Are you ready for a family vacation?

Flying Squirrel



If you’ve spent the holidays in the company of extended family and everyone is still speaking to one another, you may be thinking: We should do this more often.

If your house is full of grandparents, siblings, cousins and children, it might be worth discussing whether your family would like to travel together in the future—as in, take a vacation together, multi-generational style.

There are many good reasons for considering this. When on vacation, extended families get to know each other better. Kids have the opportunity to spend time with and learn about their grandparents. Mom and Dad can use the time away to enjoy a respite of their own.

There are several options to consider if a group vacation sounds appealing.

Resort cabins with a common dining area are one possibility. Growing up, my extended family would often vacation this way.



With this approach, you’ll have cabins around a recreational lake with a main dining hall where everyone gathers for meals. You’ll often find these properties in the Midwest or Northeast. Googling “family resort lake” is a good starting point to explore this option.

Depending on the size of your group, you might also consider looking for a large house rental. We’ve done this in locations such as Martha’s Vineyard, Yosemite and Colorado’s ski country. Again, an online search with your destination (e.g., “Yellowstone”) and “house rental” will get you started.

You may not have meals or activities included with this approach, so if doing your own cooking isn’t appealing, you might consider an ocean cruise for your multigenerational family vacation. The variety of accommodations and activities makes this an especially popular option.

On a cruise ship, you have stateroom categories in a range of prices. If everyone is paying their own way, inside cabins can be budget-friendly, whereas the grandparents may opt for a larger suite with more amenities.

Many ships built in the last two to three years also have expanded the selection of adjoining stateroom options, which makes it easy for larger groups to stay close and share a common area.

Activities on a cruise ship can also appeal to a wide variety of tastes. The family might choose to do one excursion together as a group, then leave the rest of the week free for everyone to venture off on their own. Those who want a more relaxing, low-key experience may also choose to enjoy the ship’s activities.

For extended families looking for a beach vacation, all-inclusive resorts in the Caribbean, Mexico and Central America can be a nice option. Again, you have a variety of accommodations, with oceanview rooms at the higher end of the budget range and garden/ resort-view rooms at the entry-level. Look for family-oriented resorts that also have great programs for the kids.

How to get started in planning your family trip?

The first step is to decide where you want to go, what you want to do and when everyone’s available. Whether it’s Alaska, Hawaii, the Mediterranean or one of America’s national parks, make sure everyone agrees on the choice.

The second step is to make sure your destination fits everyone’s budget range. When estimating costs, include not only the accommodations, but also airfare, food and activities. A good travel professional can help you ballpark these numbers so you have a starting point for the discussion.

Lastly, make sure everyone agrees from the start. If a family member has hesitation about the group’s choice—especially one who has “veto power”—it’s better to discover that upfront, before you do substantial work and put down deposits.

I’ve seen instances of a group trip falling apart because one family member didn’t speak up in the beginning, instead waiting until the final payment was due to announce they didn’t like the choice. At that point, the rest of the group is forced to decide if they’ll still go on the trip, even if it means creating friction within the family.

If your family enjoys spending time with each other, the memories of a group summer vacation can be a gift that generations will long remember.

Thor Challgren is a travel writer who lives in Thousand Oaks. Email questions to