Meanwhile, park biologists just tagged their hundredth bald eagle.

Action Plan: Add the islands onto a long weekend in L.A. by driving 90 minutes northwest to Oxnard and boarding a 70-minute Island Packers ferry for a day-trip to Anacapa Island. Or sign up for one of the company’s kayaking journeys or camping overnights.

Photography: by Adrian Gaut

Make the Summer Last

So you missed your chance for that epic summer road trip, that languid island holiday, that family ranch vacation you’d been dreaming of all winter long. And now, suddenly, summer is over. Or is it?

In a few of our favorite retreats, September, October, and sometimes November are in fact better—dare we say, even summerier—than June through August. The crowds are fewer, the prices are lower, and the weather is perfect. Of course, for many of us, fall is also the busiest time of year, which is why we polled our editors and travel specialists for trips that maximize your experience in the shortest time possible (okay, along with a few longer breaks). Consider this your green light to slip away—and have another round of summer on us.

Photography: Adrian Gaut

2. Jackson Hole, Wyoming

Deep shoulder-season action, without the crowds, for the outdoor adventurer.

Why Now: These days, Rocky Mountain resorts can feel as overrun in summer as in winter, with climbing, fishing, and wildlife-watching as much of a draw as skiing and snowboarding. That makes relatively quiet September ideal for checking out Yellowstone and Grand Teton national parks and the nearby national forests.

What’s New: The rustic-cool Hotel Jackson opened in June off Jackson Hole’s town square. For live bands and dancing, hit the iconic Silver Dollar Bar at the Wort Hotel and its just-expanded music space. The area’s famed trail system has also gotten more expansive: Key routes (like the southwest portion of Jenny Lake) have been reopened and improved.

Action Plan: Take a four-day jaunt in September or early October, devoting a full day to each of the two national parks as well as the nearby Bridger-Teton National Forest, leaving you one extra day to explore downtown Jackson Hole.

Photography: Gallery Stock

3. San Isidro del General, Costa Rica

A hacienda-style resort in Central America’s inland mountains.

Why Now: Far from the coastal areas that bear the brunt of the season’s storms, Costa Rica’s rain-forested southern mountains have just-right temperatures in the fall. The arrival of the 864-acre, 50-villa resort AltaGracia this June has also brought luster to the rugged terrain. Ride horses on the resort’s private trails, take a flight in an ultralight, and make time for a hot-stone treatment at Central America’s largest spa.

What’s New: After operating independently, AltaGracia came under the management of Auberge Resorts (famous for Napa Valley’s beloved Calistoga Ranch) this summer; that means plenty of upgrades, including a food festival in October featuring guest chefs from Auberge’s other properties.

Action Plan: Make a long weekend of it: Fly to San José or Liberia, then take a three-hour drive to AltaGracia and settle in for three nights.

Photography: AltaGracia

4. Desert Southwest

Take a classic road trip—upgraded, and without the stifling summer heat.

Yes, you can do it all in six days: Las Vegas to Phoenix via the icons of Zion, Bryce Canyon, and Grand Canyon national parks, plus Lake Powell, with stays at two of our favorite spa resorts. Southwest super-agent Caroline Bach Wood shows the way in The Perfect American Southwest Road Trip.

Photography: by David De Vleeschauwer

5. British Columbia, Canada

Go biking through some of North America’s most dramatic landscapes.

Why Now: The warm early fall days on Canada’s southwestern coast are great for active travel, especially biking. Several of the Gulf Islands (just east of Vancouver Island, itself a few dozen miles off Vancouver) have excellent paths, as does the Okanagan Valley wine region (a 50-minute flight east of Vancouver), where old railroad track beds have become the Kettle Valley Rail Trail.

What’s New: The seven-room Sproat Lake Landing opened in July on Vancouver Island making for a perfect stopover between the Gulf Islands and Tofino, where the luxe Clayoquot Wilderness Resort has a new cloud camp at 4,500 feet, accessible only by helicopter.

Action Plan: Contact Cari Gray, formerly of Butterfield & Robinson, whose active-travel company, Gray & Co., specializes in ultra-high-end bespoke biking and hiking trips around the world, with a particular expertise in this region.

Photography: Michael Turek

6. ABC Islands, Caribbean

The Caribbean during storm season? Believe it.

Why Now: Known for their outstanding scuba sites, the Dutch Caribbean outposts of Aruba, Bonaire, and Curaçao (a.k.a. the ABC Islands) lie just off the coast of Venezuela, which puts their peaceful turquoise waters outside the hurricane zone. And here, summer sticks around all year.

What’s New: Aruba has invested $100 million to upgrade hotels, including adding the new Riu Palace Antillas, and the island’s airport also got a face-lift. Bonaire’s Divi Flamingo will wrap a multimillion-dollar update this fall. Curaçao kicked off its reef-restoration eco-initiative in May, and there are new villa-style suites at Baoase Luxury Resort, freshly decked-out rooms at the Hilton Curaçao, and gussied-up villas at Papagayo.

