MJL wrote:
Others have recommended we fly round-trip to London to make it cheaper
and use London as the start and end-points of our trip. While it
would be nice to include London, I don't want to plan too much for one
trip. I feel like we would waste a significant amount of time getting
to Rome from London and then getting back to London at the end.

While I am looking for the cheapest option, I don't want to waste any
of our travel time just to save a few bucks.

This is exactly right. (And would you really "save a few bucks" when all is
said and done?)

I mean, London is one of the world's great places, but if it is not on your
short list don't go there this time.

If anyone has any advice or any ideas, I would greatly appreciate it.

It's hard to advise without knowing what you want to do or how you like to
travel. Here are a few tentative thoughts.

Don't shortchange the countryside! Adding a few days in hills, mountains, or
by the sea can also provide a welcome change of pace in the middle of an
ambitious fast-paced itinerary such as yours.

If you are splitting your time between Italy and Iberia, you have about two
weeks in each place. That is a nice amount of time, but you will still have
to pick and choose. What are your priorities?

How will you travel to Spain from Italy? It is a long train ride, depending
on where you are leaving from. Another poster suggested flying to
Barcelona--a good plan if you can afford it.

Getting to Portugal from Spain is not as straightforward as you might think,
either, at least from the south. So, I suggest saving Madrid (and Toledo)
until after you've seen what you want to see in Andalucia and the south. If
this doesn't work for you consider flying.

In Spain, I'd suggest several days in Granada. In Portugal, visit Sintra.
I've done this as a day trip from Lisbon, but I think it would make an
especially romantic place to spend a night or two.

I don't know if any of these ideas speak to you. Have a great trip!