Traveling to Hawaii for 5 Weeks with an Infant

Traveling to Hawaii for 5 Weeks with an Infant

Are we crazy?  Nuts?

Perhaps, with a side of determination.

Traveling to Hawaii for 5 Weeks with an Infant


the rationale

My husband has always wanted to live in Hawaii but has never been there on vacation for more than two weeks.  He loves Hawaii so much that he travels every year to Hawaii.  His ultimate dream would be to retire in Hawaii, except there are issues with that, namely that neither of us are American citizens.  He loves Hawaii so much that we even got married in Hawaii last year.  It was an amazing wedding (to say so myself) and we have fond memories of it, the scenery was just stunning.  We even were seriously considering purchasing a condo-tel (is that what they are called?  A combo of a condo and a hotel) so we would have some place to stay when we come to Hawaii.  In the end we didn’t end up going through with the transaction.

One of my dreams was to be nomadic somewhat during my maternity leave, so we thought what better way to spend the dreary rainy season of Vancouver than to go to Hawaii for a month or so?

Here’s the plan so far, it’s quite dependent on how baby turns out to be, but I’m pretty sure we will make it happen anyway.

the airfare (travel hacking)

We plan to use Aeroplan points since they are going to expire on June 30, 2020 (if you haven’t heard Air Canada announced they won’t be using Aimea anymore and will have their own points program instead of having it contracted out).  One of my ultimate dreams was to use my 100,000 points for a mini-round the world (RTW) trip, but given that the points will expire soon thought we might as well use some points for our flight to Hawaii.

A one way flight from YVR to HNL ranges from 45,000-50,900 Aeroplan miles and $75-196 in taxes.  A regular price airfare to Hawaii from Vancouver is about $580, so we will be saving $380 to $500 by using points.  Of course, traveling with a child under 2 years of age is free.  I got the majority of these Aeroplan points from travel hacking and signing up for a TD Infinite Visa Aeroplane card a few years ago.

Using 80,000 Aeroplan points, we travel hacked two return tickets from Vancouver to Honolulu tickets and it cost $150.

Unfortunately my husband’s Aeroplan points expired and he didn’t realize it, so we used mine.  Baby GYM will be in our lap because we are too cheap to pay $70 for the bassinet seat on Air Canada.

We might also island hop to Maui for a week or so as I have never been.

the accommodation

We plan to stay somewhat near Waikiki or perhaps in the Kailua area, somewhere were we won’t need to be renting a car very often.  The Manoa area is nice too but it seems a bit far from groceries.  The cost for accommodation isn’t cheap but doing a quick search on VRBO and Airbnb it’s over $100-$120 CAD per night to rent a 1 bedroom condo (or something similar).  So estimated cost is around $4000-5000 or so depending on if we stay 4 weeks or 6 weeks.

We will need to make sure the accommodation has:

  • Laundry
  • Gym (can take it or leave it)
  • Pool (can take it or leave it)
  • Full kitchen
  • Close to groceries
  • Walkable to the beach
  • Accepts infants
  • Internet
  • Quieter area
  • Has a pack and play or an infant crib provided

I think it would be difficult to find month long rentals, I even tried Craigslist Honolulu and was out of luck.

In the end, we booked an Airbnb in Waikiki for around $4000 for the month (Canadian dollars).  Not particularly cheap that’s the best price for the Waikiki area…and it included everything we wanted, including a in-unit washer and dryer (such a useful thing when you have a baby that is spitting up, pooing, and peeing almost a dozen times a day!).

the plan

Since the sleep pattern will be not completely set when baby GYM is an infant, we plan to do the sleep training while we are in Hawaii or when we return from Hawaii.  Baby will be sleeping with us in our room anyway since that’s what the pediatricians recommend.  We are fully aware we won’t be doing much sight seeing with the little one but will likely be relaxing by the pool, going to the beach, and just enjoying the sun (of course baby will not be in the sun, we don’t want the little one to overheat or get a sunburn!).

It would be a good opportunity to see if we end up getting island fever (I have a feeling I will acquire “island-itis” more so than my husband) if we were to move to Hawaii ever in the future.

I will be posting a breakdown of our expenses and costs for our month in Hawaii once we return.

