I was the GCS at Penina for a rather brief time in 1997-8.
The course was built on a former rice paddy, the terrain was completely flat, and only a meter or two above sea level. Cotton built it there because the land was cheap, not much good for anything but rice. Drainage was a challenge.
I haven't been back since '98, but then there was a "championship" 18 hole course, along with a 9 hole par 29 on the sea side of the coastal road, and another par 36 nine on the inland side.
The main course was remodeled in 1996. I didn't see it before the work. The new green complexes were fairly well done, but all of them were raised up to allow for some drainage, as were the tees, so it could be a bit monotonous always hitting either from a plateau or onto one. The fairways were dead flat, period. The only earthworks went into the greens and tees, and the occasional fairway bunker.
In the remodeling, they put a pretty narrow strip of sand about 15 cm deep down the fairways, and planted bentgrass. Outside the fairways was the old, dense, clay. The result was a crowned, hard, dry fairway kicking balls off into the muddy, poorly drained rough. The tee-fairway carries were also wet.
I mean wet now, in the winter. With the Mediterranean climate, you have cool, wet winters and hot dry, summers.
The routing is interesting, I suppose, but no way great. The holes do play in a good variety of directions. The nines aren't exactly balanced, par 35-37. Even that is somewhat contrived. The one par five on the front nine should really be a four, and the 16th hole is a par 3 but would be better as a short 4 from the back tees, so the course could easily be 34-38.
The opening hole is the longest, toughest, par 4 on the course, which I think is an interesting choice. One feature is that there are four par-fives on the back 9, holes 10,11, 17, and 18.
Cotton loved trees, and so planted thousands of eucalyptus and casuarina, which in my opinion are more like over-sized noxious weeds. They lined the fairways all the way around.
Water, lakes and streams, comes into play on 4 holes.
The other smaller courses at Penina are less interesting. You would be better off to go play San Lorenzo, Quinto do Lago, Vilamoura, or one of several other good course in the area. The are several new ones that have come on line since I was there, but I don't know anything about them.
Cotton only designed a very few courses, none of which have gained anything near the attention Penina did. He put it on the map by organizing pro tournaments there.
Winter is the busy season for golf in the Algarve.
Portugal is a nice country, populated by gentle, polite, people but with the worst drivers this side of Turkey. Be careful on the roads.
When I was there, it was fairly inexpensive. There are loads of good resaurants, mainly specializing in Mediterranean style seafood. And the wine isn't bad. I like the reds from Alentejo. "Vinho verde" is the locally produced wine that is sold to tourist everywhere, but never got a tase for it myself. Try the Sagres beer.
There are beautiful beaches, many are sort of clothing optional, and some of the women laying around there are amazing, from all over Europe, but the beaches will be quiet this time of year.
Sightseeing you can check out the towns of Faro and going out west Sagres. Past that is the Cabo de San Vincente, a spectacular rocky prominentory at the very southwest tip of the country, and of Europe. It's where people once thought the world ended.