We will arrive in Portugal about 10 -11 days before we start a food and wine tour that takes us from Lisbon to Evora through northern Alentejo to Porto and then back to Lisbon. We will be touching on the sights between Porto and Lisbon with the tour but will have little time in Lisbon nor do we do much around Evora or anything in more southern Alentejo. I've read many of the excellent suggestions on a prior post on things to do around Evora but I wondered about things in more southern Alentejo, which seems a bit off the tourist trail. We will have a rental car and one of our best trips was driving through Asturias, Cantabria, and Galicia in Spain and finding smaller castles, ruins, and local museums that were absolutely charming. We love ruins, castles, and a good place to stop for lunch. I'm open to all suggestions, including heading to a different area of Portugal if that is best. This will be in mid-late October so we won't need beach time but a good view of the Portuguese beach would be nice. All help is appreciated as I plan this trip.

If your time in Lisbon doesn't include a visit to Sintra I would make that a priority. We were on a day tour that went to Sintra, the marker for the westernmost part of continental Europe, Cascais and then along the coast back to Lisbon. My relatives went during a February school vacation and stayed 2 nights in Sintra, 2 nights in Cascais and 2 nights in Lisbon, traveling exclusively by Uber.

Thanks for your quick response. Our tour includes Sintra, Cascais, Belem, and the most popular places north of Lisbon to Porto. We also do most of our tour inland in the northern part of Alentejo visiting farms, and doing cooking classes and wine and port tastings until we get to Porto. I think this may be my only trip to Portugal so I wanted to see more of the country than just the highlights of the tourist areas. I've reached my lifetime limit on visiting cathedrals (I actually reached my lifetime limit at 16 when my mother and I refused to continue to Rome and opted for the Italian Riviera during our trip! We'd been on the road for a long time and just wanted to STOP. It was a great decision which I remember as one of the highlights of that summer.) I plan to stay in Lisbon a few days extra to hit some of the museums that are not on the tour and to be able to sit at a cafe and enjoy some long lunches. I might even go to some of the places on the tour so I can have some time to actually see and enjoy them as I fear the tour will be more of a walk through instead of wander and enjoy. This is the first tour we've ever done and I must admit I'm very hesitant. My husband and I are very spur of the moment kind of travelers once we are on the road. We've always changed some plan once we arrive because something seems interesting that we'd not known about. We once spent an entire day looking for a giant tree that someone mentioned to my husband. It really was a spectacular tree but we were probably the only people that actually made a special trip to see it (It wasn't even in a town with a road - you parked at the main road and walked to this mountain town through the roaming dogs and chickens, past the cemetery,....)

We enjoyed two visits to monasteries.. The first is Batalha and the second is Albacoaca but I am not sure of the exact spelling. Because we had been to these two monasteries, we did not go to the Jeronimos monastery in Lisbon, especially as the line to get in was especially long on a warm-hot mid-June day.

North of Porto we really enjoyed the historic city of Guimares. We had also intended to stop in Braga however we didn't as we were driving north in the mountains and it was foggy and misty so we missed the turnoff plus we did really need the time to explore Guimares. We did it as a day trip from Porto but we had friends who did it as a larger driving trip and spent the night.

In the Alentejo, I enjoyed Elvas in addition to Evora. YMMV.

"Our tour includes ... the most popular places north of Lisbon to Porto."

That doesn't tell us much. If you list the places you will visit, you might get more informative responses.

As kja suggests, could you list the particular places that your tour will include north of Lisbon and to Porto?
Is your tour taking you to the Minho----Braga, the ecclesiastical capital, and the UNESCO World Heritage City of Guimarães and Viana do Castelo---?. There is great food and wine there (the alvarinho grape) as well, plus these are 3 beautiful northern cities. This is my favorite part of Portugal.

Southern, coastal Alentejo is a somewhat "off the beaten path" destination, popular with families during the summer and with surfers, because of the pristine beaches of the Costa Vicentina. And there' the celebrity-filled Comporta, sometimes called the Portuguese St. Tropez, which has.become a "getaway" place for the rich and famous.

For my explorations of the Alentejo region, I always refer to the Alentejo, the Bradt Guide by Alex Robinson. It enriches my enjoyment of traveling in this region.

