Why Shoulder Season Might Be the Best Time to Travel

Timing can make a big difference when planning a vacation. Traveling just outside of the busiest months can mean fewer crowds, better pricing, and still-great weather. Lynn Farrell of Windy City Travel recently shared why “shoulder season” is one of her favorite times to travel, along with a few clever travel tips every traveler should know.

What exactly is shoulder season?

Shoulder season is the period just before or after a destination’s busiest travel season. In Europe, for example, summer is typically packed with families, weddings, honeymoons, and vacationers from around the world.

Once Labor Day arrives, things begin to change. Kids are back in school, Europeans are back at work, crowds start to thin out, and prices often begin to drop.

When is the best time to visit Europe?

If your schedule is flexible, May and September are two of the best months to travel to Europe.

You can still enjoy beautiful weather, but without the peak summer crowds. Hotels, flights, tours, and other travel expenses may also be less expensive. Depending on the trip, traveling during shoulder season can save around 20% — and sometimes even more.

September is such a great time to visit that Lynn is heading to Greece with a group this month!

What are some easy packing tips that can make traveling easier?

Start by making your luggage easy to recognize. So many suitcases look alike — especially black ones. Add a brightly colored luggage tag, ribbon, or piece of tape so you can quickly spot yours at baggage claim.

Another simple tip is to take a photo of your luggage before you leave. If the airline misplaces your bag, you’ll have a picture showing exactly what it looks like.

What’s the “shoe in the safe” travel trick?

This is one of Lynn’s favorite tricks!

If you use your hotel room safe for your passport, jewelry, extra cash, or other valuables, put one of your shoes in the safe, too.

When you’re packing to leave and can’t find your shoe, you’ll immediately remember to check the safe — making it much less likely you’ll accidentally leave something important behind.

Should travelers keep a photo of their passport?

Yes. Before leaving home, take a photo of your passport and keep it accessible on your phone. Having a copy of your passport information can be extremely helpful if your passport is lost or stolen while you’re traveling.

Can you renew a passport online now?

Yes! Eligible travelers can now renew their U.S. passports online, making the process much easier than it used to be.

Some Windy City Travel advisors recently completed the online renewal process in less than 10 minutes and received their new passports surprisingly quickly. Just remember that processing times can vary, so don’t wait until the last minute before an international trip.

Is now a good time to book a cruise?

There are often excellent cruise promotions available as cruise lines work to fill upcoming sailings. Depending on the cruise line and sailing, travelers may find offers such as reduced fares, percentage discounts, second-guest savings, or promotions for kids.

If you’ve been considering a Caribbean cruise or another cruise vacation, it’s worth talking with an advisor who can compare the current offers and help determine which one provides the best overall value for your trip.

How can Windy City Travel help plan your next vacation?

From finding the right time to travel to navigating current cruise promotions and helping with all the little details in between, working with an experienced travel advisor can make planning easier.

Whether you’re dreaming about Europe during shoulder season, a Caribbean cruise, or somewhere completely different, the Windy City Travel team can help you find the right experience, timing, and value for your vacation.

Ready to start planning? Connect with the team at Windy City Travel and let our experienced travel advisors help turn your next vacation idea into an unforgettable journey.