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How to Vacation with Friends

2019 January 8

I think that one of the coolest things we have given our kids is the gift of traveling with friends. Don’t get me wrong, I love my parents and they have traveled more of the world than most people I know (including me), but I only ever went anywhere as a child with them and my sister and I think my kids are really lucky that we choose to travel with friends so much and so often. Not only does it give them companions their own age to hang with, it allows us to explore new places that we might not if we only traveled as a nuclear family, it lets us cut costs here and there, and it keeps everyone – old and young – entertained and engaged on a different level.

We travel with friends often and just got back from another week away with two other families we adore and it got me thinking of the tips and tricks that have worked with us and our nomadic gang of “family friends”, as we call them, that others might find useful. If you don’t avidly travel with friends, here are some things to think about when you do (because you should!):

Pick your traveling buddies wisely. Traveling with families is more complicated than a solo girls or boys trip because you have to be able to manage and enjoy so many different personalities. The adults, the kids, even the dogs (if you are traveling with me and it’s within driving distance…Luna is always on board). You need to give careful consideration to the families that you can truly travel with and be honest with yourself if some of your friends just aren’t that type. They can be great dinner party friends instead. Look to book adventures with people that you truly believe you can not only live with, but dine with and hike with and beach with and be yourself with…otherwise, it’s no vacation.

Book separate accommodations. All that said, even if you are traveling with some of your favorite people in the world, when it comes to group trips, you need a little space. If you are sharing a house, make sure it has plenty of room – indoors and out – for people to break away when they need to. Otherwise, opt for separate but neighboring condos or hotel rooms so everyone can enjoy some solitude when they need it. And make sure to respect the signs when someone needs their space or has to tend to a child who needs theirs. You can’t take anything personally when traveling with friends. If you do, see above. You picked the wrong ones to go with. Oh, and always one bathroom (minimum) per family. Always.

Plan a few solo activities. Maybe you appreciate a spa day while your girlfriend would rather shop. Perhaps your kids want to go to a museum and their buddies prefer the beach. Or maybe you just need a night off from the big crew and want to get in some quality time with your nuclear tribe. Make sure you discuss as a group and plan for a few solo blocks of time ahead of your trip so that everyone has a chance to a) get a break from the group dynamic and b) check off their own personal must-see list without having to worry about keeping everyone happy.

Use Splitwise. This easy app makes it simple to keep track of group expenses throughout the trip and then divide it by couple, single or group at the end of the trip so no one gets stuck with one massive dinner bill or that extra three rounds of drinks inadvertently. Make sure everyone downloads it ahead of time and commits to using it throughout the trip.

Make it fun! Seriously, it is so cool that your kids (and you!) get to travel with friends so keep that spirit going when you are abroad. Let the kids have sleepovers in each others’ rooms or condos. Take turns hosting family dinners to give yourselves a break from eating out – and the cost of it. Take video and pics (the one above is of my son with two buddies in Lake Tahoe last week) and create a shared album so everyone can keep them. The memories and the people making them – both big and small – will be worth hanging onto. I promise.

Did you know? I share my favorite family-friendly (yet always cool) hotels and destinations on Instagram @_neverleaving.

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