Preparing for Solo Travel to Italy

Actually, it’s my first time trying solo travel anywhere! I have waited 49 years to travel by myself. I have taken solo road trips and flights before, but I have not experienced a whole trip solo.

How do I feel?

Beyond excited and scared to death.

From all that I have read about solo travel, and I have read plenty, these are normal feelings to experience.

This year has been challenging and transitional. I set out on one path in business, deviated to another, and then finally settled on where it feels right. I thought I would try and advertise a couple of group tours before the end of the year. That was always going to be difficult.

I am trying not to be disappointed, I had big plans for lots of personal travel this year. I wanted to go on a road trip through Scotland with my partner, Dan. But Scotland will always be there, and we will go.

But what I want, and need is to get on a plane.

By myself.

To have time to be me, rest and breath.


Italy is the perfect country to solo travel. #italy #tuscany #lucca #verona #florence #solotrip


Why Solo Travel?

There have been challenging health issues to contend with this year (all normal but challenging nonetheless), a lot of changes both in business and personally, and to keep our relationship healthy, I need time.

We both do.

Dan and I live and work together. We do most things together. And most of the time that’s fine. But there comes the point where we need to be individuals pursuing our own interests.

My interest and passion is travel, and it has been too long between trips.

And I just want to be able to do my own thing, when I want to do it.

Solo travel is a tremendous growth opportunity. Travel has always increased my confidence, pushed me past my limits and allowed me to find out who I am away from life’s routines. The thought of solo travel is frightening, but this quote comes to mind.


There is freedom waiting for you on the breezes of the sky. And you ask, “What if I fall?” Oh but my darling, what if you fly? – Erin Hanson


I plan to fly.

Italy I am on my way.


How I am preparing for my first solo trip

I chose Italy for a couple of reasons.

I love it and I feel at home.

This will be my third trip to Italy, and I am going to take the opportunity to explore further. Even though I haven’t stayed in any of the places I have included in my itinerary, I feel comfortable in Italy.

Meeting people I have connected with.

There is also an opportunity to connect with someone I have been friends with online for a few years. This is too good a chance to miss.

I am looking forward to meeting in person, having a good chat that my sketchy internet has denied us and spend time over meals enjoying delicious food and wine.

I hope to come away armed with local knowledge about what to see and do away from the tourist areas, and maybe explore new places together. If time and opportunity allow.

And for the rest of the time, I want to keep it simple.


Where to in Italy?

I am starting in Florence and basing myself there. The rest of the list goes something like this: Lucca, Verona, possibly Bologna and hopefully Montepulciano.

Solo travel can be daunting, but heading to one of my favourite countries, Italy makes it a lot easier #italy #italytrip #solotravel #tuscany #florence #verona #luccaSolo travel can be daunting, but heading to one of my favourite countries, Italy makes it a lot easier #italy #italytrip #solotravel #tuscany #florence #verona #luccaItaly is the perfect country to solo travel. #italy #tuscany #lucca #verona #florence #solotripPonte Vecchio Florence – Photo by Mark Boss on Unsplash


Solo travel can be daunting, but heading to one of my favourite countries, Italy makes it a lot easier #italy #italytrip #solotravel #tuscany #florence #verona #luccaSolo travel can be daunting, but heading to one of my favourite countries, Italy makes it a lot easier #italy #italytrip #solotravel #tuscany #florence #verona #luccaCastel San Pietro, Verona – Photo by Zoltan Kovacs on Unsplash

If I make it to Montepulciano, I will be joining a wine tour so that I can learn more about that AMAZING Brunello di Montalcino and of course indulge in some tastings. I have my eye on a tour company, but I will write more in depth about my adventures when I return.

You can also keep an eye out on Instagram where I will be posting daily while away.


Making loose plans is harder than it sounds

I like being in control, and I like to have a well thought out plan. For me, another challenge of this trip is to keep things loose and relaxed and to see where my days take me.

I’m not sure yet if this is going to be entirely possible, but I am happy to see how I feel. Travel and anxiety can go hand in hand, so I will keep things simple until the time comes where I need to plan it out more to alleviate any stress.

This trip is about challenging myself, not stressing and allowing myself to be nervous but not anxious. It’s a balancing act and a good way to push my limits.


What I plan to do first

I will organise accommodation in my first destination for as long as I feel I will need it. Airbnb will be one option. I am a huge fan, and you can get a discount if you click here and book for the first time.

I like to cook so having even a basic kitchen is a bonus for me when travelling, I am one of those freaky people who love exploring supermarkets overseas.

From there I will have a list of accommodation in the other locations that I can book on short notice. I will be travelling in the shoulder season so booking with little notice should not be a problem.

