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Winter Holiday Getaways and Multigenerational Trips


Are you saying to yourself next holiday season will be different? A vacation to spend time together with family and build memories in a new place is what you are looking for. Thanksgiving and the month of December are some of the busiest travel days in each year.


If you've ever booked — or attempted to book — a family vacation during the holidays, you know you're going to want to have time on your side. With most children off from school and college, especially toward the end of the month, it's a popular time for family trips.

Multigenerational groups and large family trips take time to plan, so be sure to give yourself at least 12 months to book the trip. Popular resorts in the Caribbean islands, ski resort towns like Aspen, Colorado, or European Christmas markets book up a year or more in advance.


Hotels and airlines expect a seasonal rush of travelers during the holidays and typically raise prices to maximize revenue during this period. For example, a standard three-star chain hotel room, which usually starts around $250 to $300 per night in the low season, can jump to $700 per night and go up from there. I can't say this enough. The early bird gets the best and most affordable worm.


Pulling off the perfect multigenerational or large family vacation, start with a good plan. Start with a poll to gauge availability with all the travelers. Below are some of the questions our travel advisors will help you sort through.

  • How many days do I have available for PTO?

  • Are there restrictions from my work when or where I can travel to?

  • When are the kids off for break?

  • Are there weddings planned in our family's friend circle?

When planning a year or more in advance, not everyone will be able to give you a definitive "yes" — but as long as the majority of the group agrees, stick to those dates and start planning.

Next, think about the demographics of your group and where everyone calls home. Are the older family members generally in good health, or does someone have mobility issues? Will you need a destination and lodging that accommodates people using mobility aids like canes, walkers, electric scooters, or wheelchairs? How about the kids and young adults traveling with your group? Will you need baby accessories like cribs and highchairs? What about the self-employed family members or those who could be on call during travel? Will they need an office space with a computer and printer so they can work during the vacation? All of these elements will inform the type of destination and accommodations you need to book.


Any travel with complexity needs planning to ensure it goes as smoothly as possible. The bottom line is whether you want to book every element of your trip yourself or lean us, booking significant trips a year in advance or more improves the odds of you getting an affordable luxury experience.

Are you the one who always plans the trip? If your answer is yes, click here to schedule a planning call and we'll get started on your next holiday getaway!

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