There’s a Little Secret Seasoned Travelers Know
Hi friends,
There’s a little secret seasoned travelers know: the “best” time to travel isn’t always the most popular one.
Shoulder season and low season trips can quietly deliver some of the most meaningful, comfortable, and surprisingly joyful travel experiences out there. Fewer crowds. Better value. More breathing room. And often, better weather than you might expect.
Let’s start with “fun in the sun” destinations.
Fall travel to warm-weather spots can be exceptionally well priced. Kids are back in school. Holiday travel hasn’t ramped up yet. Resorts and hotels are more relaxed. Flights tend to be more reasonable. And you? You get the same turquoise water and golden sunsets—just without the peak-season buzz.
Late fall is especially lovely in places like Cabo. The days are warm and bright, but not scorching. Even better? Whale watching season begins. There’s something quietly magical about being out on the water and spotting a humpback whale breach in the distance. It’s the kind of moment that feels bigger than a vacation—it feels like a story you’ll tell for years.
And then there’s Europe.
Spring and fall are arguably Europe’s sweet spots. The weather is often mild and cooperative—cool enough for walking cities all day without melting, warm enough for café tables and open windows. Gardens bloom in spring. Vineyards glow in autumn. Markets feel local instead of rushed.
The biggest gift, though, is space.
You can actually step into a museum without being swept along by a crowd. You can linger in a village square and hear the church bells instead of tour group headsets. Restaurant reservations are easier. Guides have more time. Locals feel less overwhelmed and more present. There’s room to notice things—the smell of fresh bread drifting out of a bakery in Florence, the way light hits the stone buildings in Prague at dusk.
And often, the pricing reflects the season. Flights and accommodations tend to be more affordable than peak summer. It’s not about chasing a deal—it’s about finding that sweet balance where experience and comfort meet.
Africa’s low season might be one of the most overlooked opportunities of all.
Many travelers assume there’s only one “right” time to go on safari. But low season can be extraordinary. There are significantly fewer people in the parks, which means sightings feel more intimate and unhurried. You’re not jockeying for position at every lion sighting. You’re simply there—watching, waiting, absorbing.
Landscapes are often lush and green after seasonal rains. The light can be dramatic and beautiful for photography. And yes, pricing is typically much more favorable. In some cases, even single supplement waivers appear during lower-demand months, making it more accessible for solo travelers who don’t want to wait for a companion to say yes.
There’s also something special about traveling when a destination feels like it’s exhaling. When it’s not bracing for the next wave of peak-season visitors. When you can move at your own pace and connect more deeply with the place itself.
Shoulder season and low season travel aren’t about settling. They’re about shifting perspective.
Instead of chasing the calendar’s most popular dates, you’re choosing conditions that support curiosity. You’re choosing comfort over chaos. You’re choosing space—to wander, to notice, to savor.
And sometimes, that space is exactly what turns a good trip into an unforgettable one.
Your Globetrotting Friend,
Joy