I will also have a list of the activities/tours I would like to do in each location and my laptop, making bookings effortless.

The reason for already creating the lists is that I don’t want to be wasting my time researching. Travel days are too precious for that. But I am also not worried if I don’t use my research, keeping my plans fluid and seeing where the days take me.

Once I have established where I am going, I will join a walking tour in each new location. I love walking tours for getting oriented and the chance to chat with the local guide and get recommendations and also the opportunity to meet other travellers.


Packing Carry on only

Because I am trying to keep it simple, and because next year I am walking the Camino (and will be forced to pack light), I am attempting carry-on luggage for the first time.

Am I crazy to think I can pack for 2 – 3 weeks for colder weather in carry-on only?



I am whittling down my toiletries, this week I am trialling a locally made shampoo bar, firstly because it is all natural, secondly so I don’t have to be concerned about having too many liquids in my luggage. So far so good, but I will also be writing a post about the toiletries I take in the hand luggage that should do me for the entire trip.

I prefer natural products and am slowly replacing items. You can read more about my healthy travel essential and the products I used. I will be revising this post to include the new products I am using now and would highly recommend.



I haven’t admitted this to anyone but Dan, but clothes cause me anxiety. Or at least wearing the appropriate outfit for the proper event causes me anxiety.

Years ago, I packed suitcases full of clothes for just in case situations. Thankfully, years of travel experience has taught me how casual the world is, and that if I really need something, I can buy it. Although, that has not happened yet.


Being true to my style

Fashion is a lot more casual here in the Blue Mountains, and I can dress in “my style”. Comfortable and relaxed with a uniform of nice jeans and boots, a nice top or good t-shirt and scarf and a good coat. At least that is what I am wearing this winter, come summer I will need to think again of course.

My summer wardrobe will probably consist of a couple of light summer dresses, dressier shorts and comfortable, cool tops. Because it is cooler here a lot of the time, I can get away with a light pair of jeans, top and summery sandals.

For this trip, my current autumn/winter style should easily carry over into travel. My style at home and travelling seems to be the same. Therefore, I can save on buying new clothes for travel and just include some accessories or a few extras that my wardrobe is missing.

I have been frantically reading everything I can about packing light and I came across this insightful website that covers it all – Travel Fashion Girl.

It is going to be my saviour to be able to pack light and I feel that what I want to do is achievable.


Finding the right bag

The next thing I needed to do is find a good backpack that I can use for this trip and also use on the Camino.

I found an Osprey Sirrius 36 lt backpack locally, but you can find one here. Eventually I would like to buy a small carry-on suitcase for trips like this and leave the backpack for hiking trips, but for now, it seemed silly to buy two bags and I thought the backpack would give me a bit more freedom to get around cobblestone streets and upstairs.

By not having to check my luggage and then wait for it at the other end (with bated breath hoping it appears) I have one less thing to worry about. With a backpack, I can keep my handbag secure without worry about pulling a suitcase along, particularly when I get to my destination, over cobblestones, and possibly up flights of stairs. It also means that hopping on trains is easier.

I will keep you updated on how I go. If I can achieve this, then anyone can, because I was the Queen of “just in case” packing.


Solo travel can be daunting, but heading to one of my favourite countries, Italy makes it a lot easier #italy #italytrip #solotravel #tuscany #florence #verona #luccaFlorence, Italy – Photo by Tolga Kilinc on Unsplash


Never say never about solo travel

For those of you thinking you could never solo travel, never say never. For years I thought those that travelled alone where crazy. Why on earth would you travel alone???

But to be the best version of ourselves we need to be happy with the person we are and not reliant upon someone else to provide our happiness. We need to grow and challenge ourselves, and I don’t know anything else that builds us as people more than being alone and being perfectly fine with that.

I have lived on my own, been single for years and love my own company and space. I also love being in a good and healthy relationship. But I have lost a little of myself as tends to happen in a relationship, and it is time to find me again.

Dan will happily travel with me, but he also knows that travel is my passion. He understands the need for us to be the individuals we were before we met. And he is also ready for his own time, whatever that may look like to him.

I am lucky to have his support and trust but also knowing that my travelling alone does not threaten our relationship. In fact, it will only strengthen it.



Learning to listen to the signs

I have realised that when the need, and yes, it is a definite need, to travel nudges me, it can only be denied for so long.

It doesn’t matter the destination. I have destinations on my wish list that I will see; it doesn’t matter the date. Life is forever teaching me the lesson of patience.

But Italy has always been in my heart, and if I could only ever travel to its many destinations, I would be happy.

Hurry up and get me on that plane!


Cindy x


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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.

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