I would cut a night from Toledo and a extend the stay in Madrid.
If you are not interested in museums in Madrid, there are several day trips you can make including the beautiful Segovia.
Sevilla is rather small.... 5 nights with no day trips would be too long for me.

With the cities you've outlined you may want to drop the 1-nighter in Cordoba and visit as a daytrip from Sevilla. It's a great place for an overnight but I personally hate 1-nighters. Another option would be to take a night from Barcelona and have a couple of nights in Cordoba. Carnival in Cadiz is huge and runs in 2013 from Feb 7-17. You may want to take a couple of nights and stay in Cadiz during this time - but you'll need to book accomodation soon and except premium prices. As an alternative you could visit as a daytrip from Sevilla where you'll likely be surrounded by fellow partygoers heading to Carnival. You're a little short on nights in Madrid but since you're overnighting in Toledo it may be OK. I'd daytrip to Segovia.

The current outline gives you an overview in 23 days of 3 areas of Spain. You're not seeing all of them in depth but it's a well paced overview. It's a good itinerary for someone without a car.

It's interesting that you mention your love of food and wine but you're leaving out the Basque Country and La Rioja. It's off season for this area but I'd especially try to find 5 days or so for San Sebastian. This would give you time to visit San Sebastian and do some daytrips. La Rioja is a little more difficult without a car but you could spend a couple of nights in Haro and visit a few bodegas also grab a bus to Briones and visit the wine museum and bodegas there. I'd add these days in I wouldn't take it out of the days you have outlined as you have a good pace in the cities above. I'd try to find somewhere else in your overall trip where you could cut back.

SS is worth visiting but 5 days in a rainy season would not be my choice.
One can easily fly Vueling to SS or Bilbao from Barcelona for a shortEr visit.

Three days in Malaga is too much. You could rent a car and visit the many worthwhile towns near Madrid besides Toledo including Salamanca, Avila, and Segovia.

PS
Often overlooked Valencia is a fantastic city.

the OP does not wish to rent a car!
Malaga is small and lovely...perhaps two nights would be enough.

And, seven nights in Barcelona is too many.

Is this on top of or including your trip to Portugal?
http://www.fodors.com/community/europe/itinerary-set-additional-suggestions-needed-for-18-days-in-portugal.cfm

Personally I don't think 3 nights in Malaga is too much if the OP is planning on doing daytrips, which I assumed was the case from many of the cities. From Malaga you can daytrip easily to Antequera, Nerja, Almunecar, etc....a 1-2days in Malaga itself and 1-2 daytrips would work well.

Salamanca would be a good overnight for a couple of nights but it's a very long daytrip from Madrid at nearly 3 hours each way by train.

Would dump the night in Cordoba (Seville is an hour away by train). Would forego Segovia and add a night to Madrid so you can daytrip to Salamanca or take a night from Toledo so you can overnight there (the preferable alternative). Salamanca > Toledo > Segovia. Segovia is really not impressive after seeing Toledo or Salamanca.

Does that 1k/week budget include the lodging or is that already a sunk cost? If it's meant to include lodging, you're going to have to scrimp a bit and the wine will have to be really cheap.

Go to the articketbcn.org website for a 7-museum pass that will save you money if you visit three of the sites.

If you're going to visit Montserrat and Girona, 7 nights in BCN won't be too many.

Given the interests you list, you might consider cutting 1 night from Seville (so you have 3 days there), adding a night to Cordoba (I loved my 2 full days and nights there), adding at least night to Madrid (so you have at least 3 full days there), and cutting a bit from Barcelona.

Sounds like you are going to have a wonderful trip!

Looks pretty good. 7 nights in Barcelona is a lot for me. 5 would be better. 4 nights is better for Madrid. I would take Cathy's advice.

If you stay 7 nights in Barcelona, you can do 2-3 easy and worthwhile day trips (Girona, Montserrat, Figueres etc...) Here's a link:
http://gospain.about.com/od/barcelon1/a/barcelonadts.htm
There's also plenty to do in Barcelona.

This is all great - and yes it's in addition to the 2.5 weeks in Portugal and will be followed by a few more weeks in Italy.

@CathyM I would love to fit in San Sebastian – is 3 nights there enough? Does it make sense to put it between Madrid and Barcelona?

