Spain + Portugal Combined in 10 ish days? Am I crazy?

I totally understand the desire to see as much as possible within one trip. It just depends on what your priorities are. The more you see, the less time you have in each place. If you prioritize nights per city, you have to cut places from your itinerary. For my taste from having travelled to both Spain and Portugal many times, I would vote for Seville over Madrid. It is farther away from Barcelona, but has much more charm and feels more like Spain to me. Madrid has a lot to offer, but mostly feels like any big city in Europe.

So are you the planner for a group, including husband and friends? Are they on board? I have to say if I embarked on a plan like this with friends, it is unlikely we’d be friends after, nor would my marriage be in good shape. I’m joking, but 10 days is a fantastic amount of time, so really think about how you want to spend those days.
If you want to go to Morocco, I’d go there only. Portugal and or Spain seem to be the obvious choice, you just need to scale back.

I would drop one city or leave Madrid in late afternoon(maybe that's your plan?)

I would drop one city or leave Madrid in late afternoon(maybe that's your plan?) I have been to both Granada and Lisbon and think Granada is more interesting than Lisbon.

What time of year is this trip? The weather in Spain varies massively between the northern coast and the rest of the country. Andalucia is highly likely to be miserably hot in the summer, so if you're traveling then, I would not push to include Seville, Granada, Cordoba (or even Madrid) on this trip. You have to make a lot of hard choices, so I'd take weather into consideration.

As you have discovered, there are very limited ground-transportation links between Portugal and Spain. This is why so many people end up deciding not to try to go to both countries on one trip. Ten days is a short time just for Portugal, and Spain is much larger. Attempting to go to too many places scattered around the Iberian Peninsula will not result in seeing more, but rather in spending a lot of time on trains, buses and/or planes.

Thanks for the input so far!

I would definitely prefer Seville over Madrid; however, the travel logistics are challenging, as are those for Granada. Super open to ideas on how to make that work.

This part of the trip is with my husband, myself and one other couple that we've traveled with before, and we are all used to changing cities/hotels. 3 cities over the 10 days would really only leave us 2 cities, as we do need to get to Barcelona, and the other 3 members of our travel party will meet us there for a few days before the cruise.

This is a late May/early June trip; all of the Spain and Portugal parts will be late May.

If I had 10 days I would certainly not be looking at staying in more than 3 cities. And if one of them was Barcelona, it would be 2 cities in total. Many top sights in Barcelona require pre-purchased, timed tickets, which makes scheduling a challenge.

Seville is likely to be very hot in late May: https://www.timeanddate.com/weather/spain/sevilla/historic?month=5&year=2025.

It's not a time of year I'd want to visit Madrid, either: https://www.timeanddate.com/weather/spain/madrid/historic?month=5&year=2025

Temperatures do vary from year to year, so I encourage you to use the drop-down box at the right, just above the graph to check May in other years. You can use the Search near the top right to see data for other cities.

With just 10 days (how many nights on the ground in Europe?) I'd consider something like Lisbon/Sintra + Barcelona, Porto/Douro Valley + Barcelona, or Basque Country + Barcelona. However, I am a retiree who can take long trips, so I have the freedom to spend considerable time in cities that have a lot to see, and I do especially love Barcelona for its architecture.

Ground in Europe 10-11 days total, 9-night cruise. Likely to head straight home from cruise, at most adding one day (Rome) just to not rush. We may be booking a pre-cruise 3 night package in Barcelona so that we can handle all of the ticketing challenges; it's just easier.

I suggest that you pick a country and don't try to do both Spain and Portugal.
You could spend three weeks, just in Portugal alone and won't see the key cities, places in Spain in a month.
Cut your traveling.

For Example, one day in Madrid is ridiculous. You a missing much in Madrid. Also, from Madrid you would need to do two day trips to Toledo and Segovia.
Do more research, find out WHAT you want to see and plan accordingly.
TripAdvisor.com is a great source.

One more vote for "pick one". Are you also factoring in the hotel check-in/out time, getting to the airport several hours in advance, or getting to the train station in time to buy tickets and find the track? And you're moving in a group. Don't underestimate the time it will take to get everyone on the same page at the same time. Every time you move, you're eating up a good bit of the day. With only 9 full days on the ground, so visiting so many cities is going to eat up nearly 3 days of your trip. Since you'll need to end in Barcelona, I'd stick with Spain, although they both merit an extended trip.