How to Pack 3 weeks Carry-on Luggage Only: Italy in Autumn

Down the road I went, in the ridiculous heels I had packed that went with one top, maybe two, and I hadn’t worn them once during the month-long trip. So, determined to prove that I didn’t pack unnecessarily, I stubbornly wore those heels to the pub down the road. Yes, the pub. For dinner with my family. And for someone who doesn’t like to look out place, I certainly did that night as I walked into that casual neighbourhood pub in Boston.

After dragging two huge suitcases, two large carry-on pieces, my large handbag, two kids’ backpacks and two smaller bags, I had had enough! It was crazy that we had so much luggage for a family of four. Admittedly we had attended a black-tie wedding at the start of the trip, but still, there was no excuse for the amount of “just in case” outfits I had thrown in.

At one point in the trip, we had to upgrade our rental car because we couldn’t fit all the luggage into the original one.

It has taken me a lot of trips since then to work my way down to one bag. I did it on a previous trip to Italy, but I checked the suitcase and still brought a huge carry on bag.

Not this time. This time I was determined to master it.


Taking carry-on luggage makes travelling a whole lot easier. No more dragging around large suitcases. #travel #traveltips #carryon #luggage #packing


Don’t try and fit in

I am not a stylist, that’s for sure.

You could say that since moving to the mountains my style has been reduced to being ultra-casual. I work from home, so I do not need work clothes apart from the occasional outfit required for meetings and networking. Our social life here in the Blue Mountains is casual too.

But I started to panic when I thought about my packing list to Italy. Shouldn’t I be more stylish? Should I update my wardrobe?

Then I stopped. This will be my third trip to Italy. Previous visits have been a combination of city and country and not once have I ever felt out of place or that I did not fit in.

I will never dress like the Italian women as much as I would like to. My life does not warrant it and as much as I don’t want to look like a tourist, I always will.

The minute I open my mouth I am quite obviously a tourist. So, I don’t worry anymore about fitting in. But I also don’t need to look like an unwary tourist who would attract the attention of pickpockets and the like. I want to be safe when I travel. I want to look like a confident traveller.

I have realised how I dress at home is how I dress travelling.

You are who you are and just because you are jetting off to a new destination does not mean you need to change your style. My style has always been casual but classic, meaning classic shirts, jeans or pants, boots or heels, coats or jackets.


Learnt how to pack carry on luggage. #travel #traveltips #carryon #luggage #packingComfortable at home

Packing List

You can find my generic packing list on Your Guide to Packing Light: Carry-on Luggage Only.

The list below are the items I took and/or swapped out during my trip to Italy last November/December.

This list has been edited to include the clothes I came home with, and what I would take again.

I had extreme difficulty in deciding what to bring. I had the issue of dealing with hot sweats and menopause.

I didn’t know how I would cope or how hot I would be. As it turned out, my symptoms decreased just prior to the trip which was a huge bonus. But that meant the cooler items of clothing I had packed were not enough to keep me warm. So I had to take myself shopping.

Not such a hardship when you are in Italy.


Packing List for Italy in Autumn for carry-on luggage

1 x Dark wash jeans

1 x Mid wash jeans

1 x Natural coloured merino jumper

1 x Grey jumper

1 x Emerald Green 3/4 sleeve merino cardigan

1 x Nude singlet top

1 x Grey singlet top

1 x White polo neck long sleeve top

1 x Grey merino long sleeve top

1 x White t-shirt

1 x Grey t-shirt

1 x Emerald green blouse

1 x Black Ecco ankle boots (these replaced the inadequate ankle boots I took)

1 x Tan Ankle Boots

1 x Pair Black Gloves

3 x Pairs of Wool Socks

1 x Green, Grey & Navy Infinity Scarf

1 x Grey Plaid wool scarf

1 x Grey Warm hat

1 x Black Rain Jacket

3 x Bras

5 x Underwear

1 x Pair of sleep shorts




To help plan my packing list I made sure to check the weather. Although I misjudged how cold it would get it still helped overall.

I travelled to Northern Italy – Verona and Bologna, and to Florence with a couple of nights in Milan travelling from mid-November until early December.

The temperature ranged from 18°C down to 3°C at night at the end of my trip. I had quite a few rainy days. On the warmer days, my jacket with a light top underneath was perfect, but at night I had to add more layers underneath.


