Picking a vacation spot is usually the hardest part of any trip. You start with a big map and a million ideas, but then the reality of weather, flight costs, and “peak season” crowds starts to narrow things down. If you’ve ever booked a “dream trip” to Europe in July only to find yourself sweating in a line behind five hundred other people, you know that timing is everything.
The good news is that 2026 is looking like a fantastic year to get out there. Whether you want to stay in the States or finally use those passport pages, there’s a perfect spot for every month. Here is a guide to where you should be heading and when, keeping things practical for the average American traveler.
January: The Virgin Islands
Most of us are scraping ice off windshields in January, which makes the Caribbean the ultimate escape. The U.S. Virgin Islands (St. Thomas, St. John, and St. Croix) are a massive win because you don’t need a passport, you use the U.S. dollar, and the “winter” weather is a steady 80 degrees. January is just past the holiday rush, so the beaches aren’t quite as packed, but the water is still crystal clear for snorkeling.
February: Colorado
If you’d rather lean into the cold than run from it, February is when the Colorado Rockies really shine. This is the sweet spot for snow quality. Places like Breckenridge and Vail have a deep base by now, and the “champagne powder” is real. If you aren’t a skier, the après-ski scene in towns like Aspen is just as fun, with heated outdoor pools and great breweries.
March: New Orleans, Louisiana
March is arguably the best month to see the Big Easy. You missed the absolute chaos of Mardi Gras (which usually falls in February), but the spring festivals are just starting up. The humidity hasn’t turned the city into a sauna yet, making it the perfect time to walk through the Garden District or eat beignets at a sidewalk cafe without melting. The azaleas are in full bloom, and the energy is just right.
A Personal Note: I remember walking through the French Quarter on a Tuesday morning in March a few years back. The air smelled like jasmine and fried dough, and a brass band was practicing on a street corner with absolutely no audience but me. It’s those quiet, accidental moments that make New Orleans feel like a different world entirely.
April: Kyoto, Japan
April is “Sakura” (cherry blossom) season. Yes, it’s a bucket list item for a reason. Seeing the ancient temples of Kyoto framed by soft pink petals is something you have to see once. For Americans, the flight is long, but 2026 is a great time to go as the exchange rate remains relatively favorable. Just be sure to book your hotels months in advance for this one.
May: Washington, D.C.
Before the school groups take over in the summer and the D.C. humidity hits its peak, May offers a beautiful window of mild weather. The museums are world-class, most are free, and the city is incredibly walkable. It’s a great “middle-of-the-road” trip that feels patriotic and educational without being a bore.
June: The Canadian Rockies
June is when the turquoise lakes of Banff and Jasper finally thaw out. If you love hiking and mountain views that look like a Windows screensaver, this is your month. The days are incredibly long this far north, giving you plenty of sunlight to explore. Just watch out for the mosquitoes—they’re the size of small birds in the early summer.
July: The Amalfi Coast, Italy
Italy in July is iconic. It is hot, yes, and it is busy. But there is something about sitting on a balcony in Positano with a cold drink while the sun sets over the Mediterranean that makes the crowds worth it. To save some sanity, try staying in smaller towns like Cetara or Minori rather than the main hubs.
August: Portland, Oregon
While the rest of the country is suffering through an August heatwave, the Pacific Northwest stays relatively comfortable. Portland is a vibe in the summer. You’ve got the Rose Test Garden, endless food carts, and easy day trips to the Columbia River Gorge for waterfall hikes. It’s a low-stress domestic trip that feels like a real getaway.
September: Paris, France
“La Rentrée” happens in September. The locals come back from their August vacations, the city hums with new energy, and the weather is crisp and perfect for walking. The light in Paris during September is legendary—soft and golden. It’s much more pleasant than the sweltering heat of July or August.
October: Seoul, South Korea
If you want fall colors but are tired of the New England crowds, head to Seoul. The mountains surrounding the city turn brilliant shades of red and orange. The street food scene is next level (try the hotteok), and the mixture of high-tech skyscrapers and traditional palaces is fascinating. It’s a very safe, easy-to-navigate destination for Americans.
November: Sydney, Australia
As we head into winter, Australia is just starting its summer. November is the sweet spot before the intense December heat hits. You can hit Bondi Beach, take a ferry across the harbor, and enjoy the outdoor lifestyle. It’s a long haul, but waking up to summer in November is a pretty great feeling.
December: New York City
There is nowhere like NYC in December. The Rockefeller Center tree, the windows on 5th Avenue, and the holiday markets at Bryant Park create an atmosphere you can’t find anywhere else. It’s expensive and it’s crowded, but for a “grand finale” to your travel year, it’s the only place to be.