Action Plan: Ditch the turkey. Direct flights from the States (especially to Aruba) mean a Thanksgiving getaway that gives you nearly four full days on the ground—and in the water.

Photography: Gallery Stock

7. Cornwall, England

An extra-long weekend on the U.K.’s idyllic—and surprisingly chic—southwest coast.

Beyond its garden tours and heritage homes, Cornwall is an unexpected center of haute gastronomy, luxe adventure, and glam hotels. By now, the summer crowds have gone, but thanks to the jet stream, the weather’s still balmy. So here’s an idea: Take two days off around Columbus Day weekend and book the perfect getaway—Five Ideal Days in Cornwall, England—through the travel specialists at Black Tomato.

Photography: Luke Hayes/Courtesy Watergate Bay

8. Cartagena, Colombia

Who knew sultry South America could be such a short hop away?

Why Now: Summery weather sticks around 12 months of the year in Cartagena, making a quick jaunt there—to admire the colonial architecture, scarf down street vendor arepas, and hit ceviche restaurants like El Boliche or La Cevichería—a solid idea at any time.

What’s New: Recently added three-hour JetBlue direct flights from Fort Lauderdale to Cartagena simplify travel from Florida, and the new InterContinental Cartagena de India’s waterfront location is worth checking out too.

Action Plan: Make it a three- or four-day weekend, spending your days shopping the traditional Bazurto food market or taking boat excursions to nearby islands and your nights hitting salsa clubs like the classic Café Havana and Bazurto Social Club. Book the recently upgraded Sofitel Legend, which has one of Cartagena’s most stunning pools.

Photography: Getty

9. Portland, Maine

New England’s little foodie mecca is at its best during harvest season.

Why Now: With a trio of James Beard Foundation Award nominations this year, Portland—as renowned for lobster and oysters as for centuries-old streets and ocean views—has built itself a seriously buzzy restaurant scene. Temperatures remain comfortable through September and early October, and fall’s bounty is put to great use at JBFA nominees Eventide Oyster Co., Central Provisions, and Miyake.

What’s New: Autograph Collection’s Press Hotel opened in May as the city’s first real high-design stay. Its 110 1920s-evoking rooms and farm- and sea-to-table restaurant, Union, occupy the brick-and-stone building that formerly housed the Portland Press Herald.

Action Plan: Direct flights from nine cities on the East Coast—as well as Detroit and Chicago—make three-day weekends a breeze.

Photography: Getty

10. Brazilian Beaches

Catch summer on its way in with an exotic coastal getaway—sans jet lag.

An easy overnight flight (with not much of a time change) gets North Americans to and from Brazil, where summer’s approaching just as winter hits the States—the ideal time for a Rio de Janeiro getaway followed by a sailing trip in Angra dos Reis and Paraty. South American travel experts Dehouche show us how it’s done in Best of Brazilian Beaches: A Week-Long Trip.

Photography: Richard Powers

11. Austin, Texas

Where the country’s best summer music festival happens in October.

Why Now: Fall may be the finest time to visit Austin, period. After a long, hot summer, temperatures finally become bearable (in the '70s and '80s), and the cultural calendar fills with shows and art openings. Come October, the Austin City Limits Music Festival pulls into town for two sunscreen-soaked weekends, with 100-plus acts ranging from Florence and the Machine to Deadmau5 and The Strokes.

What’s New: Two hotly anticipated hotels arrived over the summer: the mid-century-inspired South Congress Hotel, home to Top Chef winner Paul Qui’s next-wave sushi bar Otoko, and Kimpton’s music-themed Hotel Van Zandt, just off lively Rainey Street. Another well-situated newcomer is the Westin Austin Downtown, one block from Sixth Street’s bars and music clubs.

Action Plan: Three days is plenty of time to take in the best of the city— four if you’re devoting a full weekend to the Austin City Limits Music Festival. But book your flights, rooms, and festival tickets early: Everything sells out well in advance.

Photography: Getty

12. Azores, Portugal

Your next European beach holiday could be only a five-hour flight away.

Why Now: A little more than halfway between the East Coast and Europe, the nine volcanic isles of Portugal’s Azores archipelago deliver sunny-but-cool weather year-round. And thanks to direct flights from Boston, beaches like the white sand Baía da Praia Formosa, on Santa Maria, are just five hours away. Fall ushers in Terceira’s Angrajazz Festival (October 1 to 3), followed by the Wine in Azores event (October 23 to 25) and the Outono Vivo world-music festival (October 30 to November 15).

What’s New: Last year brought in a wave of hotels and spas, including Design Hotels’ Furnas Boutique Hotel, with 55 rooms and a spring-fed thermal spa, on the island of São Miguel, above. There are also new museums and hiking trails to explore, including the nearly 50-mile network of the Great Route on Santa Maria.

Action Plan: Book one of SATA International’s nonstops from Boston to São Miguel, which take off daily through mid-October and then thrice a week. Spend four or five days island-hopping and filling your days with thermal pools, nature preserves, and whale-watching voyages.

Photography: Getty Images/Moment RF