Taking carry-on luggage makes travelling a whole lot easier. No more dragging around large suitcases. #travel #traveltips #carryon #luggage #packing


What Didn’t Work

Lighter Clothes

My T-shirts were okay but needed to be layered more than I thought. Even though I have worn most of them under a coat in winter here at home and have been fine, they weren’t for this trip.

Firstly, I decided to take out my wool coat at the last minute. It just weighed too much. It would have been ok had I not needed my laptop.

Secondly, I realised that even though I have worn these clothes in similar temperatures at home, I’m not outside all day like I was when I was travelling.

And thirdly, the hot flushes that have plagued me since March stopped. Or mostly, they have been few and far between and very mild. Who knew?!!! The theory of carbs, sugar and wine contributing to them flew out the window in Italy.

Suddenly I was feeling cold again.


My Shoes

My ankle boots were okay for the most part. And I felt they dressed things up a little as they had a small heel. I also threw in inner soles which made them more comfortable.


They were not suitable for the marble walkways in Verona. Once it rained they became slippery. I feared for my safety and after two falls, one in Florence and another in Verona I wasn’t taking the risk anymore. That and the soles were not sturdy enough for Italian cobblestones.

Neither pair of boots I had packed were suitable. I had also brought my long leather boots which are incredibly comfortable at home. They kept me warm and were great on rainy days, but the soles were not solid enough for travel.

So, I bought a pair of Ecco boots, on sale woohoo! They are not the most stylish pair of boots, but the store had limited choices in my size, and I was desperate.

Apart from the look, I am totally in love with them. They are heavenly on my feet, totally waterproof and I felt safe walking in these.

Because of my poor choice of shoes, my feet paid a considerable price. There were more times than I care to admit that I was reduced to tears from the pain in my feet and the painful blister that formed on the bottom of one of my toes. Compeed became my best friend.


What Worked

Long Sleeved Merino

My long-sleeved merino t-shirt was the best. I will be wearing this all the time on the Camino this year. I wore it under everything! Next time I will bring another one of these, in a different colour.

My jacket worked like a treat. Not thick, it’s only a waterproof jacket. But with all the layers underneath and a lovely wool scarf, I was toasty. It is thick enough to keep the wind out. I will consider a light puffer jacket next time, or vest,  if I am going any later in December, but this worked quite well and was a big hit on the rainy days when it kept me snug and dry.

I was warm enough with my jeans, but there were a couple of times it was a little chilly. I had packed a pair of tights to wear underneath, but I didn’t bother. I wasn’t cold enough. Next time if I travel later in winter I will take a pair of light merino thermals to wear underneath my jeans for extra warmth.

I did get sick of my jeans so just to change it up next time I might buy a different colour pair of jeans, or find a dress that I can wear over leggings or tights. But I am pleased I turfed my black jeans out of the suitcase. They would have been too light, and they aren’t my favourite jeans, even at home.



What would I add next time?

A Dress or Skirt

I want to buy a dress or skirt that travels well, can be worn in spring as it is with perhaps a denim jacket. But that can also be worn in autumn/winter with tights/leggings, and my boots. Throw on a jacket or coat and layers underneath.

There are some great travel dresses on the market so before my next trip; I will need to do a bit of research. It’s essential that I find something for at home and travelling.


Let me know what you think? Do you pack carry on only? From now on I won’t do anything else. The freedom of not worrying about heavy luggage was terrific. Apart from falling over and sore feet, I felt great. No aching back or stiff neck and headaches from hauling and lifting heavy bags. It made getting to and from train stations and hotels a breeze, and I will never go back.

Hope this helps you in some way pack a little lighter and feel a whole lot freer.


Cindy x


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Learning how to pack carry on luggage will give you greater freedom when travelling. #travel #traveltips #carryon #luggage #packing


Learn how to pack carry on luggage. #travel #traveltips #carryon #luggage #packing


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Cindy Reid

Cindy is the founder of Travel Charm and her exclusive Travel Club. She is passionate about travel and planning and loves nothing more than helping travellers plan their best trips and fulfil their travel dreams.


  1. Kara on July 28, 2019 at 11:31 am

    Thank you Cindy! NZ next week for an August trip in a campervan and I thought I’d quickly take a look at your list. x

    • Cindy Reid on July 29, 2019 at 4:13 am

      Have fun, Kara. Stay warm! It sounds like it will be a lot of fun. Travelling around NZ in a campervan is high on my wishlist. Unfortunately, my partner is not so keen.

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