1 PUERTO VIEJO DE TALAMANCA, COSTA RICA

More daily flights make for a well-timed visit to Central America’s Caribbean coast.

Starting November 2, American Airlines launches daily direct flights to San José, Costa Rica — a significant upgrade on the Saturday-only direct hauls American and United currently offer. November sits at the tail end of Costa Rica’s rainy season, but travelers and Ticos in the know head straight to oceanside Puerto Viejo de Talamanca on the lesser-known Caribbean coast for abundant sunshine and calm seas.
While there: The 15-room Hotel Aguas Claras (from $247) is a modern-meets-whimsical property. Set near the soft sands of Playa Chiquita, it features a palapa-covered beach bar and an Afro-Caribbean restaurant. New this year: a pair of two-bedroom bungalows.

2 ATHENS RIVIERA, GREECE

You can get your White Lotus fix at this renovated wellness retreat.

Boasting two private Aegean beaches, terraced bungalows, and an open-air gym, the 139-room Cape Sounio (from $857), less than an hour from Athens, has long drawn a health-conscious crowd. Now the resort has launched its Elevations of Wellness program, featuring alternative treatments like a gut massage layered with craniosacral therapy. It’s the creation of L.A.-based osteopath and health guru Vicky Vlachonis, known for working with Gwyneth Paltrow and Katy Perry. Bonus: Vlachonis will be onsite this fall until the hotel closes for the season November 8.
While there: Across the sea on the Cape Sounion promontory is the ancient Temple of Poseidon. The best way to see it is on a 90-minute hike led by the resort’s yoga instructor.

3 BRECKENRIDGE, COLORADO

The dining scene here is more elevated than ever.

Mountain towns aren’t usually known for their gastronomy, but this Rocky Mountain destination shows you can have both adventure and great food at high altitude. That’s thanks in part to 2024 James Beard Award winner Matt Vawter. This year he built on the success of his restaurants Rootstalk and Radicato to open the Breckenridge Farmers’ Market (Thursday evenings through September 25), where visitors can buy everything from wagyu beef to Palisade peaches.
While there: With an elevation of 9,600 feet, Breck sees some of the earliest fall foliage in North America. Hike Cucumber Gulch via the Pence Miller Trail from town, through tunnels of golden aspens. You may even spot a moose.

4 BARDSTOWN, KENTUCKY

A fancy new hotel makes an ideal base for a bourbon-infused vacation.

The new 95-room Trail Hotel, which opened this spring, brings upscale lodging to the Bourbon Capital of the World, offering easy access to the Kentucky Bourbon Trail’s many distilleries and tasting rooms. The hotel (from $186) was designed for bourbon drinkers, especially its amenities: “Bourbon butlers” curate itineraries that keep the party going, and in the Rejuvenation Room you’ll find bougie hangover therapies like an infrared sauna, cryotherapy, and IV hydration.
While there: Don’t skip Heaven Hill’s new $200 million distillery, which can produce 150,000 barrels of whiskey a year.

5 SANTA CRUZ, CALIFORNIA

A beachfront hotel opens in time for Cali’s secret season.

The best time to visit Santa Cruz is late September through November, for long sunny days with temps in the 70s, powerful swell for ideal surf conditions, and beaches and parks at their least crowded. Another reason to go: the 155-room La Bahia Hotel & Spa, set to open in September (from $505). The first luxury beachfront property to come to this laid-back town promises outdoor terraces with every room and a perch across from the Main Beach and Santa Cruz Boardwalk.
While there: A mile from the hotel is Bad Animal, a restaurant housed in a wine and rare-book shop. Thailand native Lalita Kaewsawang, formerly a chef at Chicago’s Grace, serves artful plates like apple-ginger mieng and tom kha goong with white coconut curry.

6 ROME, ITALY

The Chicago-born pope offers a new excuse to make a pilgrimage.

If south suburban Dolton doesn’t scratch your papal itch (see “Bob’s House”), there’s no better way to celebrate Chicago’s Pope Leo XIV than by visiting the Eternal City in this jubilee year for the Catholic Church. You can see the Holy Father in the flesh on a handful of Sundays a month, mainly at St. Peter’s Basilica and St. Peter’s Square. Track his schedule (typically released a month in advance) and request (free) tickets on the Vatican’s website.
While there: The Holy Year, which takes place every quarter century, means rituals that include the opening of the otherwise-sealed Holy Door at St. Peter’s Basilica.

7 ORLANDO, FLORIDA

Universal has a new mega theme park.

The 750-acre Universal Epic Universe, the first entirely new theme park to open in Orlando in 25 years, debuted in May with more than 50 attractions, making it Universal’s biggest park and one of the world’s largest ($139 for adults, $134 for children). Among the attractions are a dual-track roller coaster (where near crashes are part of the thrill) and the biggest Harry Potter ride ever built. Through November 2, nearby Universal Studios Florida stages its wildly popular Halloween Horror Nights.
While there: To escape theme-park madness, stay at the art-focused, high-style Alfond Inn (from $257) in Winter Park. Owned by Rollins College, the 183-room property packs a revolving collection of impressive contemporary works.

8 COLUMBIA RIVER GORGE, WASHINGTON

A new glamping spot lets you embrace Pacific Northwest wonders in style.

Want to sleep under the stars without sacrificing comfort? The recently opened Under Canvas Columbia River Gorge, boasting views of Mount Hood, offers elevated safari-style tents complete with West Elm furnishings, en suite bathrooms, and gas fireplaces (from $249). Set on 120 acres within the White Salmon River Valley and open through October 27, the camp provides easy access to waterfall hikes, rafting, and fly-fishing. While onsite you can enjoy morning yoga and fireside s’mores.
While there: Under Canvas is in the heart of wine country, with 10 vineyards within a 10-mile radius.