Hawaii Prep for a 28 day stay

Everyone knows Hawaii is expensive. So what do you do if you are planning to stay there for a month and need to maximize your dollars? You have to work hard on finding the best deals! My max budget was $6000, but I was able to get things lined up for $3800 for a total of 28 nights. Which is pretty awesome!


Spent: $913
I could have found a flight with one stop for about $650 but opted for a direct flight from Chicago to Honolulu. One of the reasons being that the weather is way more unpredictable in the winter and I don’t really want to waste a lot of time waiting for planes or getting rescheduled with possible overnight stays. Found on GoogleFlights.

SurfBoard/Paddle Board

Estimate: $350
I will be able to get a board from my surf instructor for $15/day. But the house that I am staying at also has free surfboards available for us to use. In addition, I will be taking my inflatable Naish SUP with me.


Budget: $2500
Spent: $1730
I opted to stay in an Airbnb and this particular one is catered to digital nomads and entrepreneurs. So it will be fun environment working on my business ideas and finding that “work from anywhere” kind of job. This one was by far the best deal available. Found on Airbnb.


Budget: $1300
Spent: $775
I had a harder time with this one. In order to save I had to go away from the airport otherwise it would have been at least $1200. Found on CarRentals.


The roof rack rental would have added additional cost and maybe even forced me to change to a different car size. So I bought a soft roof rack for $45 to transport my surfboard around. It will useful in future too and if I don’t need it I can always lend it out.

I decided to get my own snorkel mask and fins for $100, something that I would need anyway.

I am hoping I can find somebody or something to leave all my gear with until I return in May. I will have to pay an extra bag fee at $35+ for my inflatable, paddle, and roof rack for at least going out to Hawaii.

One thought on “Hawaii Prep for a 28 day stay

  1. Good plan going with a direct flight. What a good shopper – great deals on everything. Is there a ‘learning curve’ on using the soft roof rack? I’m not familiar with that style of rack. Hope you have safe travels, no glitches, and a wonderful adventure. Hugs!!

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s