Like many people here I am a combination of planner/spontaneous traveler. I enjoy the research part and you need to do research in advance for many things. DH and I just did 10 day trip to Portugal in June. We decided to go in early spring for mid-June so I immediately looked for best airfare I could find to firm up dates, then he did car rental as we decided on our driving plan and then figured out the itinerary and then I did intense hotel research based on how many nights needed in each of the places. After booking hotels, I made some lists of what we wanted to see but didn’t make any dinner or tour reservations in advance although I noted some restaurants and we did bring several guide books with us. We did have some info from several people we knew who had gone on similar trips and so we had their information but we didn’t necessarily follow what any of those people did. We used the concierge or front desk in each of the hotels for restaurant suggestions and enjoyed great meals. We also made some adjustments in places that we stopped to tour based on conversations with people we met as well as hotel front desk either adding or subtracting places. Weather also plays a part in what you plan to do. We let hotel front desk recommend and book a tour for us to go to Sintra from Lisbon on our last full day and that worked very well. Didn’t reserve any tickets in advance for any of the monasteries or palaces we toured but we got to many places early to avoid crowds. Glad that I hadn’t pre-booked a boat ride in Porto for example as when we were there the weather was overcast and moisture in the air because it takes some time for fog to burn off and water looked choppy. Did add a refreshing gondola boat ride in Avierno which we weren’t 100% decided on stopping in at all and we really enjoyed both that boat ride and the entire experience of seeing that town.
We are going to a wedding in Big Sur in June for friend of younger d and so I did book those accommodations already but haven’t yet decided on how many nights overall we are going to go for and whether we will do wedding first and then some additional touring or tour first and end with the wedding. Plenty of time for that.