If you'd like to explore more of the Alentejo region in addition to Evora and the northern Alentejo (Estremoz plus Marvão, Castelo de Vide in the Serra da São Mamede in the Portalegre district), I concur with venturing east to Elvas at the border and also to Beja to the south (each which has a Pousada).
If you'd like to stay or just have lunch in a beautiful hacienda (herdade) that produces fine wines, olive oils, has cattle, horses and great food, I can personally recommend the Herdade da Malhadinha Nova in Alberola near Beja.

https://portugalconfidential.com/her...ouse-alentejo/

Thank you everyone for all your suggestions. Our tour concentrates on food and wine, cooking classes, and farm and vineyard visits. After leaving Lisbon we move to Evora doing a walking tour and having the afternoon free before our evening cooking class. Next we leave Evora and visit a cork factory and have a winery tour as we go up into the mountains. On day 4 we visit a sheep farm and learn about cheesemaking, on to breadbaking and a visit to Monsanto. Day 5 is a trip into the Douro Vally and a cruise on the Douro Rive and end in Porto. We have the next day in Porto, all day. We leave Porto and go to Coimbra in the morning and Tomar for the afternoon and to spend the night. The following day we stop by Obidos and on to Sintra to visit Pena Palace and then return to Lisbon to sleep. We don't spend much time in any of these places, it really is a "taste" of Portugal. My plan was to spend a bit of extra time in Lisbon and also to do a deeper dive into Alentejo or another area. This tour has not been our style of travel but we are going with friends and, as we get older, I want to see if we can enjoy tours when we are too old to want to drive and do all the luggage schlepping.

So far our "must do's" are visits to the Megalithic sites and dark sky star gazing. After that I figured we'd find castles and ruins so all your suggestions are very helpful in fleshing out these 10 days. I'll try to map out everyone's suggestions in the Alentejo district to see if we can make it work. If you can provide more info on what we should see in the areas or which are good spots to spend a few nights and do day visits I'd appreciate it. I'd love to be able to have only 3 places to sleep during this Alentejo adventure. We've done the one-night driving trips before and although we enjoyed them I prefer to stay for 2-3 days in one place.

You all have always been so helpful. I think I even recognize some names from my other trips! Thanks!

Re: the megalithic sites: As of this past April, the road to the Almendres Cromlech was in such bad state that driving on it was strongly discouraged. I suppose it could have been repaved / repaired since then....

As I mentioned there are Pousadas, the Portuguese inns, mostly historic, similar to the Spanish government -run Paradors, in Beja, Estremoz (a castle), Vila Viçosa (the marble town), Elvas, Arraiolos (the handwoven tapestry town), Crato (s monastery), Marvão (breathtaking mountain views) and Alvito (strolling peacocks), in addition to the one in Evora, and we have stayed in all of them except for Beja. They're no longer government-run by instead run by the Pestana hotel group and offer very good senior rates.

I'm glad that kja mentioned the condition of the road to the cromlechs, dolmens. If you do want to tour them you might contact Ebora Megalithica to see if they are now able to offer their guided jeep tours from Evora.

There are castles galore (empty) in the Alentejo region, including the one at Monsaraz, where you may want to stay nearby for your dark sky Alqueva experience. There's a beautiful hacienda style property in this area, São Lorenco do Barrocal.

Your suggestions have really helped me focus on what I might want to see/do on this Alentejo circuit. Please continue to indulge me and provide some comments on my current thinking;
Our arrival day in Lisbon will just be a recovery day nothing is scheduled. We'll head off to Evora the following day.
Day 1 - leave Lisbon late (after seeing the Tile Museum which is not on the tour list of things to do) and arrive in Evora in the late afternoon
Day 2 - Evora - hang out in town - museums, etc
Day 3 - Day trip from Evora - Morning tour of Megaliths,etc with Ebora Megalithica - afternoon in Evora
Day 4 - Day trip from Evora to caves and Vila Romana
Day 5 - Drive to Marvao, stopping at Evoramonte and Estremoz on the way
Day 6 - Marvao day
Day 7 - Drive to Monsaraz, stopping at Elvas
Day 8 - Day in Monsaraz with evening Stargazing
Day 9 - Drive to Lisbon - stopping at anything we find intriguing
Day 10 - extra day in Lisbon before start of tour

This schedule has no "one night stands" and only has a couple of times where we are stopping en route to see things. I do hate to leave the car when we have everything packed in, even though I'm very careful to never have anything visible it's still a risk with a rental car. It's very clear that I could spend tons more time searching out interesting sites (and rocks) but I feel like I need to nail down my dates so I can make some hotel reservations. It seems too soon to have to make reservations but Portugal is currently so popular I need to at least get my extra nights in Lisbon scheduled.

At your suggestions I'm looking at some of the Pousadas. Has anyone experience with the one in Marvao? Or other hotel suggestions? We don't look for luxury accommodations and prefer something in town so we can walk around and find a cafe or small restaurant for dinner.

And, truly, thanks for all your help.

With 10 to 11 days you have the time to visit the Algarve and the area along the coast on your way back to Lisbon to join your tour. You might want to take a look at my trip report:

Trip Report: Portugal, May-June 2019

and here are the relevant photo albums:

https://flic.kr/s/aHsmELyB7t

https://flic.kr/s/aHsmENSCvb