An 11-Day Hawaiian Vacation for 3 for Under $2,000!

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An 11-Day Hawaiian Vacation for 3 for Under $2,000!

Million Mile SecretsAn 11-Day Hawaiian Vacation for 3 for Under $2,000!Million Mile Secrets Team

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Welcome to the next installment of our Reader Success Series where Million Mile Secrets Readers share how they booked a trip with miles & points to get Big Travel with Small Money!

Allen is our newest reader success story to show folks it’s possible to travel without spending a lot of money.

An 11 Day Hawaiian Vacation For 3 For Under 2000
Family Fun Before Breakfast at the Aulani

A big thank you to Allen for sharing his story!

Please introduce yourself to everyone and tell us how long you’ve been involved in the miles & points hobby.

My name is Allen Benjamin Joseph Wing and I have been involved in the hobby since May 2015.  My first card was the Citi / AAdvantage Platinum Select World Elite Mastercard, a card I still use to this day and have gotten great value from:  3 round-trip flights and over $600 saved in checked bags so far.

What was the goal of your trip?

The goal of the trip was rather simple, plan a “family-moon,” a vacation that my fiancé and stepson could enjoy and serve as the first official memory that we had, as a family.  I was married on May 5, 2017, and we embarked on our family vacation the very next day.

How long did you collect miles and points for your trip? 

I know I will draw some dirty looks from those in the miles and points community, but I am a points hoarder.

An 11 Day Hawaiian Vacation For 3 For Under 2000
At the Hawaiian Royal Palace

I collect points with no forethought about how, when, or where I am going to use them.  My personal philosophy when it comes to points is that it’s better to have them when you don’t need them, than to need them and not have them.  I apply to credit cards in 6-month cycles, one round which focuses on hotels and the second round for airline miles.

Which points did you save to take your trip?

To get my family of 3 from Philadelphia to Hawaii, I used a combination of points and flight credits.  My son is a stranger to flying, so I knew he would not be able to endure an almost 11-hour direct flight to Honolulu, and broke the trip into 2 days.

Day 1:  Philadelphia to Los Angeles – I used my British Airways Avios points to book 3 one-way flights.  I booked the tickets in August 2016 for the May 2017 flights, and only had to use 12,500 points for each ticket.

I stayed at the Wingate by Wyndham LAX Airport hotel, which I got for free, thanks to my Barclaycard Wyndham Rewards credit card.

An 11 Day Hawaiian Vacation For 3 For Under 2000
The Face You Make When You Only Paid $75 to Stay at The Ritz-Carlton and Get Upgraded to a Suite

Day 2:  Los Angeles to Honolulu –  I used my Citi ThankYou points to get 3 one-way tickets for free.  And I used my Citi Prestige card for Admirals Club access at the Los Angeles airport.

I knew my family would be jet lagged our first night in Hawaii.  And I did not want to spend money for a day at the Disney Aulani that I knew we would spend sleeping, so I used my Wyndham points to stay at the surprisingly nice Ramada Plaza Waikiki hotel, which I actually enjoyed due to its friendly staff and 1960s chicness.

Then my family spent 6 days and 5 nights at the Disney Aulani.  The Aulani is EXPENSIVE.

When I plugged the dates into their website, the cheapest room I could find was $2,875 for 5 nights.  I am a massive fan of all things Disney, so I knew that many people use Disney Vacation Club points to book discounted rooms at Disney resorts.  But I used a respectable and highly recommended website to book a Disney Vacation Club room at the Aulani for 6 days/5 nights for only $1,300.

An 11 Day Hawaiian Vacation For 3 For Under 2000
Grounds and Beach at The Ritz-Carlton

I have the Chase Disney credit card, which I used to book 4 other Disney trips with several of my friends and co-workers.  So I had a sizable amount of Disney Rewards dollars that I used for meals while I was at the Aulani.

We left the Aulani and flew from Honolulu to Maui for free using the $250 flight credit on my Citi Prestige card.  We stayed at The Ritz-Carlton, Kapalua for 3 days and 2 nights, paying just the resort fee of $35 per night, thanks to my Chase Ritz-Carlton card.

