First time visitor to Portugal - Going in late September or October

As far as hotels, I usually use booking.com and I have had good results.

I will be in Lisbon late October and got a deal through booking.

I am staying at Be Poet Baixa Hotel

We will be back in Portugal for a few days when you are visiting - you will not be disappointed! there is lots to do and see in Lisbon on your own, but tours are plentiful if that is a preference. Word of caution ... the Lisbon marathon is running (sorry) October 7-8 with registration beginning Oct 5. They are preparing for 44,000 participants for the various events and I noticed hotel prices rising and availability dropping even though we will be departing on the third. Sintra is the definitive day trip for a first timer - It will be crowded, and tourist driven but for good reason - The train to Sintra is easy but not so easy to get to the palaces etc once there. Again tours are plentiful and often grouped with Cascais and Roca .. I feel like I'm passing the buck but with short time it will give you a taste of things you might want to see more thoroughly at another time. Porto is lovely but hilly - plan your footwear accordingly. We were lucky to have a wine salesman in our group so had some VIP tours and tastings at the port houses. We were very pleased with our stay at Hotel Carris Porto Ribeira. Nice decor. helpful staff, and friendly bar to sip a nice Porto when day is done. Try Ginja (spelling?) - a cherry liqueur and in Porto perhaps Francesinha- a traditional sandwich (be hungry)

thank you both for the responses, and especially for the heads up about the marathon. We can definitely work around the dates. I assume that weather, etc. holds out through October?

Early October is usually great - weather wise. It’s still warm and little or no rain until later part of the month.