Travel type gear needed in Italy during November

We had friends that went to Istanbul a few years ago and really surprisingly enjoyed it.

Get yourself some packing cubes on Amazon. It’s a great way to keep yourself organized and help you pack a light. I bought all three sizes.

I don’t think you need boots just some great walking shoes.

We mainly travel in winter, so much more chance of rain, and we do carry on only (we check bags coming home, but never going over). I have a pair of waterproof Merrill brand shoes - I think they are technically called a hiking shoe - and have used these for several trips now. I really like them. The sole is grippier and firmer than my Asics running shoe (my normal everyday shoe), which is good for irregular terrain and cobblestones. I have never felt I needed a boot, and the Merrills definitely keep my feet dry and warm. I take three pairs of smartwool socks (wear one, pack two) and I can wear a pair for days before they get stinky.

I also take a water resistant outer layer. This depends on when and where I travel. For cold weather, it's a Lands End coat with a hood that hits me just below my rear end. Not their super heavy one, just the lightly lined one. I wear this on the plane. I take layers for warmth - three Lands End fleece (wear one, pack two), long sleeved tshirts (these pack super small so I may take 5 or 6). If I'm traveling in warmer weather, the outer layer is a standard packable rain jacket that folds up pretty small. Everything else is the same except a short sleeve shirts instead of long sleeves, one or two fleece instead of three.
Carry on only is definitely the way to go, especially when you're changing locations frequently and have to manage your luggage on and off trains, stairs, etc. You can do it!

Oh, I forgot to address the question about purchasing along the way. Simple answer. NO! I mean, yeah, if you realize you need an extra layer or something, you can totally pick up things, but no way I'd be comfortable buying core items as I go. Learning to live with a limited wardrobe is just a part of traveling light and lots and lots of people (including most here on this forum) do this even on long trips. Lots of tricks and tips here.

I spent two weeks volunteering in Sicily in November 2021. I was surprised how cold it was at times. And I’m from Minnesota! There were days when a light cardigan was enough, but at other times I wished I had brought more long sleeve shirts, and a warm cashmere or wool sweater, fleece and so on. Most days had no rain, but when it rained, it poured! So a rain jacket (that will go over all the layers) is a must. Good walking shoes should be fine, no need for boots. But do bring two pairs of shoes in case one needs to dry out (or your feet just need a change). I like wool socks from Smartwool and Bombas. I’ve also heard Darn Tough is a good brand. I have compression socks from Bombas that I like.

I also took the RS Sicily tour and it was great! I wouldn’t count on being able to just buy what you need. You don’t always stay in big shopping areas and time is limited. Of course, I’m not much of a shopper, so maybe I just didn’t notice. This tour was in March and, again, there were some surprisingly cold days, particularly when it was windy on the coast and up on Mt. Etna (I literally wore almost every item of clothing that I had brought on our Etna day!). Other days were pleasant.

I don’t think you need to buy a lot of special clothing for this (or any other) trip. Bring clothes you already own that you are comfortable with and make sure your shoes are broken in.

When you say that you are traveling on two different airlines, are you booked through on one ticket or two separate tickets? This is an important distinction since, if you are on one ticket, the airlines cooperate on transferring luggage and all you need to do is make your way to the next gate since you will be all checked in. They will also be responsible if the first or second flight is late and you miss the next flight. But if you have two separate tickets, you will need to check in again with the second airline (after retrieving any checked luggage) and likely go through security again. This obviously takes more time and can be financially risky if your first airline is running late. I never book this way unless I have an overnight layover.

By the way, it’s too bad your daughter nixed Istanbul. It’s an amazing city. Consider the Rick Steves Istanbul or Turkey tours in the future.

Do not buy a single item until you decide what you need and what will work for you.

Peruse the packing forum here and see what has worked and not worked for folks here.

Basically, for outerwear, think layers. A lightweight waterproof, not water resistant rain jacket and a warmer underlayer (a fleece or down jacket/vest) will take you through a large temperature range.

And mind the weight of everything you pack. Packing cubes are great, but some are heavy and some are extremely lightweight. See what your options are before panic buying.

It looks like you plan to be gone about 2 weeks. Pack for 1 week and plan on doing laundry along the way. I prefer to use a laundromat and be done with it. Many others do sink washing every night or 2.

Trial your toiletries at home for the same amount of time you will be in Italy. Many products can be decanted into smaller containers, such as contact lens cases, to save weight and space.

I wouldn't count on buying clothes during your trip, especially during your tour. You may come across something, but I would be too stressed if I knew I had to shop. I have a hard enough time shopping for clothes at home.

Excellent tour and advice given thus far is spot on. You're right on the money regarding lightweight layering outerwear options and I use a waterproof shell jacket by Rain I got on sale at Nordstrom that combines with a slim quilted 32º label jacket sourced from Costco which nicely cover temperature swings and conditions in combination or solo. Merino wool is a great choice for socks and sweaters, I am happy with items I have bought at Uniqlo. I was just in Rome at the end of February and alternated wearing leather Chelsea boots by Caslon bought at Nordstrom Rack and vegan Skechers I found at TJ Maxx, each handled the rain and slick surfaces wonderfully. If purchasing footwear shortly, be sure to break them in for comfort before you're on the road. I am a carryon traveler, always bring a small umbrella, use lightweight packing cubes, make a complete packing list including absolutely every item I bring and plan for the best case scenario - avoiding the 'what if' additions that would weigh me down. Have a great trip, Sicily is fantastico!

We were in Sicily last November. I found I wore my down jacket several times and my merino wool cardigan most nights. I also take a merino wool crew neck as a base layer as needed. I like the brans WoolX for these. And I also took a Gortex jacket for rainy days. I like all these items because they are lightweight and pack easily. As for socks I like Smartwool; I no longer wear compression socks for flying. I found them uncomfortable for day to day wearing. For shoes I wear BrooksRunning which have excellent support.

They make waterproof models. I always take two pairs of shoes. Casual clothes where just fine in Sicily.
I do not like buying needed clothing items while I travel since it ia often hard to find the right size and it takes away time from enjoying and sightseeing.

I agree with waterproof shoes. I also like a waterproof rain jacket long enough to cover my rear end. Merino wool pullover sweaters are good in all temps. Silk long underwear which takes up little space under clothes and in your luggage.

For compression socks, I like Sockwell, which offers some merino content, as well as a range of sizes and levels of compression. They also have some fun patterns. And they are warm, so I will wear them in cold temps, as well. For regular socks, I like Wrightsocks, which have a double layer to prevent blisters. But Smartwool is great, too. I buy socks from Sierra.com, which is a great source for travel gear, clothing and shoes of all kinds.
Costco is a good source for lightweight, packable (waterproof!) rain jackets, as well as puffer jackets (which I prefer to fleece, as they squish down and can double as a pillow on the plane).
Both Costco and Sierra have good return policies, so don't hesitate to try something out. REI also has a good selection of travel gear, clothing and shoes, and a great return policy. REI's prices tend to be higher, but not always.
Weighing your clothes and your gear with a kitchen scale is a great way of making choices of what to bring. Packing cubes, for example, vary wildly in size and weight. I have a collection of Lewis N Clark "electro light" compression packing cubes that I have used for many trips. I'm not sure they make them anymore. REI does a good job of indicating the weight of products, which is helpful when ordering online. Sierra is inconsistent about listing weights. Merrell lists the weight of its shoes on its website, which is really handy because some of them are very heavy.