Family in Costa Rica

How to Plan a Family Vacation Everyone Will Enjoy

Family in Costa Rica

Families are the original brainteasers. Their individual parts can be combined in many ways, but they don’t always fit together perfectly. It takes time and energy to sort out who connects best with whom… all the more so when a family is traveling and spending much more time than usual in one another’s company.

Of course, figuring out how to plan a vacation with family is tricky. But crafting a good time for a family– with its range of ages (especially in a multigenerational group) and interests, and tricky dynamics – can be even more challenging. Just remember, the benefits of traveling with kids make it worth the trouble!

To help the process along, here are nine key tips on how to plan a vacation that everyone on the family will enjoy, as identified by many family travel experts:

1) List Your Family Interests

Think about what you would like to do, alone, in small groupings and as a full family. Then ask your family members to do the same. This can be an individual exercise, and then you can compare all your notes together.

Two important results are likely to emerge. First, if there are lots of overlapping interests, then you’ll know precisely how to make the best use of your group time. Second, you’ll have all you need to help decide where to go. If everyone craves warm sun and soft sand, then don’t bother with the sparkling glaciers of Patagonia!

2) Set a Budget (and a Division of Cost)

On a family holiday, no one is happy when they’re stressing about money. So don’t count pennies. Come up with a reasonable travel budget (per person, per day, or for the total amount) and plan around it.

During budget discussions (especially among a multigenerational family travel group) you may discover that one generation– often the grandparents– is willing to shoulder a larger financial burden than others. This may increase the overall budget or help ease the stress of an expensive plan. Having clarity about who is responsible for what (and paying for it directly) can also help you avoid post-trip arguments.

This is where booking a trip organized through a tour operator like International Expeditions can save travelers a lot of time and trouble. Since the vast majority of expenses are included in the cost of IE’s tours, unexpected financial outlays are minimal.


3) Look at the Calendar

It’s time to find time! Look at your individual agendas, think about the season and weather, and lock in your travel dates. This can be hard, especially when school and work commitments limit your wiggle room. Prepare to make some sacrifices.

And consider this: Travel during calendar holidays is costly. When schools are out of session, most people hit the road, so high-season premiums usually apply. A better idea is to travel during low season. The crowds are thinner, availability better and the rates more affordable. But yes, it may mean missing some school!

That’s for the lucky few who hit the road at all. Unfortunately, according to Project: Time Off, 55% of the American workers surveyed left vacation days unused in 2015. Don’t be part of that unfortunate statistic!

4) Create Your Itinerary

What activities are actually available in your chosen destination? In what order should you take them in? Develop an itinerary and activity calendar that takes into account everyone's particularities. If your family group includes people who move at different clips (toddler pace, grandpa speed), take that into account.

Here again, booking a trip through IE can save a lot of headaches and hassle. Simply pick your destination and either choose one of our organized itineraries or allow us to customize one to suit your family’s needs.

Don't cram too many activities into one day, especially for the full group. In fact, build in downtime for everyone, alone time for people who need it (naps for little kids, screens for adolescents, sports TV on weekends) and couples-only time for pairs who will be grumpy without it. To ensure sufficient buy-in, make everyone part of the planning process, especially the kids. If their opinions are heard and honored, they're more inclined to hear and honor others' desires.


5) Lock in Critical Reservations

One more advantage of working with International Expeditions’ Travel Planners? Reservations — from accommodations to guides to activities — are handled for you. Not only does this make the planning process less problematic, but it often ensures lower prices than booking independently!


6) Check Your Important Documents

No one wants to get caught out at the last moment. Are you traveling overseas? Does everyone have a valid passport and any required visas? Satisfy and document the immunizations and insurance you need, especially for kids and seniors.

Will anyone be driving? Do they all have valid licenses (and credit cards, in the case of rental)? If an international drivers license is recommended, get one! Will there be any parents traveling with kids, but without a spouse? Make the effort to secure a permission to travel letter or similar affidavit.


7) Leave Time for Packing

Last-minute packing is a desperate art. Avoid it if you can. That means reviewing luggage weight/size restrictions and costs in advance, and determining how to deal with them.

If choosing small carryon bags, you must pack light, which can force tough choices. This is especially true when traveling with small children or seniors unable to manage their own bags.

If you require extra gear– for sports, young children or family members with special needs– make sure to account for it. Contact your travel providers, accommodation and anyone else who should know.

8) Be Flexible

In short, plan for plans to change along the way ESPECIALLY if you are in a country like Cuba, where life travels at a different pace!


9) Collect Memories

Live your vacation fully. Don’t hide behind a camera or in social media.

But also don’t forget to chronicle your experiences, for yourself and your friends who love to see how you lived it up!

It just might help convince them to step away from their desks and enjoy some family adventure time together, too.


As a writer, Ethan Gelber has agitated tirelessly for responsible/sustainable travel practices, family travel, a focus on keeping things local, and quality and relevance in publishing and destination marketing. He started The Travel Word blog and is editorial director of the Family Travel Association.