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Best time of year for a two week “Tour” of Italy

My husband and I are planning to go for two weeks and do Milan, Venice, Dolomites, Cinque Terre (maybe) Pisa, Tuscany/Florence, Rome, Pompeii/Naples.

I read on a travel blog that November is typically very rainy, and we are very interested in walking/hiking/exploring on foot. Would October 24th - November 8th be pushing our luck in terms of weather? Should we try to bump it up earlier in October?

Posted by
2135 posts

I think that timeframe is fine--we're starting our trip a week earlier than you. Difference is that we're starting in Sicily and only going as far north as Rome.

It will be less crowded overall--a real plus for me. You probably will encounter some rain, but not cold temps, probably no lower than 50 at night.

Posted by
1258 posts

Best in terms of crowds or weather? Historical weather trends are interesting but they're history. Weather is not predictable in the least. And you are visiting several different climate zones that are not directly related to each other.

Posted by
6 posts

I would say both, and also local events/festivals. For example, on the same blog I read that one of the best times to go overall is the fall because there are some great local food/wine festivals going on (in addition to less crowds and more temperate conditions). I just didn’t know if the rain too was similar to going to the Caribbean in November when it is definitely rainy/hurricane season (aka stupid).

Posted by
2135 posts

Just for what it's worth--unless you like moving from place to place, even without Cinque Terre, that's a lot of places in 14 days. Look logistically at it re: travel time, and how you're going to get from place to place. Have priorities and cut to 3, 4 max stops in my opinion.

Enjoy your planning!

Posted by
5429 posts

Agree with Jay--you can't do anything about the weather (for the record, I'd take the risk of late fall travel), but you can make sure you don't try to do too much. Sketch it out day by day to get a more realistic picture of your itinerary (including travel time). I'd cut it in half.
CT will be out in the rain, and I'd delve more into weather in the Dolomites as I am not familiar with that region and its seasonality.
Do you have flights yet?

Posted by
2218 posts

Sketch it out day by day to get a more realistic picture of your itinerary (including travel time). I'd cut it in half.

I totally agree. My rule of thumb is no more than one region per 2 weeks. I consider Milan/northern Italy as one region, Venice/Florence/Rome as another region, south of Rome to Sorrento another region, etc. We spent 10 days just in Tuscany and didn't feel it was nearly enough time. Doing a detailed day by day itinerary will really help you get a better idea of how little time 2 weeks is.

I looked up average November rainfall for Rome and found it to be the same as Atlanta. Be aware that the second most rainy month is October. Look up the festival schedules. I think most are late September/early October. Late October on will be iffy for the Dolomites. Read this.

I'd start by definitely throwing out CT and probably Pisa. What mode of transportation will you use? That will have an impact on how much time it will take from one place to another. One possibility would be to fly open jaw into Milan and out of Rome. See Milan, rent a car and go to the Dolomites, return the car to Milan, then take the train to Venice and work down through Florence and Rome. It still think that would be a lot, but certainly more reasonable than your current plans.

Posted by
944 posts

I agree with suggestions to select fewer sites, and at that time of year it probably makes sense to drop the Dolomites and Cinque Terre. We have been to all of the sites on your list except for the Dolomites, and it took us two very busy 2-week trips to do so.

Have a great trip. Italy is amazing!

Posted by
7473 posts

Welcome to the forum!

A “2 week” trip usually means 13-15 nights on the ground. It’s important to know exactly how many NIGHTS you have.

If 14- you have listed 8 locations (9 if you count Florence and Tuscany separately). That means each location will only get a 1-2 night stay.
A 2 night stay is really just 1.5 days. Every time you change locations you lose a half day at least.
Your “tour” of Italy will consist of the inside of trains and train stations and checking in/checking out of hotels most every day.

For 14 nights cut back to 4-5 locations at the most.
Most of the locations you have listed deserve a 3 night stay minimum.
(Pisa can be done as a day trip from Florence or skip it.)

I’d move dates to late September/early October if possible. We were there at that time this past fall and the weather was lovely. It was our 4th trip and we concentrated on northern locations- Stresa, Bologna, Verona, Padova, etc- we had 17 nights.

Slow down so you can enjoy where you are and spend less time in transit.

Posted by
15111 posts

I did Rick's Best of Italy starting Sept 30, ending Oct 16. Weather was variable, some rainy days but not too many. I will tell you that I was more affected by the heat in Rome at the end of that time. Your profile doesn't reveal anything about where you live so if you are intolerant to heat, I'd go with your original dates. I think that this Fall was hotter than "normal" whatever that is any more, lol. For myself, I'd be more concerned about heat than rain.

