Want to Improve Your Relationship with Your Teen? Take Them on a Parent-Teen Vacation

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My 16-year-old son Jonathan and I are in that delicate stage of our relationship where nothing I do for him matters much and everything I say easily tunes me out of his life. It’s not fair because I’ve worked extra hard to always be an engaging dad, but such is life with a teen boy, and I’ve learned not to take it personally.

This fall a media executive friend of mine, Alberto Vasallo of El Mundo Boston, prodded me to come to Beantown with my son as his special guest. Knowing that this VIP invite would give me some much needed quality time with my son, I jumped at the opportunity.

Over the course of an artificial long weekend (my son had to miss one school day), Jonathan and I would take in a major Red Sox-Yankees game with prime seats, meet Red Sox great David “Big Papi” Ortiz, visit Harvard and take a history trip through Colonial Boston. In the process, my son and I got some special bonding time from two of the great things he and I most have in common: our love for sports and our passion for travel.

If you’re in a similar situation with your son or daughter, here are some tips on how to create a great parent-child vacation.

Keep the Conversations Light

As with most relationships, my son and I are navigating through some challenging moments in our lives, with each other, our peers and/or our colleagues. Even though I’m one who’s prone to trying to dig deep into what’s happening, I recommend that you don’t force your family trip to probe into everything.

If the conversations you want to have happen, let them take place as organically as possible. Certainly, it doesn’t hurt to try to talk about the things that matter, but be sensitive to the fact that your son or daughter may not want to talk about everything you desperately want to discuss.

Do What Your Child Likes

One of the most sacred ground rules of a parent-child vacation is to plan around their interests – and not necessarily any, or at least just very little, of your own.

During our trip to Boston, I made my son tell me what kind of food he most wanted (clam chowder) and we went out of our way to eat it every single time we could.

Unlike me, Jonathan preferred to sleep in on most days rather than eat breakfast, so I let him sleep and did breakfast on my own every day except the last one.

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Make it Memorable

The best way to make a trip memorable is to plan for it. Working with my friend Alberto, who in addition to being a major media personality in Beantown is also truly the unofficial Latino mayor of Boston, I plotted a trip that was as colorful as it was memorable. Jonathan and I walked Boston, rode Beantown’s subway system, got an insider’s tour of historic Fenway Park and met Big Papi. Hey, if that’s not a memorable itinerary right there, I don’t know what is.

Spare No Expense – within your means, of course!

I’m fond of saying that I don’t often go to concerts, but when I do…I get front row seats! The same principle applies to my vacation style. I work hard that when I do take time off I don’t want to count the pennies to experience what I toil so much to see.

During our trip to Boston I told Jonathan that barring any crazy requests, I would honor most of his travel wishes. During our stay we ate at some expensive restaurants, including one of Beantown’s best Sushi ones (Thelonious Monkfish) and I barely looked at the bills that I was signing because darn it, I wanted my son to know that I would spare little to no expense for him.

One of our most extravagant bills was for the Red Sox jerseys, caps and baseballs that we bought for the Boston game. It cost a pretty penny but hey, we weren’t going to go all the way to Boston from Miami and not totally fit in! It was totally worth it.

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