We'd like to spend 2 days in Cinque Terre. Here's our rough itineray for a trip in October...when should we plug in CT and how should we travel there? Also, where and how or if can we add a 1-2 day side trip to Bologna?

Venice-4 nights
Florence-2 nights
Tuscany/Umbria-7 nights
Amalfi Coast-3 nights
Rome-4 nights

We will mostly travel by train except for Tuscany/Umbria where we plan to rent a car.

Thank you for your help!

It would be easier to help you plan a trip you would enjoy if you described your reasons for allocating your time as you have already, and why you want to add Cinque Terre and Bologna as destinations.

Are you most interested in history and art? Or food? Or beaches? Do you want a "survey" of famous Italian sights or are you looking for something off the beaten track or with maximum relaxation?

Where were you thinking of staying on the Amalfi Coast? There is no train past Sorrento.

Nessundorma,

After doing research (and still doing research...and enjoying it!), we've begun to narrow our trip down to these places based on what we'd like to see in each region.

1) Venice-for a romantic and uniquely magical experience and for the Art/Architecture. We'll probably spend the bulk of our time getting "lost" in the city. On and off the beaten path. We'll attempt to see/hear a performance (theatre/opera/music).

Florence-all day tour (mainly to see the Uffizi and David), second day...getting lost and exploring the city.

Tuscany/Umbria-Countryside, old towns, food/wine, relaxing and romance. Staying in farmhouses and villas. Taking a cooking class, visiting winery estates and learning about olive oil and agri.

Amalfi-probably staying in Positano. Explore Ravello. Maybe a day trip to Capri...(might be too much). Looking to hang out on our balcony and enjoy the coastline.

Rome-honestly, we've added Rome, but it's not our top choice. We'll do the main tourist stuff here and see the "must-sees".

Bologna-food, food and more food.

When we travel, we like to experience it all...Art, Nature, Food/Wine, off the beaten path, Culture/Lifestyle, Rustic lodging and Luxurious lodging. A little bit of it all...from one extreme to the other.

I was thinking about scrapping one coastline...and go to either CT or Amalfi, but after research...I find that each is so very different than the other. So it makes sense to us to do both. One for a more rustic and the other for more resort.

In all regions, we'll immerse ourselves in eating and drinking the foods of that region...more like the locals, not necessarily the top expensive choices.

Hopefully that answers it all.....

Cinque Terre is unreal and you shouldn't pass it up! I would say a good order for this itinerary would be in this order but you could start on either end of it:
Venice to Tuscany then down to Almalfi Coast or Rome (these 2 can be switched), then continue to Florence, when you leave Florence stop by Pisa (you only need about 2 hours to see the tower) on your way to Cinque Terre. Or, Tuscany can be done on the way to Florence.
I did this same itinerary with the exception of the Almalfi Coast where we ran out of time and Tuscany and it worked out pretty well.
I saw Rome last year for the first time and I don't REALLY enjoy history that much but seeing all of it in person was definately worth it! I would keep it in the itinerary.
Good luck!

Yes -- at least you know who you are and what you want!

Since you are unwlling to forego one of two coastlines -- and why should you? They are quite different in feel -- the obvious advice is to scrap Rome, and I say do it!

Your problem is, as you've probably noticed, that there is no convenient train itinerary that includes all these places. Would you be willing to drive your rental car for a longer period of time?

How about this as an interary:

Venice 4 nights
Train to Bologna 2 nights

Pick up car drive to sights in Umbria, Tuscany and Cinque Terra -- 9 days

Drop of car in Firenze (2 nights)
Train to Naples. 2 nights (one day spent touring Pompeii; evenings spent eating!)

2 nights Positano.

Fly out of Naples.

PS: I added Naples to your itinerary because you said you like off-the-beaten track -- and believe me, Naples is now off the beaten track for a lot of American tourists because of its reputation, but it is an amazing city as Venice.

In fact, if it were me, I'd hang out on the balcony of this hotel

http://www.hotelsanfrancesco.it/

and spend all my time in Naples, taking a ferry to Capri, and to the Amalfi coast. And seeing the astonishingly wild and flamboyant mannerist art of Naples, which matches the overstimulated culture of the Neopolitans.

I added Pompeii to make up for the loss of Rome, but obviously you might prefer something else.

