Need Itinerary Help for Spain 8 days (Barcelona/Madrid)

Toledo is my #1 recommendation around Madrid. I adored it. It has a huge historic district, great for wandering around, as well as a lot of actual sights to be visited if you choose to do so. I enjoyed the circuit of six or seven secondary sights that are part of a wrist-band package sold at the Toledo train (or bus?) station. Most include short guided tours, typically bi-lingual. However, Toledo is on a spur rail line. To get anywhere by train, you must go through Madrid, so it's not a good choice as a base city for side-trips. What I'd recommend is staying in Toledo just for the time you want to devote to Toledo itself--2 or 3 nights (depending on when you plan to arrive and depart; I'd want more than one full day there) and spending the other nights in Madrid for the convenience of side-tripping.

Segovia and Cuenca would be my top choices for day-trips from Madrid. Each is worth an overnight, but you only have so much time. Cuenca (which is on the way to Valencia) is viable for a day-trip only via the AVE train, which gets you there in less than an hour. The AVE fare will be reasonable if you buy the tickets about as soon as they go on sale. Bought at the last minute, the tickets would be prohibitively expensive for a day-trip.

Thanks:) Toledo does look beautiful. Any hotel/food recommendations?

I'm a budget traveler, always looking for the cheapest place I can find with private bath, Wi-Fi and air conditioning. I seldom end up in memorable places. I can tell you that I stayed at Hotel Medina de Toledo for 57-78 euros per night, single. I hit a festival, thus the spike in the hotel rate. The location of the hotel is not really ideal. It's on the road that zigzags its way up to the historic center, so you have to walk uphill to nearly all the sights or look for access to the escalators at a midway point (which may exist; I didn't mind the walk so didn't try to find it). I think most people would prefer to stay on the upper level. For budget travelers, I think this hotel is a perfectly OK option. It's always important to look at photos on sites like booking.com to check the size of the rooms, though. I had some very tiny ones.

I tended to just stop somewhere and eat in Spain, which frankly was not a very effective approach. It's not like Italy; you're doing the right thing by seeking recommendations. Unfortunately, I have nothing particularly good to suggest in Toledo except for the marzipan. Quality varies. TripAdvisor will probably get you to the best places. I liked the Pasteleria Santo Tome right on Plaza de Zocodover but do not claim that it is the best Toledo has to offer.

Thanks for putting Toledo on my radar:) Now i am torn between Toledo and Segovia! Wondering if I should jus do as a tour together ( i have seen options for this) or, if each place warrants a full day trip from Madrid if I end up basing myself there for three nights.?

There is truly more to see in Toledo. I really liked Segovia (and spent two nights there), but I'd choose Toledo alone over a day divided between the two. Although I'm sure you could find some people who would disagree with me, I believe the vast majority of people who have had the opportunity to spend the night in Toledo would agree that it's not a half-day destination. Toledo gets a lot of day-trip traffic, so the area between P. Zocodover and the Cathedral is full of tourists. You need to have time to wander off that path to get the best of Toledo. With a half-day and traveling Madrid-Toledo-Segovia-Madrid, you wouldn't have time to do more than walk to the Cathedral and tour it.

Are you sure you didn't see a day-trip that combines Segovia and Avila? I'd opt for a pure-Segovia tour if I wanted a tour, but the Segovia/Avila combination makes somewhat more sense than Segovia + Toledo.

Day
1-4. Barcelona (4N)
5. AVE train to Madrid then Toledo (2N)
6. Toledo
7. am. Train to Madrid (3N)
7. pm. Prado, Retiro Park
8. Royal Palace, Plaza Mayor, Reina Sofia
9. Day trip to Segovia
10. Fly to Porto