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  • Melissa Lipari

How To Plan A Family Vacation

Updated: Jun 19, 2022

Planning Your Family Trip: Organization, Scheduling, & Booking

One of my favorite aspects of travel is getting to share the experience with loved ones. It ignites a bonding experience that can be relieved for years to come. I’ve traveled abroad with my extended family and have had hundreds of local trips with my parents.

Whether you have a clan full of people or are just traveling with your immediate family, it’s important to have a guideline of where to start and how to get yourself and your family prepared for an environment that you all might not be familiar with.

It might sound simple, but the first step is to plan all aspects of your destination. It’s pivotal to sit down with your family members and block out the days you’ll be going on your trip. We all have different work or school schedules, making it difficult to get together at times.

But if you’re planning a trip, especially one overseas, you want to make sure that the dates align for everyone. You might not be able to visit this place again- make sure you make the most of it! Getting on the same page with excursions, arrival and departure dates, and lodging are key elements of success that we will cover today.

How to Plan a Family Vacation.
How to Plan a Family Vacation.

Get Organized with a Group Calendar

With a family calendar, everyone can put in the dates that they’re working, have appointments, social gatherings, etc. to block out for booking. From personal experience, the more people who are involved with the trip, the harder it is to get an agreed-upon arrival and departure date. Instating a group calendar can get the organization process going without one person needing to keep track of everyone’s schedules.

Google Calendar

The Family Setting on Google Calendar makes it simple for you to add the Emails of your loved ones so you can collaborate in one space. All you must do is add your events to the calendar and everyone can view them.

Once you see a window of mutual free time, you can begin scheduling your trip! I even use the Family Setting when correlating trips with friends, too. The older we get, the less free time we have. Why not use an app that can track exactly what days

work for each person?

Get organized with Google Calendar to keep track of your family’s schedule
Get organized with Google Calendar to keep track of your family’s schedule

Schedule Activities in Advance

So, you’ve found a week where you can all come together for a vacation, awesome! But what are you going to do during your stay? If you’re going to a nearby city, you might want to visit places that are less tourist-based, since you could probably visit this place again. If you’re traveling overseas, you might not get a chance to come back. These are things you want to weigh when preparing group activities.

Airbnb Experiences

My favorite way to find activities for the entire family is through Airbnb Experiences. Let’s say you want to find a balance between over 21 and under 21 activities, Airbnb has you covered!

You can check out tours of famous parks, museums, etc. from locals, book a bar crawl, or try an experience that your hometown doesn’t offer. All your activities will live on this app, making it simple to access. Stay tuned for Pedacitos Tours- a similar service that we will be launching soon!

With Airbnb Experiences, all your tours and activities will be booked in one space.
With Airbnb Experiences, all your tours and activities will be booked in one space.

Booking Your Stay on a Budget

You’re organized, have your activities planned, and now you’re ready to book your family trip! Except, this can be pricey. We have “The Best Online Travel Resources” as a part of our Pedacitos Tips series. This can be a great checkpoint on where to find the cheapest flights and lodging. However, there are services specifically for family stays that can be a lifesaver.

Southwest Vacations

If you’re taking a trip to a spot in the U.S., Mexico, or the Caribbean, Southwest Vacations could be a great place to find an all-inclusive stay. I took a trip to Cancun with family, and Southwest Vacations was simple and effective to use when finding a package for 10 people.

Not only do they give you a list of participating hotels and resorts- but they also offer suggestions for activities and how to include them in your existing package.

If you’re looking for something all-inclusive, Southwest Vacations can be a great help for large families
If you’re looking for something all-inclusive, Southwest Vacations can be a great help for large families

5 General Rules of Thumb

Your schedules are cleared, your activities, flights, and lodging are booked- and now you’re counting down the days! But before you go, let’s discuss some general rules of thumb when it comes to traveling with family.

As much fun as it can be to share this time with loved ones, you have to prepare for things to possibly go awry or for unforeseen circumstances. To ensure your trip goes smoothly, let’s chat about some common aspects to keep in mind, as we round this article out.

Give Yourself (and Your Family) Time

When you’re traveling solo, it can be easy to just get up and go. But when you’re factoring in people of all ages- you need to give everyone time to get to the airport, to an activity, and virtually anything you might do. Instead of booking things back-to-back, make sure you leave time for some wiggle room.

Try Not to Overpack

I know this is easier said than done as I’m a serial over-packer, but I learned this tip the hard way when my entire family was dumping their suitcases on the floor of the Philadelphia airport before our flight to Bogota, Colombia.

If you’re traveling internationally, try to repurpose your outfits, accessories, etc. so you’re not bringing more than you’re allotted. You also should factor in gifts or anything you might buy on your trip. The weight limits at airports can be difficult to prepare for, as all scales vary, so it’s better safe than sorry to leave your luggage with some emptiness.

Don’t Be Afraid to Splurge a Little

Whether you’re doing a family camping trip, going to a new country, or just taking a short road trip, I think it’s important to have a budget that works for everyone. With that said, it’s okay if you all don’t stay consistently on a monetary schedule. I’ve always created a spreadsheet to monitor holiday spending but give yourself some extra money for yourself (or your loved ones) as a treat. Souvenirs are always a great idea!

Things Might Go Wrong... and That’s Okay!

Let’s be real- when you’re traveling with a large group, something is bound to go off-schedule. Someone might lose something, get sick- the likelihood of something wrong occurring is almost impossible to avoid. With that said, it’s okay to factor that into your planning. Accepting these things early on will save you a lot of stress in the long run.

Enjoy the Moment and Have Fun!

At the end of the day, you’re making memories with your family that will last a lifetime. Live in the moment and have the best time. Whether you’re planning this vacation as a family reunion or yearly occurrence, make this experience special.

My motto has always been, nothing at home matters when you’re on vacation. You won’t be able to get this time back, have the time of your life.

Enjoy your Family Vacation to the fullest
Enjoy your Family Vacation to the fullest

We hope this blog gives you some helpful tips regarding your next family stay. Whether you’re stumped on how to book for a family-friendly budget or what kind of activities would be fun for the whole family, we’ve given a baseline for your next family trip. Enjoy yourself and spend this much-needed vacation with loved ones!


Want to know more? Are you interested in becoming a contributor for Pedacitos? We'd love to hear your stories! Send me a message and I will get back to you!

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