Destinations: Four Seasons Hotel Firenze

My teenaged son Stevie and I have been slowly travelling the world since 2011. We left the U.S. and adopted a nomadic lifestyle because I wanted to infuse more life into our everyday living. After working in health care for a few decades, I began to notice a common theme from people near the end of their lives—regret. I decided I didn’t want to live a life full of regrets, and it was important to me to instil this spirit in my child.

As any parent with kids over the age of 10 knows, there is a difference between travelling with a younger child and doing so with a teen. When they’re 9 years old, everything is magical and exciting. At 13, things that used to really interest my son, for example, elicit little more than a shoulder shrug.

Fortunately, over the last four-plus years spent travelling from Asia to South America and beyond, our relationship has become quite strong. We tend to function as a team, and my son rarely hears the typical (and sometimes ineffective) reasoning of “I’m the parent, that’s why,” when it comes to our travel decisions.

Here, I’ve gathered some of my best tips and tricks for pulling off an excellent vacation with teenagers and making the most of your time together. A family holiday helps ensure you’ll get quality time and make good memories, but it will take some extra effort. From itinerary planning to packing to using travel to train your teens for their independent future, here are some of the things I’ve learned as a globetrotting parent.

Involve your teen in trip planning

Involving your teen in trip planning is key. My son and I recently collaborated on mapping out a trip to Europe, during which we went to Paris for my birthday and then visited a place on his list: the Pantheon in Rome. Photography courtesy Eustaquio Santimano and Gary Ullah

Even though your son or daughter will likely respond with a casual “whatever,” it’s important to include them in the trip planning process. Just like adults, teens want to be heard. And the more they’re involved in the early stages, the more likely they will be engaged and the less likely they are to complain during the trip.

This is also a great opportunity for kids to learn about compromise. My son and I discuss locations, things to do, costs, methods of transportation and so on. In fact, he usually picks our next destination himself. If either one of us has a particular interest, then we pay attention to that as well during the planning phase. For instance, this year we celebrated my birthday in Paris, and when we were in Rome, we made a point of visiting the Pantheon because it had been featured in one of my son’s favourite video games.

Use packing to teach accountability

Let teens be in charge of packing their own bags; it teaches accountability and the importance of planning ahead.

So many parents pack for their teen in a panic: What if they forget their toothbrush, their underwear, their iPad? But part of growing up is learning accountability. Will the world really end if they have to buy a new toothbrush or, heaven forbid, endure a morning with bad breath? (I see the self-proclaimed control freaks wincing at this notion.)

On the other hand, my son has a tendency to forget important items, which often ends up causing both of us some frustration. Packing is a great time to teach your teen the value of planning and generating lists. Sit down with your kid and have him or her come up with a packing list. That way, things don’t get left behind and travel days are much less stressful.

When they want to pack too much, just remind them they are in control of their bag, which means they will be carrying it through the airport, lugging it to the car, and pulling it into the hotel. If you are flying, make sure they understand that bags need to be under a specific weight. If they need to make adjustments, it’s better to let them make those decisions. It’s all part of the growing up.

Plan for downtime

Downtime is crucial for teens, even on holiday. They may want to hang out in the room all day, which means you can make the most of hotel amenities, such as the contemporary Australian cuisine at Mode Kitchen & Bar at Four Seasons Hotel Sydney.

Downtime is crucial for teens, even on holiday. They may want to hang out in the room all day, which means you can make the most of hotel amenities, such as contemporary Australian cuisine at Mode Kitchen & Bar at Four Seasons Hotel Sydney.When travelling with teens to a new place, there is an incredibly strong temptation to rush about and not miss anything. However, a jam-packed day of sight-seeing just doesn’t work for teens.

Most teenagers sporadically get into hermit moods when they need their space. You may want to spend time together, but your child will be happier with some time alone during the journey—or at least time when they aren’t constantly on the move.

When my son and I have had an all-day excursion or a few days with a lot of movement, I make sure to follow that up with a lazy day. Sometimes this means he stays in the hotel to relax while I go out exploring on my own, and other times I hang in the room with him, or we spend some time at the pool. On some lazy days, I’ll even order delivery or room service. At Four Seasons Hotel Sydney, for example, I certainly didn’t mind spending a day relaxing by the pool and sampling the fresh flavours at Mode Kitchen & Bar.

