Ditching the Spreadsheet and Finding Your Special Destination

Please note this site has financial relationships with American Express and this post may contain affiliate links. Read my Advertiser Disclosure policy here to learn more about my partners.

Some trips, some places, some moments are just special. I don’t mean special as in someone else made your coffee and you didn’t have to go to work that day special, though of course that is special. What I mean are the places that are really and truly breathtakingly special. They are the places where you feel at home even though you may be thousands of miles away from your own bed. They are the destinations that imprint on your soul. They are the moments when your heart rate and your breathing slow down and you feel at peace with everything around you.


I hope most of us have found some of those special places, but if you don’t have yours yet, you have something to seriously look forward to when miles and points take you to your own spot.


This morning I was reminded of one of my own special spots in the world when I read a post by The Frequent Miler as he debated the best use of his SPG points for an upcoming family trip. He is very analytical and numbers driven, which in the miles points world can be a very good thing. As such, his post outlined lots of equations pointing towards the best overall use of his points. He was debating many options, but one major decision was between the St. Regis Princeville on the North Shore of Kauai or the Grand Hyatt Kauai on the southern side of the island…among a few other contenders.

None of the math will point towards the St. Regis Princeville being the best use of points (or cash for that matter), and yet as I tweeted him after I read the post, what the numbers and analysis can’t quantify is that there is something special and magical about Princeville that should not be missed if you have the opportunity to go.


Based on previous discussions I have had both online and off with those who have also gone there, and a quick look at the comments on his post, I know I am far from alone in that belief. The location of the St. Regis Princeville and its dramatic view of Hanalei Bay, the Na Molokama mountains, epic sunsets, and more is beyond memorable. It is a spot and a moment that can imprint on your soul and become a part of who you are.




I have been yearning to return to that spot since the moment we drove away over two years ago, and even though the math will probably never point to that hotel offering the best return for points or dollars, I know that it provides something special that cannot be quantified in a spreadsheet. I know that I want to return.


Sad to be driving away from paradise

The vista over Hanalei Bay is not the only spot where I yearn to return. I have similar feelings about being on top of a snow covered mountain in The Rockies where the only sound you hear is the sound of your skis slicing into a turn.



Or driving down the “Sea to Sky” winding Highway 99 from Vancouver to Whistler where the lakes, the sky, the waterfalls, and the mountains are almost too much to take in…and that’s all before you even get to Whistler and experience its own majestic mountain magic.


There were also special moments on trips that weren’t just a feature of being in a special place, but more a combination of being in the right place at the right time with the right people.

Taking a ride around a classic carousel with my four year old ride in Boston as fall fell upon the city falls in this category.


As does riding horses as a family of three along side the lakes, streams, and mountains of Alaska.


Taking a kid-free relaxing vacation around the world with Josh in a period of calm before a number of stressors would hit our family is in this category of special moments.




Having a light snowfall start just as the Macy’s Thanksgiving Day Parade in New York City ushered out the turkey and welcomed Santa and the Christmas Season was special. If that wasn’t special enough, it was also the last trip I took with just Little C before we shared the news with her that a sister was on the way.


Experiencing the emerald magic of Ireland with Josh for the first time.


I have also had lots of special moments where the ocean meets the land, especially as the sun brilliantly announces the beginning or end of that day in your life.





Note that none of these places or moments were tied to how many square feet were in your room, whether breakfast was an included benefit on your stay, or if your upgrade cleared…though those things can set the stage for a more rested and relaxed state of mind, so they are not to be totally discounted. Just as Frequent Miler did, do the math, calculate the value of your redemptions on paper, stretch your dollars and your miles as far as you can, but don’t forget to factor in the intangible. For me, what makes a trip special is something that you will never find on a spreadsheet. It can only be found in the moment. I look forward to our next special travel moment, and I’d love to hear about some of yours!


Editorial Note: The opinions expressed here are mine and not provided, reviewed, by any bank, card issuer, or other company unless otherwise stated.

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. I guess it really depends on what you want out of it. We stayed at the Grand Hyatt Kauai this summer, but had a meal and sunset at the St. Regis Princeville, and walked around the property. If you want beach, the St. Regis is probably better. If you want sunset, most people think it’s better, but I honestly disagree. (I wasn’t that impressed with the sunset in Oia, either. What is wrong with me? I prefer sunsets with things in the foreground. Just the sun over the water seems boring, and seems like less vibrant color.)

    The pools at the Hyatt blow the pools at the St. Regis away, though. The lagoon, the lazy river, the waterslide. I found the restaurant selection better, too, and easier to get to the local shops. I had enough SPG and Hyatt points to stay at either one, and I’m glad we decided on the Hyatt.

