How To Travel For Free: Hawaii Trip Update

How To Travel For Free: Hawaii Trip Update

Hello everyone! I hope you didn’t miss me too much. Just finished up another busy tax season, got promoted at my day job and tried to see my family in between. It’s been nuts!

During that time, I also kept the wheels a turnin’ on our epic Hawaii trip plans. Last we left off, I had put all the puzzle pieces together on getting 7 free tickets to Hawaii for our family, and was about to book the tickets. Let’s see how that turned out.

7 Free Roundtrip Tickets To Hawaii

We are heading to Hawaii to celebrate my mother-in-law’s 50th birthday, and to have a 10 day getaway from reality. Since we’re bringing a sizable crew, I knew finding tickets wouldn’t be easy. Here’s what happened:

  • I checked for availability of 7 tickets in September for 2014 on Alaska airlines out of Seattle. NOTHING.
  • I checked out through October and November. I could only find 4 tickets at a time, and couldn’t get 2 flights close enough to make it work out.
  • I started to panic, but then I realized the #1 rule of booking travel rewards flights is…

Then I started to think a bit more creatively. Maybe there were more flights out of other cities. After searching around a bunch, I found a RT flight out of San Diego. WOOT! So I immediately called British Airways, gave them the Alaska airlines flights details, and booked the flight on the spot! They were going to charge me $30 per person, but I told them I got an error trying to book the flight through their website (true), and they waived the booking fee. So we just paid the standard $5 fee per person, and I booked 7 tickets to Hawaii for $35! BOOM!

But, Now How Do We Get To San Diego?

We’re up here in Seattle, San Diego is all the way down there. Crap. But not to worry, because remember, I’ve got this free travel ON LOCK! So I had one of the people in our crew sign up for the 50k bonus mile Southwest Airlines credit card. The bonus comes up like twice a year, and our timing was perfect. It’s now back to 25k. I knew that flights from Seattle to San Diego were about 5,500 points each way, so about 11,000 RT. With the 50,000 bonus and the $2,000 spend on the card to get that bonus, we’ll have about 52,000 miles to work with.

If we do the math, though, we’ll actually need almost 80,000 miles to get us all there. OH NO! Again, not to worry, because I’VE GOT THIS! Another member of our crew was already working on the Chase Sapphire Preferred, which gives a 40k point bonus after $3,000 spend in 3 months. And whaddya know! Chase points transfer straight to Southwest at a 1:1 ratio. BOOYAH! So we’ll pony up another 30,000 miles to Southwest, and there’s our trip to San Diego. I’ll be booking these flights when they come available on

Rental Cars

I talked in the first post about how we’re using the Barclaycard Arrival World Mastercard to book our rental cars in Hawaii. We were going to hop on and look for the best deals and hope to get 2 sedans for all the peeps in our party.

But then I was on a travel forum and saw someone link to Holy crap. These are the absolute best prices I’ve ever seen on car rentals in Hawaii, heck, almost anywhere. We’re talking $150 a week for a sedan. CRAZY! You can even get the ever popular convertible mustang for a mere $57 a day (off peak). And since we’re booking in off-peak season, we’ll get the deepest discounts available.

We’re already got 43,000+ miles on one of our Barclaycards, so that should cover both car rentals. BOOM!’

San Diego Hotels

One extra piece of the puzzle is that we need to head down to San Diego the day before because our flights leave very early to Hawaii. We also need to stay a night there when we come back because we’ll be coming back there so late. So I need to book a couple hotels for 8 people. Luckily, the second Barclaycard will cover those bookings because you can book any travel related expense and erase it (love this card!). SAWEET!

Since we have a crew of 7 + infant, we’re going to need 2 rooms. We used about half our miles for my wife and MIL to head up on a small cruise to Canada, so we’ll have about 30,000 ($300) left for the hotels. That’s $150 per night available, so we’ll need to find a $75 per night rate hotel near the airport. A quick perimeter search shows us some promising options. No, we won’t be wine’d and dine’d at a 5 star palace, but since this is just a stopover, who cares πŸ™‚

Maui Condo Rental

As I mentioned in my previous post, instead of trying to rack up like half a million hotel points to stay at some fancy pants resort, we opted to find a good condo on And it didn’t disappoint. We found a great, 2/br 2/bath condo on a private beach with FREAKING SEA TURTLES THAT COME ASHORE for a mere $200/nt. We’ve pooled out Christmas/Bday monies for 2 years and just booked 9 nights at this super awesome location. We’re talking private pool, BBQ area, full kitchen, ocean front balcony, the works. And the people booking it seemed SUPER NICE, so we’re pretty stoked about that. Done and done!

