Plan Sintra - you seem to be listing too many places to visit in my view. I would aim for one in the morning & one in the afternoon only.

The Belem Tower was closed recently when I was there and many say the Monastery is not worth the entrance fee as you are limited to the cloisters. The Church is free and the carvings on the outside are pretty spectacular.

Investigate where to eat in Alfama as many are tourist fodder restaurants.

On Saturday's the flea market takes place behind the Panteao Nacional in Alfama.

We loved Lisbon on our recent trip. Wandering about is part of the fun.

As for the St. George Castle (Castelo de Sao Jorge), I cannot agree with the first comment. It's true that major restorations were undertaken in the 1930s, but there are portions that exist from many past ages in the past, including the 11th century, if not earlier. Furthermore, you'll see the castle looming above you from almost everywhere in Lisbon; it will be difficult, if not futile, to resist seeing it up close.

Keep in mind that you don't go to the castle, just to see the castle. You go there, as well, for the spectacular views of Lisbon and the Tejo estuary beyond. As to how long you need -- it's hard to say. I suppose you could just traipse through in an hour or so. But if you really want to enjoy the views, perhaps sitting on a bench sipping good Portuguese wine from the wine cart (I can't say whether it's still there), and maybe even have lunch in the restaurant, you could do as I did and spend an entire afternoon there.

Also, as for the Alfama, I do want to put in a good word for a museum that doesn't always get a lot of mention, the Museum of Resistance and Liberty, also known as the Aljube Museum (after the original name of the old building in which it is located). It's devoted to the resistance against the long conservative dictatorship of Antonio Salazar (1932-1968). If you're a dedicated fascist or authoritarian, perhaps you may not like it; otherwise, you may find it informative and inspiring, as I did. Most of the displays are labelled in English as well as Portuguese.

I recommend the national Azulejo (tiles) museum

https://en.wikipedia.org/wiki/National_Museum_of_the_Azulejo

A bit east of Alfama along the river and railway

Agree that the tower of Belem is not that interesting.

I would highly recommend doing a foodie tour with Treasures of Lisboa as a great way to taste great food and wine and to visit Alfama. Belem is on everyone’s must see list but it wasn’t our favorite day. Did go into the Maritime museum which we liked a lot as well as the Coach Museum and the Jeronimos Monastery. Walked on the waterfront, etc but Belem didn’t knock my socks off.

Definitely have dinner in the Bairro Alto area as it comes alive at night. We loved Lisboa a Noite but it may be too low key for your age group. We enjoyed O Fado for dinner and a show a second night.

We didn’t pay to go into the Castle (line was huge and heard it was a disappointment. But we were very glad we visited the adjacent neighborhood as it was quite lovely.

I think your list is mostly do-able. I disagree regarding Torre de Belem we loved that area as it seemed slow paced compare to central Lisbon. Also along the River with the MAAT museum offers amazing views of the place. As for restaurants to check out in addition to Barrio Alto and Alfama, I would highly recommend checking out the restaurants in Pink Street. You can check out the list here https://www.itsallbee.com/2019/03/pink-street-lisbon-restaurants-bars-rua-nova-do-carvalho/ as that whole areas is charming with some cute and unique places to eat.

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