Deal with screen time

Fact: Teens are glued to their phones. Give a lesson in compromise by working with your teen to decide when and where screen time is appropriate while on vacation.

It can get frustrating always looking at your teenager’s face over some sort of electronic device. On holiday, some parents encourage their kids to leave their electronics at home. But I’ve found this is another opportunity to teach compromise.

Work out periods of time when screen time is acceptable. On the airplane, the train and long bus rides, why not let them disappear into their devices? It will make getting their attention much easier later on. For gamers, work with them to come up with times like these that are a win-win for everyone.

After all, it is their holiday as much as yours, and you’re never going to convince them to ditch the digital world entirely.

Photograph like a teen

I involve my son (pictured here diving with me) in all facets of travel. As a result, we tend to function as a team and have explored much of the world together. Photography courtesy Talon Windwalker

Your child may take 20 selfies in five minutes, but that doesn’t mean they will pose graciously for you when you want a family picture. Usually the first few times will be met with cooperation, but after that, expect “the look.”

If you have a surly teen, try to restrict the number of photos you take with them. Make sure they are really worthwhile shots, in worthwhile locations. Alternatively, you can invite them to join you in a selfie. This works better than other methods because they understand the value of selfies in social media, and generally are happy to lend their cool factor to your profile. It is even easier to capture a photo with your teen if you have them take the photo with their own device, allowing them to edit and post it on their own social channels.

Avoid repetition

On occasion, let your teen hang out at the hotel while you go out exploring. The rooms at Four Seasons Hotel Firenze, for example, are incredibly comfortable and can be a cultural experience all their own.

Teens don’t always share our penchant for history and culture. After spending a lot of time in South America with Stevie, I began to hear “More ruins?” in an exasperated tone. In Thailand, it was “Another temple?” After a few months in Europe—“I’m tired of churches and castles.”

Again, this is where compromise comes into play. If we spend a day doing mostly things I’m interested in, the next is all about him. While visiting Ecuador, we spent one day visiting cathedrals, churches, cemeteries and local markets—not exactly riveting attractions to a teen. The next day was his, and he opted for a lazy day, which meant we didn’t see the outside of our hotel room. At Four Seasons Hotel Firenze, he stayed at the historic hotel while I went out to see the sights. Other times, he will tag along and hang out outside the “boring” church/castle/temple while I go exploring.

Compromise with food

Don’t stress if your teen is not as eager to try new foods as you are. Even hamburgers and hot dogs can turn into memorable meals when ordered in other countries. Photography courtesy Verjus Bar à Vins (L); Photography Virginie Garnier (R)

For many adults, one of the joys of travelling is experiencing new food. Any time I’m heading to France, I dream of the fabulous wine, baguettes, cheese and crêpes. When looking at a menu with items such as tongue tacos, however, my son will sigh and tell people, “My dad will eat almost anything.”

Most of the time he can find something to satisfy his finicky appetite, but sometimes he just wants something that is familiar. While watching your teen eat macaroni and cheese in Thailand may make your inner foodie weep, give the kid a break and withhold that “but-you-can-get-that-at-home” plea on occasion.

It kills me when we’re in Paris, looking over a menu offering such tasty items as grilled stingray wing, and he picks a hamburger—but at least we can both enjoy the meal. Luckily, most places usually manage to add a local interpretation of even the simplest things, such as adding gourmet cheese or fresh bread to a hot dog.

Expect post-trip abandonment

Teenagers may run off to spend time with their friends once you return home, but they’ll always cherish the times you spent travelling together. Photography courtesy Thinkstock

Don’t take it personally when you return home and your teen quickly puts distance between you—it doesn’t mean they didn’t enjoy the journey. At this age, their world revolves around their peers. It’s all part of stretching their wings as they prepare to leave the nest.

I’ve had plenty of lovely talks with college-age adults who reminisce about how they complained almost non-stop during family vacations, but add that those times remain some of their favourite family memories.

Someday your kids will thank you. It may not be until they’re 23, but it will happen.