'Why, a decade on from heartbreak, I returned to the City of Love alone'

'Sitting there on the river Arno, I realised: I am my own plan A.'

Francesca Specter in Florence
(Image credit: Getty Images/Francesca Specter)

Curious about Solo Travel? We teamed up with Francesca Specter, author of Alonement: How To Be Alone & Absolutely Own It, for a week dedicated to celebrating the joys of Solo Travel. Here, Francesca herself returns to the City of Love—where she had hoped to return with a partner—alone.

While some favour Paris or Venice, for me there is a clear winner when it comes to naming the most romantic city in the world, and that’s Florence. Typically, it’s known as the birthplace of the Renaissance. But it isn’t the city’s world-leading collections of 14th, 15th and 16th art that does it for me; it’s the present-day romance pulsating through its streets.

After spending part of my gap year in Florence, I know the city intimately; the marble statues of Greek and Roman gods that punctuate every corner, the best places to enjoy sunset along the river Arno; the winding, cobbled streets to walk down hand-in-hand with a lover and the hidden-gem trattorias to enjoy a glass of Montepulciano and plates of pasta with. For me, Florence’s defining characteristic is the romance, flowing through its every artery.

The reason I’m so keenly acute to all this: the last time I was here in Florence, a decade ago, I was heartbroken. A couple of months prior, I’d been unceremoniously dumped by my high school boyfriend and First Love (a man who, unhelpfully, held a strong resemblance to the strong-nosed, sharp-jawed Roman statues that lined the Florentine streets). At the time, I thought it was the worst feeling ever, and in a sense I was right; it was the kind of primal feeling that inoculated me against future heartbreaks. And while retrospectively I’m grateful to have got it out of the way earlier, I was still very much embroiled in it at the time. 

I look back at that experience as one of the richest times of my life—but, at the same time, the loneliest. I was in such aching proximity to love, beauty, sex and yet I was unable to enjoy it first-hand. That’s not to say I didn’t have flings while I was out there: an American soldier, a local artist, someone from back home—I was ticking off all the cliches much faster than I completed my Italian homework. But fundamentally, I was lonely; a 20-year-old living away from home for the first time, who’d never understood that there was another other way to be alone. 

Fast forward ten years. Aged 30, I’m the author of a popular self-help book, Alonement: How To Be Alone & Absolutely Own It, and the host of a podcast of the same name. My book was first conceived months before the pandemic, off the back of another break-up—in the wake of which I’d decided to lean into the experience of heartbreak by learning to respect, rather than stigmatize, by newfound solitude. A rule I’ve held for myself, over these past three years, has been that if there’s something I enjoy with other people, I want to be able to enjoy it alone too. Not as a replacement to doing those things with other people; simply as a complement. And so I challenge myself; everything from solo cinema trips to travels to South America.

Florence represented something of a final frontier. For so long, I’d hoped to return there with a partner. A Happy Ever After to finally pacify my lonely, gap year student past self; see, it all worked out in the end. But when I found myself craving a trip to Italy, I had to be honest with myself that the reason I was avoiding travelling there was because I was waiting for this hypothetical other person. And that wasn’t something I allowed myself to do anymore. 

So, armed with my newfound confidence, I decided to take a four-day trip to Florence as a belated 30th birthday present to myself. Because, as the Italians say, Non aspettare. Non sarà mai il momento giusto. (Don’t wait. The time will never be just right.)

Il suplemento unico: ’The single supplement’

The single supplement is the bane of every solo traveler’s life, and this trip it was no exception. For the uninitiated, the single supplement is the extra ‘supplement’ you have to pay when travelling alone, compared to what you would pay in a couple or family—e.g. for a hire car, or a hotel room priced for two sharing. 

No situation is perfect; it is what it is, and I guess the single supplement is the literal price you have to pay for the wonders of solo travel. And I will add that, however basic the hotel room, I love the blank canvas of a neat room, and sometimes knowing you have it all to yourself (and any ‘floordrobe’ situation will be of your own making) is bliss. Although I only had hand luggage, I used my friend Clare’s tip and took along a couple of items to make my surroundings feel more luxurious: a sheet mask and a pair of satin pyjamas. 

Francesca Specter in Florence

(Image credit: Francesca Specter)

Anyway—where to stay in Florence. For solo travel, I do accept that I’m likely going to stay somewhere considerably less nice than I would if sharing the cost so I prioritise a clean space in a central location (for ease of getting around—after all, how much time do you want to spend in the hotel room?). Most major cities offer hostels with private rooms (which I consider a priority, but again, if you’d rather spend your hard-earned holiday budget elsewhere then dorms can be an even more affordable, and sociable, option). For hostels I found two options: Plus Florence and TSH Florence Lavagnini. Both are conveniently located (near Santa Novella station). I stayed in the former for my first night in Florence. 

