Euro Trip 2019 Planning: Booking initial hotels (Part 1)

In the previous installments in this series, I wrote about having a blank slate for this year’s journey and selecting our transatlantic flights. I then discussed how I decided where we would actually go once we arrived in Europe. Today’s article is the first of two which will cover booking our initial hotel stays. I will describe my general strategy for making lodging reservations, along with the short-list of properties that I am considering and why they made the list. I will use Milan, Italy for this detailed discussion though I employed this approach for all bookings for this trip.

One multiple-night stay or multiple one-night stays?

For my recent trip to Miami, I had to decide between a two-night stay at one hotel or two one-night stays at two properties. The decision came down to whether immediate bonus points or SPG Gold Preferred status for 2016 was more valuable.