The 15 Best Places to Visit in October

1. New York, Ny

• Why We Recommend It: tons of activities, fall foliage, family friendly

The city that never sleeps is back to its usual buzzing and it seems like outdoor dining is here to stay, which means NYC is even more cosmopolitan and European in vibe than you’ve likely experienced on a past visit.

Some of our favorites for a classy night out on the town include Sola Pasta Bar, and yep, you totally read that right. The “pasta bar” is packed with delicious favorites, like a yummy squid ink pasta, crowd-pleasing cacio e pepe, and spaghetti alle vongole, as well as a take on the classic Aperol Spritz that uses Italicus bergamot flavored liqueur. Other outdoor stunners include Match 65 Brasserie, which boasts a melt-in-your-mouth steak tartare; the fancy pants, dreamy floral garden display at Scarpetta; and, the charming neighborhood feels of The Leroy House, with its tables and outdoor dining structure positioned on a popular stretch of the West Village’s Hudson Street. Pro tip: If it’s on the menu, get the burrata.

Halloween is also sure to be a blast in late October, especially since all those events that had been put on pause during the pandemic are back in full swing. New York City’s legendary Halloween parade is back on, and it’s likely to draw a pretty epic crowd this year and some of the wildest, most innovative costumes you’ve ever seen.

Where to stay:

• Cozy Renovated Brownstone (4 guests): $165/night
• Garden Property (4 guests): $139/night
• Large Park Block Duplex with Garden (8 guests): $338/night

2. St. Lucia

• Why We Recommend It: beach vacation, refreshing waterfalls, lots of history

Just a hop, skip and jump from many points on the Eastern seaboard, you can be sipping a rum punch on white sand beaches in no time. The island’s charms center on gorgeous mountaintop vistas of the Pitons, gorgeous aqua blue/green waters, and warm hospitality all around.

One of our favorite activities on St. Lucia is the drive-in volcano, La Soufriere. It’s here where you have the rare ability to see the actual crater of the volcano since it imploded in on itself during a past eruption.

While this island can be all about relaxing, we'd suggest not sleeping on a stop at the Diamond Falls Botanical Gardens or the colorful Immaculate Conception Church, either. Travelers can also experience a detoxifying sulphuric mud bath (a stone’s throw from La Soufriere) which will leave the skin milky and hydrated. Let a guide paint your body with mud in splatters, handprints, patterns, shapes and even animal figures. It’s super cheap to experience, and the photos are Insta gold.

Where to Stay:

• Elegant Villa on the Gros Piton (8 guests): $392/night
• Luxurious Bay View Apartment (6 guests): $124/night
• Castilla Bella (6 guests): $313/night

3. Miami, Fl

• Why We Recommend It: buzzing nightlife, tons of culture, great restaurants

Miami—like Paris, New York, and London—is always a good idea, but especially so when you consider all the goings on this month. Jack Harlow, Demi Lovato and even Keith Sweat are all expected to blow through MIA in October. Not only that, but the week of October 1 to October 9 will see the return of Miami’s lively cultural experience Carnival—there will be tons of bands, tons of music and of course, a copious amount of food and drinks.

Those who love cruises will be delighted to embark on the freshly minted Scarlet Lady—a new cruise ship from Virgin Voyages. With high design elements blanketed in Virgin’s signature red, more than 20 eateries—some from Michelin starred chefs—plus an impressive spa and even guest quarters and “seabeds” that can be rearranged to maximize space, no wonder Cruise Critic dubbed this yacht-inspired beauty Best New Cruise Ship in 2021.