This would be another good opportunity to test out a mini-retirement for the GYM family, even though it’s a actually a month long vacation.

Readers, have you traveled with an infant?  What surprised you about traveling with an infant and was it easier or more difficult than you had expected?  Any tips for the plane ride?

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About genymoney

GYM is a 30 something millennial interested in achieving financial freedom through disciplined saving, investing, and living a minimalist lifestyle.

15 comments on “Traveling to Hawaii for 5 Weeks with an Infant

  1. That sounds like an awesome trip. I want to retire in Hawaii too, but I’m thinking the Big Island. You can still get some acreage there. Maybe north shore Oahu. I need to explore more there.
    We didn’t travel much when our kid was an infant. I think Hawaii is good because it’s easy. You don’t need to worry about anything strange. We visited the Big Island when our kid was 3.
    Did you see our Waikiki trip report?
    I love Hawaii. 🙂

    • @Joe- Thanks for visiting!! (insert excited emoji here!). I’ve never actually been to the Big Island, I have always wanted to, the only islands I have been to are Kuaui and Oahu. North Shore Oahu is really nice too, the you could have garlic shrimp all day! Yes of course I saw your Waikiki trip report 🙂 There was a recommendation for a place (Maguro brothers) to eat on there that I wanted to try!

  2. Haven’t traveled with Baby with Cents yet but we are looking into going on a hiking trip or a cruise next year. We got a hiking backpack Mother with Cent’s cousin and it has a baby carrier so going hiking is a possibility. Cruises should be fine since they lots of programs for babies and toddlers.
    I think you guys should be okay with the baby going to Hawaii especially having an AirBnb place over there. A vacation that long should give you both an outlook if you want to consider retiring in the islands.
    Kris recently posted…Expense Chronicles – September 2017My Profile

    • @Kris- Ooh a hiking trip, that sounds really nice! I have always wanted to be ‘that family’ that goes hiking with their infant/ toddler. Super badass. My sister in law goes on a lot of cruises with her children, it works well for families, everything is taken care of.

  3. 5 weeks in Hawaii sounds great! I will be there at the end of November for the first time but only for 2 weeks.
    I traveled with my kids extensively when they were younger and it was never a problem. For the plane ride, you need to make sure you pack everything they may need, and more! There is that one time, it was really tough. My son, an infant at the time, started being sick once we got to the airport and had diarrhea for most of the flight (7 hours) and we hadn’t packed enough diapers and change of cloth. It was a LONG flight.
    Caroline recently posted…Grocery Budget – Sept. 2017My Profile

    • @Caroline- Okay got it, oh gosh that hadn’t even crossed my mind- thanks for sharing your experience. Sorry to hear your poor son had diarrhea on the flight— poor you AND him! I can’t imagine what infant diarrhea on the flight would be like- not fun!! I will make sure I bring at least 1-2 diapers for every hour of the flight, thanks!

  4. Ohh you’re going to have fun here!! The weather is still a little warm but it’s slowly getting colder….well for me anyway lol. I’m excited you’ll be staying for a month and I have to say that it will be a bit expensive. You’re good for using any type of travel hacks as fares can be pretty expensive. If you have any questions about Hawaii, let me know! I’m happy to answer any questions 🙂

    • @Melanie- I didn’t know there were different temperature variances in Hawaii lol! It’s always like 25 degrees + (Celsius). Thank you I will definitely message you! 🙂

  5. We traveled to Denmark when Baby T1.0 was 10 weeks old then back. The bassinet was great but you have to remove the baby from the bassinet whenever there’s turbulence. We used the bassinet for Baby T1.0 and Baby T2.0 for other travels too. Once the baby can sit up, Air Canada wouldn’t let you use the bassinet anymore.

    • @Tawcan- 10 weeks old! Wow, #babytravelgoals how did baby T1.0 do on that flight? Interesting- yeah, my baby doesn’t like the bassinet so much (he can sleep in it only at night, he can’t sleep in a bassinet during the day) so I don’t know how he would fare.

    • @Gabe- Baby will be around 4-5 months 🙂 How long is the flight to Mexico? Bring lots of diapers (as Caroline from Money Scrap recommends)!! So many decisions ahhhh what have I got myself into haha..

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