By Andrea Khan Special to Published May 01, 2017 at 2:03 PM Photography: Andrea Khan

Greetings from Family Travel Week, sponsored by The Family Backpack, a new online guide that connects you to the best family travel blog posts. Enjoy seven days of family travel stories that will help you plan your next adventure, reduce pre-vacation stress and provide useful tips for once you arrive at your destination. Wheels up!

Before planning a vacation, I encourage you to take a morning coffee break, a date night or a casual, before-bed chat with your spouse, partner or yourself to determine your family’s top 10 – or top 5 – travel bucket list.

If you are more of a pen-to-paper type, go for it; otherwise consider starting a pin board on Pinterest to save your thoughts and then you can add to them in the future. Your list could be further divided into U.S. and international travel. Our family’s Pin boards can be viewed here

The number of people in your travel group and the ages of your kids are important when considering where you might go and when. New Orleans with a newborn might not be a marvelous idea, but New Orleans with older kids is totally do-able.

Our hope at The Family Backpack is to provide you with easy, searchable travel advice so you can make that bucket list happen. My family of five includes three kids, ages 9, 7 and 3, and we’ve learned a lot during our travels. We've experienced incredible memory-making moments and unexpected let downs and a lot in between – all of which we want to share with you.

Here is my step-by-step approach to planning the right family trip for my clan and hopefully for yours, too.

Determine a budget

The budget is the bottom line for any family vacation. According to the American Express Spending and Saving Tracker, 80 percent of Americans spent an average of $941 per person or $3,764 per a family of four on a summer getaway in 2016. Of course, families spend a lot more or less on their travel. is a great tool to use when calculating driving versus flying. After you provide basic information, it calculates the total cost of each, the time spent and even the CO2 impact. 

Decide on a location

This is usually dictated by the budget as well as the time of year which will affect the weather. We live in Wisconsin, so for us, spring break needs to be somewhere "guaranteed" warm to help us break up the long, long (did I mention long?) winter.

 In the summer, I think about friends or family we would like to visit or meet up with first to see what options might be there. I also revisit any places that my husband and I went to alone that we might want to share with our kids. 

After reviewing our bucket list, if the places don’t seem plausible due to budget or timing –Arizona in the summer is just too hot – I do random airline searches for sales. Southwest Airlines is usually my go-to airline to start with in the U.S. because I have found great deals through them. 

Now that our youngest is 3, we are starting to plan one big trip out of the country each year. Budget will continue to dictate where we go as there are so many locations that would be amazing, but it will come down to which one is the most affordable that particular year.

Looking for ideas or inspiration?

Check out The Family Backpack's Inspiration section.

Flying vs. driving?

Once I have decided on a location, I look at airfare prices first, as this is the biggest cost for us as a family of five. If we are road tripping, I consider stops we can make along the way to break up the car ride. Are there friends we could stay with for a night? Is there a site or attraction to check out along the way?

For airline travel, I again look at Southwest first and then I use Kayak to see how the rest of the airlines price out. A lot of the budget airlines like Southwest do not show up on Kayak thus the need for two searches. 

From there, I try two different searches, one from Milwaukee and one from O’Hare in Chicago. We are lucky to have two airport options to choose from.

My rule is if we are flying more than three hours and airfare is under $300 then I am almost ready to book. If airfare is over $300, then I try some other creative options like two one-way tickets instead of a round trip. This could be on different airlines. If none of that works, then I wait a few days and check again. 

I realize this isn’t very scientific, but it has worked well for me in the past.

This January, we got round-trip tickets to Cuba for $274 per person out of Chicago. Last January, our tickets to St. Martin were $264 per person. I have also found that airline tickets purchased too far in advance, unless there was a sale going on, are ridiculously expensive. 

I love direct flights, and that is my preference, but as my kids get older, I am less concerned about making connections. They are all fast runners.


Before I book airfare, I make sure that we have a place to stay, especially if it’s a busy travel time like spring break. Our first preference is to rent a house. All-inclusive resorts are great and sometimes you just need that. However, we like the personal space a house gives us, the privacy (you don’t have to share a pool with anyone) and the money it saves. Our go-to sites are AirBnB and VBRO. 


I haven’t personally tried it yet, but there is another site for family house travel called Kid & Coe. Their team has researched and handpicked kid-friendly houses across the world. Additionally, they provide you with insight from local parents on the destination you are traveling to. It’s a brilliant concept; however, take the reviews with a grain of salt because there has been some controversy on fake reviews being posted.

Another resource is This website focuses on helping families find kid-friendly places to stay, and it functions as a full-service travel agency (in full disclosure). I love the way they write their reviews of hotels and resorts. Each review includes topics like "Our Favorite Features," "What Families Should Know" and a system to highlight how well a hotel accommodates your kids’ ages.

Fun with the fam

Traveling with kids has made me realize it’s great to have a tentative itinerary, but it’s just that: tentative. You might not get to all of it, especially if you have any kids under the age of 10. But it is good to have a game plan and some things need to be booked in advance, especially if you are traveling during peak times like spring break or Yellowstone in July.

I always find it fun and entertaining to sit down with our kids and discuss what they want to do on the vacation. One of our favorite books to consult is "101 Places You Gotta See Before You’re 12" by Joanne O’Sullivan. It ranges from #1: A lighthouse to #70: A floating museum. We have gotten some great ideas from here. 

If you are traveling overseas and staying in an area for more than three days, I would recommend hiring a local tour guide for one day. I usually choose to do this on our second day. This helps provide a lay of the land and gives us additional ideas for things to do that we might not have come across otherwise – not to mention the wealth of information the guide provides. Some guides will even give you discounts into various museums and other points of interest. 

We recently tried a newer website called Mom-aboard. For $50, they will plan a seven-day itinerary for you that includes "Things We Know You Need" like insider tips, cultural nuances, kid-friendly restaurants, age-appropriate activities and doctors. There is a "Mombassador" in each city that has met certain criteria, including that she has kids of her own, who completes the itinerary for you after you fill out a survey. They are continuing to grow their reach around the world with 50 destinations to date. This is a service we will definitely use again.

There are plenty of great ideas here just search under Family Backpack Destinations.


If you are traveling out of the country, make sure everyone has a passport that is up to date. Every country is different, but many require that your passport is six months or longer from expiring.

Passports usually take 4-5 weeks, but there is a rush service. Always check the passport website to see what the processing times are in advance.

Wheels up!

What does "Wheels up" mean? Go here.

Andrea Khan Special to

Andrea Khan is the founder of The Family Backpack, and a kids and family content contributor at OnMilwaukee. 

She was born and raised in Wisconsin and first ventured out of the country to France in high school. That trip changed her life and she has been traveling every since.

Three kids, over 24 countries and 20 plus states under her belt she still has a lot of world to see!

She considers herself a foodie, participates in a CSA, hits her local farmers market and also has her own backyard garden.

When she’s not traveling or planning their next trip she enjoys reading, cooking and playing games like Rummikub with her kids.