How I Took My Family to Maui for a Week for $573

We made it to Maui!


This past Christmas, I spent a week on Maui with my family.

This is remarkable for a few reasons:

  1. None of us had ever been to that island.
  2. My mom and brother had never been out to Hawaii, at all.
  3. My mother never thought she’d go to Hawaii.
  4. We’re not rich.

We, in fact, had a grand ol’ time, a private cottage, and a multitude of flights for roughly $4000.



So How Did We Do It?


Getting There…

I'm having a good time, I promise. :)

With $5 Flights, of course! :)

I advised my mother and brother what credit cards to get, and we all had enough points for our round-trip flights. Here were the itineraries (these are the total investment costs: annual card fees + taxes):

  • Brother: LAX-Maui-LAX (1 round-trip): $168
  • Mom: BOS-LAX-Maui-Oahu-LAX-BOS (2 round-trips + 1 one-way): $230
  • Me: LAX-Kaui-Maui-Oahu-Big Island-San Diego (5 one-way flights): $175

So total flights for ALL of us = $573.

That is about HALF (if not a third) of what ONE round-trip flight could cost at Xmas from LAX to Hawaii.

Instead, we spent less on the entire WEEK in Maui than if we had paid normal prices for three round-trip airfares—and we had a whole lot of fun… (more below).

So is this insane? Yes.

Possible for you, too? Definitely: here’s my course to help you do this! <— seriously, check that out. :)


Obviously, with so little on flights, that left a lot of room to spend our money on the QUALITY of our trip, from where we stayed, to where we ate, and what we did.

With travel hacking, I love that instead of spending all your money (or the majority of it) on getting to a place, you can spend it when you get there—and do cool things like support the local economy! :)


Getting Comfy…

Our AirBnB Cottage

Yup, this is the PRIVATE cottage we rented on a sweet 300 acres, with ocean views, fresh fruit trees, and all the country quiet you can handle!

Thanks to, we scored an outrageous deal and saved even MORE money than if we went a “traditional” route (hotel, travel agent, etc.).

If you’re not familiar with this site, it allows individuals to rent out their homes, apartments, and rooms to travelers, usually at a MUCH cheaper rate than you’d find at a hotel. All the comforts of home, while being on the road! :)

Again, we had quite the find! We were “upcountry” in Haiku, but still SUPER close to the Road to Hana and Jaws beach (major surfing spot), and centrally located for plenty of other activities. We even learned that surfer Laird Hamilton used to live on this street (you can see the lanai of the place he owned)—but our place is closer to the ocean. ;)

Even at $1700/week, this place is a STEAL, but we caught the owners when they had just bumped up the price, and we were able to negotiate a deal. (Hint: ALWAYS ask; the worst they can say is “No.”)

If you want to check out this place, you’ll see my review on the page—and be sure to let Beth know where you heard about it! :)

Rental for the Week: $1615. (includes AirBnB fee)


Getting Around…

our trusty steed!

My brother found a deal online for Avis in the sidebar of for this 2-door Jeep Wrangler. I got the strong up-sell at the counter for the 4-door, but stayed firm on what we had—and it was perfect for 3 people.

We did pay the extra driver fee and pre-paid for a gallon of gas (cheapest price on the island).

Total cost: $837. (including gas)


Other Activities…


Ziplining – Skyline Eco Adventures

  • $297 for 3 adults – all gear and 5 “zips.”
  • They are America’s original zipline company—and they own the domain—pretty sweet, right??
  • The tour guides were HILARIOUS and were worth the price of admission; seriously awesome to see these guys have so much FUN at work!! And they easily got everyone (including those of us terrified—like me) laughing and smiling.
  • I never thought I’d enjoy this so much—but you feel so ridiculously safe, how could you NOT have a good time?! :)
  • They have two spots on Maui, and we went to the Haleakala location.

Snorkeling – Seafire Charters

  • $165 for 3 adults (full price) – all gear, snacks, and a 3-hour excursion.
  • VERY friendly and awesome crew!
  • The views were AMAZING! This was the first time ANY of us had been snorkeling and this trip didn’t disappoint—it’s like looking into a whole other world. And the reef drop—all I can say is WOAH! :)

Sunrise at Haleakala: $10 to enter the park, waking up at 4 am, and mind-blowing views. Do it. :)

Hike to Redwoods (yes, on Maui!): free and a 6-mile drive on dirt roads! More info.

Road to Hana: free

  • Don’t believe any of the signs of “last stop for food before Hana”—there’s probably a dozen of those places, many on the honor system—and many with banana bread (how can they all be “Maui’s Best”?! ;)
  • In Hana, seek out the Red Beach: totally worth it!

Total Activity Costs: $472.



our homemade luau


  • Mana Foods: a GREAT natural foods grocery store with fantastic prices (better than Whole Foods); plus, a salad/soup bar and other goodies available
  • Paia Fish Market: right in downtown Paia on the corner, the quality and quantity of the food here was excellent. Our zipline guides said that if you go to Mama’s Fish House, you’re paying (a lot) for the view; the Fish Market’s food is just as good (if not better)!
  • Flatbread Pizza: how could this Massachusetts boy not hit up a place whose only other locations are in New England?! And yeah, it was damn good pizza—I went for a red pie loaded with local veggies: OUTSTANDING!

Total Food Costs: $490.


Getting It All Together…

So how much did we spend?

  • Flights: $573
  • Cottage: $1615
  • Car Rental: $837
  • Activities: $472
  • Food: $490
  • Other Incidentals/Misc.: $83

Total for 3 people for a week on Maui: $4070.

That’s it! Nothing else. For three people for a week on Maui, in a private cottage—at Christmastime—that’s all we spent.

CRAZY—and very awesome!

By the way, I love how the cottage cost 3x our flights (instead of the other way around)! :)

Perhaps the thing I’m most thrilled about (even more than the savings) is that I was able to help give my mother and brother an experience that they might not have otherwise ever considered.

welcome to the jungle, guys...


Me saying at Christmas in 2011 that “we should go to Hawaii next year” I’m sure sounded like only a pipe dream to everyone else; but I knew it was possible.

I’m now looking into and planning a trip with my Uncle (who hasn’t taken a vacation in years): maybe we’ll go to Italy or even Thailand. It won’t cost that much to get there, so why not!? :)



So yeah, it’s possible to have an AMAZING tropical vacation—and not break the bank; in fact, with these rates, you’ll probably have money left over from your vacation fund!


So my only question: when’s YOUR trip? :)



From the road…





Former life: actor/office worker/virtual assistant; lived in Los Angeles for 11 years. Since then: sold nearly everything, took a $5 flight to Hawaii, lived there for 3 months, wrote an eGuide about all of it, and still traveling. Currently: digital nomad – looking to improve myself, have fun and serve others.