Should You Plan Holiday Travel Now?

“Many U.S. airlines have eliminated blackout dates and now make a large number of flights available to book with frequent flier miles, even during the holiday season,” says Julian Kheel, the founder and CEO of Points Path, a free internet tool that displays the points needed to travel alongside cash prices among flight search results. “That means it’s much easier than it used to be to redeem your miles for holiday travel.”

Like cash prices, the total amount of points needed to fly a given itinerary tends to rise and fall with demand. Kheel recommends searching for holiday flights to be paid in points at least 90 days before departure. If you book a flight with points, many airlines will refund your points should you cancel, which allows fliers to hedge their bets. In the event a points price falls, travelers can cancel the original booking and rebook at the lower rate.

Using points over the holidays might even score you an in-flight perk or two. “Holiday periods can offer opportunities to use points for extra comfort, as many business travelers opt out of flying during these times, potentially freeing up seats,” says Gilbert Ott, travel expert at Point.me, a search and booking engine that prices flight itineraries in points.​

4. Jump on lodging reservations

Many families use the holiday breaks to vacation and often travel to warm weather destinations such as the Caribbean and Mexico.

“We are seeing more and more multigenerational families — grandparents, parents and grandchildren — traveling together,” says Tully, noting that the quickest rooms to sell out from safari lodges to cruise ships are “suites that can comfortably accommodate three or four in a room, or which offer connecting rooms. So, if you’re planning on traveling with family, we strongly suggest booking well in advance to avoid disappointment.”

Even if you’re traveling solo or coupled, don’t wait. “If you book early, you can snag the entry-level rooms at a reasonable rate,” says Katie Carew, a New York City-based travel adviser with Travel Edge. “If you wait too long, you will be stuck with booking a higher category room, and you may not like the price tag.”

While beach resorts boom over the holidays, consider destinations in their low season for more space and tranquility. Ocean Edge Resort & Golf Club on Cape Cod, Massachusetts, began opening over the holidays about six years ago. “I often hear from holiday season guests that they visit to appreciate the calmer seasons of Cape Cod where they can admire the quiet beauty and nature that winter affords,” says Brendan Carey, marketing director for the resort, which uses the slower season to offer mixology workshops, wellness retreats and painting classes.

5. Unwrap gifts and buy Rockettes tickets

The holidays present unique travel challenges, starting with luggage. If you can, travel with just a carry-on bag that will remain in your control in the event of an airline snafu. Unchecked baggage should only contain gifts that are not wrapped because they may be inspected — and unwrapped — by airport security agents.

Once you know your destination, consider any activities you may want to do over the holidays — concerts, museum exhibits, light shows — and get reservations as soon as possible. “Book your restaurants ahead of arrival, as the popular restaurants often get booked very far in advance — particularly for prime-time seating,” says Zurbin-Hothersall.

Once gathered, put next year’s plans on the agenda. “My best suggestion this year during the holidays,” says Senora Kelly, owner of Missouri-based Paradise Travel Services, “is to sit down with family and talk about next year.”

Editor's note: This article was originally published on August 14, 2023. It has been updated to reflect new information.