The other day, I realized we now have five international trips booked between now and next June: Montreal, Ireland, Kenya, Liverpool and Southeast Asia. I didn’t really plan any of these for 2022-23, but it just worked out that way. For example, the Kenya trip has been rescheduled three times and was originally scheduled for January 2021.

How do you plan for these types of trips? For us, some of these trips are based around dates we have to travel and some are based around wanting to travel somewhere combined with finding availability for business class flights.

For Montreal, I had promised my older daughter I would take her there, as I took her sister to Alaska last summer, and I “owed” her a trip. In the end, she wanted to bring her boyfriend, so my wife is joining us too. We had to plan around a holiday weekend, so we picked Labor Day. My wife and I ended up needing to be in New Jersey to move our younger one into her dorm right before that weekend. We’ve now booked a flight from Newark to Montreal and a flight back from Montreal to Atlanta using Air Canada (one way on points and one way in cash). Our daughter and her boyfriend can drive to Montreal in about five hours from where they live in Connecticut.

For Ireland, our younger daughter asked us if we could travel somewhere during her fall break in the third week of October. We ran through a few options and decided on Ireland. We have set dates to travel to and from Newark (near her college) and have just booked economy award tickets (on United using LifeMiles for the outbound and Aer Lingus on the return) as it’s only a 6-7 hour nonstop flight. At one point, I had business class award tickets for the return on Air Canada, but they kept changing our connections in Toronto by so many hours that LifeMiles allowed me to cancel those tickets for no fee.

For Kenya, as I mentioned, this is now the fourth time I have booked our flights. A local safari company in Nairobi will be handling most of the arrangements on the ground so I don’t have to worry too much. I booked us in Qatar QSuites for our outbound flight about 11 months out for New Year’s Eve when I could see four seats available using American Airlines miles. Included in the same award ticket, I was able to book three of us on AA connecting flights from Atlanta to Chicago (with our older daughter meeting us flying AA from Hartford to Chicago) and then we will all take Qatar Airways all the way to Nairobi via Doha. For the return, we are flying KLM business class with a 10 hour daytime layover in Amsterdam so we can show the kids a bit of the city in-between flights. Those were trickier award tickets to book with Flying Blue as I had planned on Turkish Airlines, but they have not been making as much award space available. I probably paid a bit more in points and fees than I would have liked, but our dates were pretty locked in after booking the AA/Qatar award.

For Liverpool, my wife has wanted to join me on one of these trips (I’ve been there for Liverpool matches five times between 2016 and 2020) and we decided on a long weekend (Wednesday-Monday) in April when I was sure a match would not be rescheduled away from that weekend. I had 72,000 Singapore KrisFlyer miles sitting in my account from an old attempt to fly their Houston-Manchester flight that did not work out. I ended up finding two seats in business for the outbound flight so I transferred in another 72,000 points from American Express and booked it just before Singapore raised their redemption rates. For the flight back, we are flying Virgin Premium Economy direct from Manchester to Atlanta using only 32,500 Virgin points each (and paying a lot less in fees than Virgin’s business class award tickets).

For Southeast Asia, I previously wrote about how I found business class space on ANA for next June. We’ll visit Vietnam, Cambodia and Singapore. That trip is still coming together, but the main challenge of the long-haul flights has already been solved.

I don’t think I’ve ever had five international trips planned at the same time before, but they are reasonably spaced out so we won’t have too many issues with missing work. We have two trips for just the two of us, one with each grown kid alone and one with both kids. That’s a perfect summary of Empty Nester Travel life!

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