A few honest conversations ahead of time can pave the way for a fantastic vacation.

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Credit: Kalamurza Iryna

Intergenerational travel can be tricky—when you land in a new city, your favorite thing to do might be to get a cup of coffee at an outdoor café to take in the scenery, while your 5-year-old grandchild can barely sit still long enough to stop terrorizing the pigeons. Or you and your adult children might be adventurous eaters, wanting to hit every insider-only hot spot in town, while your teenage grandkids just want to order room service. It's no surprise that when you're traveling with a group, especially a group that may range from 9 months old to 90 years old, conflicts can arise. “It's important to think about the different needs of everyone in your group, so the more active members can run as hard as they want, while others can have a more relaxing pace—and everyone has a good time,” says Valerie Grubb, author of the new book Planes, Canes, and Automobiles: Connecting With Your Aging Parents through Travel. Try her tips when you're planning your next family getaway:

Discuss financial expectations beforehand.

Yes, talking money can be awkward—but better to hash it out at home than argue over the check while the waiter hovers uncomfortably nearby. “Before you leave home, discuss your budget and decide who will be paying for what during your trip,” says Grubb. If you offer to pay for your children's families' flights, for example, they may assume that also means hotel, meals, and activities, so it's better to make it clear in advance who's covering what.

Go over childcare expectations, too.

You love your grandkids—but that doesn't mean you want to spend your entire vacation inside the hotel with them while your adult children get to explore the destination. “Remember, it's your vacation too,” says Grubb. “Ahead of the trip, make a schedule or at least discuss with your children how much you're willing to babysit.”

Don't spend every moment together.

Even the happiest families need some space, and no one wants to feel like they're getting dragged around on someone else's dream vacation or constantly compromising to please the group (not to mention an indecisive group can spend a whole day just deciding where to have breakfast). “It's tough to be in constant contact all day, particularly in small hotel rooms,” says Grubb. “Before the trip, pick one activity or meal that you’ll all do together each day. Outside of those times, let everyone book his own activities to have some freedom and down time from the group.”

Pick a destination with activities for all ages.

“You want to make sure older folks and younger folks can each go at their own pace and do what's interesting to them,” she says. That could mean splitting up to explore, or making time for activities that are typically fun for all ages, like aquariums, zoos, boat rides, and interactive museums. One of Grubb's favorite all-ages destinations is Costa Rica, since adventurers can tour volcanoes, zipline through the clouds, and trek in the rainforest, while less active visitors can get a great geology lesson at Poás Volcano National Park; it also has a wheelchair-accessible visitor center and a paved trail that makes it easy for both wheelchairs and strollers to get a good view. Plus, Costa Rica is in the Central Time Zone, so you get to leave the country together without having to contend with much jetlag, which otherwise can throw off kids' sleeping and meal schedules and make for tougher travel.