@BigRus yes, the budget includes lodging and for the most part I’m doing hostels to keep the cost low so I can spend more on food and wine. Thanks for the tip about the museum pass.

Given the number of UNESCO sites around Madrid I’m beginning to wonder if I should spend more time there and cut out Barcelona altogether.

How's this revision:
Seville – 5 nights (I’ll get in late my first day, and do a day trip to Cordoba)
Malaga – 3 nights (day trip to Antequera)
Granada – 2 nights
Madrid – 4 nights (day trip to Toledo)
Salamanca – 2 nights
San Sebastian: 3 nights
Barcelona – 4 nights (at least one day trip)

Is this the right order for things? From Spain I’ll be heading to Italy (either Florence or Naples).

Bubbly...you again? Just left you in Portugal, now here you're talking Spain. What an excciting trip you're about to take! Here are a few familiarization pix to prep you for Barcelona and Seville (we were once there for Holy Week)' Hope the Portugal pics were a little illuminating for you, too.
Stu

https://picasaweb.google.com/stuarttower/SevillaHolyWeek#

Bubbly...and here is Barcelona. With day trips to Girona, Figueres (Dali Museum).... 7 nights would be just right for Barcelona. It's an electrifying city. (I only have very old, not yet scanned pics of Madrid and Granada.)
stu

https://picasaweb.google.com/stuarttower/SelectedBarcelonaScenes#

The updated itinerary is good - it's a little moving around but you don't have any 1-nighters and the 2 nighters are wedged between 3 and 4 nighters and not together. You're also still young so can travel a little quicker. I've also found it's easier to travel solo (pace wise) then with a larger party.

I must say that so many people plan trips trying to cram way too much into a trip. But both of your itineraries are a good pace.

Regarding San Sebastian: 3 nights would be enough to just visit San Sebastian in the off season. The challenge will be the travel day from Salamanca to San Sebastian will be quite long. It will be a 6 hour trip with a transfer by train Vallodolid or Palencia. So 3 nights in San Sebastian will really be just 2 days. It's such a beautiful area that it seems a shame to visit for just this short time. You won't have time for daytrips or visits to the countryside. Are there a few days you could carve out of Portugal or Italy to add time to this area? Admittedly I'm quite biased towards this area but it is quite different and exceptional. If you only have 3 days I may be tempted to skip the Basque Country(this trip) and add the days back to Madrid & Barcelona since you'd already be in these areas. Or even spend a couple of nights in Cadiz, Toledo, Cordoba or Girona - not such large cities.

The quandry is 3.5 weeks seems a long time but Spain is a large and diverse country with so many wonderful places to visit!

Salamanca is wonderful and well worth 2 full days.

I would have found a day trip to Toledo very frustrating - there's too much there that I wanted to see to have fit into that time frame, and Toledo is one of those places that is magical in the evening after day trippers have left. But to each his/her own!

As CathyM says, there's just too much to see in Spain to fit into 3.5 weeks, so difficult choices are necessary. (I ended up skipping Barcelona and San Sebastian so I could focus on central and southern Spain. I'm looking forward to a trip that includes those cities and other parts of Spain.) At least you'll see some wonderful things no matter what you decide!

You're all right - there is SO MUCH to see and do in Spain and it's a huge country. I'm going to skip Salamanca this trip and do Toledo instead. That way the travel is shortened for getting to SS and if I fly I can do both SS and Barcelona.

You can get non-stop flights from Madrid to San Sebastian [expensive] and San Sebastion to Barcelona [very reasonable on Vueling.com] You could also look at kayak.com

Both flights in air about one hour, plus at least another hour on each end of a flight. So, 3 to 4 hours each flight.

Train Madrid to San Sebastion may work better--not sure.

To get from Salamanca to San Sebastian it's probably best via train. In order to fly you'd have to get back to Madrid (3 hours), then get to the airport from the train station, check in at the airport (probably at least an hour in advance for the flight) and then fly an hour to San Sebastian, wait for luggage, then get into San Sebastian from the Hondarribia airport. By the time you go through all of this you might as well have just taken the train from Salamanca to San Sebastian with a transfer in Palencia or Vallodolid (approx 6 hours). Train Madrid to San Sebastian is 5.5 hours at best. But you'd first need to get to Madrid from Salamanca so it would be best to not go via Madrid by train.