Where to stay:

• Modern Two-Bedroom (6 guests): $134/night
• Brickell Waterfront Luxury Apartment (4 guests): $199/night
• Casa Blanca Tropical Paradise (5 guests): $150/night

4. Las Vegas, Nv

• Why We Recommend It: lots of partying, tons of outdoor activities, great food

Between the casinos, mesmerizing bright lights and all that accessible shopping on the strip, a trip to Vegas practically sells itself. Add the fact that the post-summer rush has long died down and the holiday season madness has yet to start and visiting Sin City in October is truly a no-brainer. Usher’s wildly popular residency at the Park MGM will be nearing its close, but you might be able to roll the dice and snag some last-minute tickets.

If you’re feeling a little more adventurous, head over to FlyOver—an immersive flight ride that allows you to experience a multi-sensory journey in 8K video through popular destinations across the American West. In the most Vegas turn of events ever, that means you can see all the glittering natural beauties our country calls home from the comfort of a chair—including the volcanic peaks of Oregon’s Cascade Volcanic Arc and the valleys of the Grand Canyon, plus plenty of other attractions in California, Montana, Colorado, Wyoming and beyond.

Where to stay:

• Vdara Condo (4 guests): $162/night
• Deluxe Condo at Wyndham (8 guests): $209/night
• Private Vegas Casitas Pool (6 guests): $203/night

5. Istanbul, Turkey

• Why We Recommend It: great architecture, lots of history, vibrant nightlife

One of Istanbul’s major tourist attractions is The Hagia Sophia, a symbol of the Byzantine and Ottoman Empires, and today a museum housed in a domed mosque where beautiful Biblical scenes are depicted. Leiter notes that October is a great month to visit Turkey because of the cooler weather and fall foliage. Restaurants, parks and markets are open, making it the perfect time of year for a lovely stroll around Cianger (the city’s trendy nabe) or along ​​Istiklal Caddesi—the main artery bursting with shops and restaurants.

Other points of interest in the place where Eastern and Western cultures collide include the Grand Bazaar, the Blue Mosque, Galata Tower and the Basilica Cistern. If you’re big on Mediterranean food and BBQ (and who isn’t), this is the town for you, especially at crowd-pleasing favorites with plenty of kebab options, like Last Ottomon Cafe & Restaurant, Bitlisi, Siva Restaurant and the super affordable and tasty Hidden Garden.

Where to stay:

• Spacious Ottoman Style Apartment (6 guests): $53/night
• Elegant Apartment with Beautiful Apartments (7 guests): $280/night
• Homely Apartment Near Galata Tower (5 guests): $157/night

6. Orlando, Fl

• Why We Recommend It: lots of theme parks, family friendly, tourist hub

Orlando is divine in the fall, not least because the prices are cheaper. It’s still hot enough to hit the pool (or the lake, or even the manufactured beach at some of the top water parks), and we all know by now that Disney World is high levels of fun even when you’re an adult. Through the end of October, Universal Orlando Resort will also be hosting its beloved Halloween Horror Nights, featuring haunted houses, scare zones, creepy characters and all-new mazes that deliver family-friendly thrills.

Where to stay:

• Mills Cottage on Small Lake (4 guests): $188/night
• Elegant College Park Cottage (4 guests): $157/night
• Cozy Modern Full Apartment (5 guests): $131/night

7. Lisbon, Portugal

• Why We Recommend It: amazing food, ornate architecture, lots of history

The best time to visit Lisbon is in October, when the summer crowds start to thin and the temperatures hover around 85 degrees. It’s also going to be a particularly cheap time to visit, with the summer vacationers long gone at this point. Portugal is already a more bargain-friendly way to visit Europe, and rates on top hotels are too good to pass up.

Some top attractions in Lisbon include the mind-blowing aquarium Oceanário de Lisboa, the adorable, picture-perfect neighborhoods of Alfama and Barrio Alto, and the gothic architecture and cloisters of Mosteiro dos Jeronimos. You can see most of it by foot or by the city’s glorious trams, some of which offer spectacular hilltop vistas. Our favorite way to see Lisbon is by grabbing a pastéis de nata (a local custard tart) and taking the Route 28 tram through some super narrow city streets until you disembark at Portas do Sol. With a birds eye view over the city and sea, it’s about as dreamy as it gets. The resort town of Cascais is also an easy 40-minute day trip from Lisbon, and may provide you one last jaunt at the beach before it starts to feel too chilly.

