Places to Vacation in September

By VI | Disclosure: I use affiliate links

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If you want fewer crowds and perfect weather, I always suggest traveling in September. It’s my favorite time of year to plan getaways. You’ll find places to stay in September with incredible views, better rates, and that peaceful, in-between-season charm. Honestly, it feels like one of those travel secrets I almost don’t want to share—but it’s too good not to.

Where I’ve Traveled in September (and Think You Should Too)

Explore the New England coast – I love going before the leaf-peeping crowds arrive. Towns like Kennebunkport and Rockport feel extra serene this time of year, and the seafood is still top-notch.
Wander through Italy or Greece – I’ve strolled cobbled streets and dined al fresco in weather that’s still warm but not sweltering. The crowds have thinned, and everything just feels a bit more relaxed.
Relax in wine country – September is harvest season in California’s Napa Valley and Oregon’s Willamette Valley. I’ve watched grapes being picked while sipping wine on sunny patios. If you love vineyard views and fall flavors, this is your time.
Discover cooler temps and quieter trails in the Canadian Rockies or national parks like Glacier and Yosemite – I’ve hiked under golden aspen leaves and felt like I had whole views to myself. The lighting this time of year makes everything feel extra vivid.
Enjoy tropical bliss in Hawaii or the Caribbean – I’ve found lower prices and warm water in September without the summer crowds. Whether I’m snorkeling, reading on the beach, or just chasing the sunset, this month always delivers.