So, you’re ready to plan a vacation. You have your vacation time blocked for 10 days in July (or October or whenever). You can get a pet sitter (or neighbor) to watch the pets. How do you decide where to go? Do you look at your point balances with Hilton or Marriott or Hyatt and try and figure out hotels that will reward your status with free breakfast and a possible upgrade or do you first figure out where you want to go and see how your points, miles and status will help you get there and get more out of your trip?

These days, I almost always figure out where we’re going first, and then see if I can get us there using airline miles (in business class if it’s overseas) and which hotel points might work for us when we get there. I look for saver-level space in business (or economy if I have to) and work from there. Then I look at what hotel chains have desirable properties in the locations we want to stay and then look elsewhere at independent hotels or Airbnb if necessary.

For example, we decided to go to Ireland in October during our daughter’s college fall break. It was up to me to figure out how to get there and where to stay. My wife and daughter will just be along for the ride as they (mostly) trust me to fit in activities and sights that we will all enjoy. One key thing to remember for this trip is that the dates were not flexible. We needed to leave on a Friday evening and return on the following Saturday (just to give us a margin of error so she does not miss class on the Monday and has a day to recover from the travel).

I started with the flights. We would have to fly out of Newark Friday evening as that is the closest airport for our daughter. I easily found that we could get there using Avianca LifeMiles (which you can get by transferring from several point currencies like American Express Membership Rewards) in economy for 20k LifeMiles plus about $50 in taxes and fees per person. But, I didn’t book right away. Why? Both United nonstop flights and even the Aer Lingus nonstop flight (available for 13k Avios plus ~$120 per person) were available for booking in economy and I knew it would be unlikely they would all sell out quickly.

For the return, I found flights in business class from Dublin to Toronto on Air Canada (again using LifeMiles for 60k + ~$50 per person). The kicker here was that Air Canada also had business class saver space on the connecting flights to both Newark and Atlanta. Thus, our daughter could connect to Newark and we could connect to Atlanta while we could still all fly together on the lay-flat business class from Dublin to Toronto. I went ahead and grabbed those flights as business class saver space does not usually stay available for very long, especially for the Canada-US flights. This would also save us booking a positioning return flight for my wife and me from Newark to Atlanta.

For the hotels, I first mapped out a rough driving itinerary, starting at Dublin Airport and working anti-clockwise around southern Ireland figuring out where we should visit. I ended up booking a couple of smaller independent hotels that offered triple rooms (cancellable until a couple of days before the stay), an interesting looking Marriott Autograph Collection hotel that is basically a country estate for one night using a 35k Marriott free night certificate, and an Airbnb in Dublin as there were fewer city hotels that allowed three adults to share a room. For the Airbnb, I took advantage of the $200 vacation rental credit that was offered on the Capital One Venture X Card so that reduced the cost considerably.

As the months moved forward, I decided to go ahead and grab the most desirable economy flight on United (using LifeMiles) for our outbound flight. As a United Premier Silver, I should be able to move us into Economy Plus seats with extra legroom and recline for the short overnight transatlantic flight. I booked one-way Delta flights to Newark for my wife and me to arrive a few hours ahead of the transatlantic flight.

I obviously checked many other programs besides LifeMiles (Star Alliance) including Delta, Air France, American, British Airways, etc. but ultimately those other options were either too many miles, too many connections, high taxes/fees or just not available. I also looked at using Hilton points in Dublin, but having to book two rooms made the Airbnb option more attractive.

I hope this gives you some ideas as you look to book future trips. Life is short and there are many places we still want to visit. Sure, hotels like the Park Hyatt in Paris and Waldorf in London look great, but I’m not going to plan a trip around their availability for reward nights as long as there are other places I still want to explore.

If you enjoyed this post (or have questions), let me know in the comments or send me an email at emptynestermiles@gmail.com. If you are thinking about opening a new credit card, please use one of my links.