Trip Planning

Family Vacation Planning Simplified: A School Year’s Worth of Travel in 6 Easy Steps

Paris is a perennial family favorite

The weather is turning cooler, lunches are made each morning and the kids are out the door. You finally have some uninterrupted time to get your family organized for the coming year. Back-to-school season is the perfect time to proactively plan your family’s precious vacation days and lock in key travel dates before other commitments fill up your calendar. Here are six steps you can take to plan your 2019-2020 school year vacations now. 

Family Vacation Planning 2020
Kids always enjoy a visit to the Leaning Tower of Pisa!

6 Steps to Family Vacation Planning for the Coming Year

Gather 2019-2020 school calendars and block out key dates.

This is the very first thing I do when the kids head back to school. We have children in different schools, sports and activities, so it is critical to get a full view of all of our commitments for the year. Gather up all the schedules for academics, sports and activities, highlight free time in your family calendar, and then check for overlap or gaps. Are there key sports tournaments or recital dates that you can’t miss? Where do you have some flexibility? Are there commitments you can decline in order to make a bucket-list trip or a long weekend getaway possible? Asking these questions will help you get a broad view of your time for family travel and where you can carve out breaks.

Family Vacation Planning 2020
Amsterdam is a perennial family favorite

Schedule a family vacation planning meeting.

Get your kids involved in the planning. Traditionally, after the dust of new school schedules settles, we plan a family dinner where we talk about our breaks for the year. What new places do we want to explore? Where in the school year will we need a sunny break or time to unplug and recharge? Who do we want to travel with? Our kids are now 15 and 11, so they are much more vocal about their opinions and equally busy. We also have just a few summers left before our oldest heads off to college, which makes planning these trips even more important to us. 

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Family Vacation Planning 2020
No trip to Vancouver is complete without a stop at the Capilano Suspension Bridge

Determine your 2020 travel budget.

What have you earmarked for your travels for the year? Once your family has a good view of the time you have to travel, you need to understand what you have to spend. In our family, the travel line item in our budget is one of our most important and largest discretionary spends. When was the last time you sat down to do your budget and included vacations in your financial planning? Making travel a part of your annual financial planning helps determine how much you can afford to travel, where you can go, and most important, how you can save for those bucket-list trips. 

Family Vacation Planning 2020
The Galapagos Islands are among the hottest destinations for adventure-loving families

Check fare sales and sign up for airfare alerts.

Planning ahead will save you money. In the fall, we start tracking airfare for our key dates for the year. This is often the most significant expense of a trip, and it has the most variables and likelihood of costing more the longer we procrastinate. If you have school-age children, especially middle or high schoolers, it becomes increasingly difficult to pull kids out, which leads to less flexibility. You will most likely need to travel during peak times when everyone is traveling, which means higher fares.

If you are traveling abroad in 2020, you should have airfare booked for big summer trips by the end of 2019 for best rates. October is also a great time to lock in mileage rewards and take advantage of airfare sales. Don’t forget to check those miles and companion fares for expiration dates!

Family Vacation Planning 2020
Looking for an under-the-radar European getaway? Belgium calls!

Leverage a travel advisor to put the whole year together.

Time is one of our most precious commodities. If you don’t have hours to search online, consider outsourcing your 2020 family vacation planning to an expert who can recommend where to go, where to stay and once-in-a-lifetime travel experiences for your family. Ciao Bambino Family Travel Advisors are experts in pulling together everything from a sunny spring break getaway to a spectacular trip your family will remember forever.

We’ll match you with an advisor who will reach out to set up a time to talk over your wish list and how we work. They can brainstorm destination ideas with you, design a custom itinerary or simply book a resort, villa or hotel stay for your family. Ciao Bambino luxury family travel planning services empower families to enjoy meaningful experiences and collect lasting memories.

Family Vacation Planning 2020
Put a helicopter ride over San Francisco on your family bucket list

Learn to say no so you can say yes to precious family time.

We only get 18 precious years to spend time with our kids under our own roof. Make the most of it and be unwavering in your commitment to carve out this time to travel together. There will always be another soccer game or another invitation to participate in an enriching opportunity on which you worry your kids will miss out. Say no to those extra commitments and say yes to plugging in together — it gives everyone permission to step off the hamster wheel of the school year for a moment, deepen your family connection and raise more compassionate, culturally aware kids with no regrets. They will thank you for it.

Relevant Links:

18 summer vacations to take before your kids grow up

We’re feeling the love! Praise from our 2019 family travel planning clients

10 family vacations that will change kids forever

10 great places to take kids … while they are still kids

Editor’s Note: Photos courtesy of the individual families pictured.

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