    • Alan, I compared the two here and largely agree with you on many things – especially the pools.
      Ultimately though they are just very different properties even though they are on the same island, so which is better will depend on what you are looking for out of your trip. No spot will be “special” to everyone, but to me the St. Regis Princeville is very special while the Grand Hyatt Kauai is an awesome family resort with lots to do and fabulous pools. I love it and want to return, but it doesn’t conjure up the same feelings for me that Princeville does…if that makes sense. Wherever your special spot(s) are, I advocating going there as often as you can, even if the scales don’t always tip that way in a spreadsheet.

  2. I agree with you 100%, Summer. Special spots are far more important to me than getting the most value from points. The St. Regis Princeville has left an indelible mark on my soul. During my first visit 9 months ago, I had no desire to leave during the day and didn’t! I had been to Kauai a number of times over the years, so I wasn’t missing out on the sights. Went back a few months later and WAS able to wander during the day! Thailand also left a mark on me and can’t wait to go back.

  3. Are you sure it was the St. Regis that left the imprint? Because I feel that way about every nook and cranny in Kauai in general (Polihale beach… especially for sunset. Allerton Gardens, Na ‘Aina Gardens, all the various farmers markets and small towns… Hanapepe, Koloa, Hanalei, etc.. Head back there 4 weeks from today for our 4th year in a row, and planning our wedding there next year too. Havent bothered visiting the other islands (except in 2005 on day excursions via cruise)… because what would be the point? We have about 120k SPG points between us, but Im a Hyatt loyalist and other than in Bora Bora dont know where Id want to stay at a Starwood hotel.

    We’re certainly not spreadsheeting our honeymoon, headed to Australia and Madagascar and paying cash when needed… though we will be taking advantage of our point collection for SQ suites and more.

    P.S. I think I recognize those crossed palm trees from our trip earlier this year 🙂

    • Yes and no. If the hotel as it stands was picked up and plopped down say here in Houston, it would probably not feel anywhere near as special as it does in Princeville (no offense, Houston). However a 2.5 star hotel in the same spot also wouldn’t put me in the same mindset for it to feel that special. So, the location by itself on the North Shore of Kauai is absolutely special and worth a visit no matter where you stay. However, the exact spot the St. Regis is on, and the mood the hotel and service sets (for me), is special in its own unique way outside of just the overall specialness of Kauai.

  4. My most special travel spot to date is an unlikely winner. The beaches of Hollywood, Florida, a tiny town between Miami and Fort Lauderdale, where I watched my girls gather shells at sunrise in front of our 400 square foot Airbnb rental, not another soul in site… Beautiful translucent man-of-wars littered the beach… It was a difficult time in the life of my little family, but those moments felt so peaceful.

    Second would be Maluaka Beach on South Maui. A little known spot with an strikingly green background and blue water full of sea turtles… Magic.

  5. Though I do get alot of good information from many of your blog posts I think I enjoyed this one the most. You really hit the nail on the head! I also agree the feeling that you get from spending time in these “special” places brings more gratification to me than the value of the points spent to get there. The Princeville area of Kauai just seems to put me into that magical state as well.

    Keep up your good work and happy travels!

  6. I love this post! It seems like most points bloggers are so cutthroat that if you pay for something out of pocket or don’t use the points to the best ability, then it’s an epic FAIL. We’re headed to Banff next week and ended up paying more points for our flights just to have a better connection and return at a better time. I think that’s worth it, too.

    My most recent favorite memory- I won’t forget being able to watch the Australian Open in Melbourne with my husband. It had been a dream of his to go to a Major tennis tournament and thanks to points (and some intense saving) we took our family of 5 all the way down under. I won’t forget his kid in the candy store smiles!

    • That is so awesome to have that memory with your family – and I think Banff is an excellent choice. It is also on my list. Thanks for your nice comment!

    • I think using more points for a better flight is such a great idea. It makes it more relaxing, so you can enjoy your trip better.

      We just got back to Banff. It was amazing. I want to go back now. I hope you have a great time.
      That is the first time we have traveled on points and now I am hooked. I hoping to do more and figure this game all out.

  7. Your post really got my travel juices flowing, because I think that’s why we all travel…the endless search for that special spot. This past summer it was Hong Kong and riding the sky tram over Lantau Island to the Giant Buddha. And now, I’m looking for that next summer destination for our family trip and the possibilities seem endless…all thanks to points. I think your right, sometimes you gotta forget the analytics, because its not how many points you spent that you’ll remember but its the special moments that will stay with you forever.

Leave a Reply

Your email address will not be published. Required fields are marked *