Where to stay:

• Lisbon House (6 guests): $122/night
• New Duplex with Fantastic View to Tejo River (7 guests): $115/night
• House River and Rossio (4 guests): $71/night

8. Punta Cana, Dominican Republic

• Why We Recommend It: beach vacation, tons of history, lots of activities

Favored for clear, turquoise Caribbean water, Punta Cana is the ideal spot for a beach vacation — ya know, after beach season ends. In October, high temps are around 87 degrees, rarely falling below 84 degrees. It’s also the end of the wet season, meaning your chances of rain are slimmer than traveling over summer months, so that extra PTO you have saved up over the past year can finally be put to good use. In October, there’s also a long weekend dedicated to salsa and bachata dance, a major Halloween bash at the gorgeous and splurge-worthy Breathless Resort & Spa and a Swing & Sip Golf Experience at the beautiful Casa de Campo.

Where to stay:

• Premier Beachfront Condo (5 guests): $145/night
• Luxe Beach Condo at Hard Rock Punta Cana (6 guests): $159/night
• Beachfront Condo in Beach Bavaro (6 guests): $100/night

9. Scottsdale, Az

• Why We Recommend It: tons of outdoor activities, scenic views, great weather

Escape to the good life in this upscale enclave, a city part of the larger Phoenix metro area that very much has its own distinct identity. Beyond the stunning landscapes and desert beauty, there’s plenty of luxe spas, golf courses and other recreational activities, not to mention good grub that lures travelers here year-round.

But come October, when the weather is beyond pleasant at 86 degrees, there are even more reasons to visit, including a free concert series that runs each week into October and features local bands and musicians, plus an art walk featuring works from over 30 galleries, a super spooky Scottsdale Zombie Crawl and an Oktoberfest celebration housed on a nearby train through the Verde Canyon. An afternoon spent at Butterfly Wonderland, home to thousands of species of butterflies and where you might be lucky enough to have one land directly on you, is another favorite activity of visitors.

Where to stay:

• Remodeled Home in Old Town Scottsdale (6 guests): $139/night
• Scottsdale Oasis with Heated Pool (6 guests): $195/night
• Southwest Villa in Scottsdale (5 guests): $164/night

10. Aspen, Co

• Why We Recommend It: beautiful foliage, great shopping, fewer crowds

In the know travelers seek out Aspen in October, generally known as “off-season” or “mud-season”. The fall is quickly becoming a more popular season to visit the mountain paradise as the weather is gorgeous, trees and leaves are changing colors and the prices are affordable compared to peak winter and summer months.

Rent an E-bike from Four Mountain Sports and cruise around town or take the bike on the 20-mile round trip pedal up to the Maroon Bells, one of the most popular destinations in the entire country. The Roaring Fork Valley (home to Aspen and Snowmass) was previously awarded a Gold Level Ride Center from the International Mountain Bike Association, meaning there are plenty of other roads and trails to check out if you’re big into mountain biking. Visitors to Aspen this time of year are also fond of The Rim Trail and the Ute Trail. Neighboring Snowmass has 90+ miles of hiking trails, and 2.8 million acres of adjacent wilderness to be explored, providing accessible and scenic hiking for any and all abilities.

And after a long day out on the trails, there’s lots to do in town, too. A swirl around Aspen’s impressive art museum is never a bad idea, as is a swirl around the handsome lobby bar at Hotel Jerome. Dinner at BOSQ for contemporary American fare is a highlight for most visitors to Aspen, as is a trip to Silverpeak Apothecary—a great dispensary with knowledgeable staff if you happen to be into cannabis tourism (yep, it’s legal here).

