We’re excited to bring back our monthly ‘Where to Visit’ column, sharing top destinations and chic boutique hotels to match each month. If you’re craving a last-minute getaway before October wraps up, check out our recommendations below and start planning your escape before fall fades into winter.
Santorini, Greece
With its unmistakable limestone white-washed buildings and cobalt blue domes set against the sparkling sea, Santorini is always memorable. Still, few travelers consider visiting beyond summertime. The famed sunsets are particularly awe-inspiring this time of year, and it’s still warm enough to spend afternoons along the waterfront or on a boat. Plus, without the scorching temperatures, visitors can more comfortably spend time outdoors, whether hiking the caldera, uncovering ancient ruins in Akrotiri, or sipping crisp Assyrtiko at a local vineyard.
Why visit in October? In peak season, hordes of tourists flood the beaches and make walking the narrow streets of Oia and Fira nearly impossible. However, once the chillier fall winds creep in, the crowds begin to clear and travelers will have unmitigated access to the island’s chicest hotels, most coveted restaurants, and top sites.
Where to stay: Since opening earlier this year, Domes Novos Santorini already stands out from the locale’s boutique accommodations – literally and figuratively. Expect pinkish-hued façades inspired by Santorini’s volcanic sand beaches. Minimalist interiors evoke the island’s essence through modern Cycladic artistry. The well-appointed villas and suites offer refined spaces for relaxation and rejuvenation, with private Zen pools mirroring the tranquility of the Aegean Sea.
Mexico City, Mexico
Mexico City—perched 7,349 feet above sea level, making it one of the world’s highest metropolises—is a vibrant hub of design, cuisine, and culture. A must-see is the Frida Kahlo Museum, housed in her iconic cobalt blue home, showcasing her life and artwork alongside Diego Rivera’s pieces. For a dive into the city’s fashion and art scene, head to Colonia Roma—CDMX’s creative heartthrob—then stroll down Calle Colima, lined with independent boutiques and galleries featuring work from Mexico’s top designers and artists.
Why visit in October? With Day of the Dead celebrations kicking off in late October, planning your trip at the end of the month guarantees front-row seats to the festive El Día de los Muertos parades that take place throughout the city until the holiday ends on November 2.
Where to stay: Casa Polanco is a beautifully restored Spanish Revival mansion that resides in the chic Mexico City neighborhood of Polanco. The 19-key stay boasts spacious suites, classic retro furnishings, and antique Mexican artworks.
Puglia, Italy
Puglia, Italy’s sun-soaked heel, becomes a captivating autumn escape with its blend of history, charm, and natural beauty. Stroll the winding streets of Alberobello and Ostuni, where the iconic trulli houses pop against fall’s golden hues. For food lovers, the season offers fresh seafood, handmade orecchiette, and locally harvested olive oils and wines—especially around the olive harvest. Visit medieval castles like Castel del Monte, explore Romanesque churches, or join local festivals. Whether you’re relaxing on Polignano a Mare’s beaches or exploring the countryside, Puglia’s autumn magic leaves a lasting impression.
Why visit in October? With off-season pricing, you can enjoy luxury stays at a fraction of the cost while experiencing authentic local festivals and food tours in mild temperatures—allowing you to soak in the warm hospitality that defines Puglia.
Where to stay: At Tenuta Negroamaro, the tranquility of nature meets the rich heritage of Puglia. Inside its minimalist rooms, guests discover a harmonious blend of traditional and contemporary architectural styles, offering a secluded haven amid the seven-hectare estate along the Ionian side.
Sonoma County, California
Sonoma County is part of Northern Californian wine country; its acclaimed food & wine scene plus picturesque rolling hills comprising top-notch vineyards are just a few of its famous hallmarks. Just 30 miles north of San Francisco, tourists will find over 425 wineries, towering redwood forests, and inviting small towns such as Healdsburg or Petaluma between county lines. This gem-like California stretch of land is a must-visit spot if you’re a wine connoisseur and food enthusiast.
Why visit in October: The weather couldn’t be more ideal in Sonoma County during the month of October, with temperatures in the mid-to-high 70s—perfect for frolicking through wineries aplenty.
Where to stay: Harmon Guest House offers 33 eco-chic studio-style guestrooms just steps from Healdsburg Plaza. Committed to sustainability, the hotel features recycled furnishings and uses harvested rainwater for irrigation. Guests can enjoy California’s autumn warmth at the vibrant indoor-outdoor rooftop bar while sipping some of the region’s best wines.
Morocco, North Africa
Nestled at the crossroads of Europe and Africa, Morocco blends ancient traditions with vibrant modernity. From the bustling streets of Marrakech to the serene Sahara dunes, this North African gem is rich in history, flavor, and hospitality. Savor traditional Moroccan cuisine influenced by Asian, African, French, and Italian cultures. Relax in Essaouira, a charming coastal city known for water sports and handmade goods, or explore Casablanca, Morocco’s largest city, alive with nightlife and stunning architecture.
Why visit in October? Morocco is the fall getaway you’ve been dreaming of. Experience the vibrant harvest season with flavorful dishes like harira, roasted chestnuts, spiced meatballs, and stuffed squash.
Where to stay: Riad Jardin Secret is a lush sanctuary featuring seven uniquely designed rooms, each infused with rich Moroccan elements and a blend of traditional charm.
Ridgedale, Missouri
Ridgedale, Missouri, is a hidden gem for East Coasters accustomed to the Hamptons and Nantucket. Nestled near the Ozark Mountains and Table Rock Lake, it offers a nature lover’s paradise with activities like hiking, biking, wildlife watching, kayaking, and golfing. Explore nearby state parks, such as Table Rock State Park, for scenic hikes, or visit Branson for more attractions. If you prefer a more leisurely pace, enjoy local festivals and farmers’ markets that celebrate Ozark culture. Ridgedale is an ideal destination for outdoor adventure and cultural experiences.
Why visit in October? As summer fades and peak leaf season arrives, Missouri’s mountains are transformed into a vibrant tapestry of red, orange, and yellow. It’s the perfect time for fishing and hiking, as well as enjoying Ridgedale’s festival season, which celebrates the local harvest with delicious food and family-friendly activities.
Where to stay: For an authentic mountain getaway, check into The Ozarker Lodge, an alpine-chic retreat located just a 15-minute drive from the heart of Ridgedale in Branson.
New York City, New York
New York City is one of the most exciting places to visit in the fall, buzzing with even more energy than during peak tourism months. From New York Fashion Week to Central Park’s vibrant autumn foliage, art festivals, and crisp, comfortable weather—perfect for embracing autumn fashion trends—fall showcases the city at its best. A true cultural melting pot, whatever you hope to discover—or eat—is always within reach during this breathtaking season.
Why visit in October? Throughout October, New York fully embraces Halloween with Upper West Side brownstones decked out in spooky decor and events like the iconic Village Halloween Parade.
Where to stay: The Hotel Chelsea, built in the late 1800s, is an iconic creative hub that has housed legends like Janis Joplin, Bob Dylan, Patti Smith, and Mark Twain. After a chic makeover and reopening in 2022, the hotel now offers high-end aesthetics and expensive cocktails while retaining its rock-and-roll spirit.
