How to Plan a Solo Season in Italy

We have all had that fantasy of running away to Italy, checking into a beautiful hotel, and dropping our bags. But if you do not have a plan for your solo season, the first day in that hotel room can hit you with a sudden, overwhelming feeling of: "Now what?"

To avoid this, you need a context. The absolute best way to start your first solo season is to enroll in a month-long class. It could be an Italian language course, sculpting, painting, or Renaissance history.

Suddenly, you are not a lost tourist; you are a resident with a purpose. You have a schedule, you have somewhere to be, and you have instant interaction with a community. It gives you a platform to stand on while you get your bearings. Many of these schools also offer student lodging right in the city center (with options for single rooms).

It is the perfect, soft landing into your solo season life.

During that first month, you can start looking for a real apartment and go on showings. While AirBnB is fine for a quick landing, it is usually far too expensive for a proper solo season.

In Italy, you are looking for an affitto a lungo termine (long-term rental), and you want to make sure it is arredato (furnished). The most common websites to search like a local are Immobiliare.it and Idealista.

We rent our Florence apartment through a property agency and we pay them a monthly fee. The owner commissions the agency to handle the contracts, which gives us a great layer of security and avoids scammers. We rent it fully furnished, and we simply read and report the meters for our electricity and water consumption each month.

A quick word of advice: always compare agencies, as some charge exorbitant fees just for drawing up the contract.

You do not actually have to do a "solo" season entirely alone. My solo season in Florence began in the most unforeseen and unexpected way when my grown daughter invited me to be her roommate - and her Italian Greyhound's nanny - while she studied a 2-year diploma in art restoration at LdM here in Florence.

She had lived abroad for years, so she had her own independence, and this became a beautiful opportunity to spend time together as adults. If you propose a stay abroad with your grown children, the secret to success is tending to the "separate lives" border.

If you both take language courses, go to different schools. I gave my daughter space, and she gave me space. It was important to me that she could fully live the free student life, and I never made her feel supervised. You do not want to be seen as a unity, you want to fully experience the "solo" phenomena where new connections arise simply because you travel solo.

By establishing that we were living independent lives under one Florentine roof, we both got the true "solo" experience of interacting with the city, while getting to share a coffee in the kitchen the next morning and create unforgettable memories together during the joint experiences.

The most common question regarding a solo season is, naturally, how to afford the time away. Most people assume a stay in Italy requires either draining a savings account for a sabbatical or waiting until traditional retirement.

But a solo season is not a retirement; it is a relocation of your daily life. To do this sustainably, you need an infrastructure that travels with you.

For me, this meant stepping away from my heavy, client-dependent agency model and stepping into the modern knowledge economy that is projected to hit 1 trillion USD 2028-2030.

Because however ”free” my agency was, my income was tied to being at a fixed desk. Instead I built what I call my "Handbag Office" work model.

By utilizing simple SaaS (Software as a Service) automations and daring to upgrade my '90s PC skills, I created an automated digital administration that does the heavy lifting.

I decoupled my income from my hours. I do not take client calls, I do not hold physical inventory, the marketing model is ”rejection-free” (those not interested just scroll by) and my entire business now fits inside my baby blue Italian leather bag.

Finally, the absolute best reason to plan a solo season in Italy?

Finding your own Italian (that even your husband will love).

For me, that "Italian" is Sid, my daughter's Italian Greyhound. He is the only boss I need to report to, and his strict 5:00 PM dinner deadline is the reason I log off my laptop every afternoon.

If you are dreaming of a dog, taking a month-long art or language course in Italy is the perfect way to spend your time while waiting for your Italian puppy to reach the age when you can finally bring him home. It gives you a profound reason to be here, and it guarantees that you will never be truly "solo" on your long, beautiful walks through the city.

Read more in the article "How to find your own Italian" about the best practice of getting and living with an Italian Greyhound and why they are your ultimate social passport to truly live an authentic Italian life.

Living these solo seasons requires a structural shift. If you want to stop trading hours for dollars and step into the new economy by building your own portable work model to fund your solo seasons, you do not have to guess how to do it.

Midlife entrepreneurship is not a quiet hobby; it is a global movement. You are entering an intersection of three massive trends:

• The Knowledge Economy: According to Global Market Insights, the eLearning market is projected to reach $1 trillion between 2028 and 2030 [1].

• The Solo Travel Shift: The solo travel market is projected to hit $1.6 trillion by 2033, driven by up to 85% women investing in culture, history, and their own autonomy [2].

• The Demographic Advantage: Startups by women over 50 are the fastest-growing group of new entrepreneurs. What's more, demographic research confirms that a 50-year-old founder has twice the success rate of a 30-year-old [3]. We are actively rewriting the rules of business later in life. Long gone are the days of our mothers and grandmothers, when midlife women were considered to be of "no use." Now we create our own companies in multiple sectors and services, and we do not have to wait for someone to eventually hire us. Our customers are each other, as we work across different sectors, as well as serving the rest of the world in the international market 24/7, simply by connecting to WiFi.

This is us, this is now.

To help you claim your seat at this multi-trillion table, I have put together two free resources:

1️⃣ The Seven Days Email Series: Start here to get your mindset right and receive my free "But How?" Toolbox (a complete guide to setting up your own Handbag Office infrastructure). Seven Days to Find Your Next Chapter →

2️⃣ The Digital Renaissance Blueprint: Click here to explore the exact framework I use. You will learn the mechanics behind the engine that powers every online transaction, step by step. The Digital Renaissance Blueprint →

Your solo season is not just a daydream. It is simply a matter of building the right infrastructure.

With love from Florence,

Pernilla

Midlife in Italy 🍋