FEATURE STORY
Summer is almost over. And honestly? Good.
If you've followed me for a while, you know I barely travel in the summer. And when I do, I stay away from the popular spots. There's a reason for that. Everyone is traveling to the same places at the same time. It's crowded, it's chaotic, and you're paying the highest prices of the year for the privilege.
Here's the thing most people get backwards. Peak season isn't the best time to travel. It might be the worst.
Now that summer is winding down, this is the window I actually wait for. Fewer crowds. Lower prices. A better experience all around.

Take this summer as proof. Europe just went through one of the worst heat waves on record. Western Europe had its hottest June and July ever. France and the UK broke national temperature records. Spain, France, and Italy fought serious wildfires. And here's the part a lot of Americans forget. Much of Europe doesn't have the air conditioning we take for granted. So if you had booked that dream summer trip, you might have spent it sweating through a heat wave with nowhere to cool off. No thanks.
So what changes when summer ends? Almost everything, and in your favor.
The prices fall off a cliff. Right after Labor Day, domestic flights drop around 25 to 40 percent off their August peak. Europe drops even more, sometimes 30 to 50 percent. Hotels come down 20 to 40 percent too. There's a sweet spot between Labor Day and late October where the summer rush has died down but the holiday rush hasn't started. That gap is where the deals live.
And the weather? Still great in most places. The crowds thin out the second school is back in session. Same destinations, half the people, a fraction of the cost.
One heads up though. This secret is getting out. More people are catching on to fall travel, so those shoulder season discounts are shrinking a little every year. Translation: this is a book it now thing, not a wait until next year thing.
Here are a few places that shine right now.
Spain. Once that brutal summer heat breaks, Madrid and Barcelona are perfect. Warm days, cool evenings, and far fewer tourists.
Portugal. Lisbon and Porto are gorgeous in the fall. Still sunny, still golden, minus the summer mobs.
New Orleans. By October the temperature settles into the 70s, festival season is back, and hotel rates drop. The French Quarter actually feels livable again.

So many choices
One important note before you book any of these. Pay attention to the calendar and the forecast at your destination, not just at home. The weather might be perfect where you live but rough where you're headed. And local holidays can quietly spike prices and crowds. A five minute check saves you a ruined trip.
Now, I'm not just preaching this. I'm doing it.
I've got a trip coming up. I won't say where just yet, but you'll see soon. And I basically paid nothing to get there.
Here's how. I kept my options open and tracked a few different destinations on Google Flights instead of locking into one. When I spotted a place that was cheaper than usual, I jumped on it and booked the flight with my Chase points. My older points still redeem at the higher 1.5 cent value, so between the cheap fare and the points, my out of pocket for the flight was basically zero. The accommodation was a steal too. A full week, nice and relaxed, for next to nothing.
I broke down the whole points move in a past issue. If you want the step by step, read it here.
So here's what I want you to take from this.
You don't have to travel when everyone else does. In fact, you probably shouldn't. Wait a few weeks. Let the crowds go home. Then go have the calm, cheaper, better version of the trip they just fought through.
That's the end of summer reset. And it might be the best travel decision you make all year.
What's stopping you from booking a shoulder season trip this year?
Recommendations
THE PLUG

✈️ Cheap Flights

🛟 Insurance

🎒 Travel Gear
The Backpack Everyone Notices
Your backpack says a lot before you even say a word. Find the newest Sprayground collection and start the school year your way.