Where to stay:

• Adorable Aspen Condo ($4 guests): $437/night
• Charming Aspen Condo (4 guests): $353/night
• Deluxe Aspen Condo (6 guests): $642/night

11. Yountville, California

• Why We Recommend It: great art, lots of wineries, highly-rated restaurants

No matter what time of year you go, seeing Napa is quite the experience, but catching it in October—at the tail end of harvest, when grapes at many of the vineyards that make your favorite wines are being picked—is truly something else. Our perfect day in Napa in this season involves spending a sunny afternoon picnicking on the lawn of Domaine Chandon, the house that produces some of Napa’s best bubbly. (If you need a recco on which California Sparkling Wines to drink while there, our money would be on the Rosé Brut, Blanc de Blancs, and Etoile offerings). Chandon offers a plethora of tastings—both solo and guided—along with mixology classes, private cabanas on the lawn, and tree-covered, al fresco dining spots to soak in the sun as you enjoy the healthy, bright California cuisine coming from the kitchen. Menu items include charcuterie, hummus and crudités, cheese plates, seasonal sandwiches, and more.

The charming town of Yountville, steps from the Chandon property, is Napa’s crown jewel, and a Disneyland of food and wine. Within walkable distance, you’ll find everything from fine restaurants and tasting rooms to a spa and salon where you can get primped with a glass of vino in hand.

Where to stay:

• Yountville Villa (4 guests): $350/night
• Home in the Heart of Wine Country (7 guests): $300/night
• Charming Farmhouse (4 guests): $158/night

12. Cancun, Mexico

• Why We Recommend It: bustling nightlife, tons of outdoor adventures, great food

Dirt-cheap fares put the ’Cun at the top of our list this month when “rainy season” means you may see a cloud or two during the day. What that also means: Plenty of time still to enjoy the pool (and its swim-up bar), jet skiing or parasailing along the coast or spending a rather wild night out at one of Cancun’s many popular nightclubs. Whether it’s your first time or one of your favorite fly-in-for-the-weekend spots, it’s never a bad idea to organize a tour or simply hire a taxi for the day to take advantage of the region's incredible cenotes—natural sinkholes formed by a collapse of limestone that reveal gorgeous aquamarine water ripe for jumping and swimming in. During October, especially toward the end of the month, many resorts offer Day of the Dead cultural experiences. One of note and authenticity is the annual Day of the Dead festival, Festival of Life and Death, that happens in Xcaret Park, roughly a 75-minute drive from Cancun. It features concerts, ofrendas (or paper flower) making activities, and even access to Mayan healers, plus a whole lot of food.

Speaking of eats, back in Cancun, we recommend La Destileria and Tacun for authentic grub, and the immersive video dining experience—where the table you sit at is a giant video screen that is paired to take you through a multi-sensory, multi-course meal celebrating Mexican food—at La Joya. And while there are plenty of yummy Mexican bites to be had, when you’ve officially had your fill of chips and guac, consider splurging on Le Basilic, one of Cancun’s most celebrated French fine dining spots.

Where to stay:

• Ocean View Two-Story Penthouse (6 guests): $220/night
• Hopelchen Beach Getaway (6 guests): $80/night
• Ocean View Apartment on the Beach (6 guests): $145/night