IF you do go that late in October, I'd start in Milan and do the Dolomites early on as they will be the most impacted by weather, I think. When we spent our 2 nights in Castelrotto (Oct 2-3) it was very pleasant temps but some of the seasonal restaurants and activities were starting to wind down.

I'd also agree with the recommendations to trim your wish list. The Best of Italy covers everything on your list in 16 nights except Pompeii/Naples and that was moving very quickly with a guide and bus driver who are familiar with the areas and the hotels and can get you places quickly. Doing it on your own will mean more time spent in transit, locating your hotel, figuring out public transit if any, etc.

Posted by
420 posts

The weather is not predictable! We were in Italy for 2 weeks in October this year, North and South. It rained one day and was sunny the rest

Posted by
10805 posts

For hiking in the Dolomites, you need to check the lift schedule to see if they are running during the inter-season. We were there in early June and the lifts had just restarted. The shuttle bus up the hill where we were staying hadn't restarted yet. Huffing and puffing up the hill, we learned that operations close down between summer hiking and winter sports seasons.

Posted by
498 posts

October 24 is definitely too late to visit the Dolomites. We were there in October 2022, we left October 12. Things were really slowing down, many hotels, b&b's and restaurants were down till ski season. Only a few lifts were still running.

Posted by
1140 posts

Echoing Bets- the lifts to Seceda and Alpe di Siusi usually shut down mid October. That being said, October is hands down my favorite month to visit Italy. The first two weeks are optimal.

Posted by
6 posts

We currently have flights booked Oct. 9th into Milan and Oct. 25th out of Rome. My current predicament is figuring out our priority list because there are so many places I want to go. This is what I have so far:
Milan for 2 nights
Either onto the Dolomites next for 2 nights OR just scratch because of the time of year and maybe drive through "on the way" to Venice
Venice for 2 nights
(maybe) Cinque Terre for 2 nights, but I think I will end up completely scratching this from the list as I've seen the hiking trail between the towns is closed until 2024, and that was one of the main reasons for us going...unless its still worth it to go. So I'm wondering if we can do the Amalfi Coast after all.
Florence for 3 nights
Sienna/San Gimignano for an overnight in one of those locations
Rome for 4-5 nights, and either a day trip to Pompeii, or adding in Amalfi for 2 nights (taking those away from Cinque Terre...)

Hopefully this made any sense at all.

Posted by
5429 posts

Milan for 2 nights Either onto the Dolomites next for 2 nights OR just
scratch because of the time of year and maybe drive through "on the
way" to Venice Venice for 2 nights (maybe) Cinque Terre for 2 nights,
but I think I will end up completely scratching this from the list as
I've seen the hiking trail between the towns is closed until 2024, and
that was one of the main reasons for us going...unless its still worth
it to go. So I'm wondering if we can do the Amalfi Coast after all.
Florence for 3 nights Sienna/San Gimignano for an overnight in one of
those locations Rome for 4-5 nights, and either a day trip to Pompeii,
or adding in Amalfi for 2 nights (taking those away from Cinque
Terre...)

There are many many paths in Cinque Terre--the alternate trails are actually better because you have fewer people. However, midOctober is more iffy for this region, so I would make it a flexible plan.
This the official website: http://www.parconazionale5terre.it/Esentieri-outdoor.php

I would choose between Dolomites, CT, and Amalfi Coast. I think you need more than two nights in places to account for travel time.

Posted by
6 posts

It is sounding like we may just need to plan a trip back for some hiking in the Dolomites...maybe paired with Switzerland.
Now just need to pick between CT and Amalfi, but it is sounding like Amalfi may be the safer bet, and lends itself more to adding in Pompeii (maybe even Naples if it's worth it).

Posted by
5429 posts

Yeah the hardest part is choosing between so many good options, but I would add those Dolomites nights to Venice (would want at least three nights--many say that helps you have time to acclimate to the crowds and explore back streets) and to Tuscany.
I always say choose either CT or Amalfi Coast because both offer coastal hiking and you can eliminate some travel time. If you are seeing Pompeii anyway, I say press on to the coast. With a two week trip, I would want at a minimum two stops of at least four nights, but that is just a personal peculiarity. I do understand some like to move faster. It can be practical as well--time to do laundry, etc.