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…
- Be FLEXIBLE.
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 Southwest.com.
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 hotwire.com 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 http://www.discounthawaiicarrental.com/. 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!
Sign up for your $460 in free travel rewards HERE (<- affiliate link)
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
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 VRBO.com. 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!
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!
And for those just getting started, I recommend signing up for the Barclaycard Arrival World Mastercard (<- affiliate link), because it’s the simplest card to use with a $460+ signup bonus to get you moving. Make that $920+ for you couples out there. You can check out my review of it here. HAPPY TRAVELS!
Disclosure: If you sign up for this card through my affiliate link., I do receive a commission. Thank you for any and all support, and enjoy your free travel rewards.