There are 2 buses a day Salamanca to San Sebastian but they take between 7-8 hours.

Hence my comment that it's alot of travel to get to San Sebastian for only 3 days - it basically cuts out an entire day.

CathyM; It seems like the OP is skipping Salamanca, so that's why I suggested flying Madrid to SS. By dropping Salamanca the OP could add another day in SS or elsewhere.

But your thought about the train gives the OP an idea of time. I think train time is reasonable.

Then there may be a bus.

The flight is expensive.

Geez..just saw the note about skipping Salamanca for Toledo. Sorry.

So you will need to get from Madrid to San Sebastian:

-Train is comfortable but 5.5 hours.
-Bus takes nearly the same amount of time - I'd consider if you could get the supra bus which doesn't have as many stops and also is more roomer (like flying premium economy vs economy).
www.alsa.es

-You can also fly from Madrid to San Sebastian. I don't think Vueling flys direct Madrid to San Sebastian - you may have to make a long connection in Barcelona. but I could be wrong. It may be cheaper to fly Madrid to Bilbao and then take the shuttle directly from the Bilbao airport to San Sebastian - it runs frequently and takes an hour, 15 minutes. Note: Vueling has extremely tight luggage restrictions. What could seem like a great fare could become extremely expensive with add on fees for luggage. Given the lengh of your trip you may have alot of luggage.

San Sebastian is a bit out of the way logistically between Madrid and Barcelona. So I'd really suggest adding more time. Salamanca is incredible and the entire old town is an UNESCO World Heritage site....but yes, there's so much to see!

I like the idea of taking a bus. Your luggage will be more secure in the locked compartments in the undercarriage of the bus.

Thanks all for the travel advice - much appreciated!

I'm starting to plan out more of the details for Seville, but need help picking an area to have an apartment for my 5 nights there. I need it to be easy access to the bus station since I'll be doing 2 day trips (Jerez and Cordoba), plus coming in and out on bus.

The one I like best is located opposite the Fine Arts Museum Square: http://www.vrbo.com/258394#ownerprofile. It fits my budget and has great reviews. Thoughts? Would I feel safe from muggings in this neighborhood by myself at night?

Others I'm considering:
http://www.ownersdirect.co.uk/spain/S7061.htm
http://www.only-apartments.com/en/seville/AZUL_2637/Search/2,29/01/2013,02/02/2013,32,1,0,0
http://www.only-apartments.com/en/seville/ABADES2_12111/Search/2,29/01/2013,02/02/2013,32,1,0,0

My favorite area is El Arenal. It's very central and has a lively tapas bar scene. It's close to everything yet has a neighborhood and local feel. I also like the are around Plaza Alfalfa in El Centro. I spend a week or so in Sevilla every spring traveling solo and have never felt unsafe walking around at night (or during the day).

I'd try sevilla5.com for apartment rentals - used them last year and they were very responsive and professional. The apartments were exactly as they appeared in the photos.

I'm starting a fan club called "Spain Travelers Heart CathyM" because you are so helpful - thanks!

if you are headed to malaga i would make the journey to marbella and go to Puerto Banus. There are loads of restaurants on the port where you can sit outside, sip wine, and look at all of the luxury yachts. Also you can eat in a few places that have a menu of the day for well under your budget. Or if you dont want to go as far down as Puerto Banus you could always goto the port in Marbella and sit outside, have an amazing view of the sea and enjoy a nice menu of the day. Then after that it is a short walk to old town Marbella where there is cobble stone roads and plenty of little shops.

Sounds like a fabulous plan! Close to what I would have done for a roundtrip with the same amount of time after 25 years of intense travel in the country. The Málaga and Antequera part of the trip tells me you know what you're doing...

You've already got loads of great suggestions. I just add some hopefully to the point tips for some of your cities/towns with a focus on laid-back atmosphere, wine and food.

Sevilla:
Start an evening in some of the tapas bars/cafés along Calle Betis in the wonderful and vibrant Triana district on the other side of the Guadalquivir river, a cradle of flamenco culture. Plenty of bars and clubs long into the night in this neighbourhood. http://www.sevilla5.com/activities/goingout/betis.html

Córdoba:
Has got lots more to offer than the obvious tourist atractions such as the Mezquita, the Alcazar etc. Go a little North of the major tourist atractions to find "Roman" Córdoba around central Plaza de las Tendillas with excellent and affordable tabernas on every corner and a much more local atmosphere.

