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How to Choose the Perfect Time to Take a Family Vacation

Updated: Nov 1, 2019

Determining the optimal time to whisk your family away for a life-changing adventure can infuse it with extra joy + serenity.

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While a huge factor in when you go on a trip is when you start planning, components of travel such as weather, best time of year to engage in various activities, school schedules and more, all play in to when you depart, and how long you’ll be gone.

Because Bailey is always angling for longer vacations, and Eric is constantly bringing her back to Earth with bank statements and school schedules, following are the steps we use to diplomatically select dates and time frames for our getaways.

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Research the best time of year to visit your destination.

A snowy pine forest that's best to visit in the winter

This one is pretty subjective, as there are multiple reasons for visiting a particular destination. For example, if you’re heading to Taos, New Mexico, you may want to go for the intense ski slopes, the mesmerizing fall colors, or enchanting walks through historic sites amid the warm summer breeze. Researching what your destination of choice offers during the various seasons will help you hone in on when you want to visit.

Decide the trip’s span.

Date book used to select the best time for a trip

When you’re figuring out how many days you can get away, do everything you can to give yourself at least ten. For many people, it takes a minimum of three days to settle into vacation mode, so when you’re in and out in seven, it’s easy to feel like you only got a long weekend’s worth of vacation. This longer expanse of time also gives you more freedom to craft an itinerary with ample down time and opportunities for spontaneity. With that said, we understand a shorter trip is sometimes all hectic schedules allow, and have had amazing adventures in under seven days.

You’ll also need to factor in your family’s unique preferences. For example, if you don’t have an abundance of funds for the trip, but have the desire for luxury accommodations, you may have to go with a shorter vacation. On the flip side, if you’re cool with staying in more budget digs and don’t need to eat out every day, you’re in a good place to stretch your trip by a few days, without busting that budget.

Examine family schedules.

Laptop, notebook and cell phone being used for family travel planning

Ready for another family meeting? Great. Gather the troops, instructing everyone to bring their schedules to the table. Together, look at school calendars, big events like weddings or graduations, or anything else that impacts when you can and cannot skip town.

Request the time off.

While money is the biggest hurdle some families face when planning an epic vacation, others have a tricky time getting enough time off to immerse themselves in a vacation that doesn’t feel like it's over as soon as it begins. But when you give yourself ample time (ideally 12 months) to plan and prepare your employers, colleagues, employees and your child’s school, you should be able to secure a solid chunk of time off.

Travel Savings Tip: If you’re looking to save big, and are comfortable letting the kids play hooky, taking an offseason vacation can often save you hundreds of dollars.

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