We need a little or lot of help with a planned 3-week+ (plus a couple of days for the transatlantic flights) trip to Italy and Spain next mid-September through first week in October. I hope some of you can comment and/or make suggestions about alternatives to what I’ve outlined below.

Some context - the “we” will be two couples (I’d like to say middle-aged, but I’m afraid we’ve just passed that threshold). DW and I have been to Italy 3 times, but only one of those times was for an “extended” period of time (2 weeks, with one week based in a villa just outside Orvieto with numerous day-trips and the second week in Positano/Capri and Rome); other than one-day wonders when cruising when we “visited” Barcelona and Vigo, we’ve not spent time in Spain. The other couple has never been to Italy (or Spain), but they spent 3 wonderful weeks with us in France in 2008 (Paris, Provence and the Riviera), so they do enjoy traveling; whatever the collective itinerary will be, they plan on getting to Rome a few days earlier than us to “do” Rome. We love beautiful scenery, good food, wine, amateur photography, and art (particularly in churches, not so much the galleries). And, believe it or not (based on how “stuffed” this preliminary itinerary is) we enjoy time sitting in outdoor cafes, drinking nice glasses of wine, and people-watching.

At the moment we are thinking that we’ll “do” Tuscany (for one week), visit Cinque Terre (couple of nights), the Lakes area (probably 3 nights) and Milan for a couple of days (mainly for the Duomo and The Last Supper). After Italy, we’re planning on taking a BudgetAir or EasyJet flight to Malaga and spend a week in Andalucia and the Costa del Sol and then train to Madrid for a few days.

As of now, our itinerary looks like this (hope the specific dates here don’t put people off; it’s the only way I can keep track of a real calendar and the need for Saturday to Saturday accommodations in Tuscany and Spain):

Day 1 (9/13/12) - leave the US
Day 2 (9/14/12) - arrive Rome; train to Orvieto and spend one night (Hotel Virgilio?)
Day 3 (9/15/12) - pick up rental car in Orvieto and drive to an accommodation in southern Tuscany for 7 nights (currently leaning toward Sant’ Antonio apartment near Montelpulciano)
Days 4 - 9 (9/16/12 - 9/21/12) - visit Montepulciano, Montalcino, Siena, the Val d’Orcia, Assisi, San Gimignano and Florence (by train)
Day 10 (9/22/12) - drop off rental car in Chiusi and train to La Spezia for two nights in the Cinque Terre (no accommodations identified, looking for something in the range of 90-110 euros/night/couple)
Day 11 (9/23/12) - visit some of the villages of the Cinque Terre
Day 12 (9/24/12) - train from La Spezia to Milan and then on to the Lakes region; (still considering alternative locations, suggestions welcomed) to stay for 3 nights (Residence Il Borgo in Bellagio - http://www.borgoresidence.it/eng/index.html or someplace in Varenna; looking for accommodations in the range of 90-110 euros/night/couple)
Days 13-14 (9/25/12 - 9/26/12) - day trips by ferry to visit Varenna, Menaggio, and Bellagio
Day 15-16 (9/27/12 - 9/28/12) - train from Varenna to Milan to stay two nights (no accommodations identified, looking for something in the range of 90-110 euros/night/couple) to visit the Duomo and The Last Supper
Day 17 (9/29/12) - fly to Malaga by EasyJet or BudgetAir, pick up rental car, drive to accommodation to stay for one week [currently considering an apartment in Ronda (VRBO 279421) or condo in Nerja (VRBO 6776) - either a “white village”/Ronda or seaside]
Days 18 - 23 (9/30/12 - 10/5/12) - day-trips to Malaga, Ronda, other white villages, Granada, Cordoba, Seville
Day 24 (10/6/12) - train to Madrid (no accommodation identified) to stay for 3 nights; no accommodation identified (same approximate budget preferred of 90-110 euros/night/couple)
Days 25 and 26 (10/7/12 - 10/8/12) - “do” Madrid and day-trip to Toledo
Day 27 (10/9/12) - fly back to the US

I realize that we’re trying to cram a lot into a fairly short period of time. Unfortunately, 3+ weeks is all we can afford to be away from home, from both a financial standpoint and family obligations back home standpoint.

