Spring (April–June) and Fall (September–November) when the cities bloom and the autumn leaves turn Instagram gold. Summers can be hot and muggy, but this is still my favorite time to visit because I love sunshine! Winters can be, well, frigid.
Late fall to early spring (October–April) when humidity takes a vacation and hurricane season is safely at bay. Summers are hot and steamy, but hey, that’s what beaches are for!
Late spring (May–June) and early fall (September–October). Winter? Let’s just say unless you’re building a snowman, you might want to skip it.
Fall (September–November) and spring (March–May) when the desert heat won’t fry your flip-flops. Summer can reach serious oven status.
All year, depending on what you’re after! Spring and fall bring the best weather for cities and hikes, summer is glorious on the beaches, and winter is perfect for Northern California wine country.
Winter (December–March) for ski enthusiasts; summer (June–September) for hikers and national park junkies.
Alaska: Summer (June–August) for long days and mild temps.
Hawaii: Spring and fall (April–June, September–November) when it’s less crowded and still warm.
Embrace the road trip. Rent a car and hit the highways—some of the best experiences hide between the big cities.
Whether you’re chasing the bright lights of New York City or that off-the-beaten-path diner in Kansas, the USA makes getting there an adventure all its own. Touch down at the big hitters like JFK, LAX, or Chicago O’Hare—think of them as your travel launchpads. Domestic flights are everywhere, but if you want to take the scenic route, Amtrak’s long-haul train rides let you soak up the rolling hills, deserts, and small towns you might otherwise miss (pro tip: snag a window seat). For the ultimate road trip? Rent a car and get lost on Route 66, or take the Pacific Coast Highway—trust me, I’ve done it, and it’s worth every mile.
Ports like Miami, Los Angeles, New York, and Seattle welcome cruise travelers in style. You can dock in bustling cities, hop off for local excursions, and reboard with a sunburn and a smile. Popular cruise lines (Carnival, Royal Caribbean, and Norwegian) make it easy to start or end your journey by sea, perfect for those who want to see the skyline from a deck chair with a piña colada in hand.
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Confession: my newsletter is where the good stuff lives. Not the polished, edited-for-the-grid stuff, the “here’s the hole-in-the-wall I almost skipped” stuff, the packing lists I actually use, the “don’t book this hotel” warnings before you waste your money on them.
The newsletter is basically me texting you before a trip instead of after one. Sign up and you’ll be the first to know where I’m headed next, plus a few things I’ll never post here.
Link in bio if you want in. ✈️
Yes, it’s only July. Start planning anyway. Fall books faster than people expect, and a few of these destinations are worth getting ahead of. Here are five places worth putting on your radar right now.
Ireland: Cooler temps, moody skies, dramatic coastline fall was made for it. Tourist crowds drop, the green stays, and the whole country feels a little more like itself.
Great Smoky Mountains, TN/NC: Fall foliage in the Smokies is the real thing. The color peaks mid-October and the views from the ridgelines are hard to argue with. It’s also one of the most visited national parks in the country, so going on a weekday makes a real difference.
New York City: Fall is NYC at its best comfortable temps, the energy of the city shifting into a new season, and every neighborhood doing something worth showing up for. It’s also just a great walking city when it’s not brutally hot.
Japan: Fall foliage season is as good as spring cherry blossoms and somehow less talked about. The colors are dramatic, the temples and gardens are stunning, and it’s worth planning around peak dates by region.
Mystic, Connecticut: Small, walkable, genuinely charming Mystic in fall feels like exactly what a New England autumn is supposed to look like. Easy to pair with a broader New England road trip if you want to extend it.
Full guides linked in bio 🍂
There are two kinds of travelers: people who plan a trip and then figure out where to eat, and people who book a restaurant and then build the rest of the itinerary around it.I am the second kind. I will not apologize for this.
The reservation gets locked in first. The hotel search happens within the same 24 hours. The flights get compared around the restaurant’s hours of operation. The rest of the trip exists to fill the days before and after the table I actually came for.
If this sounds unhinged, I completely understand. It has also resulted in some of the best meals of my life, so I’m going to keep doing it.
Drop a 🍽️ if you plan your trips around food too.
Let’s talk about when to actually book that Dubai trip you’ve been pinning for two years. I get asked this constantly, so here’s the honest breakdown: October through April is your window. Anything outside that and you’re basically touring in a sauna!
October and November give you warm days and cooler nights, which is basically the sweet spot for wandering around without melting. December through February is peak season: gorgeous weather. March and April are the quiet insider pick, right before summer heat shows up and ruins everyone’s plans.
Saving this for later? That’s what it’s here for. Full breakdown linked in bio.
If you’re chasing energy, beaches, nightlife, and nonstop luxury, Dubai takes the crown. If you’re craving culture, iconic architecture, and meaningful landmarks at a slower pace, Abu Dhabi shines.🤍
My advice? Base yourself in Dubai and do Abu Dhabi as a day trip! The perfect balance of excitement and culture in the UAE.
Want the full breakdown? Check out my Dubai and Abu Dhabi guide for tips, itineraries, and must-sees!
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