13. Montclair, New Jersey

• Why We Recommend It: no crowds, artist hub, quiet getaway

Jersey is often the butt of a lot of jokes in the U.S., but the Garden State has some truly beautiful landscapes, seaside communities, mountainous enclaves and charming towns. One said town, Montclair is located about 45 minutes west by car from New York City and is an idyllic autumn destination if you’re looking for leaf-peeping opportunities and that small-town-meets-big-city charm. Filled with ex-Brooklynite families and lots of historical charm, this trendy community is packed with lots of artsy and cultural activities, like an afternoon at Montclair Art Museum. The nearby Van Vleck House & Gardens was built as a country estate for a prominent Brooklyn family in 1868, and seeing the Italian-style villa and its lush gardens—which feature a beehive and butterfly garden—can easily fill up an afternoon in town. The locals in Montclair are spoiled when it comes to food from distinguished chefs. It’s easily one of NJ’s biggest foodie destinations, with dining options Allegory, Turtle + the Wolf, Raymond’s, Laboratorio Kitchen and Faubourg Restaurant and Bar of note. It’s also home to Montclair Brewing Co., where craft beers are always being changed up so you can discover something new. At night, after the brisk fall air starts to turn chilly, you’ll want to consider checking out what’s on the marquee at the Wellmont Theater, Montclair’s entertainment venue where you can catch everything from comedy acts and live music to theater and drag shows.

Where to Stay:

• Duplex Apartment in Downtown (8 guests): $245/night
• Spacious One Bedroom Apartment (4 guests): $107/night
• SoHo-Style Townhouse (4 guests): $180

14. Vancouver, Canada

• Why We Recommend It: great shopping, gourmet eats, great nightlife

There’s so much to love about Vancouver that you’ll likely need to plan a return trip as soon as you board the plane home. A healthy mix of cosmopolitan life surrounded by lots of British Columbia’s natural splendors, it may sound a bit cliché, but this place truly has something for everyone. Start your day downtown, cruising through Vancouver’s historic streets of Gastown, now one of the city’s trendiest neighborhoods. Meanwhile, the lively Robson St. corridor is also packed with restaurants and shops worthy of exploring—and doubles as the home of “Terminal City” gay nightlife. Take a walk around Stanley Park and Jericho Beach to enjoy the incredible mountains that seem to surround the city at every angle, or get a little adventurous by walking across the Capilano, a 400-plus-foot suspension bridge among the trees that you have to see to believe. Vancouver also boasts lots of great clothing shops and one of the country’s finest is Holt Renfrew. Think of it like the Saks of Canada. Whether you’re there to blow the down payment you’ve been saving for a house or are just window-shopping in awe, it’s a beautiful department store that’s worthy of your time.

Where to stay:

• Crosstown Crib (8 guests): $250/night
• Brand New Three Bedroom Suite (6 guests): $279/night
• Modern Central Condo (5 guests):$189/night

15. London, United Kingdom

• Why We Recommend It: famous sights, lots of museums, vibrant culture

Jonesing for a trip to Jolly Old London Town? In this cosmopolitan city, even if you went and never saw the Tate Modern, St. Paul’s Cathedral, Buckingham Palace, London Bridge, or bothered to take a ride on The London Eye, you’d still feel overwhelmed with things to do. We’d recommend doing all of the mentioned, then taking a stroll through the fashionable Covent Garden and Soho neighborhoods, mingling among some of the best hipster culture Europe has in Shoreditch, and going on an Ab Fab-esque shopping spree in Knightsbridge.

And we haven’t even mentioned the premiere part of traveling here in October, besides the light leather jacket-appropriate weather: London Cocktail Week. A pass here—roughly $20 or less—gets you access to the U.K.’s biggest cocktail festival. We’re talking pop-up bars, immersive cocktail-making experiences, street food and more—basically, lots of vehicles to get a cocktail or good grub in your hands. If you’d prefer a more sophisticated nightcap, splurge on a night at Scarfes Bar at the Rosewood; the sophisticated, art-filled ambiance complete with live singers and piano players and cocktails inspired by some of your favorite musical acts will not disappoint.

And if you needed one more reason to consider London this month, besides cozy fall walks, you can consider attending the 2022 BFI London Film Festival will begin on October 5 to 16. Screenings are of course on the agenda, as are talkbacks, DJ parties and even a few crash-worthy red carpet galas.

Where to stay:

• Chelsea Charm in Historic Neighbourhood (5 guests): $219/night
• Spacious Apartment in Bloomsbury (5 guests): $262/night
• Spacious Two-Bedroom Apartment (6 guests): $195/night