How we spent 14 days in Hawaii for less than $1300/person

Disclaimer: The above picture was taken from one of our hikes on Oahu.
I can’t begin to say enough about the payoffs from racking up hotel points, credit card and frequent flyer miles. Over the course of the last two years, we have literally saved thousands of dollars we would have otherwise spent by redeeming rewards for travel or by erasing transactions via our Capitol One card.
The number one thing you should know if you are planning new to take a vacation using rewards, is plan far in advance in order to allow yourself plenty of time to rack up points or fulfill the spending requirements on new credit card bonus offers. If you’re like us, you might not plan more than 6 months out for your next vacation. This vacation idea formed from a few friends joking around about how awesome Hawaii is and how awesome it would be to get a group together to take advantage of all the natural splendor Hawaii has to offer.
1. Go on the off season
Is there really such this as an off season in Hawaii? Come on – I mean it’s perfect weather all year round. However, this alone will save you $600+ on flight costs. The best times to go to Hawaii are after the holidays from Feburary through May. By the middle of May comes around, you’ll see a dramatic spike in flight costs from the mainland. Additionally, even though it may cost a little bit more, I recommend only allowing yourself one layover if you are flying from the East Coast (your tired self will thank me later).
2. Save up those miles early!
Save up your miles now! Save up miles through carriers such as Delta, Alaskan or American. We were lucky to have enough Delta Skymiles to pay for one of our flights round trip. That ended up saving us over $850! Since Sean travels a bit for work, he managed to rack up Gold Status (more on the benefits of gold status in a future post) and got upgraded to first class on the way to and from Seattle to Hawaii. Disclaimer: if you do have status with an airline, check their policy on companion upgrades. Since I was booked via a reward ticket (e.g. Free!), I could not get upgraded to a better seat (translation: 6+ hours of crying babies in coach).
3. Home share whenever possible
Travel with a group through an Airbnb or Homeaway to make your money go further. The house sharing economy is still largely unknown to most tourists, but given the number of amenities and convenience a rental house provides, it’s a no brainer. We stayed in three houses with washers, dryers, beach towels, kitchen amenities and really anything you could think of on two different islands  throughout the trip. Cost of splitting housing for 14 days = $50/day per person. No too bad for being in paradise AND we could have easily found cheaper places! This was between 5 people for two bedroom homes. One of the houses was even on the beach.
Here’s a breakdown of how we spent our 14 days in Hawaii:
  • Flights – $850 (one flight free and did I mention 1st class?)
  • Lodging – $1400 (for 2 people)
  • Food – $200 (give or take, some meals out and many home cooked meals)
  • Car Rentals – $150 (we took advantage of corporate rates for Hertz in order to get upgraded & one free day)
Grand Total = $2570 or less than $1300/person
With a little bit of advanced planning, it is totally possible to get away to one of the most beautiful places on Earth. In fact, when I was a poor recent college grad, I went to Hawaii for less than half of that by bumming with a friend.
Until next time…
Travel more, be awesome!