I am overwhelmed please plan my trip.

Congratulations on your 40th anniversary!
Having been to most of your cities, I suggest flying into Lisbon and returning home from Barcelona. Buying an open-jaw ticket will preclude the need to backtrack to fly home.

I would fly into Lisbon and stay for the first 3 nights. Then take the high-speed 2.5 hour train to Porto for two nights. To make your way of getting to Spain extra special, you could take the Trenhotel Lusitania overnight train from Lisbon to Madrid. The train has grand clas sleeper compartments each with its own toilet, sink and shower. Lusitania leaves from Lisbon in about 9:30 pm which will give you plenty of time to return to Lisbon from Porto on the day you depart for Madrid,
You’ll arrive in Madrid the next morning about 8:30 am. Madrid for two full days should be sufficient if you’re not drawn to the city’s many art museums By adding a third night to Madrid you could take a daytrip to the medieval capital of Spain- Toledo. Toledo is a beautiful city and it’s only a 35- minute train ride from Madrid.
You can leave Madrid for Seville on a high-speed AVE train from Madrid’s Atocha train station and arrive in Seville 2.5 hours later. Seville, the capital of Andalusia, is another one of Spain’s showcase cities. Plan on three or four nights in Seville.

Flying to Barcelona from Seville in 90 minutes for your final three or four nights rounds up your trip.
You can search for your flight tickets at www.Skyscanner.com. Train schedules to get an idea of times can be viewed www.Omio.com. Online train tickets can also be bought on the Omio site. There’s money to be saved by booking your Madrid to Seville AVE train ticket as soon as possible on Spain’s national train company website at Renfe.com
For a look at info on the Lusitania overnight train and how to get discounted tickets for trains in Portugal and Spain check www.TheManInSeat61.com

Have a great Trip!

OK, here’s a start for some quick suggestions. For routing, I would fly into Barcelona, train to Madrid (2.5 hours) and then train to Seville (2.5 hours). Fly to Porto from Seville and then train to Lisbon which would be your departure city for home. Barcelona has the Sagrada Familia and other Gaudi sites, Barri Gotic, Ramblas and the Boqueria Market. Madrid has the royal palace and Retiro Park and is a good jumping off point to go to Toledo for the day by a quick train ride although I would spend the night and also you could do a day trip to Segovia. Seville has the cathedral, the Alcazar and Plaza de Espana and flamenco performances. There is a bullring there but we didn’t do that so I don’t know when those bullfights take place. I haven’t been to Portugal so I can’t help you with that. I hope this helps. The Rick Steve’s guidebook has more info. We loved Spain and it is really easy to get around by public transport.

Gail, that’s a shame about the overnight train that Kenko suggested. I love trains and that sounded fun.

You are giving each country a surface look with only 16 days. Have you considered focusing on either only Portugal or only Spain? Your language skills will be wonderful to use in both countries.

If you can, I'd seriously consider adding Granada and/or Cordoba in Spain.

I wouldn’t try to cover that much territory with only 20 days, but that’s just me. Your must see places will easily occupy that many days. For bullfighting, check the servitoro website to see if there will be one in the area you’ll be in, when you’ll be there. There are a couple fights in Madrid province, NOT Madrid city, in early October.

After some further checking on the night train Lusitania that ran between Lisbon and Madrid I found the Trenhotel website still lists the Lusitania train in operation from Madrid to Lisbon. Several sites show Lusitania tickets from Lisbon to Madrid for sale at the train ticket websites “The Trainline” and “ Omio” and “Rail Europe.” But, alas. when you try to buy a ticket, it’s not possible.

The Man In Seat 61 seems to have it correct—the Trenhotel Lusitania has been suspended.

On the bright side, the OP can fly directly from Porto. Portugal to Seville without backtracking to Lisbon.

Chicago to Lisbon and Barcelona to Chicago is $560 on AA not bad.
Chicago to Barcelona first is about $100 more. Still affordable.
We do plan to have a carry on each, no checked bags.

I think I like flying into Barcelona stay 4 nights, train to Madrid stay 3 nights with the Toledo day trip then train to Seville stay 3 nights then fly to Porto stay 2 nights then train to Lisbon stay 4 nights and fly home.
Need to get my timing better as I prefer not to be in Porto form my anniversary.
Would prefer a meal at Cervejaria Ramiro seafood restaurant in Lisbon.
We also want to try the oldest restaurant in Madrid for the suckling pig.

Be sure in your planning that you are factoring in the time to get from the hotel to the train station, train ride and time to get to the next hotel and get checked in. That can eat a considerable amount of time. I know you are not a fan of museums but the Prado is one of the best in the world. Even if you just pop in there briefly and limit your attention to a certain few works of art, it will be worth it. A lot of venues require advance ticketing now so get those in order soon. Have fun planning your trip and Happy Anniversary.

There is no cause for analysis paralysis at all. Both countries are new to you. Therefore it is relatively easy. You look at a map and link your cities. Either a circular back to your start route or a point to point. Then you get out your RD book for the countries and apply it to your route or you use RS proposed routes for the days you want.
If you have choice problems now, it can only get worse once people start posting all sorts of itineraries for you.
There are major cities and sights within Spain and Portugal. If you use the three nights each city rule, You narrow it down to your timeframe divided by three and there you are.
You will not see everything. No one ever does unless they bomb through a country with one night stays.

