9-Day Draft Itinerary

Sintra and Cascais in a day seems rushed. Do you have particular sites you want to see in Sintra? It is an easy train ride there if you want to skip a guide. Cascais didn't thrill me, but since you like riding bikes it is about 1.5 hours each way from central Lisbon and you'll pass through Belem which we enjoyed far more. We considered riding there but the weather wasn't cooperating that day.

We liked Porto more then Lisbon, our favourite day there was across the river in Gaia where all the Port shops are. If you're interested, here's my Trip Report from September 2024.

https://community.ricksteves.com/travel-forum/trip-reports/trip-report-part-1-hills-and-castles-portugal

It looks like a fairly good balance to me. I think with the 3 towns and daytrips you have picked that a car would not be an advantage.You might be cutting Lisbon a bit short unless you have a full first day in Lisbon ( what time does your cruise dock?). I agree with Allan that Sintra and Cascais in one day is ambitious. We actually stayed 2 nights in Sintra and didn't see everything. You could possibly drop a night from Coimbra and add it to Lisbon if it is important to you to see both, but personally I would just pick one or the other. I loved Sintra, but it is very very busy now and you might enjoy strolling Cascais more.

I think the Douro will be dull in June. I’d take that day, if not Guimaraes as well, and give it/them to Porto. I’d also be tempted to skip Sinatra and/Cascais in favor of giving spending more time to Lisbon. For my taste, too much frosting and too little cake with such a short time in Portugal. Enjoy your TA!

I’ll counter that Guimaraes was a highlight for us. So, whether to go there or spend the day in Porto really depends upon your interests.

Been to Portugal twice in the past two years, more recently in September. Your itinerary has a focus on the bigger cities, so your day trips can be a way to explore some of the smaller towns in Portugal. Train and public transport will work fine for you, even if you decide to go to Sintra/Cascais or Guimaraes on your own. The Douro would be best done with a tour.

Your itinerary is well balanced for a first trip to Portugal, and for the route you’ve chosen, trains and guided day trips make more sense than renting a car. Lisbon–Coimbra–Porto is very easy by rail, and parking in historic centres can be more hassle than help.

I agree with others that Sintra and Cascais in one day is ambitious. Sintra alone can fill a full day, while Cascais works better as a relaxed coastal stroll or bike ride if you enjoy cycling. You might consider giving Lisbon a bit more time and not overloading the schedule.

In Porto, staying in the city or visiting Guimarães depends on your interests—both are worthwhile, but Porto has more to see. One thing to keep in mind is that Porto can be seen with assistance, making it more enriching and allowing you to learn about the city's history and landmarks. This overview of tuk tuk tour options was helpful to me: https://www.tuktourporto.com/en/

Overall, you’ve chosen excellent bases. Leaving some space for wandering and slowing down will make the experience even better.