September is hands-down the ultimate "shoulder season" sweet spot. The chaotic summer crowds have packed up, flight prices drop, and the weather gives us the absolute best of both worlds.

Whether you’re trying to hold onto summer forever, chase peak sweater weather, or sneak away for a cozy trip with your favorite person, I’ve got you covered. Here are the top spots to add to your September travel wish list!

☀️ For Warm Weather

San Diego, California — Avg temp: 65–75°F

I’d visit Coronado Beach and the world-famous San Diego Zoo! It’s warm, sunny, and much cheaper than summer school-holiday pricing. Plus, September actually brings some of the clearest, warmest beach days of the year without the oppressive heat waves.

Lets get you some Zoo tickets!

🍂 For Fall Vibes

Vermont, USA — Avg temp: 50–70°F

If you want early autumn foliage, crisp crisp mornings, and pure rustic charm, head to Vermont in late September. Take a road trip down Route 100, go apple picking at a local orchard, and grab fresh cider donuts. The maple leaves start turning brilliant shades of red and gold, making it the ultimate cozy getaway.

Let me know if you want to know about a sunset picnic cruise!

💕 For a Romantic Getaway

Santorini, Greece — Avg temp: 70–82°F

September in Santorini is pure magic. The scorching July/August heat cools down into perfect golden-hour weather, and you can actually walk through Oia’s cobblestone streets without bumping shoulder-to-shoulder with tour groups. Book a cliffside suite with a private plunge pool, sip local wine at sunset, and enjoy post-summer serenity with your favorite person.

Check out this PRIVATE 3 DAY Tour. 

Where Are You Traveling Next?

I’d love to hear which of these September spots is calling your name! Drop a comment below with your dream destination, or tag me in your travel photos over on Instagram @TravelsByVivi.

Don't forget to subscribe to the newsletter so you never miss a travel guide!

Safe travels and happy wandering,

💕 Your Travel Bestie

You Might Also Like