Itinerary review before and after RS tour

Toledo's a short train ride from Madrid, and buses are available as back-up. I'm risk averse on days with transatlantic flights but wouldn't be concerned about making that flight. However, I know I wouldn't do anything in Toledo on the morning of Day 23 except grab breakfast and get myself to the train station to assure a timely departure for Madrid. I'd have to squeeze all my Toledo sightseeing into Day 22 after traveling from Seville (3 to 4 hours), getting to my Toledo hotel (non-trivial due to the geography), checking in, etc. Nightfall comes late at that time of year, so I'd figure on a generous half-day in Toledo, but with time out for two meals.

You have to decide whether it's worth trying to do that. You're just not getting a lot of sightseeing time in Toledo. On the other hand, you have to sleep somewhere (Seville's clearly too far from Barajas), so I guess it may as well be Toledo (a city I adore).

It's a shame you can't start your Spanish segment with a couple of nights in Toledo and see Madrid right before the flight home, but that's not possible with a 10 PM arrival time in Madrid.

Hmmm, that itinerary sounds familiar ☺☺

Did you read the tripadvisor article about Renfe? It's long, but it is excellent. You can save money by buying your tickets now at "promo" prices. Also consider getting the tarjeta dorada (gold card) for €6 each if you are 60+ to take advantage of discounts if you can't get promo prices. You can compare prices by checking "tarjeta dorada" on the Renfe site - then you can compare the promo and reduced prices.

Back to your question - you'll see that there are frequent trains from Toledo to Atocha. There are a couple places at the train station where you could kill some time and have lunch if you want to allow more time for your transfer. 2.5 hours is enough at the airport. If you get there earlier, you can relax at one of the restaurants or window shop in duty-free. If you get to Atocha by 1 pm you should be fine. If you're worried, take an earlier train from Toledo. That still gives you time for a leisurely breakfast and packing, even a walk around town. It shouldn't take more than 10-15 minutes to get from a central hotel to the Toledo train station.

This might work a little better ...

Day 18: tour ends in Porto;
fly to Madrid; train to Seville (2 nights),
Day 19: Seville,
Day 20: train to Cordoba for visit to Mezquita; then train on to Madrid (3 nights),
Day 21: Madrid,
Day 22: day trip by train to Toledo,
Day 23: return to MIA.

Lagos may seem too much effort for a short 2 night stay. You have further interesting options from Lisbon.

Day 2: arrive Lisbon,
Day 3: Lisbon,
Day 4: day trip to Sintra,
Day 5: day trip to Cascais,
Day 6: day trip to Mafra,