It was about 8 years ago when I posted a question on social media to some friends: “Ireland or Hawaii?” The responses were as diverse as the two locations themselves. As you may have guessed, Ireland (All Points Lead To Ireland) was the early winner and the trip we chose to do at the time. However, many of the comments we received responded with some variation of “Go to BOTH!” Of course, we could not do so at the same time, or even in the same year for that matter. However, the seed was sown and our interest in Hawaii was such that it was probably the “next” destination on our list.

The flight to Dublin, and everything we experienced in business class, was out-of-this-world amazing. Aside from the glitz and glamor of the lounge and onboard amenities, my favorite part of flying business class was the lay-flat seat, the actual sleep I got on the way to my destination, and waking up the next morning ready to dive into the experiences of the day. (That, and I was able to avoid a trip to the chiropractor when we returned...) A trip to Hawaii, however, isn’t that bad. One flight to the west coast of the US, followed by a 5.5 or 6 hour flight to the island of your choice. One big problem, however, is that return flight (traveling east) is certain to be a red eye. Ick. Not anyone’s favorite, and something that immediately caused your’s truly to have flashbacks of our 40+ hour trip to Thailand in economy. We did not yet have enough points saved up for another business class ticket (let alone two), so I had to get creative. In this instance, I discovered that United allows travelers to book legs of a flight in separate classes. (Alternatively, I’ve come to learn that if the airline does not specifically allow this, you can book two separate flights, one in business, and one in economy, and then ask the airline to merge the reservations). With this knowledge, I booked the “long” legs (and most importantly, the overnight leg) of the trip in United First, and the other legs in economy. The price was much better than booking the whole thing in First. In fact, with flexible dates and a bit of searching, the cost was about the same as our economy tickets to Thailand. II found some solace and justification in paying this cash price for a flight with a total travel time of nearly 12 hours, partially in first class. THAT SAID, first class on the domestic airline, even to Hawaii, was less than stellar. Just your typical domestic first class product. No lounge access, a seat that is slightly bigger than economy, and critically, does not lay back more than a few inches. Moral of the story is to ensure you know exactly what airplane (and seat) you are booking. Just because you find a good price on “first” or “business class,” does not mean you are getting a world-class product.

Sometimes, we are able to travel on points for flights and accommodations. This was not one of those trips. However, we were able to use points (and a Hilton Honors Certificate!) on the accommodations! After staying at our second Conrad property (Thailand and Ireland), we learned that not all Conrads, and not all luxury hotels for that matter, are created equal. For that reason, I made it a point to find the best and most luxurious accommodations I could find for my points. Bang for the buck, if you will. This led me to discover a website that will forever live in infamy. A Complete Map of Hilton Hotels by their HH Category. I had no clue it existed, and stumbled upon it by accident. Woah. What a find. (Ok, ok... I’ll share it with you:

Hilton Hotels Category  

 The worldwide map is searchable by “category.” Categories range from 1-10, with (as you might imagine) 10 being the cream of the crop. *NEW life goal. Visit all the 10’s! Well, maybe not, but I now could see a rated difference between the Hilton in Koh Samui, Thailand (Category 10) and Dublin, Ireland (Category 7). It wasn’t just my imagination after all. Equipped with this new tool, there was little doubt the island in Hawaii we would visit; it would be Maui, home of the Grand Wailea (Waldorf Astoria). It is a HH Category 10 property with redemption rates around 90,000-95,000 points. With the cash price of the room easily exceeding $1,000 per night, I had found my next dynamite points redemption. Together with a certificate for a free night and points we had saved up, we booked our five nights in Hawaii at this immaculate resort, for free. Here's how we accumulated lots of points and got that reward certificate! Hilton Surpass  

For five days, we were able to escape reality and live the Hawaiian dream. Of course, we always have to remind ourselves when we travel - especially staying at resorts of this caliber - that normal life, even in Hawaii, wouldn’t be this glamorous if we were to sell everything and move here; but, it’s hard not to dream about it. We took the opportunity to try scuba diving, drive the road to Hana (we survived!), and bike down a volcano after watching a sunrise. Incredible scenery abounded, including at the resort, which boasted one of Hilton’s best spas (which we did get to visit). Coming home and telling the kids about the 7 interconnected swimming pools, which included a “water-elevator” to get to the top, only made them jealous that they did not join us on this trip. The kids were getting older, though. Maybe it is time that they could start traveling with us? That means needing more points and finding more creative ways to get places. That’s all right. We were starting to get the hang of it, and it’s become somewhat of a hobby to put it all together.