Portugal and Morocco -- need help with the initial planning!

Well, just a personal preference, but I'd save Morocco for when you could do a more extensive trip. I mean what happens if you get food poisoning (not an unheard of occurrence),? Then your trip is dunzo because there is zero wiggle room.
Your Portugal stops could definitely be longer, and I would try to avoid going all the way north and then all the way south. Have you scoped out the flights yet? This kind of trip just requires a lot of legwork--I realize you are just getting started.

You’ve really got a lot on your 16-day agenda. Does your timeframe include inbound and outbound to home flights? Think about the logistics a bit. How will moving about with a party of 5 be? Do your travel/vacation styles match? Is everyone ok with getting up early (or late)? Is everyone comfortable with a scheduled itinerary, or conversely, comfortable with playing it by ear? Will everyone want to do everything together? Wanting to use public transportation is great, but the proposed itinerary doesn’t account for travel time between destinations (several hours to a half day, if not more). For 3 full days, you’d have to add transportation time, plus arrival and departure administrative tasks. Even checking in and out of hotels eats up time, along with unpacking and repacking, eating, etc. What are your must-sees? How much time will you realistically have to see them? Three days can quickly morph into more than four. With all these stops, you can see how much time that adds up to. On top of that, you’re contemplating changing continents! For me, less is more. Every city on your list is worth seeing, no doubt, I just don’t think it will be physically possible within 2 weeks. I’d suggest either Morocco or a scaled-back Portugal trip rather than both. It’s easy to spend two weeks in either of these wonderful countries. Visiting both in one trip would be shortchanging both.

You might have perfectly good reasons for visiting Casablanca, but after 3 trips to Morocco, I can't think of any. You might want to do a sanity-check on what your expectations are for what you'll find worthwhile in Casablanca. Morocco is awesome, but it's a large, diverse country, and it deserves more time...and personally, I wouldn't waste any of mine in Casablanca.

Your trip is short enough just visiting Portugal alone, I would echo the comments about about re-considering the side-trip to Morocco, and perhaps spend all your limited time in Portugal, saving Morocco for a later trip when you have some more experience and when you can give it the time it deserves.

Perhaps worth noting: You start off by describing your trip as "two weeks" and then say you're thinking about an itinerary that totals 16 days. What exactly is "two weeks" then? I would suggest you begin by being completely honest with yourself, and look at actual dates (even if you're unsure of the specific date right now), because until you start referring to specific real-world dates, it's very easy to set yourself up for an unrealistic timeline. Don't count the days you will be away from home/off work, count actual days and nights on the ground at your destination. Don't count your arrival day or your departure day, those are consumed by travel. And remember, each time you pick up and move yourself from place to place, you burn most of that day. So take into account the fact that 2 nights anywhere equals just one day actually being there (generally, # of nights – 1 = # of days).

Depending on how you define your "two weeks" you may have as few as just 11 full, usable days on the ground. But your initial itinerary adds up to 16. Need to reconcile those things - get out a calendar and write on it (in pencil...).

@valadelphia — good point about the food poisoning. I will keep this in mind for when I plan, if I decide I still want to go to Morocco then I will try to be strategic about it. I still haven’t started planning yet. I like to gather information to have an idea about what to expect, best routes, duration, etc. Your information is very helpful. Thank you!

@Wanderlust58 — thank you for your feedback. This is really helpful for me to know that I need to cut back on the amount of destinations. My friends and I have traveled as a group every year for the past 8 years, and we are very close friends. We have traveled to 9 countries together so we know each other’s style very well. I’m not too concerned about that aspect of the traveling. We also are flexible on our timing, so we want to see how many days are ideal for a trip like that before actually deciding. We have initially decided on 2 week ish but can totally extend the number of days a bit too. We are not sure if we want to visit Morocco on an extended trip, hence we had an idea that maybe if we visit Morocco for a few days this trip and end up wanting more, we can then decide to visit it again in a future year.

For public transportation, did you mean it generally takes a long day to travel between destinations, even within Portugal? Would you recommend renting a car instead? We are not opposed to renting a car, we just prefer to rely on public transportation but if it’s not efficient, we would then rent a car! This is such good information. We will keep this in mind for when we plan!

@David from Seattle — I love that you brought up Casablanca in your response! Honestly, the reason why I want to go there is really silly. I listened to the song Casablanca when I was a kid and loved it, and even though the song was about two people watching the movie Casablanca, I had growing up romanticized the idea of visiting Casablanca for some reason. It is completely silly, but I love the idea of giving the little kid in me the satisfaction of “I made it to the place I’ve always wanted to go”. BUT now hearing what you said about it, I realized I knew nothing about it, and not sure if I even want to visit it now. :-))

I meant to say “about 2-weeks” because my time for this trip is pretty flexible. We can go up to 25 days, but I’ve found in the past about 14 days, I start getting homesick and missing my kitty cats at home so I wanted to see if we can take this trip for 2 weeks, and go from there. If we need to add more time, we could do that. Or we might consider cutting back the number of stops.
Thank you so much for your insight!

I am so glad to hear that your group has lots of experience traveling together! I had visions of all sorts of potential pitfalls…And, it’s good that you could have a few more days to play with. Yes, I’m terrible at math but I just couldn’t fit it all in 14 (16) days. The time it takes to travel between cities really depends on how you prioritize your itinerary. Have you considered open-jaw flights? That would save time in backtracking by moving in one direction. Once you finalize your list of cities and maximum number of actual full days on the ground and how many days you want in each, take some time to sit down with train and bus schedules. Add in the car option, but be aware that Google maps and similar tools often underestimate driving times, sometimes by an hour or two. Got to factor that in.
In my planning, I print out blank calendars, start with everything we want to see and the total number of days we have, use a map to establish the route, then pencil in transportation times. Then it’s time to start adjusting my goals based on realistic transportation times, the number of must-see sites, time necessary for each and availability of total days. It’s like fitting a puzzle together. We do move slowly and have the luxury of extended time away from home, so it’s a bit easier for me to plan. And I confess to being an over-planner, but this works for us. I’m currently working on a trip to Poland and using this method has led us to chop a few stops or reduce the time in some/each. A couple of day trips to smaller towns away from major cities have had to go. In one city, my husband and I are actually going in different directions for a couple of days, a first for us, so that we both are happy! Again, depends on your priorities.

How do you normally plan your trips? If it’s been successful, why mess with succes? Everyone here has their own process. My technique might be overkill for you. The beauty of all this is that you are wisely starting your planning now.

It is definitely a major bonus that you have already have so much experience traveling together. And thanks for the cute Casablanca story! I wondered the same thing but just based on hearsay--I'd love to get to Morocco one day. Friends have had fantastic trips there, and you can definitely fill two weeks and then some there.

With the time you have available, an all-Portugal trip would be my choice, but it's not a crazy idea to dip your toes into Morocco to see what you think about a longer visit in the future. I can tell you now that, if you're at all adventurous, you're going to want to go back.

Casablanca is a mostly modern city, so I agree with David--not worth sightseeing time on a quick visit. However, you may well need to go through Casablanca upon arriving or departing, for logistical reasons. I'd just make that as quick a visit as possible.

Air Maroc flies nonstop to Casablanca from the US, and many European cities have flights to places like Marrakech and Fes. I think there are nonstops to Marrakech from Lisbon, Porto and Faro.