Outside of winning the lottery, setting travel goals is the most effective way to make your dream vacation a reality! While achieving your dream vacation doesn’t require wading into the points and miles hobby, it can certainly speed things along and make it better, longer, and/or more luxurious than you would otherwise have thought!
Becoming Inspired
As detailed in the series on my trip to Pebble Beach, that was the trip that got me started towards the deep end of the points and miles hobby. Before that trip, I had some miles in a couple airlines that we could use to get free tickets, but I was’t really aware of much more than the very basics of a couple programs.
When I needed a new credit card for an unrelated trip I discovered the value of signup bonuses. My wife was spending a few weeks in Canada and all the cards we had at the time charge foreign transaction fees for any purchases made outside the US. My research pointed me to a card offering no transaction fees as well as tens of thousands of points in the IHG Rewards loyalty program after meeting a minimum spend threshold in the first 3 months of owning the card.
In addition, the card also gave me complementary elite status in the IHG program as well as one free night in any IHG hotel worldwide each year for an $89 annual fee. The free night alone could easily be worth more than the annual fee alone.
While I wouldn’t call getting that card part of any goal setting, it did inspire our family to set a goal to go to Hawaii two years later.
Setting Goals
For our family Hawaii was the place we always wanted to go. My wife and I had planned 5 different trips to Hawaii, but had only been able to actually go there once, just before we had kids. We had always had to cancel the trip for various work and other reasons. After our latest plans had fallen through for 2015 for a trip with just the two of us, we decided that we would set a goal to go the summer of 2017. The kids would be 6 and 8 and hopefully old enough to more easily handle the time change and length of the journey.
Coming up with a Plan
Setting a goal is one thing. Following it through is obviously another, but we were committed to making it happen. We were hoping to use points and miles for our flights and at least some of our hotel stays.
On the logistics front, we wanted to make sure the kids would be able to handle the trip. By the time we were planning the kids had been on a few flights, but nothing more than 3 hours in length and one time zone away. To that end, we decided to make a test trip to LA in 2016, the summer before we were planning the Hawaii trip. We figured if they could handle that trip, which is essentially halfway to Hawaii, they could handle the full trip the next summer when they were a year older. Plus, we had never been to LA other than for work so why not?
Executing the Plan
On the credit card signup front, I had decided that since we had some American Airlines miles we would try to gather as many of those as possible to pay for our flights. I signed up for the Citi AAdvantage World Mastercard Elite MasterCard which was offering a 75,000 miles bonus at the time. This was my first premium card and it had a $450 annual fee. With the signup bonus and the perks, I easily got that much value out of the card. Some of the perks included a $100 statement credit for getting TSA Global Entry and access to American Airlines Admiral Club lounges. I had never been in lounges before that time and was looking forward to how that changed the travel experience.
In addition I also signed up for a Citi Checking account which was offering 50,000 points for new accounts. I had to open an account with a minimum amount of cash and use their bill pay to spend a certain amount of money in the first three months in order to get points. I ended up calcualating money we would be spending for car payments and put that much into the account so that it would be empty by the end of the three months. I would then close the account once I got the bonus points credited. The account was simply for the bonus points as there aren’t any Citi branches near where I live so it was quite inconvenient to use as a regular bank. It was worth the bonus points, though!
On the hotel side, we knew we needed to gather points and status, though at the time the only status we had was through the IHG card I had. We were going to be staying on Maui and there were no IHG properties on the island. There were several SPG properties, though. My wife signed up for an SPG Amex card and started focusing her work travel to that chain when possible. Through her travel at work and our own travel plans we were on track to achieve Gold status by the time we went on our trip.
Goals can Change
Goals can get you headed in one directions, but don’t be afraid to change direction if things just aren’t working out. As we got about 10 months out from the trip, I came to the realization we just weren’t going to have enough miles with American to buy all the tickets. We could buy one or two of the tickets, but doing the math, we weren’t getting a great value for the al the points we were spending. It was disappointing that we had spent so much effort gathering these miles but wouldn’t be able to use them on the trip we intended. We were also able to use the American Airlines miles for a bonus trip to Paris in February of 2017 so they didn’t go to waste!
We had to rethink our plans and either get points in another program or buy the tickets outright. I had been traveling frequently for United at the time and had quite a few points, but not enough for all our tickets, but it was a start. This was at a time United was offering a bonus for buying their miles. While buying points is rarely a good deal, I did the math that with the bonus, buying the points was cheaper than buying the tickets outright. While it wasn’t a fantastic deal and I’m not sure I’d do it the same way again, it did get us to Hawaii which was our ultimate goal!
Be flexible
On the hotel front we had focused on gathering SPG points and had found a few properties that fit what we were looking for, but only for about half of our trip. We didn’t have any place we could redeem SPG points for the rest of it. We wanted to spend time on different parts of the island so we were thinking we’d have to pay for a stay on the other part we wanted to stay at.
Then I learned that Marriott and SPG were the same company and that we could link our accounts and transfer points and status between the two! While the programs have now been merged, at that time they were still separate, but you could transfer points between them instantly for free and could match status between the programs as well. This opened up several more properties we could book and few the same or fewer points. We were able to book the Ritz Carlton for the same points as the Westin. For our stay on the other side of the island, we decided to save money and book a stay at a Marriott that looked okay on the site, but we weren’t all that enthused about it. We were going to save a ton of money by staying there and figured we’d manage. It turns out that is our favorite property on the island!
Enjoy the Planning
As a planner by heart I admit I’m a bit biased. I do think planning and looking forward to the trip gives you almost as much enjoyment as actually going on the trip. By planning and coming up with a strategy for using points and miles, you focus on what you want out of the trip. You become aware of the compromised you are making and get a better feel for what compromises you are willing to make. You’re less price sensitive when choosing hotels because there may be several with the same price in points that have wildly different cash prices. You can choose the hotel you think works best for you rather than what works best with your wallet.
Expanding your Bucket List
Before points and miles, my bucket list was pretty empty. I just considered things out of reach and too unrealistic to even bother putting in my bucket list. Now my bucket list is overflowing! Focusing your spending and credit card applications to a specific goal takes time and discipline, but most of it happens in the beginning. You figure out where you want to go, determine what types and how many points you’ll need, and research a plan for gathering those points. Every few months you re-evaluate your progress and if there is anything you can take advantage of that will get you to your goal more quickly. In the end the waiting game of building up points balances can be boring though it gives you time to dream about and get excited about your destination which is the ultimate goal!
Tomatico Travels 
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