I just booked our flight to Portugal for a 3 week trip! We are leaving in earl May and fly in and out of Lisbon from JFK. While I haven't booked any hotels, car rental and specific itinerary I am leaning to the following: 5 days in Lisbon ( including side trips to Sintra, Cascais), 2 days in Evora, 3 days in Coimbra ( including side trips to Aveira, Tomar), 3 days in Duoro Valley, 5 days in Porto ( side trips to Braga, Guimaraes). My plan would be to pick up a car after leaving Lisbon, drive to Evora, up to Coimbra, up to Duoro Valley and finally to Porto ( drop car off). Train back to Lisbon from Porto for flight home ( arriving the night before). I would appreciate any suggestions/comments on this plan including recommendations for hotels/B & B's), side trips/itinerary, must see sights. I would like to rent the car in Evora ( take train from Lisbon to Evora) and drop it off in Porto, however, couldn't find a car/agency that would allow me to do this. Thanks!

For your trains - book our own tickets at www.cp.pt - Portugeuse Railways' official site - book early for possible discounts. For lots on Portugeuse trains check www.seat61.com- erudite info booking own tickets online; www.ricksteves.com and BETS-European Rail Experts.

Itinerary and days sound great - I'd try to drive by Batalha Monastery - UNESCO WORLD HERITAGE SITE en route to Porto.

Thanks PalenQ. I have a question regarding where to start our trip: Lisbon or Porto.
Option 1: Flight JFK to Lisbon. Stay 4-5 nights and pick up rental on way out to Evora. Visit Evora ( 2 days, Coinbra ( 3 days), Duoro Valley ( 3 days) and drop off in Porto. Take train to Lisbon night before we head home.

Option 2: Flight JFK to Lisbon. Taxi/Uber to train station for 3 hour travel to Porto. Stay 4-5 nights, pick up rental on way to Duoro Valley, drive to Coinbra, Evora and finally drop off in Lisbon. Stay in Lisbon for 5 days before heading home

Where is it best to start this 3 week trip? Should I rent/ drop off in the city or at airport?

Can't see much difference but if ending in Lisbon for some days a car is useless there so drop it at airport or train station or wherever upon getting to Lisbon.

We covered Most of the places on your itinerary. We picked up our car at the Lisbon airport as we were leaving the city.we stayed in Losbon, Obidos( mistake), Evore, Coimbra, Guimares and Porto.

HappyTrvlr - Why you do say that staying in Obidos was a mistake? I'm curious because I'm planning to spend a night there during my upcoming trip.

Many say Obidos is way too crowded during the day to appreciate - the proverbial neat old walled town that is too popular with bus tours, etc. But at night it takes on a whole different serenity - folks who stayed there say. I just day tripped in and in off-season so was nice but anyway that's what many others say.

Okay. I have decided to stay in Lisbon for 5 nights at the start of the trip and rent in Lisbon on the way out to Evora. Now I need Hotel reservations in Lisbon ( Baixa/Chiiado), Evora, Coinbra, Duoro Valley and Porto. Is 3 nights in Coinbra a good decision? Really trying to limit the number of places we stay. As of now it's 3 weeks and 5 locations to stay.

Coimbra itself is IMO a one day thing at most. But could be a good base from which to hop to Batalaha Monastery - a UNESCO WORLD HERITAGE SITE or such but for Coimbra itself I'd say a day at most.

Porto has good day trips too- like Guimares and Braga - two fine regional historic towns.

Thinking of booking My Story Hotel in Baixa district. There are two hotels: My Story Hotel Rossio and My Story Hotel Ouro. Does anyone have any suggestions which one would be best?

A few decisions I have made so far: Booked MyStory Rossio hotel in Lisbon and Hotel M'ar De AR AQUEDUCTO IN EVORA.

As I have mentioned my thoughts are to rent a car when leaving Lisbon and drive to Evora for 3 days and do a few side trips from there. Then I would drive to Coimbra for a few days with a side trip or two. Next to drive to the Duoro Valley for 3 days and eventually into Porto where I will drop off rental, however, I am a bit confused here.
Should I stay in Coimbra for 2 days or somewhere else after leaving Evora?
Should I base in more than one location in the Duoro Valley?
Should I plan on driving to either Braga and/or Guimares before driving to Porto or plan on taking train from Porto to see these two places?
Should I not travel by car into Duoro Valley at all and just take train there?

Keep the car until Porto then take day trips by train to Guimares and Braga - short train trips and save on car rental money and hassle of returning to Porto with car at night. But if you can hit one on way back to Porto do it.

IMHO Obidos is too disneyesque. Consider visiting Monsaraz instead as a side trip from Evora.

My plan is to drive from Coimbra to Douro Valley before heading to Porto and drop off car rental. I am not sure whether to base our 3 days in Lamego, Regua or Pinhao? I definitely would rather stay in one place rather than move around.

I also like the idea of stopping in Guimaraes before heading into Porto.

Can you suggest best base for us? Suggestions for hotels or quintas? Specific wineries? Restaurants?

Thanks again!

I now have reservations in Lisbon, Evora, Coimbra, Lamego and Porto. Now I need advice on which train to take from Porto to Lisbon the day before we head to the airport for our trip home. Also need a suggestion for a hotel for the day before. Would you recommend Parque Das Nacoes if arriving at the Oriente train station?

What sort of advice??? According to bahn.de they are virtually all InterCity trains taking around three hours. Porto (Campanha) to Lisboa (Santa Apolonia).

RaiEurope has trains and arrives into Oriente rather than Santa Apolonia.

So it does. So does the Portuguese train company www.cp.pt, which is where you should buy your tickets, although I don't think I would bother buying ahead for this route. RailEurope is a reseller and should be avoided.

Thanks so much for your advice thursdaysd!!

Still looking for suggestions where we should stay the night before we leave out of Lisbon. I have booked a train from Porto to Lisbon with the Portuguese www.cp.pt arriving at Oriente station in Parque Das Nacoes.