Itinerary for Review and Suggestions

If you want to spend most of your trip in a car, it seems doable. I’m not seeing lots of time to rest and explore in any depth. I understand the desire to see lots of little towns, but there is also something to be said for seeing less but taking in the people, relaxing, etc.

Consider 2N in Sintra. Assume that even in April the main sights will be crowded. I haven't been to the south.

Do not look at distances for driving in Portugal! Look at driving times and add 50%, except for travel on the toll roads - and be sure to rent a toll reader with your car. I had a Garmin which not infrequently led me astray. I also used google maps and a road map will be useful. The only map I found was the free tourist map of Central Portugal that all the TI's in the region had. I didn't find a similar map for other areas, sadly. I picked up the car at Oriente Station in the city, it was about the same price as going out to the airport. Unless there's considerable savings, either is fine. It was easy to get out of central Lisbon and onto the tollroad around 10-11 am.

I visited 4 monasteries. Alcobaca and Baltalha were my favorites, daytripped to both from Tomar. Belem was good, I liked the Naval museum there as much - went while staying in Lisbon. Least interesting was the one in Tomar.

I went to this cork factory while I was in Evora - you don't actually tour the factory, but they do explain all the processes, from acorn to finished products, in the large warehouse, complete with all the equipment and a couple demonstrations. The shop is full of creative products. I bought a small purse (something I'd been looking for, not from cork specifically, for years). I never saw another like it. The prices in the shop were reasonable and I didn't see better ones in other places.

It looks like Nazare is out of your way. It was the place I least enjoyed - actually, didn't like it at all.
I don't think Viseu needs a whole day. I stayed at Quinta de Marroccos for 2 nights (near Pinhao) and loved it. The dinners were excellent and the wines were wonderful. They offer a tour with tastings. I also took a walking tour in Porto to wine cellars and tastings.

An exhausting pace, spending as long in the car as you would be visiting places on some days. You are going to rack up quite a toll road bill and these roads are dull in comparison to the smaller, slower local roads. You have far too many short stays which is going to be exhausting.

Why bother travelling light if you are going to have a car most of the time? You are going to waste time trying to get things washed and you will have moved on before any washing is dry! Pack a decent sized bag each which will fit in your hire car boot so it won’t be visible when parked places.

Day 7. I would visit the charming Aljezur with its castle rather than the bleak windswept surfers hangout that is Sagres.

Day 9 - if you take the N125 rather than the toll road A22, this took me over 3 hours the last time I drove it. From Tavira, a great day out is to drive to Vila Real do Santo Antonio and take a boat trip over the Guadiana River to Ayemonte to have lunch. Canela Velha is also charming, but you haven’t got any free time for pootling round places.

Day 17. Nazare is overrated and will be dead in April.

The sea maybe rough in April, so kayaking in Lagos may not be possible. I have seen fit young men struggle with the currents here in June and they had to be rescued.

I will echo the other posters - you have way too much time driving from place to place - and no real time to savor Portugal. I recently did a road trip to northern Portugal and had planned to ‘see on the way’ a number of small towns. Rarely were we able to see all the things we had planned to see ‘on the way’.

I would encourage you to drop the one night stays - plus several of your stops. You cannot see all of Portugal in 22 days. I realize cutting places out is difficult, but you will enjoy Portugal so much more if you slow down and give yourself time to enjoy the people, places, food, etc., rather than racing from place to place.

I'm going to put on my "Rick Steves" hat and repeat some of his advice.

First, allow some down time in your schedule. You need some recuperation time and time to do laundry, replenish supplies, etc. Also, you have to allow for inclement weather or road detours or getting lost (which I do a lot). Don't pack your schedule so full that one delay upsets everything.

Second, avoid one-night stays. Pick a few destinations and stay two-nights. Whatever you can hit to and from those destinations is what you will see. You will still have a great trip if you drop a few of the smaller towns from your itinerary. I ended up not going to one of my "must sees" Sintra because I decided I didn't want to deal with the crowds. I still had a great trip and don't regret skipping it.

Third, assume you will come back. This is a Rick phrase. Know that you can't do everything. Know that you can come back someday and see the rest. Though I realistically know I may not come back to the destination, I do keep this phrase in mind when planning so I don't stress out.

Lots of great points and suggestions from everyone. Back to the drawing board.... I will post an updated itinerary with changes.
Thank you for the help!