I love Taberna El Gallo in C/Mária Cristina, 6, two minutes from Plaza de las Tendillas, and next door to the Roman temple ruins. Great wines - try the dry Amargoso - and excellent tapas. In one word: Genuine!
http://www.tripadvisor.com/Restaurant_Review-g187430-d2098252-Reviews-Taberna_el_Gallo-Cordoba_Province_of_Cordoba_Andalucia.html
http://cordobapedia.wikanda.es/wiki/Taberna_El_Gallo

Málaga:
You don't find more laid-back and true Andalucian atmosphere anywhere. Loads of tapas bars, cafés, clubs etc just east and north of central and pedestrian Marqués de Larios street. El Pimpi is an institution in town and a must at night: http://www.bodegabarelpimpi.com/launch_eng.html

Antequera:
I love the bar/restaurant/terrace in the corner of the peaceful square in front of the Real Colegiata de Santa María la Mayor, the first partly Renaissance-style church in Spain (built 1514-1550). Up here it's totally peace and quiet. Next to the recently excavated Roman baths beneath and looking up on the 13th century Moorish alcazaba/fortress. Great views over unique landscapes (the spectacular Torcal limestone mountain etc.). http://www.wild-about-travel.com/2011/07/5-reasons-visit-enchanting-antequera/

Granada:
Perhaps go for the Thursday night performance at Peña Flamenca La Platería, one of the oldest exisiting flamenco clubs in Spain. In the unique Albaycín district close to the center and Plaza Nueva. This would be the real deal, and you could be up for an excperience to remember for very long. Sometimes they also have performances on Saturday nights. The entrance is only some 10-12€ with one drink included. Also a restaurant: http://www.laplateria.org.es/

One of the greatest up and coming flamenco dancers in the world today, Patricia Guerrero, literally grew up here, and the greatest local flamenco artists perform here on a regular basis. This clip gives you an idea of the place and the atmosphere. Here, the extremely popular singer Diana Navarro from Málaga performs. She is not a traditional flamenco singer, but she has a beautiful voice and is fully capable of creating magic: http://www.youtube.com/watch?v=qgPrfjinEgQ

Madrid:
The Madrileños are called "Los Gatos" (the cats) and never goes to sleep. Start a long days journey into the night at hard to find Casa Granada on the 6th floor of an apartment building just off local feel Plaza Tirso de Molina right in the middle of everything. Great terrace: http://www.tripfilms.com/Travel_Video-v63831-Madrid-Where_To_Eat_in_Madrid_Casa_Granada-Video.html

Watch the sunset over the Guadarrama mountains from the terrace at El Ventorrillo in the Vistillas park. Great pollo al ajillo (garlic chicken), some say the best in town. Map, video and some pictures: http://11870.com/pro/restaurante-ventorrillo

Café Central, just off bustling Plaza Santa Ana, is a fabulous jazz venue with live performances from the best artists every night at 10. Entrance 15€. Good food also. Populart, a little further down the street, is also a great place. http://www.cafecentralmadrid.com/

San Sebastián:
My favourite city on the planet, and I could go on for ages. Shall limit myself to say that you can't do much wrong going for the world famous pintxos in the Parte vieja/Old town. All about, suggested routes etc: http://www.todopintxos.com/home/home.php?lang=en

For nightlife there are several laid-back music bars just behind the cathedral that probably are the best bet in San Sebastián for a really late night out when (if) you are over the disco age. The Reyes Católicos area thus is one of the very the best area for nightlife in San Sebastián (Udaberri, Pokhara, El Nido, Splash etc etc).

Traditional Bar Restaurante Casa Vallés from 1942 is one of my absolute favourites in the city when you get tired of the gourmet hype and in the same area: http://www.barvalles.com/
http://www.frommers.com/destinations/sansebastian/D51870.html

I also highly recommend the jazz/blues/funk Bar Be Bop on the seaside in the outskirts of the Parte vieja. The best atmosphere, and often great artists performing here.
http://www.barbebop.com/contacto/

Barcelona:
I very much recommend the Poble Sec district, the small and very local feel area just between Montjuich and Avenida Paral.lel. Great cafés and restaurants, the best atmosphere and several great theaters close by. http://www.barcelona-tourist-guide.com/en/areas/poble-sec.html
http://www.youtube.com/watch?v=XU3ePGy1_Y0
http://www.youtube.com/watch?v=UGb2pcWnJaI

Wow amazing post from kimhe.

