Happy Hours in Hawaii Under $500 per Person from Vancouver

Personalized welcome brochure from the Sheraton Waikiki

Personalized welcome brochure from the Sheraton Waikiki

During the last 10 years, we have developed our travel acumen; long gone are the days we end up staying at crappy 2 and 3 star hotels we won on Priceline and Hotwire.  They key to our success has been methodical trip planning though loyalty programs and travel rewards, and being flexible.  People ask us for help and tips all the time but this type of travel doesn’t work for everyone.  The big thing is being flexible!  To get a good deal and get maximum ROI on your dollars spent to convert them into points ($1 spent could be 1 point or 2 points), you need to be flexible!  In most cases, you cannot say: I want to go to “insert destination” from “insert date” to “insert date” because the prices may not be in your favour.  It is practically impossible to find deals in places like Mexico, Hawaii, and the Caribbean around Christmas, but if you go a little before Christmas and fly on Christmas day, then you may be in luck! We also found tickets from YVR-ORD (Chicago)last year for $175US return each due to United starting up service on this route.  These are the kinds of things you need to look for to find deals and make travel affordable.

Makapu'u Hike

Makapu’u Hike

A good example of a successfully planned trip like this was our trip from BLI-HNL this past May. We had a lackluster spring with lots of cold rainy days and the stress of work and life had us craving sunshine, heat, and relaxation.  Allegiant airlines, a discount carrier had promotional fares from BLI-HNL, so we bought the tickets at $220USD return, paid the $25 insurance fee to switch the dates if needed.  While we could have used Aeroplan points to get to HNL, the 40,000 points needed are not a good ROI (Return on Investment) when this route has a lot of cheap flight options right now.  For example, for me to fly home (YVR-YYZ-YSB), it costs 25,000 Aeroplan points and the ticket is worth $1,200.  In this situation,it’s cheaper for me to buy a ticket for $220US and save my points for more expensive routes with no deals or seat sales.

Sunset swimming in the adult pool at the Sheraton Waikiki

Sunset swimming in the adult pool at the Sheraton Waikiki

Next, we started looking at hotel options.  May was a busier than anticipated time at work, so we didn’t have as much flexibility with dates, so the hotels were a little pricier than expected.  That being said, we decided to stay at the Sheraton Waikiki as it was located on the beach and we could use points to pay for our stays. While I like this hotel for the location, the balcony and its views, and the pools, it is a little loud due a club in the hotel.

View from the SPG Executive lounge

View from our balcony

Our itinerary had us leaving from BLI on Thursday night around 18:45 and arriving in HNL around 22:00, and returning from HNL to BLI on Sunday morning around 07:00.  It was a short trip to fly some 4,000 km’s but flying during the day instead of our usual red-eye routine was nice in some ways, even if it took away some time on the island.  The bonus of taking a red-eye is that you get a full-extra day in Hawaii, and that you can sleep on the flight then go to work and not have to take an extra vacation day. Allegiant is a real no-frills airline and I am surprised they do not charge you to use the bathroom. Some of the cons of the flight are: seats do not recline; they tend to assign you seats away from your companions to make you pay for seat selection, no in-flight entertainment, food and wine options are so-so, and you get lots of un-experienced travellers who do not know flight etiquette on-board.  The flight attendants were nice and attentive though. If I had to fly Allegiant again, I would as it beats the alternative of paying over $600 to fly on Alaska Airlines, Air Canada, West Jet, and other carriers that service HNL from the Vancouver area.

Outdoor patio at Kona Brewing

Outdoor patio at Kona Brewing

For the hotel, we couldn’t book the same price each night, so we had to pay for 1 night, use cash + points for the other, and just use points for the last night. Thankfully, the hotel let us stay in the same room each night, and out bill for 3 nights was under $250.  As SPG Gold members, we got a welcome drink at the bar and lounge access for 1 night.


Poke party on our balcony

While we didn’t have lots of time, we did get to relax and do things to unwind.  We did some stand-up paddleboarding on the beach;  went swimming; did a hike of the Makapu’u Lighthouse; spent a morning in Kailua; went to the KCC Farmer’s Market; met up with some friends for sushi; and had quality time together on our balcony where we enjoyed poke, beer, salad; spent a couple of hours at Kona Brewing Company; and Bubbie’s (mochi ice cream) for dessert. We also rented a Prius at about $30 per day and it was so fuel efficient that we ended up spending about $5US on gas for about 335 miles km of driving.

Walking on Waikiki Beach

Walking on Waikiki Beach

View from Happy Hour at the SPG Executive lounge

View from Happy Hour at the SPG Executive lounge

All things included, it was an affordable trip that brought us some sunshine and relaxation. while it is still a luxury to do things like this, at under $500 each for a weekend in Hawaii, it’s on par with weekends in Whistler and the Okanagan (our last 2 night 1.5 day weekend in Penticton, BC cost us $750CAD). I also get a bit of a thrill of doing fast-paced things like this to enjoy things as much as possible, even with limited time and doing it on the cheap. This type of travel is not for everyone and lots of people think we’re crazy, and maybe we are! Since we need some hotel stays and to use up some airline credits, our next trip of this nature will probably take us somewhere in California in September!

5 responses to “Happy Hours in Hawaii Under $500 per Person from Vancouver

  1. Max this is great, thank you for sharing your knowledge. I want to travel more and am all to often dissuaded by the cost. These traveling techniques are great. I absolutely agree with you about weekend getaways locally too. I can fly to Savannah, Georgia (return) for less than it would cost to fly local for a weekend. Let me know what you find for California this fall!

    • Yeah, it is insane how cheap it is to get to most US destinations if you are patient! Sometimes though you can’t chose where you want to go to get a deal; you have to go where the deals take you. Some places tend to be cheaper year round but a cheap flight doesn’t mean hotels will be cheap though.

  2. Can I ask do you book directly with the airlines or use an online service like kayak etc? :)

    • Hi Dana We use Kayak and other sites to research flight and hotels, and to see if they are cheaper at certain times of the year or days. Sometimes we book on Orbitz, Expedia, etc. just depends… Sometimes it is cheaper to do a flight and hotel package, or to book a hotel through a service site. If we are using points, companion fares, or want to get segments towards Air Canada Latitude then we book directly with the airline. Same for hotels’ if we need to build up nightly stays and the price is decent, we book directly through the hotel but if it is way cheaper to use a service, we do that.

  3. PS Good fares to LAX right now! My friend got one on Allegiant for $175 return from BLI.

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