The Rest

We still have about 9 months left to save for this trip. I’m assuming we’ll need like $50-$75 per day for food for our family (conservatively), and money for excursions and other fun activities. I’m going to put away about $2,000, but am hoping to grab another Chase Sapphire card and Chase Ink Plus card to get me about $1,000 cash back to help offset the cost. At this point, we’re taking a $10k+ vacation for pennies, but I’m always up for a challenge to save a bit more. I’ll keep everyone apprised of how this trip turns out, and how much we are able to save using credit card rewards.

Anyone else want to learn how to travel for free? Check out my Free Travel page, and shoot me an email if you have any questions. I love this stuff!

photo credit: laszlo-photo via photopin cc

Related Posts Plugin for WordPress, Blogger...


  1. Great job, Jacob! I agree that the key is being flexible. Sometimes reward flights are a pain to hunt down but they are always there! If you want to rack up some more hotel stays and Southwest points quick, I would sign up for a Marriott Rewards card. The sign-up bonus is 70K Marriott points after spending 1K in 3 months, and you earn a free hotel stay upon account approval. Marriott points transfer to Southwest too, albeit at a crappy rate since they aren’t worth as much. 70K Marriott points = 25K Southwest points. But you also get the free hotel stay. I bet they have hotels in San Diego.
    Holly@ClubThrifty recently posted..Disaster Averted: 4 Reasons I Love VRBO.comMy Profile

    • Thanks Holly. I’m up to my quota of Chase cards, and need to get the United and Ink Plus here pretty soon for FinCon, so I don’t want to jump on the Marriott, but thanks for the heads up. Good to know they transfer to a more *useful* program like Southwest. Plus a free Marriott night is all good πŸ™‚

      • Is there a quote on Chase cards? HAHAAHA
        Holly@ClubThrifty recently posted..All We Have Is TimeMy Profile

        • Well, usually no more than 2 personal and 1 business in 6-12 months. I’ve got 3 personal and 1 business in the past year. But I’m going for the second business for me, and another personal for my wife (she has 1 for the year). I just don’t want to push it too much and get blacklisted.

          • Information not exactly accurate jacob. You can get quite a few chase cards in a year (my record is 4 personal 2 biz) as long as you maintain consistent exposure. If you’re interested in the mariott card and they deny you, call them up and ask to shift some of your limit from an existing card to that card (Say take 4k from your chase saph limit and move to the mariott card)

          • Good news! Thanks Jeff. I personally have gotten 4 Chase cards in 12 months (2 personal, 2 biz), only got a “pending approval” on my latest one, but called and it was approved without begging πŸ™‚ Nice work on getting 6 of them.

            Shifting credit is definitely an option, but is usually a last resort, and only if they mention “too much credit extended” or something similar.

  2. Super sweet!! The Mister and I are going to Maui this fall for our anniversary and plan on using all of our points/rewards for pretty much everything! If you need to spread out your points for with a different bank – there’s always the AMEX Blue Sky Preferred. It might still be worth it to get some additional cash back cards in the mix! So excited to read all about the rest of your trip – we’ll need some pointers! Thanks, Jacob πŸ™‚
    Anneli @thefrugalweds recently posted..Frugal Reads Of The Week (ending 4/19/14)My Profile

    • Sweet deal. You guys using Avios, or other miles? You churning cards for the hotel as well?

      I’m not into cards without HUGE sign up bonuses, so will probably pass on the AMEX, but it is a good daily card for sure.

  3. Oooh, Maui is beautiful. We were there two years ago! I would say scan Craigslist over the next several months and see if you can grab some used snorkel equipment in assorted sizes that fit most people. Around here you can usually get used equipment for about the same as a 1 day rental of snorkel equipment in Maui. And you’ll definitely want to head out snorkeling with the turtles, which can be very cheaply done as they are so close to the shore on many parts of Maui. Plus, you can always resell the equipment when you get back home if you don’t want to keep it.

