How to Travel with Family (Without Whining like a Baby or Committing a Felony)

A year ago, my mother-in-law started talking about a family trip to the Big Island of Hawaii for everyone, that is, parents-in-law, uncles- and aunts-in-law, and siblings-in-law. She had used VRBO and found a house for all ten of us. One house. Four bedrooms. Two weeks. HAWAII.

It had the potential to be an amazing trip. It also had the potential to go wrong. The surest way to ruin a trip is to have interpersonal problems with your co-travelers. I had learned that the hard way the last time I’d gone to Hawaii. But this trip had two really big things going for it: (1) my husband’s family is way, way more relaxed than mine and (2) HAWAII.

The desire to go to Hawaii and good sense won out over my general hatred of family vacations (bred over years of sitting in the back of a family truckster), and off to Hawaii we went. We had a lovely time, and Hawaii is an amazing place. This, however, isn’t a blog post on how awesome Hawaii is; this is a blog post on how to travel with family.

Here are my tips and tricks:

• Remember that we’re all adults. It is so easy to revert back to well-worn parent/child roles when you’re on a family vacation, and for as much as children may become a little demanding, parents will forget their boundaries.

• Rent your own car. This is so, so important that it’s actually worth two bullet points. And look, I know your Aunt Susan has offered to pick you up at the airport and you can use your Uncle John’s car whenever you want, but please trust me when I tell you that these are well-intentioned lies. You are an adult, you can rent a car, and you should politely tell Aunt Susan and Uncle John that you really appreciate their generosity but that this is your vacation and you simply couldn’t impose and no, you will hear none of their begging and pleading, and yes, maybe it’s a waste of money (it’s not), but it’s your money to waste.

• Rent your own car. Really. Having your own car allows you to say things like, “I need to go to the grocery store,” when you need to have a cigarette, and “I’ll meet you there,” when you have had just about enough of your Aunt Susan’s whining, and “I’m not interested in going to the yarn museum; you can find me at the bar,” which is self-explanatory. A car allows you to escape and be an adult; it allows you to do things you are interested in, which will vastly improve your vacation experience; it provides you independence. That is SO. WORTH. the rental fee.

• Make sure you have your own space. Have a real conversation with yourself about what kind of space you need. No judgment, but familial relationships can be incredibly complicated. Do you need to find a different hotel from your family, or will being on another floor (or even simply not sharing a wall) be enough? If you find yourself saying, “It should be fine,” maybe think again.

• Surround yourself with people you like, and be honest with yourself about it, because, seriously, a family vacation where you’re sharing a house is NOT A GOOD IDEA if you have deep-seated family issues. Look, no place, however wonderful, not even Hawaii, is going to trump family drama. This isn’t the time to work on your issues. Just politely decline the trip if you can, and build in lots of extra space if you can’t.

• Speak up. If you don’t like Indian food, you need to say so before fifteen of you show up at a family-style restaurant. If you burn to a crisp at the beach, say that you need to get a giant umbrella and/or SPF 2000. If you don’t want to see a particular movie, say so and find something else to do. But above all, don’t ruin your vacation by not speaking up and ruin other people’s vacation by complaining viciously and moping around.

• Do your research and be a leader. Nobody likes to play the “What do you want to do today?” game. Have activities and points of interest researched so you can say, “I am going to check out the organic coffee farm. Is anyone else interested? I’m leaving in an hour.”

• Technology is your friend. Right up there with “rent your own car” is “make sure your Boomer parents can work their cell phones.” This will help tremendously with changes in plans, missed highway exits, and adorable local diners advertising fried mangoes that you just can’t pass up. Note: even if Boomers can work their cell phones day-to-day, make sure they have a base understanding of how to operate their cell phone once they’ve figured out how to hook it up to their rented car’s cool navigation system. (Not that I’m speaking from experience.)

• BYO Entertainment. No matter how well planned or how many things you’re interested in doing, coordinating a big number of people takes time, and you will have down time. Instead of stressing about it, just read your book.

• Debbie Downer wasn’t invited. For all that talk about boundaries and independence, this is vacation, and traveling in any group goes more smoothly when people are being agreeable. Go along for the ride when you can, and when you can’t, decline with a smile and an upbeat attitude. Every party has a pooper–don’t let it be you.