Also, if you like off the beaten track, and luxe on a shoestring, try booking yourself into the diuble rooms offered by the restaurant Da Salvatore in Ravello. They are 90 euro a night with lovely views. Ravello is much more secluded and quiet than Positano. It is a choice between a palace in the clouds or a romantic jumble of (former) fisherman's houses spilling down the hillsides.

Sorry - one more thought and then I'm done, I promise!

Are you including Umbria for October truffles?

If so, you'd do better in Le Marche (Acqualagna or Urbino).

In that case, I would say Venice, Bologna, pick up car in Bologna, head to Urbino/Acqualagna, then head straight to Tuscany, followed by CT, then Firenze, drop off car and proceed with trip.

If you could afford a flight from Pisa to Naples/Sorrento, that would be a time saver.

Grazie for the excellent options.

Don't be sorry, Nessundorma....keep those thoughts coming.

So if we were to keep the car through CT, Do we park it and train/hike in? What are your thoughts on the CT region as far as your recommendations? We enjoy long hikes, so my thought is probably train it in (dump off the luggage) and stay at one of the towns and hike the entire stretch in the 2 days. Thoughts?

That hotel in Naples is bellisimo!

My thoughts on the CInque Terre are that it is way too crowded and that the towns have become far too touristy -- annoyingly so. It has few recommended restaurants. You might have a different and lovely experience if you spend most of your time hiking, but since you are going in October, you will indeed face fewer crowds, but you also run the real risk of rain, which can make hiking the CT trails a no-go.

In October, I think you can park a car somewhere right in the CT and stay in the CT. If it rains, you can get in your car and do a day trip to someplace like Lucca, or take a train into Genoa for a great lunch and an afternoon of palazzos. But if you prefer, you could stay instead in Levanto or Santa Margherita Ligure, which probably have better restaurant option, and train into CT for hikes.

I also suggest that you give serious consideration to staying in Camogli. There is a hiking trail through the national park of the Portofino peninsula that some judge to be the best in the area, with spectacular views of the moutains and sea. The town of Camogli is very charming and has excellent restaurants. In October, you are likely to be sharing it mainly with Italians. In addition, if you get rain, you are only 20 minutes by train from Genoa. It has a range of accommodations.

Or you could split the difference, stay in Camogli, hike the Portofino trail, and the next day drive to the CT and hike a CT trail.

One thing you haven't talked about is whether you enjoy socializing with other travelers and like a bit of night life, or prefer secluded spots. In October, you are going to find very quiet nights in Camogli, and in much of CT after the daytrippers leave (although in CT, you will find fellow hikers from all over Europe). In Santa Margherita Ligure or Rapallo, you will find bars and a more upscale party atmosphere (although somewhat subdued in October.)

In October, I would be very tempted to not make hotel reservations for the CT-Tuscany-Umbria part of my trip, unless you are determined to stay overnight in the center of Siena or some other very famous Tuscan hilltown. Instead, I would keep an eye on the weather forecast and try to be sure to hit the coast during a stretch of sunny weather.

But I am quite used to driving around without reservations and bedding down in albergo ristorantes or agriturismos, or non-special hotels or BBs. The accommodations in such places are spotlessly clean, the service is great and often they have loads of charm and delicious homecooked meals. And they are cheap by comparison. But for others, a superior or famously charming hotel is an important part of the travel experience, so that's not a good strategy. And it's not a good strategy if you just feel better having booked in advance.

Ah, look what I found for you adventureseeker:

Somebody who took a hike on the Portofino peninsula, starting in Camogli, put pictures of their trek on the web. Apparently they enjoyed the solitude:

http://community.webshots.com/album/118020384gYgCvT

Nessundorma, Wow! Again...great advice and thx for the link. Bellisimo. Something to think about....

Keep 'um coming.

Thx so much for your help.

Just one more tip, and then I am off to watch The Sopranos on HBO on Demand. (Missed it last night.)

You said previously that you are interested in olive oil -- and wine. Montefalco might be a great perch for you in Umbria, with its famous and unique Sagrantino wine and its olive oil.

I stayed at Frantoio Brizi, surrounded by convents, with a view of all of Umbria, and an olive oil press (still in use) in the basement.

http://www.frantoiobrizi.it/index_e.html

Here is a picture of the olive press:

http://digilander.libero.it/frantoiobrizi/