Planning Ahead for Holiday Travel

When it comes to holiday travel, the early bird almost always wins out. But don’t despair if you’ve waited until the last minute. Here’s what the pros advise. 

A dangerous misperception about holiday travel—especially for major holidays like Thanksgiving, Christmas and Easter—is that most people are visiting family so cruises, resorts, and tours will be offering great deals.

“Nothing could be farther from the truth,” said Lisa C. Deal, VTA, CTA, owner, Deal Travel and Cruises. “By mid-September, many of the most desirable resorts and flights are sold out (for Christmas break) and have been for a long time.”

The best time to book is at least six to nine months in advance, advised Helen Prochilo, owner, Promal Vacations. “Pricing for the holidays is always high but demand this year is far higher than it’s ever been, so budget accordingly.”


Experienced travelers often book their trips for the holiday season in January, February and March, said Dave Hershberger, VTA, CTC, CBTS, president, Prestige Travel. “They know that the longer you wait, the more you pay for airfare, hotels and everything related to travel. For example, an airline fare of $300 in June will likely be $700 in October.

Book your activities in advance, as well.

Don’t count on finding a nanny or booking tee times, popular dining spots, spa treatments, or activities like yacht charters and diving once you arrive, cautioned Kristin Chambers, CTC, founder & lead travel consultant, D.A. Luxury Travel. “When our clients book a holiday trip after October 1, we make sure the activities they want are not sold out before finalizing their accommodations.”

Most travelers head for tropical beaches, theme parks and ski slopes over the holidays, but it’s also a memorable time to go farther afield. Chambers took her family to Ireland one year. “Our children saw the castles and churches lit up, heard traditional Irish Christmas music and saw how some local traditions mirrored ours and others were different.” 


Another common misperception is that there will be discounts if you wait long enough. “Increasingly vendors avoid that precisely because they don’t want to train people to wait until the last minute,” Hershberger noted. “Especially for major holidays, prices rarely drop.”

In the rare case that a vendor does lower their price, they may let you rebook at that lower price if you ask, he said. “Travel advisors try to stay on top of price changes so that if you book a holiday vacation in February and there’s a price drop in July, you won’t lose out. The big exception is nonrefundable airfares.”


If you can’t book at least six months in advance, be prepared to spend more and be flexible.

“If you are set on a specific resort, you’re likely to be disappointed. But if you are flexible, we usually can find you a great alternative,” said Hershberger.

Laurel Brunvoll, CTA, founder & owner, Unforgettable Trips, agreed. “Recently, the resort my clients had in mind was fully booked, but I found them a much nicer resort on a different island, with VIP amenities, nonstop flights, and for a lot less money!”


Travel advisors’ hands-on knowledge and connections also can keep you from making a trip-altering mistake like heading to a destination during its rainy season, said Jillian Everhart, VTA, owner, Ever Ready Travel. “I’ve been to over 50 countries, attend educational sessions, and partner with in-country suppliers all around the world to stay current.”

“The internet doesn’t vet suppliers, we (travel advisors) do,” Hershberger added. “We know which vendors are unreliable and which resorts are having problems. Plus, we have clout because of the volume we book, so vendors are going to prioritize pleasing our clients over individual travelers. Clout also gives us access to upgrades, better rooms, and more value-added extras for our clients.”

Equally important, your travel advisor is there for you when things don’t go as planned.

Deal had sent two couples on a European cruise and learned they were about to miss their flight home due to a delay at the port. “Before they even called to tell me, I had arranged a hotel and changed their flight to the next day,” said Deal.

A fact of life for holiday travel is lines and crowds, Deal noted. “Airports are packed; car rental lines are long…  Be prepared, stay calm and roll with it. It’s all worth it to be somewhere special for the holidays!”

By Geri Bain, travel journalist & editor


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