    I’m envious of the flexibility you guys have with this trip to keep costs low. Sadly we don’t have a whole lot of flexibility when it comes to travel over the next couple of years, so we end up paying a fair amount (either in points or dollars) because most of our travel is done at peak times.
    Mrs. PoP recently posted..A Year of Bike CommutingMy Profile

    • Good call! I’ll keep a lookout. The lady we booked with also say snorkel rentals are like $2 a day. But if we can grab a bunch of equipment on the cheap, might be even better.

      Flexibility is definitely key for free travel, especially using the British Airways trick we used. Plus, I like booking WAY out, because we get a better selection on seating, and can find off-peak times to go. Once you’re FI, though, you’ll be completely set for traveling whenever you want πŸ™‚

  4. I really love reading all your travel hacking tips! We don’t have a credit card but my hubs always go for a travel, so we were thinking to sign up for a credit card.
    Marie @ Financial Debauchery recently posted..You Don’t Need to Be Genius to Understand the Annuity FormulaMy Profile

  5. Jacob,
    Living here in Hawaii only one way off this rock. We’re travel hacking this year with a year end goal of 400,000 points. If you want any Hawaii pointers you can drop me a line. recently posted..Find Your Financial Freedom InspirationMy Profile

  6. I bet I looked 50 times before I found the saver level tickets we needed for Hawaii. Originally, we planned on going from Phoenix, but ended up finding a better deal leaving from Vegas. Flexibility is the key, even when traveling in peak times, like we have to do with a kid in school. Since the airport in SD is downtown, you have tons of options. We used Priceline a few years ago and got a great deal at a Westin or Wyndam, can’t remember which, but I feel like it was $69 per night. That’s awesome to get that many people to Hawaii, and that they all got on board. They all think you’re crazy until they realize you really can travel for almost nothing!
    Kim recently posted..6 Things That Are Cheaper on Amazon Prime than at Wal MartMy Profile

    • Absolutely. People’s eyes glaze over when they hear the details of “how”, but when I just boil it down to “I just booked 7 tickets to Hawaii for $35”, people seem to start listening πŸ™‚

      I’ll check out Priceline, and make sure we can grab the hotels. And good to know there are close by attractions in SD. I don’t want to go far from the hotel. πŸ™‚

  7. Total pro. I also like to rent out my apartment while I’m away which is great for covering costs. That condo in Maui sounds amazing!
    Stefanie @ The Broke and Beautiful Life recently posted..Budget Travel: 5 Ways I Paid For My Last VacationMy Profile

    • Hah, thanks! And nice work on renting out the apt. Never thought of recouping costs that way. Way to get creative!

      And yes, we’re pretty excited for Maui. Now the hard part is WAITING!

  8. Good for you, congratulations. I remember when i got to travel for free, there is nothing like receiving free stuff. I can pay for it but somehow its more pleasurable when somebody else gives it to you, i don’t know why. Writing you personal finance blog about your free trip is getting me excited on my free trip this June. Cheers
    Jeff @Project Ikonz recently posted..Ebay side hustle is awesome and crap at the same timeMy Profile

  9. I’ve found that airlines usually screw you, I’ve found the most availability on hawaiian on trips using miles. They have a decent rewards cards. I usually buy miles off my parents. I flew one way from the east coast for 25k per ticket and $5. I am flying into CA from HI for $188 and back east for another $178. I rate using miles only at 2 cents/mile an I usually get better. Flytalk can help score deals. Let me know if you need more tips. I also usually wait and book SD for pennies using VRBO and I make offers a week before. Also can you priceline but my DH likes security knowing where we’ll be staying.

    Also as a tip it might be worth flying into LA, LB, OC depending on one way car rental. Gives more flexibility on using miles as well. We do this as well fly into one city, car rental and leave.

    But your food budget is too low. $6 for half gallon horizons organic milk. Bananas $1.79/lb. Pineapples $1.99/lb. Just stuff I recall seeing as I sit in hawaii right now and I went to the grocery store. Food is expensive and I just filled up gas at $4.13 for unleaded. Just a heads up.

  10. This is some impressive travel hacking! Great job!
    Brent recently posted..Credit Card Rewards: 5 Unique Strategies for Hitting Minimum Spending RequirementsMy Profile


  1. […] Check out the Hawaii Trip Update Post HERE […]

  2. […] to nothing, who could say no to that? This week we offer his post about how he is crafting a sweet Hawaiian vacation for 7 people which should cost around 10 grand, and it is going to cost them ALMOST NOTHING! Check it out if you […]

Speak Your Mind


CommentLuv badge