3 weeks in Italy...questions...
 

My husband and I are planning a 3 week trip to Italy in October 2017, considering flying into Milan, exploring northern areas a bit (Lake Como, Piedmont, then over to Venice, then Cinque Terre, working our way from north to south, Naples), then flying out of Rome at the end of our trip. We'd love to experience spending time in wine country, perhaps an agrotourismo experience, and perhaps more rural than city. Our style is wanting to spend more time (3 nights) in great, centralized places rather then do a frenzied pace to get to lots of places.
Questions: How much time should we dedicate to Cinque Terre? Is Florence/Tuscany similar to Umbria? Are there any areas we should consider hiring drivers vs. taking trains? Anyone have good suggestions for great lodging places? We are budget conscious but want safe and clean, of course. Thank you.

Are you hikers? That's the biggest draw of the Cinque Terre (which I loved - I've been twice). Hiking between towns is awesome. My first visit was in October a few years ago, when the weather was still quite warm but pretty ideal for hiking. I think in October the rains may start to come at some point so you have to watch for that; the trails can close on short notice due to rain.

Also, some of the trails are closed well in advance due to slides or other closures - check in advance to plan potential hikes.

If you aren't hikers, I would lower the priority of visiting the Cinque Terre at all. The villages are lovely but small. The hikes are not all that hard but most are not easy.

Italy has a great train system. You can take the trains almost everywhere (e.g. to and through the Cinque Terre). There are buses too. I've never considered hiring a driver in Italy, though I'm frugal, but I have never needed to anyway. I expect that would cost more in Italy than in say some less prosperous European countries.

You should plot out an itinerary to see how much you can comfortable fit into three weeks and not make your travel too rushed.

It might be easier to fly into Venice, then train west to Lake Como, etc. to the Cinque Terre then south to Naples instead of flying into Milan. See if flying out of Naples is possible instead of Rome to avoid backtracking. Of course, if into Milan out of Rome is a lot cheaper than Venice and Naples, do that and take the hit of the slightly additional train travel time to get place to place.

Thank you Andrew. We are hikers. Hiking Cinque Terre is a big priority, so we'll watch the weather. Flying into Milan and out of Rome might be the cheapest right now, but I'll keep looking. We're trying to use miles, so seats are limited.

Note that if the main trails directly between villages are closed, there are many other trails you can hike that may be open - longer or less scenic perhaps but maybe still rewarding. There is a website somewhere with updated trail status info for the CT. Of course, you have a long way to go so a lot could happen in the next 1.5 years til you go...

I am not sure about similarity of Tuscany and Umbria, but Florence is really different from everything. If you have an opportunity, visit it, the architecture, the views and the vibe of the city is truly amazing!

I think three nights (which is really 2.5 days) stays are nice, I do a lot of them. But I wouldn't call it 'spending more time' in a place, it verges if not on 'frenzied' at least on 'fast paced'. And if you want to see Como, Cinque Terre, Venice, Florence, Tuscan countryside, Rome and Naples - well that's 7 places times 3 nights and there's your three weeks. And do you only want to see Naples, (not the Amalfi Coast). So basically I think you can do all this but it will be more like a tour group type trip and not terribly relaxing.

Is this your first time in Italy (in Europe)? There are pros and cons to doing a 'taste of' type trip - which this would be versus picking one or two regions (e.g. either Rome and north or Rome and south but not both) and slowing the pace a tad.

Some of the Cinque Terre trails between villages have been closed for several years because of the risk of landslides. The higher trails (not having much land above to slide) are always more likely to be open. There may be a steep climb to get to some of them, and for some hiking shoes are recommended. Here is a page that has up-to-date information about trail conditions, not just in the Cinque Terre, but in the surrounding park area.

http://www.parconazionale5terre.it/sentieri-outdoor.php

They have an English language page, but it has almost no information. (They used to have a good page in English; there must have been a budget cut.)

I suggest you click on a trail that interests you. Then copy the URL and paste it into translate.google.com . The translation isn't perfect; "driving time" should be "walking time", for instance.

It would make more sense to visit the Cinque Terre before going to Venice, either directly from Milan or from Lake Como. The order you have now has you zigzagging from west to east and back again. I don't know where you want to go in Piedmont, but I see at least three very long train trips (5-7 hours)in this itinerary, four or five if you backtrack from Venice to the Cinque Terre. To me, a trip of this length, followed by another to get to the next destination, wouldn't be worth it for a three-night stay.

Are you willing to rent a car? At least in Piedmont, it would be very useful.

Budget conscious. Be aware that Venice is one of the most expensive cities in Europe. That does not mean you absolutely have to spend millions for a decent hotel but also be aware of the geographic location of any Venice accommodation you might stay in and how far it is actually situated from the usually-visited parts of that city.

I agree that if you can do so it would be best to fly into Venice as opposed to Milan but as has been said, you can take the train from Milan to Venice (once you get yourself into the city from the airport) in about 2.5 hours.

Rather than ask if you might take a train, the issue should be "should I ever need a car?". Probably not is the answer, but if you do it will be in parts of Tuscany or if you end up a lot south of Napoli. If you do end up with a car you need to realise that they are banned in some city centres and charges are steep if you bring them in. For two people trains work out cheap, have a read of seat61.com to get an understanding.

For for first timers is Umbria like Tuscany? Probably, just steeper. Florence is a valley city so very unlike any of the hill side cities in either Umbria or the rest of Tuscany. It has virtually no walls left and those it does are 15cnt so unlike say Lucca with its 18cnt ones. Plus Florence had all the money when it was being built. Siena was captured by the Florentines after the black death so it is more caught like a fly in amber at around 1400.

Umbria is more "rugged", less "polished" than Tuscany.

The food is, on average, better in Umbria. (I know this is subjective.)

Umbria has fewer tourists.

Umbria is more rural. In Umbria there are only three cities with more than 50,000 inhabitants (Perugia, Terni, and Foligno). Tuscany has 13 cities with over 50,000 people. In Italy, Umbrians are considered somewhat to be country bumpkins.

Umbria is the only region south of the Po that has no seacoast. But there is a part of the Sibilline mountains in Umbria, which are higher than any mountains in Tuscany. (Most of the Sibillines are in Le Marche, though.)