If you really mean two weeks total - that only leaves about 11.5 days 'on the ground'. Then you'll waste some of that precious time (and money) traveling between them. Take your two weeks and pick ONE country - either Spain or Italy - not both.

You might want to read some guidebooks on whichever country you choose.

Pick one---each requires at least several weeks to see well.
In only 2 weeks, pick a region of either---you cannot hope to see much in that time---think Andalusia in Spain or Tuscany/Florence in Italy---not entire countries.

Unless you just want to see two major cities (and their close-in environs) and do one week in each, flying in between them, then I also advise picking one country to explore.
You have tons of time to check out some books from the library or peruse the internet to narrow down your options--there are literally thousands of trip options that we could throw at you, but only you know what speaks to you the most.
Also, flying all the way from the west coast means that even if money is not a factor, then flight times will make a difference. I would first plug in some flights on Kayak or some such site to get an idea of what you are in for. The best flight often makes a difference in my trip planning, to avoid layovers, many transfers etc. Have fun researching!

I think the "classic" itinerary for a first timer is to:

- Fly into Venice and stay there for 4 nights (I always add a night at the first place, for jet-lag recovery)

- Take the train to either Florence & stay 3 nights, or Siena & stay 2 nights (Florence can be overly crowded in early Sept - how do you handle crowds?)

- Rent a car and drive to the Val d'Orcia (Pienza area) in Tuscany and stay in a B&B or small hotel for 4 nights. Explore the beautiful countryside & small perched villages.

- Drive to Orvieto (1 hr), visit Orvieto, dump the car and take the 1 hr train to Rome & stay there for your remaining days.

Stu Dudley

Take a look at the Basque Country and the rest of Northern Spain. The best food in the country if not all of Europe, fabulous landscapes, lots of small villages both along the beautiful coastline as well as in the often mountainous inland. Also some fabulous larger cities such as San Sebastián, Bilbao, Santander, Gijon, Oviedo etc. etc. September is a great time of year to go up here as do many Spanish because of the August/September climate:

Basque Country: http://tourism.euskadi.net/en/
http://www.guardian.co.uk/travel/basque-country
Cantabria/Asturias: http://www.guardian.co.uk/travel/2008/jun/22/spain.green
Galicia: http://www.telegraph.co.uk/sponsored/travel/galicia/9437772/spain-holiday-galicia.html

Green Spain: http://www.greenspain.org/

Neither country has a big B & B tradition. They do have pensions and pensioni however.

I agree with eveyone above. Choose one. Each country is worth months and months, let alone a week in each.

Depending on where you go and how long you stay, a car may be more of burden than a help.

(1) Procure guidebooks of some sort. Fodors puts out a quality product (where's my freebie, dammit?) as do other companies like Fr------ and D------ K--------- and R--- S-----. I'd suggest the Fodors guides that have a lot of photos, the D------ K---------- and the Ins---t Guides for your perusal because they have lots of photos and you can look and say to yourselves: "ooh, I want to go there." This is a legitimate form of picking a place to visit - the superior half and I have used this method to great effect. [Note, I do not name non-Fodors products on these forums and Fodors STILL hasn't sent me free hotel stays or similar perks].

(2) Determine which areas interest you in which country because only ONE country will work.

(3) Determine how you'd like to get from place to place. If you will be in cities, you will not need a car because public transportation is good and both the Spaniards and Italians drive like Europeans. Trains between major cities are plentiful and fast and do not share the road with European drivers.

(4) This: "We love sightseeing, nature, beautiful towns, good food, picturesque places" - is meaningless. Both countries have sightseeing, pretty towns, good food (you have to work to find a bad meal in Italy), etc. Neither country is completely enclosed by a dome nor completely paved over, therefore each has "nature." You might as well say you want to have a beach vacation and ask about all the islands in the Caribbean.