We were in Spain last year and you may find something useful on my blog, in particular the post on Tapas in Sevilla which will at least make you hungry

http://somuchmoretosee.blogspot.com/search/label/Spain

I never got around to posting on Grenada but one suggestion is to book the first tour of the day at the Alhambra and walk past everyone who enters with you on the timed ticket, continue through the rooms and walk back. This allows you to see some of it on your own, which is a magical experience and quite different. The only difficulty is that you fight the crowds back in the beginning rooms. It may be more manageable in February, though we found it busy last March.

We'll visit Madrid in late Jan between our Portugal and Paris rental, so I can''t comment on it yet but I wouldn't cut out Barcelona. If you like museums and architecture it is a great city, MIro, Gaudi, Picasso etc.

Have you considered a rail pass it may be worth it if you're covering the entire country? I know from looking at prices on Renfe for our trip that train tickets (on the same route) vary enormously in price and it seems discounts are available when booked in advance or if there's still availability at the last minute. Given that you are planning a fixed itinerary it may be worth buying in advance?

Also, one last thought. It may be that you're most interested in the permanent collections only, but it may be worth look at what exhibits are on at particular museums when planning your trip. For example in Madrid I want to make it to the Cartier exhibit at the Thyssen before it ends on Feb 17th and I had this in mind when planning our dates..

http://www.museothyssen.org/microsites/exposiciones/2012/cartier/index_en.html

Hope this helps.

What amazing suggestions, kimhe! Thanks!

How does this look for my Southern Spain portion? Any key sites I’m missing or great restaurants I should add in?

Seville
Tues: Arr late in Seville to apt near Fine Arts Museum, tapas nearby
Weds: Triana neighborhood and market, wander old Seville, Dinner at PuraTasca
Thurs: Day trip to Jerez (Harveys of Bristol tour, Lunch: Reino De Leon Gastrobar, González Byass), dinner in Seville at Vinería San Telmo
Fri: Day trip to Cordoba, back to Seville for tapas and then Casa de la Memoria for flamenco
Sat: Alcázar in AM, tapas wandering for dinner and drinks into the wee hours

Malaga:
Sun: Travel to Malaga, Atarazanas Market and snack at nearby café, Walk Paseo del Parque, wander and visit Alcazar, tapas around Calle Larios
Mon: Cathedral, wander the city, Plaza de la Marina for shops and cafes, Walk along the beach: Paseo Marítimo, Dinner: El Tapeo de Cervantes
Tues: AM: Day trip to Antequera

Granada:
Weds: travel to Granada, walk around Old Center, Places of Worship self-guided tour and Shopping at Calle Calderería Nueva, Plaza Nueva area for tapas
Thurs: Alhambra and surrounding area in AM, Lunch at el huerte de Juan Ranas, wander Albayzín area (self-guided walk), Peña Flamenca La Platería

Many of us - and I'm one - think it worth visiting the Alhambra twice, once in the day and then visit the Nasrid Palace again in the evening. I thought it absolutely magical at night! Do book ahead.

That's a great idea - getting to see it in different light.

Your plan sounds good! In Sevilla don't miss the Cathedral. The beauty of Sevilla is just wandering around the neighborhoods. In addition to El Arenal and Triana I enjoy the Macarena area. One of the best websites I've found for Seville is ExploreSeville -a wealth of information.

exploreseville.com

Different lights and different contexts: The night tour is limited to a small number of people; during the day, there may be masses of them with competing tour guides.

As CathyM says, don't miss the cathedral in Sevilla. And don't miss the one in Grenada, either.