Mary mentioned possibly stopping at the Prado or Reina Sofía even if just for an hour or so. If you decide to do that, visit during the free admission hours to save money. On previous trips we visited both museums during the free hours and it was more than enough time for us since we’re not museum people either.

For someone who claims to be "overwhelmed," you seem remarkably well prepared. I'm sure than your ability to speak Spanish, and muddle through Portuguese, will enhance your trip, as those same abilities have enhanced mine. I don't know whether I can add a lot to the previous comments, or to your own preparation so far, but since I agree with "treemoss" above that additional itineraries may only confuse matters if you really are overwhelmed, I would just offer the following general comments:
[] Don't worry about having just to "muddle" through Portuguese -- my experience was that people in Portugal seem to appreciate it when tourists try going even that far with their language. Even "muddling" a few initial phrases of the national language is so much better than always starting right off with English.
[] As for getting around, I would strongly recommend the train, though it appears that you may require a flight for the Spain-to-Lisbon part. Spain and Portugal have great train systems (including metro systems in four of your chosen cities).
[] Given that you wanted "must-see" cities, you seem to have made the right choice. You appear to have 19 complete days (20 nights) in Portugal and Spain, which averages to four nights in each of your five selected cities. To me, this would be a minimal stay for each -- I would not advise trying to squeeze in any more nights, anywhere else (though squeezing a night in for Toledo might be worth considering). And yet, if you plan to fly in, and back home from, the same city, which I believe is usually the more economical option, that may mean removing a night or two from one of your other destinations.
[] On my several trips to Spain, and my one (so far) to Portugal, I have lodged only in the Huertas neighborhood of Madrid, and the Bairro Alto neighborhood of Lisbon. They're both interesting and quaint, and you can find reasonably-priced lodgings in both those areas. Note that the Bairro Alto is said to be something of a night-life area, though perhaps not surprisingly, it seemed rather tame during my mid-week, mid-December stay. Huertas, in Madrid, offers a lively tapas-bar scene that goes well into the night, though the area does have its quieter parts.
[] Respecting your request, I won't judge your decision to see a bull-fight, but I'll simply suggest that you read at least Chapter 6, section 6, of H.V. Morton's "A Stranger in Spain," provided you can find a copy. (It was published in 1955.)
(Incidentally, I can understand your flying to Europe from the international airports in Minneapolis or Chicago -- but Rochester?)

Thank you all for the input. If I plot my nights I have Arrival to Barcelona on Sept. 28 (4night) and train to Madrid (4 nights) on Oct. 2 then train to Seville (2 nights) on Oct. 6 and fly to Lisbon (7 nights) on Oct 8 flying home on oct 15. I think i have too many days in Lisbon even with popping over to Porto for one night. Should I add more to Seville and do some day trips from there? Realistically I have 17 nights. ...........PLAN B........... Fly to Lisbon (4 nights) Porto (2 night) Seville with Cordoba day trip (3 nights) Madrid with Toledo day trip (4 nights) Barcelona (4 Nights) ???

Is Porto worth two nights? Could add a day to Seville and day trip to Cordoba. It looks interesting.

Just returned from 2 weeks in Euorpe--we flew into Lisbon, then flew to Madrid (as the overnight train b/t the two is no longer running) and flew home from Barcelona. We did a night in Toledo which was amazing and i would recommend. The Chiado neighborhood in Lisbon and Eixample neighborhood in Barcelona are both great areas. We had 3-4 days in each city (and also 2 nights in Sitges, a beach area outside of Barcelona) and felt we had ample time to see the main sites in those cities.

Thank you all for the input. If I plot my nights I have Arrival to Barcelona on Sept. 28 (4night) and train to Madrid (4 nights) on Oct. 2 then train to Seville (2 nights) on Oct. 6 and fly to Lisbon (7 nights) on Oct 8 flying home on oct 15. I think i have too many days in Lisbon even with popping over to Porto for one night. Should I add more to Seville and do some day trips from there? Realistically I have 17 nights. ???

On this plan A, I would :
- Remove 2 nights from Lisbon
- Add 1 to Barcelona
- Add 1 to Seville (that way you can go to Córdoba if you want)

And you'd be all set, in my opinion!

If you have 17 nights on the ground in Europe, I would not look beyond the 4 city bases …

Barcelona - 4 nights
Madrid - 5 nights - with day trips to Toledo & Segovia (or El Escorial)
Sevilla - 4 nights - with a day trip to Cordoba
Lisbon - 4 nights - with a day trip to Sintra

or

Barcelona - 4 nights
Madrid - 4 nights - with a day trip to Toledo
Cordoba - 2 nights
Sevilla - 3 nights
Lisbon - 4 nights - with a day trip to Sintra

or

Barcelona - 4 nights
Madrid - 4 nights - with a day trip to Toledo
Sevilla - 4 nights - with a day trip to Córdoba
Lisbon - 5 nights - with a day trip to Sintra

I like
Barcelona - 4 nights
Madrid - 4 nights - with a day trip to Toledo
Sevilla - 3 nights - with a day trip to Córdoba
Porto - 2 nights
Lisbon - 4 nights

Three nights in Seville with a day trip to Cordoba is only one full day in Seville, which to me is way short. I normally recommend at seast 4 nights (3 days) in Seville. You're verging on "too much travel time, not enough feet-on-the-ground time" here.