(5) You really need to determine what you want to see before setting an itinerary. Stu Dudley's itinerary is a basic welcome to Italy notion, but there's a lot of city and not much town time and the fact is that the cities in these countries are historical monuments. Some towns are too (Assisi, Alberobello; Toledo [small city], Salamanca) and if you pick the basic welcome to Italy or welcome to Spain trip, you'll miss a real gem.

With two weeks and for your first trip to these countries, I highly recommend choosing one. Both are wonderful destinations but I would choose Italy.

You do not need to speak the language to have a wonderful trip but it is always nice to learn some common phrases.

The beginning of September is a great time to travel to either Spain or Italy but I would stay north in Spain at that time of year. Our favorite Spain destination, Andalucia, can be boiling hot in September. We often travel to Italy in September and it is a bit more moderate in temperature.

Do some research, internet and guidebooks, and choose an itinerary. Come back to Fodors to talk about your itinerary and get some help on details. Happy planning.

We did 2 weeks flying into Rome and out of Paris. Took the trains the whole way. Yes it was small amounts of time in each place, but worked out great. We did Rome the first few days, and I would say Rome is a must see!! We took a train to Cinque Terre. It was everyones favorite and say it is a must see also!! Then we took the train to Venice. I loved Venice, the rest of the family did not. It is very unique, but they got bored quickly. On one leg of the tour we stopped and did Florence for the afternoon. Not enough time at all, but made for a nice break.

In Spain i have only done Barcelona. It is an interesting city. When it comes to travel, you might want to check into flights on Ryan air or other air lines. Sometimes you can fly for much cheaper than train and faster than car.

I agree with mamcalice. If you decide to do one destination i would pick Italy over Spain.

When we did our trip, we came up with a loose itinerary, then used one of the on line travel agents through Rick Steve's web site. They were awesome and really helped us hammer down our plans.

You guys will love Granada in Andalucia, Spain. I studied there for 6 months on the Spring. It is one of the only regions with free tapas (food) when purchasing a drink, and there is a variety of fresh seafood from the Mediterranean, Paella, and Spanish Tortillas. Also the Alhambra is a MUST see because it lies beneath the gorgeous Sierra Nevada Mountains, and there are dozens of beautiful views (San Nicolas) to enjoy the sunset and views with a glass of wine. It is an enormous fortress built by the moors in the 1300s, perfectly symmetrical and detailed carvings with a title of being one of the 7 wonders of the old world. Not to mention the people are phenomenally friendly and accepting. Hemingway said if there was one city to see before you die, it must be Granada. Also I went to Italy for a week and loved Rome... So many sights to see! And Florence had amazing architecture with a smaller yet livelier feel to it. Would have loved to see Venice, I heard wonderful things.. Except don't go there if it is cold because you won't fully enjoy it. Some friends of mine went there in February and were disappointed by the frigid cold and lack of options to enjoy the gondolas or whatever those boats are called. Wish you the best of luck...and please ask me if you have any questions! The photos from my travels are on my website: http://jf-pr.com

Also be cautious if you go to Northern Spain or the Basque Country because they are trying to separate from Spain and are dealing with riots as well as active terrorism groups. The most English speakers reside Madrid or Badcelona too, but Granada has thousands of foreign exchange students from the U.S.

That is pure nonsense JesssssicaF.

This shows an abject ignorance of the current and historic state of affairs and secession in Spain. The ETA has had a truce for a year and then during the worst of times never targeted tourists. In Catalunya, elections indicated that the majority wanted to secede, but the future is uncertain. And even during the large demosntrations for independence back in September, there was no violence directed any tourists.
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It is one of the only regions with free tapas (food) when purchasing a drink,

That too is pure nonsense. It depends on the tapas bar and the type of tapa.
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The most English speakers reside Madrid or Badcelona too, but Granada has thousands of foreign exchange students from the U.S.

Once again this is pure nonsense. Many hospitality workers throughout the country speak some English, although English speakers are harder to find in smaller towns.