This Couple Got 13 Nights in Hawaiian Paradise Using Miles & Points!

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Update:   One or more card offers in this post are no longer available.  Check our Hot Deals for the latest offers. 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! Kyle is our newest reader success story to show folks it’s possible to travel without spending a lot of money.

A big thank you to Kyle for sharing his story!

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

I’m Kyle.  My girlfriend Courtney and I have been in the points game a little over a year – November 2015 to be exact.

What was the goal of your trip?

I’ve traveled the Caribbean pretty extensively since I was born, but I never had the chance to visit Hawaii.  I had two goals on this trip.

The first goal was to have a relaxing tropical getaway.  The second goal was to prove to my skeptical girlfriend this whole points & miles thing actually works!

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

It took about 10 months to accumulate all the point & miles needed for the trip (not including Delta miles, which I had before I knew about the points hobby).  We ended up booking everything about 4 months ahead of the actual trip.

Which points did you save to take your trip?

Chase Ultimate Rewards points were the most valuable and most flexible points in making this trip possible. 90,000 Delta miles for 2 round-trip flights from Moline, Illinois, to Lihue then Maui back to Moline (open jaw), which would have been $1,053 per person – came to 2.3 cents per mile. 175,000 Chase Ultimate Rewards points transferred to Hyatt for a 7-night stay at the Grand Hyatt Kauai.  We originally had a Garden View (parking lot view) room and they upgraded us to an Ocean View room with a lanai.  This stay would have cost us $4,501.  We paid nothing after they waived the resort fee for the entire week.

We used our 2 free Hilton weekend nights at the Grand Wailea Waldorf Astoria.  We ended up paying for one night, through a promotion from the Visa Luxury Hotel Collection offered by the Chase Sapphire Reserve.   The promotion offered the last night free, we ended up booking 2 nights, then booked 2 award nights using the 2 free weekend night certificates from the Citi Hilton Reserve.

Upon arrival there were no 1 level upgrades.  And after about 15 minutes they ended up giving us a room in the Napua Tower which included access to complimentary cocktail and hors d’oeuvres, dessert hour, and continental breakfast.  The 4-night stay at the Waldorf Astoria would have cost ~$3,716, but we paid $639.

45,000 Wyndham points (3 nights at the Wyndham Santa Monica).  Paid nothing while this stay.  It would have cost us $1,346 – this stay will be explained below.

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

• Chase Sapphire Reserve – 100,000 Chase Ultimate Rewards points which I didn’t even use on this trip, but the card perks came in handy
• Chase Sapphire Preferred Card – 50,000 Chase Ultimate Rewards points (after spending $4,000 in the first three months)
• Delta Platinum AMEX – 70,000 Delta miles
• Citi Hilton Reserve – 2 free weekend nights
• Chase Ink Business Preferred – 80,000 Chase Ultimate Rewards points (luckily I own a small landscaping company so I can also get business cards)

How did you search for and find the award flights?

Basically just Delta.com, because I already had the points.  The only difficult part was trying to book.

When I called Delta, they claimed the flight was 70,000 miles instead of the 45,000 I found on their site.  Luckily after about an hour they found the glitch and awarded the flight.

How did you find your hotel accommodations?

The two hotels we stayed in Hawaii we first saw on Million Mile Secrets – the Grand Hyatt Kauai and the Waldorf Astoria Maui.

After we decided on the hotels, it was just accumulating points for the stay.  I was able to take advantage of Chase Luxury Hotel and Resort Collection deal in late August, basically a buy one get one free night at the Waldorf Astoria.

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

Accumulating points for two hotels we couldn’t stay at.

I signed-up for the Barclaycard Wyndham Rewards card, which offered 45,000 Wyndham points and was enough for a 3-night stay at any Wyndham in the world.

Unfortunately, after I met the sign-up bonus and received the points, the Wyndham Koloa Landing at Poipu Beach Wyndham Grand Resort was no longer a Wyndham property.  Luckily we used those points for the Wyndham Santa Monica at the Pier in September to extend a short business trip.

The other problem we ran into was trying to book at the Andaz Maui, a Hyatt property.  I had over 200,000 Chase Ultimate Rewards points and even with up to 8 nights, they simply wouldn’t release a room for an award stay.  Lucky for us, the Grand Hyatt Kauai had wide open availability throughout the winter.

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

We love food!  With that being said you should definitely venture outside of your resort.

A few places that we recommend are Tiki Tacos, Puka Dog, and Hee Fat General Store in Kauai.

In Maui, Uluani Shaved Ice, Longhis, and the South Maui Fish Company which is a food truck with the most amazing fresh fish tacos.

We stayed pretty busy throughout the trip by visiting places such as Queen’s Bath, Waimea Canyon, the Road to Hana, and too many beaches to list.

What did you learn about yourself on the trip?

That the points and miles hobby can take you anywhere.  If we would have booked this trip using cash it would have cost over $10,700.  With points, miles, and other credit card benefits this trip cost less than $1,000 total for 13 days in paradise.

And that we need to move to Hawaii as soon as possible. 😉

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

A few things:   An excel spreadsheet helps keep everything in order, even if you don’t sign-up for certain cards you have your eye on now set up an account with loyalty programs early to receive more targeted offers from hotels or airlines, and get the Chase Sapphire Reserve.  The points are nice, but the benefits are amazing.

My girlfriend and I both have one and we both have the Priority Pass Select card, and Global Entry.  I’ve used the Silvercar and Enterprise discounts several times, and access to the Chase Luxury Hotels and Resorts Collection.

Now that I was able to convince my girlfriend this hobby works, we are looking at a 3-week trip to Australia, New Zealand, and Bora Bora – hopefully it will be booked completely with points & miles!

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!