How traveling with your family can be fun & rewarding

Among my greatest travel memories are trips with my family. There was the adventure to Page, Arizona, with my sister, Beth, to see Horseshoe Bend, Navajo Bridge, and Grand Staircase-Escalante National Monument. Just this year I spent five action packed days in New York City with my daughter, Jessica. And I’ll never forget the three days of trekking along the Cotswold Trail in England with my brother, Erik (see photo above).

And then there are the trips where I wanted to kill a family member. They shall remain nameless, but let’s just say I came really, really close to murder more than once.

Both types of experiences have informed this blog post. I hope these nine tips for traveling with family will help you plan memorable experiences and avoid conflict. 

First, discuss and determine your budget

Money is the source of many arguments and that certainly applies when it comes to traveling with family. Or maybe the better way to say it is that assumptions about money are the source of many problems. 

I may think splurging on a Michelin starred restaurant is worth every penny while someone else views this as wasteful. I have friends that spend large amounts on concerts, something I have no interest doing. Who is right and who is wrong? As long as you’re spending money you actually have, we’re both right. The issue is perception of how money is best spent and enjoyed.

Before you travel with family members (and this certainly applies to friends as well) have a candid discussion about your budget and what you typically are willing to spend while traveling. Or maybe more importantly, what you are not willing to spend. If your budgets are widely different, maybe this isn’t the right trip for you.

What happens when someone else is paying for the entire trip? The advice still holds, have a conversation about exactly what that means. Maybe mom and dad are covering the cost of a cruise for their kids and grandkids–a very generous offer. But if you need to fly you, your partner, and two kids across the country to get to the cruise, who is paying for that? Clarifying all major expenses before such a trip will prevent problems later. 

Discuss expectations before traveling

I find money is the biggest source of strife while traveling with family members, but number two is certainly expectations. If your idea of a vacation is rock climbing, mountain biking, and ziplining that may not meet the needs of your sister who prefers a morning by the pool followed by a few treatments at the spa. Could you combine these two types of trips? Possibly. But even before you start booking the flights and hotels, you’ll need to discuss how you want to spend your vacation. If you can’t come to terms it’s possible this isn’t the right trip for you.

Don’t do everything together

No matter how much you love your family members, you will all need a break from each other at times during your trip. I love to get up early and go for a walk when I’m in a new place. I usually follow this with coffee. My sister prefers to sleep in and meet up with me later in the morning. We’ve traveled many times together and know that we each need our time alone in the morning.

If you’re traveling with a larger family group, let it be known that there are times when the entire group will eat or sightsee together and other times when everyone can figure out their own meal or schedule. Don’t plan an itinerary expecting togetherness 100 percent of the time, this is a sure fire way to be miserable.

When there are young children joining the group, consider a dinner or two with just the adults and take advantage of children’s programs or babysitters. Adults are entitled to a break from restaurants that serve kid meals and the frequent attention required by babies and toddlers.

For larger groups, consider cruises or all inclusive resorts

Last year Jason and I had the opportunity to cruise through the Greek Islands which was marvelous. But it also reminded me how fantastic cruising can be for a large family group traveling together. Cruise ships cater to a wide range of interests. The buffet meals mean there is something for everyone to eat. A range of daily entertainment keeps kids and adults occupied during the day. Cabins of different sizes and placement are perfect for singles, couples, and families and can even accommodate different budgets.

All-inclusive resorts offer something similar, but on land. For anyone uninterested in being on water, a good all inclusive will also provide plenty of food and activity options. We took our kids to an all-inclusive in Jamaica when our daughter was 15 and our son 12. Not only was there something for all of us to do, but it was easy to do things both apart and together.

Finally, a cruise or an all-inclusive resort allows everyone to have a clear understanding of the total cost of the trip up front. While that initial cost may seem high, it will include accommodations, food, entertainment, and sometimes drinks. That can be difficult to budget when it’s pay as you go. 

Take differing abilities into account

Intergenerational travel has been growing by leaps and bounds. Grandparents want to travel with their kids and grandkids. I love this trend. However, there are some challenges that you may need to address first.

Grandma and Grandpa may be fit and active, or they may face health and mobility limitations. If the mobility is seriously limited, it may impact the choice of destination. European cities are no doubt charming but they also feature cobblestone streets that can be difficult to walk on, hotels without air conditioning, and ancient attractions without elevators. Do some research before your trip. If anyone of any age in your group has limitations then try to determine how you’ll manage. 

A common but less considered issue can be neurodiversity. A child–or an adult–in your family may have autism or something similar. Crowds and loud noises could derail the trip for them. A cabin near a lake in a serene forest may be a far better option than an amusement park or other packed attraction. 

Take dietary restrictions into account

For three years I was a vegetarian. More recently I traveled with a friend who must eat a gluten-free diet. And on a few occasions I’ve traveled with folks with very serious food allergies–the kind that require an EpiPen. While dietary restrictions won’t necessarily impact the choice of destination, they will inform where everyone eats.

Be aware of the dietary restrictions of your group. That way you won’t suggest the Texas BBQ restaurant for dinner when your niece is a vegan. Or, maybe that’s a good time for everyone to eat at different places. 

And ask the folks with restrictions to help research restaurants in advance. We live in a time of endless online information which can be very helpful when it comes to selecting your next meal. It is possible to find a place to eat that will make everyone happy.

Involve everyone in the planning

Ok, I’ll admit, this one is hard for me. I love to plan travel. Needless to say, I’m pretty good at it and usually don’t want much input. But not allowing family members to participate in the planning is always a mistake. But let me remind you, do this after you’ve reviewed the budget and expectations.

My daughter, Jessica, and I had an amazing trip to New York City in January. I had a long list of things to do and she had an equally long list of restaurants to visit. It turned out to be a good combination. I ate many delicious meals at places I would not otherwise have tried and she was exposed to a few of the city’s gems not previously on her radar.

Don’t overlook kids in this planning. Assuming they are old enough to understand the planning process, definitely give kids some input. Ask them to do some research about where you’re going and suggest a couple of attractions they would like to see. 

Set aside judgment

Anytime families get together there’s the potential for judgment–said or unsaid–to sneak into the gathering. Vacationing together makes this even more likely. But that’s a quick way to derail the trip.

If Uncle Bob shouldn’t be smoking, but sneaks out for a cigarette occasionally, now is not the time to address it. I’ve no doubt his immediate family has brought it to his attention many times. And if your sister-in-law doesn’t make the kids eat everything on their plate, keep quiet. They are her kids and she doesn’t need anyone else commenting. 

I’m not saying it will be easy, but avoiding judgment it will decrease the likelihood of conflict. 

Things will go wrong

Whether it’s a delayed flight, a traffic jam that makes you late to the show, or a trip to the emergency room, the reality is things sometimes go wrong while traveling. Often it’s your reaction to the problem that determines the ultimate experience of the trip.

When something goes wrong, take a deep breath and calmly consider your options. Set an example for everyone in your group. A calm person is more likely to get help from a customer service agent. A few kind words and a smile go a long way to putting everyone at ease.

(And I would be remiss if I didn’t remind you of the importance of travel insurance, especially in the case of international travel.)