Back in September 2021, I asked my wife where she wanted to go in summer 2022. We had mostly stuck to domestic travel in 2020 and 2021 (with a brief 4 night trip to Costa Rica being the exception). She had been speaking with her cousin, who had visited Portugal and loved it. She asked if it was possible to go to Portugal given the Covid restrictions and I told her that while it was certainly possible, it was also impossible to know what the travel restrictions would be in the summer of 2022.

Because we have an annual travel insurance policy through Allianz and because I was going to use points for most of the flights and hotels or book refundable reservations, I thought it was low risk enough to try and plan a trip. Even though it seems like booking eight months in advance is plenty of time, when I began looking for flights, it was apparent that there was not much business class award space for the summer of 2022. Some of that was due to other people booking even earlier, but some was no doubt due to airline schedules being in flux, which meant the airlines had not released all their award space yet.

I had some miles already deposited in some frequent flyer programs, so I tried to use those first as they tend to devalue over time faster than transferrable currencies like Amex, Citi, Chase, Capital One, etc. I first searched both ways using American and Delta, as I had plenty of miles in those programs. Not surprisingly, I didn’t find anything good available with Delta, but there were flights from Lisbon to Atlanta via London on British Airways with reasonable surcharges (about $350 per person) in business class on May 31^st. That would allow us to be away over our anniversary and return just after Memorial Day. I went ahead and held those flights while I looked for outbound flights to match up.

In 2020, we had booked a trip to Switzerland using Aeroplan Miles that we had to cancel. Consequently, I had a decent number of miles already in my account, so I looked for availability to Portugal. I found availability from Atlanta to Lisbon connecting in Toronto for May 21^st which worked out great with my British Airways return flights. We had planned on 7-10 days for the trip so this would meet those parameters.

I booked the Aeroplan flights which included Atlanta to Toronto in business class in late afternoon followed by Toronto to Lisbon on TAP Air Portugal in their new A321LR business class in the late evening. We would have a chance to check out the Air Canada Maple Leaf Lounge on our layover.

I also ticketed the British Airways flights which included a flight from Lisbon to London leaving late morning and connecting to the London-Atlanta flight on the brand new 787-10 with Club World Suites. This itinerary was looking good (or so I thought).

I tried to initially map out where we would visit in Portugal. Obviously, Lisbon and Porto are must-sees. We also wanted to visit the Douro Valley for some port tasting. Finally, I know that Sintra (near Lisbon) is a must-see place in Portugal. We decided to skip the southern part of Portugal on this trip as it would be too much to cover in nine days on the ground.

As for hotels, I first looked for Marriott, Hilton and Hyatt properties as I have high level status with those chains. I initially booked a Marriott in Lisbon and Sheraton in Porto. I also used two Marriott 35k free night certificates at the Penha Longa Resort near Sintra for the last two nights of our trip. I mapped out that we would start in Lisbon for a couple of days, then rent a car and drive toward the Douro Valley and Porto before heading back to Sintra and driving to the airport from there on the last morning.

I remembered that I also still had two $200 Amex hotel credits to use so I searched in Lisbon and Porto. My wife had 2x$200 credits to use on one of her Amex Platinum cards as they gave an extra $200 travel credit in 2020 due to covid-reduced travel for cards that had just been opened in 2019. All these credits needed to be used for prepaid booking by the end of 2021, but the bookings could be for 2022 stays. I found a great looking hotel in Lisbon listed with Fine Hotels and Resorts, the Tivoli Avenida Liberdade, and with the credits, I got the price down to about $200 per night for three nights. This included full breakfast for two, $100 in food and beverage credit, early check-in, late checkout, and an upgrade if available. In Porto, I found the Boeira Garden Hotel, a Hilton Curio Collection property for two nights at around $100 per night after applying the $200 credit from another Amex Platinum card. This was a Hotel Collection booking so it included an upgrade if available and $100 in food and beverage credits. As a Hilton Diamond member, I would also get breakfast for two and earn points on the stay (which turned out to be quite lucrative due to a Hilton promotion).

I next searched for a car rental. I decided to rent a car on the third day in Lisbon so we could take a day trip, park one night at the hotel in Lisbon then head out the next morning for points north. I would return the car at the airport on the last morning. I searched for an automatic car as I did not want to deal with the added stress of driving a manual (after too many years) and navigating the Portuguese roads and highways. I ended up finding a very good deal with Hertz for 350 Euros for the week including tax. Hertz also had a city office a few blocks from our Lisbon hotel which made pickup very easy.

Now I basically had the bones of the trip planned. There was still the matter of two more hotel nights to book, whether that be in the Douro Valley or somewhere nearby. I also needed to track my booked flights for changes to time or aircraft, so I set up alerts in ExpertFlyer. Things were looking good for May 2022.

Next up: Navigating changing flight schedules and travel restrictions.

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