Seeing Halle Bailey on screen as Anna in the latest Black rom-com, You, Me & Tuscany, brought back memories of my own solo escape in Italy a few years ago. Rom-coms often get dismissed as fantasy — fated encounters that transpire in ways that feel all too scripted to ever be real. But, as a regular solo traveler, I can attest that the film’s message delivers more than a happy ending and well-timed one-liners. You, Me & Tuscany was a mirror for what solo travel in Italy can feel like for Black women.
Landscapes you can get lost in. Savory pastas and wines that taste too indulgent to be true. Unexpected detours with the potential for a bit of romance. And a culture that feels inherently familial, even if not exactly like the one I grew up with.
From the busy streets of Rome to the watercolor sunsets in the Tuscan region, embracing yourself as the main character of your own feature film is almost inevitable. If you’re ready to stop dreaming and start planning, here’s how I did Italy — and how you can, too.
Why Italy Is The Perfect Solo Escape For Women
Aside from consistently ranking as one of Europe’s safest destinations, what makes Italy such a natural choice for solo travel is its built-in communal aspect. It’s rare to feel like an outsider, even while navigating new settings, language barriers, and different customs. And much like my own upbringing, food is at the center of so many Italian traditions — something that resonates both in my heart and my belly. There’s a reason the expression “chef’s kiss” originates from Italian culture.
Italy rewards spontaneity — a key trait of traveling as a woman who wants to see where the wind takes her, on a moment’s notice. Every day offers the chance to take a city tour, spend entire afternoons wandering the halls of world-famous museums, or dine at restaurants that attract guests by the thousands for their classic home-cooked meals. For those who want to make the most of their time in Italy with a multi-destination visit, the country invites you to explore it your way — by air, train, bus, or car — though I can only attest to the general ease of air and train travel.
Pro Tip: Uber primarily operates in major cities across Italy, offering select tiers, with Uber Black as the primary option. In cities like Florence or Milan, you may also find Uber Taxi or Uber Electric. When visiting small towns or rural areas, it’s always best to have confirmed transportation arranged for your departure and return.
ROME: Getting Gloriously Lost
Simone Cheri
It’s hard to fit Rome into a short stay, but the best way to experience this historic city is with a loose plan for the day, anchored by early-morning visits to iconic landmarks that draw millions of visitors from around the world. This is, after all, the home of the Roman Colosseum, Vatican City, and the Sistine Chapel.
Otherwise known as the Eternal City, Rome offers a healthy mix of dining, nightlife, ancient architecture, stunningly ornate museums, luxury shopping, and immersion into a bustling city setting. Even at its busier pace, you can easily find moments of stillness — when sunlight glistens through the windows of St. Peter’s Basilica, where the world’s tallest dome crowns the building, or after a sumptuous dinner, wandering the alleyways of Trastevere.
If luxury shopping is your version of travel days well spent, Rome delivers tenfold. Start by visiting the famous Spanish Steps, an 18th-century, 135-step Baroque staircase that sits at the center of Rome’s top luxury shopping district, near Piazza di Spagna. You’ll find every major luxury retailer alongside premium Italian designers you may not have heard of. After a full day of window shopping — or actually swiping your credit card — you’ll have earned your way through the boutiques, and there’s nothing left to do but settle into your third take on cacio e pepe and a glass of Aperol Spritz.
Staying in Centro Storico (the historic center) offers walking access to sites such as the Trevi Fountain or the Pantheon. One of the most popular areas visitors focus their accommodation searches on is in or near the Trastevere neighborhood.
With the turn of every corner, there’s a chance to brush up against 2,000+ years of history. Take an arena tour of the Colosseum, or enjoy the view and a pastry from the nearby bakery. While each piece of history is beautiful on its own, I’ve found the best way to understand these sculptural time-tellers is through locally-guided tours. Plan one or two during your visit, but the magic of exploring the city without a rigid itinerary is leaving room to witness the awe of ancient history existing alongside everyday life.
FLORENCE: Art, Culture, And Making Pasta From Scratch
Simone Cheri
Florence, by contrast, feels like exhaling after coming from Rome. The pace is more relaxed, though you can expect crowds similar to those in other major Italian cities at its most popular attractions. It’s also a great launching point for countryside vineyard experiences, as the Tuscan region’s capital and most populous city.
The city has a way of inviting you to slow down, and the works you likely studied in school come to life here — the statue of David, il Duomo, and the Cathedral of Santa Maria del Fiore. Before diving into the galleries, I found myself at the Piazza della Signoria, where I lingered over a light meat and cheese board and a glass of wine. It was the perfect prelude to stepping into the Gucci Garden Gallery, a layered journey into the house’s legacy that felt more like an immersive art experience than a retail one. Nearby, the Uffizi Gallery, open to the public since 1769, is one of the world’s first modern museums, housing Italian Renaissance art by Botticelli, Leonardo da Vinci, and Michelangelo, among others.
With sightseeing filling my days in Rome, I found the pace of Florence a better choice for checking off a longtime dream: making pasta in Italy. The group cooking class was a fun afternoon with strangers who quickly became my lunchmates. Rolling fresh fettuccine dough with the ambient sounds of local life drifting in from the courtyard delivered a moment of reflection without trying. Learning the Italian way of layering lasagna — with homemade béchamel, not ricotta — connected me to one of my favorite cuisines in a way that simply dining never could. And the end result, lunch for the entire group, served with wine, settled me into the old adage travelers speak of: finding the feeling of home in many places. Together, we broke bread before we set out on our respective journeys.
In my case, the next part of my solo trip through Italy included a day trip to the charming, UNESCO-listed town of Pienza.
TUSCANY: Main Character Energy In Pienza
Simone Cheri
With only four days in Florence, a last-minute day trip to Tuscany made more sense than an extended stay. However, if your goal is to spend more time in the countryside or explore several wineries in the region, consider a short one- or two-night visit in Siena or Montalcino.
My guided tour, booked through Airbnb Experiences, was part photoshoot, part sightseeing. Only an hour from the city by car, the drive from Florence to Pienza was peaceful, a far contrast from the city’s pace. This is the part of the solo travel story where a charming local guide offers to treat you to a Florentine steak — you know how the rest goes. Instead, I kept my eyes on the rolling hills during the drive, and on the incomparably fresh olive oil and Pecorino tastings during our stop in the Renaissance-era town center.
Pienza itself stopped me in my tracks. Every building feels storied, beautifully preserved, straight out of a romance novel. Life is visibly simpler here, and yet nothing about your time spent there feels like lack — quite the opposite. Stopping along the tour for the perfect shot brought its own thrill, and seeing the land through a local’s lens allowed me to settle into the scene and end the day with more than a few memories worthy of main-character status.
Every Woman Deserves Her Own Dream Italian Story
On the surface, You, Me & Tuscany is about a woman who follows a wild plan to Italy, which ultimately leads to love and rediscovering her calling. I didn’t find love in a vineyard like Anna, but I found something better — a softness and curiosity that had room to breathe.
Italy has a way of reminding you what matters most and gives you the space to actually feel it.
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