Sept/Oct Weather

Most of Italy will be wonderful in September and October, especially if you go early October. Might get a little rain in October but that could happen anytime.

Patti, I think the absolute best months to visit Italy are either May, or September/October. You avoid the extremes of weather, and the most crowded times. What parts of Italy are you thinking of visiting? There are so many wonderful locations, dependent on your particular interests.

October is often a "transition weather month" in some parts of Italy. There can be a significant difference between early October versus late October. .
Of course, the above is just a generalization based on averages, and no one can predict what the October weather will be in 2015 (or 2016).
The last half of September has better chances, based on averages, for better weather than October, but September is also a more crowded or popular month than October.
It also depends on what part of Italy you'll be in. Rome in October is fine, lots of indoor things to do if the weather isn't cooperating, but late October in Lake Como or Cinque Terre probably would not be the best idea, because those are "outdoor places" with not that many options if the weather isn't cooperating.

I travelled to Italy October 22 to November 7 last year from Sorrento thru Tuscany and Umbria, Venice, and Milan. I enjoyed glorious weather until the last 3 days, except for one slightly drizzly morning early on along the Amalfi coast. Dress in layers and go out and enjoy yourself regardless of the weather.

Many thanks for your responses. I'm so much a newbie that I have no idea what the itinerary should be or will be. Going to get the guidebook and read all the posts I can to help me in planning. May plan for late Sept to early Oct for optimal weather but knowing anything goes! A tour group might be a better idea for people so inexperienced but really don't like the idea of no chance for spontaneity and traveling in a bus with loads of people. I'll keep on reading, studying, researching...

Patti,
You said you're going to get a guidebook. Click below for some guidebooks you may want to consider:
http://travelstore.ricksteves.com/catalog/index.cfm?fuseaction=catalog&parent_id=155

Thank you for guidebook suggestions. Good place to start!

I've been in Italy for 3 to 4 weeks in September/October for the last 6 or 7 years. As you start planning an itinerary, my suggestion would be to start in the north and travel south, so you'll get the best possible weather in the northern cities. By mid to late October in Venice, I'm usually cold enough to add some extra layers and a warm scarf – but I'm real wimp in cold weather.

Patti,

All my travels to Europe have been in late September/early October & the weather has been great!

This is also a great time to visit Italy because most of the crowds are gone ;-)

On our most recent trip (2014) we had some light rain while visiting Varenna in Lake Como on our last day there.
I always pack a light waterproof jacket with a hood & don't bother to take an umbrella.

You can always buy an umbrella (€5) from street vendors that pop up everywhere once the rain starts!

I think early October is a great time, how long are you planning to stay? If you can arrive toward the end of September, but depart before October turns a little drizzly in some places (depends on where you are going), you should have beautiful weather, fewer tourists, shorter lines for sights. Sometimes sights may have shorter hours after the summer rush, so check guidebooks or official websites for opening/closing times.

And happy birthday!

More great suggestions--thank you all. I'm hoping we can manage (financially) a two-week trip, maybe even 16 days to allow for 2 travel days. It's definitely doable to start late Sept and run into early October. I know I need to pin down our most desired locations and, from reading so many posts, try to limit the number of cities so we can really enjoy each place we visit. It's rather overwhelming if I was really honest but I've decided to take on this planning challenge and not stress too much as it will be one of the best trips of my life. Our style of vacationing has been extended backpacking trips through the Sierra's so this European vacation is exactly the opposite of that (hah!). Thanks for great posts that will guide me well.

Yes, you're right, Europe will be the opposite of extended backpacks through the Sierrras. I've done both.
You shouldn't have to plan all this on your own.
We're trying to help, but it would be nice if your companion would help you in the planning process.
Or go on a packaged tour and pay for someone else to do the planning for you.

I find these posts very informative.We are now thinking,not this year but next a two week trip to Italy,most probably early to mid October.We chose that because if it is the same next year as this we can get great direct flights from Newark to Milan,saving 600 to 700 for two over Rome

Pepper,
No guesses on what airfares will be a year from now. Airlines buy aviation fuel in futures contracts (the technical term), and how much of any savings they pass on to the passenger is anybody's guess.