This site is great for tapas bars/restaurants in Sevilla. Azahar lives there and knows what she's talking about. http://azahar-sevilla.com/sevilletapas/

Here are two great places close to the Fine Arts museum:
Bodega Dos de Mayo: http://azahar-sevilla.com/sevilletapas/2010/02/bodega-dos-de-mayo/
http://www.tripadvisor.com/Restaurant_Review-g187443-d1749980-Reviews-Bodega_dos_de_Mayo-Seville_Province_of_Seville_Andalucia.html
Eslava: http://azahar-sevilla.com/sevilletapas/category/eslava/

You have to visit Segovia, it's very close to Madrid and can easily visited in a day trip. There is a train from Madrid, and it takes 20 mins to go there. Segovia is quite famous for the gastronomic tourism, you'll eat good and cheap (while, for example, in Toledo it's not that easy to find this combination). There is a great restaurant in the Plaza Mayor of Segovia (the one where is the town hall and the Cathedral), I think the name is Meson Mayor, but not completely sure, where you can eat for a bout 15$ with everything included (first, second dish, dessert, bread and drink). Usually this offer is valid only for lunch time (between 2pm and 4 pm usually).

If you take cathy and kimhe's advice you are almost guaranteed a great trip.

Cordoba is great for one night. I know it sounds crazy but the restaurant across from the main church is wonderful, some of the best paella I have had in Spain. Do not take any nights from Barcelona it is my favorite city in Europe, well maybe after Paris. Do not miss the Barcadero (sp) the market just off the Ramblas. Sounds like a great trip.

This is all so wonderful, thanks. I think the first part has mostly come together. What do you think of the second half?

Toledo
Fri: Hospital of Tavera, Church of Santiago del Arrabal, Zocodover, Hospital of Santa Cruz, lunch at Coleccion or Asador, Cathedral, Ayuntamiento, Santa Isabel de los Reyes
Dinner: Kumera.
Sat: AM: Begin tour at Plaza de San Andres, San Lucas, Taller del Moro, Church of Santo Tomé, Lunch: Restaurant Cafeteria Carolvs, PM: El Greco Museum, Synagogues, San Juan de los Reyes, Dinner: Casa Ludeña

Madrid
Sun AM: arr Madrid
11AM: Habsburg Walking Tour (snack on tapas after Royal Palace)
Lunch:
PM: Museo Thyssen-Bornemisza
Tapas: Plaza Santa Ana

Mon
AM: walk the Castizo Quarter
Lunch: Mercado de la Paz
12PM: Museo del Prado
Calle de Arenal & Plaza de Isabel II
Wander/tapas in Cava Baja area

Tues
Day trip to Segovia
Aqueduct, Cathedral, castle
Lunch: Jose Maria?

Weds
9AM: Sofía National Museum
Buen Retiro Park
PM: walk Gran Vía, Malasaña & Chueca
Sunset: Templo de Debol

San Sebastain
Thurs Arr in PM, Dinner in Gos area
Fri Aquarium
Hike Monte Urgull
Lunch in Parte Vieja area
Museo de San Telmo
Palacio de Miramar for gardens
Dinner in Centro area

Sat Museo Chillida-Leku
Kursaal
Wander old city center
Dinner in in Parte Vieja area
Be Bop for jazz

Barcelona (5 nights)
Walk La Rambla, ½ Day trip to Sant Sadurní d’Anoia (Cava), Walking tour of Gothic Quarter, Walking tour of El Raval (museums), Walking tour of L'Eixample, Walking tour of La Ribera, Lunch: El Roure for paella

Thoughts? Major places I'm missing?

Sounds great! Just a couple of comments on the San Sebastián plans. The Chillida-Leku Museum is regrettably temporarily closed, and Be Bop bar is not always jazz; often soul, blues, funk. But anyhow a great place!

Good to know about the museum being closed. And any music is just fine by me, but thanks.

Do you think there is time in the San Sebastian portion to venture out somewhere into Basque Country? Maybe a 1/2 day trip? I don't want to miss a single eating opportunity in SS, but wondering if I'll get a little bored considering what the weather will likely be.

Did you end up with 3 nights in San Sebastian? If so, then this will probably just be 2 full days by the time you factor in the travel time. You probably won't have time for a daytrip. But you could have a couple of ideas handy in case you end up getting the energy for one (and depending on the weather). Hondarribia is nice as is Getaria. But if you are flying into/out of the Bilbao airport you could always incorporate a daytrip to Bilbao. I wouldn't worry too much about planning out specifically where you're going to dine for the trip (unless the place requires reservations). This way you can be more spontaneous.

I need a nap just reading this.