First time to Portugal and wanting some advice.(Please)

If you want to see the best of Morocco, skip Tangier. Since you're going to PT in Oct, I would focus on seeing Lisbon and ES.

Two weeks isn’t enough to cover what Portugal has to offer, without trying to also see Morocco and if you were to visit Morocco, Marrakesh would be better than Tangier.

Anywhere in mainland Europe can have inclement weather by October. I have had torrential rain in the Algarve then, but also some warm, sunny weather in Porto.

For a 2 week trip, your first day will just be coping with jet lag and your last day will be getting to the airport. I suggest you have 5 full days in Lisbon and take the train to Porto for at least 3 days there including a day trip to the Douro, as October is a great time to visit. Then hire a car and spend the rest of your holiday driving back to Lisbon through the National Parks for hiking and seeing some of the traditional towns such as Tomar and Coimbra.

October is a great month in Portugal. There may be rain in the latter part of the month but it’s off and on and rarely an all day affair.
Spend the entire time in Portugal!

Thanks to all who gave advice! Keep it coming!!

I would spend 4 or 5 nights in Lisbon and 1 or 2 nights in Sintra. We spent 5 nights in Lisbon that included a day trip to Sintra. We did go on a bus tour because this was the end of a 3-week vacation, and we were getting tired and it was easier to take a bus tour. But we didn't see a lot. I do think that staying overnight in Sintra is a better choice because there is a lot to see and do there, and it's quieter after the daytrippers (such as us!) have left. If you want to limit the number of times you change hotels, then by all means visit Sintra as a day trip from Lisbon. If you go on your own (you can take the train), you will see a lot more than we did with a bus tour.

You mention that you like museums. I highly recommend the Gulbenkian Museum in Lisbon. It's one of the highlight of our trip! The museum consists of the Founders Collection, which is very varied with European paintings, Chinese vases and pottery, exquisite Lalique jewelry, and furniture. The Modern Collection is very interesting, too. This is in a separate building. There is a very informative historical exhibit downstairs which you should not miss.

We also really liked the Coach Museum. We didn't have time for the Tile Museum, and I know there are other interesting small museums in Lisbon.

We haven't been anywhere else in Portugal yet, so can't comment on other places.

You can easily fill two weeks in Portugal without going to the south. I take that back, it won't be easy because you'll have to choose carefully among all the options. Carolyn took a trip in November and wrote a very good report on her first week or so, including weather conditions.

With a car you could spend up to a week enjoying the scenery and small towns in eastern Portugal. I more or less followed Carolyn's itinerary, at a little slower pace. Wonderful.

PLEASE SKIP Tangier. Morocco has some great places, but Tangier is not one of them.

Enjoy Portugal, it may be chilly at times, but we love the country and its people. Lisbon is great, also Evora, Sintra, Obidos, Navarre, and especially Porto and the Douro Valley.