097| Travel Hacking for Families

travel Rewards for families
Helping families use travel rewards to travel more for less.

Today you are going to a little bit of real talk with Heidi. Maybe because I am on night 3 of a hotel to MYSELF while I’m at a conference or maybe I shouldn’t have had that second cup of coffee (by the way if you like Real Talk with Heidi version, feel free to support this buying me a coffee) Either way, I wanted to give families a valuable way to use travel rewards to supplement their travel budget, traveling longer, farther – let’s just say it’s one of my favorite optimization strategies AND after 2 people it gets much more difficult – you even heard Chris Hutchins from All the Hacks say it on episode 092.  The game is harder to play with more people.   

 And I’ll just say it, the content out there for families is eh.  I don’t think you need to pay thousands of dollars to follow someone’s system.  Once you learn the rules of the game you just need a reliable source to ask questions and find the answers you need. I also don’t think everyone needs to take online courses to understand how points and systems work.  Many of those groups want you to use their links so that they get all the referral bonus points. Just for the record, I’m not opposed to any of those things, people can make money doing things they are good at and I know that many use the referral and affiliate links to fund their work.  I just think there is a better way to support YOU through this – what can I say, we are sherpas helping families adventure.  I think families need a fair shot at the travel rewards game.   

Part of the challenge with travel hacking is that the rules change often.   It takes time to understand and let’s be frank – we don’t have time to scurry down the rabbit hole of travel rewards.  For this episode I am going to highlight some of the travel hacking resources I have and walk through three examples of how we recently used travel rewards.  I also am announcing a FREE Live Family Travel Hackers Q/A Session so stick around and make sure to register to get EVEN more tips.

First to highlight some of my previous content:

On episode 018 | Travel Rewards tips with Melissa Lagerquist.  We talk about some of the basic terminology, approaches and ways she has used points to hack cruises.  Full disclosure – Melissa is connected to the Choose FI Travel Rewards course.  If you want to go down the rabbit hole that free course is where I started when it was launched probably close to 5 years ago. 

On episode 019 | Our approach to travel rewards I walk through our strategy and I give you a free downloadable planning guide to help you through the process.  That is available at: https://ordinarysherpa.com/rewards/  

Episode 032 | How to Fly a family of 5 to Hawaii for under $500 I dive deep into Southwest Companion Pass which we have had for 4 years straight.  We are not renewing next year because we will be traveling in the RV next year and as you will soon hear we have a different strategy. 

Episode 070 | Hacks to Optimize Family Experiences without Sacrificing Value offers an updated approach to how I plan our summer vacations in particular.  

We also reference travel hacking in episode 084 with Ed Tee adventuring near and far; Episode 040 Interim Expat with Scott Barrett, and Episode 077 | Funding the Fun with Jen of Investor Mama.  

The DIY approach to learning travel hacking can seem like an uphill slog.  I may have said on more than one occasion “Can someone just tell me what to do?!” Stick around until the end to get the link to register for our Free Family Travel Hacker LIVE Q/A.  Tonight I wanted to share a few behind the curtain tips to help you travel more for less.  

Hawaii flights for 5 for under $300

It’s no secret here that we used 2 Southwest Companion Passes.  RIGHT NOW is the best time to start earning the Southwest Companion Pass to give you the maximum amount of time where one person flies free with you (-$5.50 per flight in taxes and fees). If you have ANY questions about earning the Companion Pass make sure to sign up for my Free Q/A! 

Many people tell you to design your strategy based on a destination you want to travel to.  That is one approach, but I also like to think about the experience.  From Wisconsin to Hawaii is 8+ hours of flying, and direct flights don’t exist.  Instead of designing this trip to be a long-haul with 3 kids, we broke it up into smaller segments which meant we also had so many more options on what that experience could look like and created a schedule that worked best for our family.  Instead of looking for fare sales from our home airport of Milwaukee, I look for routes to our destination and work backwards. Our route was Milwaukee-San Jose (staying a night in San Jose and making a mini-vacation of it), from San Jose to Kona (big island) for 5 nights, from Hilo (Big Island) to Honolulu (Oahu) for 4 nights, from Honolulu to Kahului (maui) for 5 nights, from Maui to Los Angeles for 2 nights, and from Los Angeles back to Milwaukee for 3 nights.  In many ways it felt like we had 5 different vacations.  

Now that might seem much longer in terms of days and number of flights overall that you want to spend, but keep in mind we were on 3 islands and planes are really the easiest way to get between them.  Because we had utilized the best fares and designed an experience, the total number of points needed for this entire itinerary was 60,168 (for essentially 5 trips).  Because we had 2 companion passes we only needed this number of points for 3 of our family members (which was 180,504).  Because both my husband and I had attained Companion Passes we earned over 240,000 points (at the time the requirement was only 120,000). Part of the reason I like Southwest is because they use a standard formula based on price/points as opposed to dynamic points systems that are difficult to figure out how many points you need to earn to redeem your family flights. 

Harry Potter World (tickets and hotel) for $0.  

This was a recent “can we do it challenge.” that we booked for 2023.  Universal Orlando (which is where Harry Potter World is Housed) often offers a 2-day+2 Day Promo (PS. It’s still happening right now for travel before March 2, 2023 if you are interested). We used a travel eraser card like the Capital One Venture X card.  We bought the tickets through Undercover Tourist (which was just under $1,500 for a family of 5 for 4 days) and then were able to wipe that travel expense out with points.  There are general rules of thumb, often a point equals a $.01 so in this case would be 150,000 points.  I can go into much more detail on how we reach those minimum spends and when we apply for credit cards as a part of our regular family budget on the Q/A call. 

I did some research into what hotel works best for our family in the area and I’ll jump into that in a bit below.  Ultimately we landed on Cabana Bay Beach Resort and used the Chase Ultimate Rewards to pay for our hotel.  It doesn’t always make sense for us to use reward points for hotels and car rentals. I can go into much more detail on what we look for and when it makes sense to pay for accommodations/ transportation to earn bonus categories vs. when it makes sense to use rewards if you want to have insight into my brain and how we approach this.

Best Hotel-hacking options for larger families.  

Hotels in general can be tricky for families.  As your kids get older it’s not as easy to coordinate sleeping arrangements.  We have found several specific hotels within the various hotel families.  As a family of 5 hotels in general are harder.  As I was finding the right formula for our family I would look at things like: was there free parking or free shuttle to the airport? Could we make a meal in the room?  Was there free breakfast or perks with hotel status that we could optimize?  Usually the selling factor for the kids, is there a pool?  Within the 3 major families of hotel Marriot, IHG, and Hilton there are several branches that offer options for families.  Three of our favorites are:

  • Residence Inn or Springhill Suites by Marriott
  • Embassy Suites by Hilton
  • Hyatt House or Hyatt Place by IHG
  • And if I am paying cash I appreciate Comfort Suites.  

As I alluded to at the start of this episode, travel rewards can be overwhelming and the content out there is not always geared towards families of 3 or more.  Register for our LIVE EVENT to answer your Questions on Family Travel Hacking for those interested in becoming a (or improving your) Family Travel Hacker skills.  To register go to https://ordinarysherpa.com/LIVE Even if you are slightly interested I would strongly encourage you to sign up.  It will be recorded AND there is a surprise that will only be available to those who register (before the rest of the community and world knows about it). 

Where to Listen

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