A Guide for Traveling During the Holiday Season & Top Holiday Travel Destinations

There’s so much to look forward to in the winter, from seeing family on the holidays to celebrating a new year with friends to finding the perfect gift for the perfect person. And now you want to take a winter trip, escape the cold of home or break out of a rut and experience something extraordinary.

Everything you need to make the most of your holiday vacation is right here.

Is Planning for Holiday Travel Different from Planning a Summer Vacation?

Yes and no. The two biggest peak travel times are during the holidays — generally from late November through early January — and when families are on summer break. Because of this, planning can be similar in that you have to account for higher prices of accommodations and activities, increased difficulty getting reservations, and more crowds.

However, it’s also different in that winter travel can pose additional hiccups. Snowstorms can cause more flight delays or cancellations as well as difficult road conditions. And whereas the summer rush might be spread over several weeks, a holiday rush at the airport, for example, is more likely to take place during a day or two.

All of this isn’t meant to scare you off holiday travel. Traveling in the winter offers opportunities you won’t find at other times of the year. Cold-weather sports, seasonal festivals, breathtaking winter scenery and holiday decorations in the streets can all make it worth the extra effort.

When Is the Best Time to Book Holiday Travel?

The general rule for holiday travel booking is to do it sooner rather than later. Yes, you can wait until the last minute to try to snag a great deal, but it’s also possible you’ll end up getting nothing instead.

Popular destinations will fill up quickly, making it difficult if not impossible, to find a hotel reservation, a vacation home in the location you want (or with the number of bedrooms you need), a table at the restaurant you’ve been dreaming of, or tickets to the show you planned on treating your family to.

If you’re not picky and are more concerned about scoring a good deal than getting a suite at the perfect hotel, you could wait until about a week before your trip. Just be prepared to adjust your plans and expectations.

Cost of Southwest Airfare, Indianapolis to Portland, Prior to Thanksgiving 2023

When is the best time to book holiday flights?

The best time to book a flight is always top of mind. When we talked about the best ways to leverage frequent flyer miles, we recommended buying tickets about a month before a domestic flight and three to four months before an international one.

When it comes to holidays, aim for the end of October. Much after that and you’ll find that flight prices increase the closer you get to Thanksgiving. If you’re flying around Christmastime, book early. It's incredibly rare for prices to dip in December, even as you get closer to the end of the month.

What Are the Busiest Holiday Travel Days?

At Thanksgiving, the busiest travel days are historically the Wednesday before and the Sunday after the holiday. There was a short-lived exception the year or two when travel re-opened after the pandemic, but trends seem to be rebounding back to normal.

TSA, which screened a near-record 2.56 million passengers on the Sunday after Thanksgiving in 2022, expects the busiest travel days to again be the Tuesday and Wednesday before Thanksgiving and the Sunday after the holiday.

For this year, we did an airfare search looking for the fastest Southwest flight from Indianapolis to Portland, Oregon. Let’s assume that the days that are most expensive cost more because of higher demand. That means the Sunday and Wednesday before Thanksgiving, both at $416 and nearly $70 more than Monday, could be particularly busy.

Compare that price to Wednesday, Nov. 15, a full week before Thanksgiving: $209.

Before the pandemic, some reports named December 17 as the busiest travel day, meaning travelers were hitting the road — or taking to the skies — one week before Christmas. Christmas Eve came in second.

With the holiday falling on a Monday in 2023, we wouldn’t be surprised if the two weekends before Christmas see particularly high numbers. For those with the flexibility to work remotely, December 15 and 16 could be prime days to fly, while those who aren’t able to be away for quite so long will still opt to fly the weekend prior to Christmas, on December 22 or 23.

Expect December 26 to also be a heavy travel day, so if you want to avoid the crowds and chaos, see if you can’t eek out one more day of vacation before heading home.

To get around the hassle of busy airports and roads, try to be flexible with your own travel dates. Maybe that means leaving a day or two earlier, and maybe it means you fly on the holiday. We know it’s less convenient, but that’s why it tends to be cheaper and less hectic.

Tips for Traveling During the Holidays

A little bit of preparation makes any trip go more smoothly. That’s never more true than when planning a trip during the holidays. You don’t have to — or even want to — schedule every waking minute of your trip, but a few hacks worked out ahead of time can be the difference between a happy holiday and a woeful winter.

1. Get TSA PreCheck.

The airport is a busy place during the holidays, and perhaps no area is more chaotic than security checkpoints (maybe the Starbucks line). Now might be the perfect time to finally get that TSA PreCheck, making it easier and quicker to get to your gate, even with increased holiday air traffic.

2. Ship holiday gifts.

Mailing your holiday gifts to your destination has two main benefits over packing them, especially if you’re flying. First, you don’t have to pack an extra suitcase or carry them through the terminal.

I’ve also had TSA unwrap presents when they couldn’t identify the object in the scanner. I understand why they did it, and it was fine. But as someone who kind of hates wrapping, it was a pain to do it twice.

Second, if your luggage gets lost or damaged, you won’t stress about if that perfect present you finally found for Great-Aunt Edna made it to Milwaukee in one piece.

3. Start a tradition with a special travel gift.

Among her tips for making your holiday road trip easier, former Seven Corners writer Ashley Fritz recommended creating a “road trip only” tradition of picking a special gift for the kids.

For Ashley and her sisters, it was the so-called Bug Juice their dad bought them at gas stations. For your kids, maybe it’s a new coloring book or game app for their phone. Or maybe you and your loved one treat yourself to a pre-flight mimosa.