To fly back from Maui to Philadelphia, I used Hawaiian Airlines miles for 3 one-way flights from Maui to Honolulu to Las Vegas.  And then I used American Airlines miles to flight from Las Vegas back home to Philadelphia.

What cards would you recommend to someone starting out with miles & points?

I would recommend getting 5 Chase credit cards over the course of 2 years and then systematically applying to AMEX cards.

How did you search for and find the award flights?

I used Google Flights, Hipmunk, and The Flight Deal to search for travel deals.

How did you find your hotel accommodations?

I have a good amount of hotel points and vouchers, so I always check to see if I can use those first, before I search for a hotel.  I prefer to use a combination of points and cash to pay for my hotels.

What was the most challenging part about planning your trip? How did you solve it?

The most challenging part was searching for multiple flights on multiple airlines.  I solved this problem by being organized – I keep a travel journal that I use to keep track of all my travel plans.

Give us a few recommendations or tips for what to do at your destination.  Parks, restaurants, hidden gems, etc.

If you are staying at the Disney Aulani, rent a car and explore the island.  Don’t just sit in the pools all day.  It’s hard, but worth it.

An 11 Day Hawaiian Vacation For 3 For Under 2000
Taking a Picture of My Wife and Son’s Selfie and the Aulani

Eat at The Pig and the Lady, one of the best meals I have ever had in life.  Go to the Shirokiya Japan Village Walk, it is a Japanese food court that is a sight to be seen and eaten!

What did you learn about yourself on the trip?

This trip reinforced my love of the points and miles hobby.  The flight from Philadelphia to Honolulu for one person round-trip runs between $1,500 and $2,000, and I was able to plan an entire 11-day vacation for 3 people for less than $2,000 dollars total.

What would you say to folks looking to plan a similar trip?  Or to those who haven’t taken a miles & points trip yet!

I tell everyone looking to get into the miles and points hobby to go slowly and carefully.  Keep all your credit card balances at $0.  And create a system to keep track of all of your spending.

Want to Share Your Story?

If you’d like to be considered for our reader success story series, please send me a note!  Emily and I would love to hear about how you travel with miles and points!

If you liked this post, why don’t you join the 36,000+ readers who have signed-up to receive free blog posts via email (only 1 email per day!) or in an RSS reader …because then you’ll never miss another update!

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Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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Any issue with Chase cards such as CSR? Do you get 3x UR for travel at this site?

Hey Mike, I don’t have a CSR, I’m 6/24 so I missed out on the Reserve craze lol… I charged the DVC points to my Disney Chase, so I could collect some disney rewards dollars for the trip.

Thanks for the tip JoAnn!

Thanks for sharing! We live north of Philly and are looking at going to Hawaii in the fall!

Hey Brad, when you are looking to book for flights, try using Alaskian Airline, if your flying out of PHL. If you get the Alaskian Airline card they offer a companion coupon for 121 total, so you can really save on a trip to Hawaii.

What website did you book Aulani through? It just states “but I used a respectable and highly recommended website to book Aulani”?

Good evening, the website is, out of respect for Million Miles, I did not want to mention another company

I’m thinking maybe he wasn’t allowed to mention it but I’m a DVC owner and have rented out my points to Dave’s who is a 3rd party. On the Ritz I’m assuming points were used for that stay, what a deal!

Good Even Boonie, yes I used Dave Vacation Rentals, I use his company all the time. Your a DVC member, can I just say that I am so envious :). I used the Ritz Carlton Credit card, which had a new member offer of 3 free nights at various Ritz Carlton’s after 5,000 spend in 3 month.

Great story, I love how you utilized your points and miles and saved so much money. As I read your story, I hoped that you knew about renting Disney points and sure enough you did! That is how we stayed at Aulani last year. Hawaii is my favorite destination. I am currently saving miles and points for what will be our third trip over there without paying airfare. On the next trip I plan to not pay for airfare or hotels. I’m hooked!

Hello Diane, yes I too love Hawaii and my wife and I are currently waiting for the Hyatt card to offer the 40,000 point bonus, rather than the two free nights, so we can use the Hyatt card, in combination with the Marriott card, to stay 28 days in Hawaii , HNL and Maui, for under 2000, using a points and pay feature to extend the trip. Renting DVC points is my guilty pleasure, there are serious savings to be had

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