Having teenagers in the house means we’re immersed in our fair share of pop culture. Despite my best efforts to trim the fat in our family budget and cancel our monthly subscription to Apple Music, the kids keep insisting that we really do use it and need to keep it. So to excessively maximize this subscription, we’ve gone to streaming music for hours on end in our house. Well, funny things happen when your ears become a bystander to popular pop music…You hear a few tidbits that are actually appealing to you as a fully functioning (at least most of the time) adult — Who knew? For me, it’s the trendy competition among current popular singers to write a “Mom Song.” Yes, you read that right. Some hot music artists write and record songs about how awesome their moms are (or grandmothers, in Ed Sheeran’s case)! How about that?

Recently my daughter and I were in the car, headed to soccer practice and singing along to Meghan Trainor’s “Mom Song”. My daughter joked that if she ever wrote a “Mom Song” about me it would have to include how I love to collect airline miles and hotel points. No joke, she really said that! So, tooting my own horn here (just a little), it’s true. My point collecting has allowed our family to travel the world and we’ve ventured to far-away places such as Australia, New Zealand, Spain, France, Italy, Costa Rica, Hawaii, and Washington, D.C.

My hope is to share with you, amazing readers (and obviously incredibly intelligent, given you’re reading this blog), how we’ve been able to accomplish this and inspire you to do the same. It’s SO doable, and really only requires a little bit of hard work and craftiness! I’ve been perfecting this hobby for over a decade now and have a wealth of knowledge to share. It’s not possible to cover everything you’ll need to know in one post, but I’ll start at the beginning and list out some basic steps to get you going.

1. Dig around online

I know, it sounds so easy. Because IT IS. There’s a big internet world out there, including an entire online community of people who collect miles/points to aid in their travels. Over the years I’ve narrowed down the websites I enjoy and that interest me the most for the type of traveling we do (read between the lines – family travel on the cheap). The comments section after each article on these websites can also be chock full of additional tips. Bookmark a few of these sites and start checking them a couple of times a week. This will help you become familiar with the lingo and stay up-to-date with the latest and greatest deals and offers. A few I like to frequent are:

2. Make friends with point collectors

Nothing is better than humble bragging and sharing your latest Gypsy scheme with a fellow miles/point collecting friend. For me, my BFF in this sphere is my father. My family refers to my father as The Oracle, and to me as The Apprentice. I love that when I’ve cooked up a new idea I can call my Dad and chat with him about it in great detail. I’ll admit that at times it’s gotten a bit excessive, to the point where when I call, my stepmom actually holds the phone out and hollers for my father, “Cara’s on the phone, you two need to talk miles.” And who else can I email my funny point collecting memes to and know they will be deeply appreciated? An online community of friends works just fine too. If I’m not sure about a specific point, I’ll often post a question in the ‘Comment’ section and typically receive multiple responses.

3. Pick a place

For reals, pick a place off your bucket list that you’ve always wanted to visit. Or maybe your spouse has a big birthday coming up, or one of your children has a graduation. Or you just decide there is no time like the present and use all the money your husband has set aside to paint the house to plan a surprise anniversary trip to Italy! (We can live with shoddy paint on the side of our house given we have memories of Rome, the Amalfi Coast and gelato.) Knowing exactly what you are working toward is a great motivator. Having a specific destination in mind allows you to narrow down which airlines fly that route and what hotels are available in your vacation destination.

4. Make a plan

This will initially involve some more online research (in addition to step 1). I’ve found the best bang for your (miles/points) buck and effort is to plan in advance. Truthfully, you rarely hit a home run with this type of traveling if you wait until the last minute (especially when you’re traveling as a family of five, and need five economy seats, all on the same flight and booked with miles, oh, and during peak holiday season). Then, this is where a little bit of hard work is involved. You need to put in time doing thorough research in order to get to your end goal. But, putting on my rose-colored glasses here, the organization and anticipation that go into planning a trip makes it even more enjoyable when the time finally arrives!

Use this Basic Plan Outline (with details, of course):

  • Where do we want to go?
  • When do we want to go (ideal season)?
  • What airlines fly there? Or what airline alliances can work for you? What airport is closest to your destination?
  • How many miles/points will you need per ticket? Look up each airline’s flight award chart. (We always fly Economy as it requires the least amount of miles, but there are lots of options too for lucky Business/First Class folks).
  • What types of credit cards/promotions do these specific airlines offer for collecting miles/points? Or is a credit card with points that can be applied to any airline a better choice for your specific needs? Then take action on those credit cards/promotions! (There are other ways to collect points as well, but credit card sign-up bonuses are often the most advantageous.)
  • What type of accommodation works best for your family? (While building up your miles/points total, look into various accommodation options, such as hotels, Airbnb, house swaps, etc.)
  • Work toward collecting hotel points & airline miles, possibly incorporating online deals and promotions. Be sure to book your flights before your accommodation, and book the local transportation after your accommodation. By focusing on these facets of your trip first, you will ensure there is availability and will likely get a better deal as you aren’t waiting until the last minute.
  • Hone in on planning fun activities once you’ve booked your flights, accommodation and transportation. This can be a ton of fun and my go-to website of choice for customer reviews on just about everything is www.tripadvisor.com. It’s also fun to talk to others who have already been there as they often have the best insider tips!

5. Break it down

Work backward from your end goal by dividing the tasks required amongst the simple steps listed above and systematically make your way through them. For example:

Where: Costa Rica
When: February (ideal weather)
Airports/Airlines: SJO or LIR
United, American, Delta, Southwest, JetBlue & Spirit
Points Needed: American: 30,000 miles per ticket/round trip/Economy Research each airline and find out which one works best for your specific needs
Credit Card: Sign up for a credit card that is offering a sign-up bonus where the miles/points can specifically be used on American Airlines or one if it’s alliance partners
Accommodation: Research accommodation option (hotels, VRBO, house swaps) that will work best for your specific needs
Tracking: Fulfill the requirements to receive your credit card’s sign-up bonus. Stay organized! Book tickets—book lodging—book transportation (in that order).
Activities: Research—online, travel books, talk to others—and plan the daily itinerary…including restaurants with great reviews!

As briefly mentioned above, generally credit card sign-up bonuses provide the greatest miles/point rewards. Of course that’s because the credit card company is hoping you’ll spend money on your new card, not pay it off immediately and then boost their profits by paying (compound) interest. A CRUCIAL point here (given this is a blog about being smart and crafty with your family’s finances)…This scheme will only work to your advantage if you use your credit card wisely! Use your new card to pay planned (and budgeted) expenses, and be sure to pay the owing amount in full before the end of the grace (interest free) period.

I promise, as you see your progress you’ll gain more momentum in your efforts. Once you have your first trip on the books, you’ll be hooked! My family’s adventures around the globe are proof this system works, and with a little effort and planning, you can make it work for your family too! Plus, gaining something positive (miles/points that can be turned into a dream holiday) for spending your money wisely (remember, no buying extra splurge items) is making your money work for you. Start dreaming, planning, and researching and I’ll provide more tips and tricks in upcoming blog posts to help you make it happen!