4. Give yourself time.

Holiday traffic — at the airport and on the roads — as well as the potential for bad weather, over-sugared cranky kids who refuse to put their shoes on, and a host of other snafus can throw off your schedule.

The key is to manage your expectations, build in extra time to get from Point A to Point B, and avoid overscheduling with every activity you can think of. There’s nothing wrong with doing less on your holiday break, especially when it helps you restore your sanity and joy in the season.

5. Plan for the unexpected with holiday travel insurance.

Mishaps can happen any time of year, but their frequency can increase during peak travel season. Adding to that travel stress can be worry over making perfect holiday memories and more expenses, for both trip costs and other festive activities.

Travel insurance can help protect the money you spent for your trip if you have to cancel your holiday travels, if your luggage is lost or damaged, and more.

Unique Holiday Travel Destinations for an Immersive Holiday Season

We’ve written before about the benefits of giving the gift of travel. This year, though, why not take it a step farther and choose a destination with real meaning. Instead of visiting the same ski resorts, lounging on the same beaches, and ingesting the same food, capture the kind of experience that goes a little deeper.

1. See the Northern Lights from an igloo hotel.

When your travel bucket list includes (1) seeing the Northern Lights and (2) staying in an igloo hotel, combining them sounds like a nice holiday trip to gift yourself this year. December through March, when the skies are super dark and clear, is usually the best time to catch the Northern Lights. Book a stay at a northern resort with glass igloos — Finland's Kakslauttanen Arctic Resort and Bubble Hotel Iceland are some of the most popular — for a holiday you won’t forget.

2. Attend the Gulmarg Winter Festival in India.

Located in northern India, in Jammu and Kashmir, Gulmarg is sometimes known as the Switzerland of India. The city hosts an annual festival to showcase its winter sports and tourism as well as to preserve Kashmiri traditions in art and food.

3. Channel your inner Viking at Up Helly Aa.

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A year’s worth of planning culminates in this epic Scottish fire festival, described by some as a northern Mardi Gras, in Lerwick, Shetland Islands.

These fire festivals celebrate the region’s Viking heritage and the coming of the new year. You’ll experience a spectacle of torch-bearing, costumed locals who march through the streets in the middle of the night, eating, drinking, and generally enjoying life before ultimately setting a Viking ship ablaze.

4. Get sporty in Buffalo.

Buffalo, New York, might not sound like the most exotic locale on this list, but its location along Lake Erie makes it one of the best places in the world to try winter sports.

Go beyond traditional ice skating and test your skill at curling or ice biking, which uses bicycles retrofitted for “skating” as you pedal, at Ice at Canalside.

5. Explore an authentic European Christmas market.

Gift yourself the perfect souvenir and sample delightful foods from a European Christmas market. A market is a good chance to get an inside look at local traditions, support small businesses, and soak in the holiday spirit.

If a European adventure isn’t in the cards for this year, more and more American cities are hosting their own versions.

What Are the Most Popular Christmas Markets Around the World?

1. Budapest, Hungary

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Advent Feast at the Basilica has been named the best Christmas market in Europe three times by European Best Destinations. In addition to the typical food and artisan booths you find at these events, Budapest’s market also has a daily light show and, even better, invites charity organizations to be part of its program.

2. Tallinn, Estonia

To get the literal flavor of the Tallinn Christmas Market, you’ll need to sample local holiday cuisine — blood pudding and sour cabbage. If that doesn’t sound terribly appetizing though, know that you can always follow it with gingerbread and mulled wine, which is so popular this time of year throughout Europe. (Depending on where you are, this hot spiced wine might be called glögg, glühwein, or vin brulé to name a few translations.)

While you munch, peruse the glittering decorations and cozy winter accessories for sale. Tallinn’s temperatures rarely get above freezing in December, so a purchase might be in order.

3. Trier, Germany

Some credit the current version of European Christmas markets to early German Christkindlmarkts, so it’s hard to go too far astray with a stop at any fair in Germany. My all-time favorite Christkindlmarkt food — Baumstriezel, or strips of yeasty dough wrapped around and cooked on a spit, then rolled in sweet toppings — was found on the banks of Lake Constance.

Dubbed the Most Romantic Christmas Market in Europe, Trier features an ever-changing daily schedule of shows and performances, along with nearly 100 booths of treats and crafts. Keep your eyes open for the Mulled Wine Queen, too.

4. Zagreb, Croatia

Zagreb’s so-called Christmas market is actually 25 individual markets spread throughout the city’s main squares that have overflowed and melded into one large celebration. Each market also has its own theme, so there’s plenty to explore as you wander the streets of Croatia’s capital.

Be sure to look for hand-carved wooden toys from the Hrvatsko Zagorje region and Licitar, heart-shaped gingerbread cookies that are typically meant to be ornaments rather than food. Both are on the UNESCO Representative list of intangible heritage of humanity.

5. Bergamo, Italy

You aren't likely to find this on too many top 10 lists, but we couldn’t not mention the Christmas market in Bergamo, Italy, about an hour’s drive northeast of Milan. I’ve been to my fair share (and then some) of European Christmas markets and found this one to have the best community atmosphere.

Hot chocolate as thick as sundae sauce, handicrafts, fair rides for kids, and twinkling lights on every building, tree, and booth were the definition of “festive.”

Happy Holidays with Seven Corners

Whether renting an Airbnb with family or getting away with friends to another country, protect your trip and your health. Seven Corners provides travel insurance for nearly every traveler, wherever their winter vacations take them. Our team of licensed experts can help you choose the best travel insurance for you.