I’d appreciate any comments on this itinerary, suggestions for accommodations, and identification of any glaring errors in this draft. We (the two couples) want to finalize at least the dates for flying to Rome and back from Madrid fairly soon so we can jump on frequent flyer seats if we can. We’ll attack other portions of this plan (e.g., restaurants, wineries, specific churches and galleries) in due course.

Thanks in advance,

Sam

Ronda is an interesting town but it is clearly not worth a week and it is a long ride to other towns.

And before that it is a busy and hurried schedule, where I hope you have an opportunity to enjoy Italy.

Nice trip---you will have fun.
I see no reason to drop the car at Chiusi---that is counter productive. Just drive to La Spezia and drop it there---much less time---or even Pisa, but not Chiusi.

Your feasible day trips in Spain will depend on your choice of locations---be sure you do that right. Ronda is a bit isolated. I am not sure I would not just stay in a Nerja for 2 or 3 days and then go to Seville. You cannot do all 3 of your day trips from one location.

I suggest that you train directly to Florence and spend your first night there, and possibly two. That way, you will spare yourself what could be a very tiring "day trip" attempting to see Florence from a villa near Montepulciano. (You can much more easily see Orvieto from a base in Montepulciano.)

Since you are spending so little time in le Cinque Terre, and since you don't appear to be hikers, I suggest you keep your car and drive it from Tuscany to the flat town of Levanto, (See San Gimignano en route.)

Levanto is a 5 minute train ride from le Cinque Terre. You can also use boats from Levanto to see le Cinque Terre. I suggest Levanto instaed of le Cinque Terre so you don't have to drag your luggage up very steep stairs and hills from the train station.

When you leave le Cinque Terre, drive yourselves to the town of Como on Lago di Como and drop off the car there. Take the ferry to Bellagio.

Are you asking for places to visit other than the lakes? If so, I highly recommend you use the car to visit Parma and Mantova. You can see Bellagio as a day trip from Milan.

From Levanto, it is a 2 hour drive to Parma, where you could stop and have lunch and see its stunning duomo with its extraordinary ceiling. From there it is only a one hour drive to Mantova, where you could spend two nights and see its amazing frescoes. From there, go to Milan, and stay long enough to go up to Bellagio for lunch if the weather is nice. Both Parma and Mantova are noted for their outstanding food.

You could either drop off the car en route in Mantova or drop it off at Linate airport in Milan and take the bus into Milan proper. Spend enough time in Milan to go up to Bellagio for lunch if the weather is nice.

Be sure when you go to San Gimignano that you go inside the churches, and I believe that the abbey of MonteOliveto Maggiore near Montalcino is very rewarding for lovers for frescoes.

I've spent much time in Nerja the past ten years. Although popular with tourists it has retained much of its Andalusian charm, lots of fabulous local bars/restaurants in the Casco antiguo/Old town. Nine beaches - small and large - among the cliffs, fabulous scenery and a pefect base for trips to great big cities such as Málaga and Granada and into the mountains. Nerja is especially known for the spectacular caves where people lived some 25 000 years ago: http://www.cuevadenerja.es/

I would recommend you to stay in the centre of town, close to the oldest street, seafront Calle Carabeo. Here you are close to everything, and on one level. Some of the more touristy urbanizations are a good - and often steep - walk from the centre. I can give you more detailed tips on where to live, bars, restaurants, what to do etc based on your interests.
About Nerja: http://www.nerjatoday.com/

Photo of Nerja, the cliffs along seaside Calle Carabeo in the old town. http://farm3.static.flickr.com/2622/...de6a8146_o.jpg

Old town street in Nerja:
http://www.minube.com/fotos/rincon/131879/629455

While you do have lots of moving around, because of your desire for one-week (or nearly) stays in villas, I don't think your schedule is too busy.

I like Zeppole's suggestion to visit Florence first, rather than day-tripping there. But I would also suggest that you consider keeping your rental car through your trip to the Cinque Terre, and dropping on your arrival in Milan. There is parking in the Cinque Terre; some of the hotels even provide their own parking (Villa Steno, in Monterosso, is one). Much less in the way of train connections, and all that.

And I would spend more time in the Cinque Terre and less time in the Lakes, but that's just personal preference.