For the second and third night of my trip, I was lucky enough to be hosted at Velona’s Jungle—a one-of-a-kind luxury, family-run boutique B&B hotel just on the edge of the old town. The ‘jungle’ theme persists throughout the house, with leopard print chairs, graphic wallpaper featuring, depending on the room, birds of prey or palm trees (by the likes of Ralph Lauren) and verdant hues of green and yellow. If you’re wondering, ‘Velona’ is the surname of the owner Veronica’s grandfather—the former owner of an antique shop. His antiques collection makes up much of the eclectic decor, with some pieces available for sale as a memento of your time. 

I stayed in the Fossey suite, complete with its own separate dressing room and palatial sized bathroom (the rainfall shower was a particular highlight after a day of walking around Florence in 31 degree heat). Another highlight was the warm, family-run Florentine hospitality: I was looked after by Alessandro, a relative by marriage of the aforementioned Grandfather Velona, and enjoyed a continental breakfast of coconut yoghurt, muesli and a vegan blueberry croissant in the dining room both mornings of my stay (incidentally, this is a great option for those who are vegan/veggie/dairy-free!).

I'll level with you; it was one of the most gorgeous hotels I’ve ever visited, and it would have been out of my budget had I not been gifted the stay. And yet, when there’s a will…After a little investigation, I found that the hotel is currently offering its newest room at the reduced rate of £130 a night—not a drop in the ocean by any means, but definitely a tempting deal for a special solo stay. The room’s name? Thoreau, as in Henry Thoreau—who famously wrote about solitude in his book, Walden. Room rates vary, with lower prices in low seasons, so it’s worth getting in touch directly to plan a stay in advance.

Tavolo per uno, per favore: ‘Table for one, please’

I set out wanting to make this trip be shamelessly romantic—and that I did. After flights and accommodation, the first thing I booked was a table for one at one of the city’s most romantic and sought-after restaurants, Il Santo Bevitore. It’s a low-lit spot with tiled floors, bare-brick walls, traditional vaulted wine cellars lining the walls and simple, white candles on every table. 

Both grand and private at the same time, it felt like the perfect setting for an intimate meal with a significant other—or indeed, myself, as I’d chosen. What made it for me was the attentive service; I arrived to find my reserved table laid out elaborately for one, my solitude respected rather than an afterthought. This was a departure from the experience I’ve sometimes had in the past, where a second place setting or even a chair has been removed, indelicately. It’s the small details like this that make you feel at ease as a solo diner. It’s worth mentioning that, traditionally, Italians almost never eat alone, so this sort of consideration was ever more appreciated. 

To me, nothing spells ‘romantic Italian dinner’ like double pasta, and so that’s what I went for, breaking all the rules in Italian dining etiquette (my favourite thing about Italians is that they consider pasta to be assuredly a ‘starter’ course). On the waitress’ recommendation, I chose tagliette in a chicken liver ragu, followed by a wild boar ravioli, as successive courses so as to prolong this delicious dining experience—technically ‘primi’ followed by ‘primi’. 

I was sitting in a corner that allowed me to look out at the entire restaurant. The restaurant was 90% couples, yet, as I’ve observed so often while dining alone, the table who looked like they were most enjoying themselves was not a smitten couple, but a group of four middle-aged women, laughing and joking, sampling each other’s meals. The other person having the most fun? Me. I sat there mindfully taking it all in, sipping my delicious wine (another recommendation from the waitress, who let me sample a couple before deciding) and enjoying the atmosphere, not alone but with myself.

Francesca Specter in Florence

(Image credit: Francesca Specter)

Strade lastricate di ricordi: ‘Streets paved with memories’

I had a mental hit list of places I’d wanted to return to during this imagined romantic trip for two. It occurred to me that the memories I’d had from Florence were, after all, with myself—not with my ex, or with the hypothetical other half I’d imagined I’d be returning with. These were my memories to remember and rewrite. So, in a way, it made ever more sense to return alone. 

Some memories were tattered replicas of what I had in my mind; the once-glamorous-seeming aperitivo bar which had been the setting of some of my Florence flings now seemed tacky, a tourist trap. Yet other places were more beautiful than I’d imagined. I gasped as I got my first look at the river Arno, lined either side with avenues of rapeseed yellow buildings, its golden hue at sunset. The peaceful piazza of San Lorenzo, where I sat one night at sunset after stumbling upon a busker’s live concert (soft pop-rock, sung in Italian), sharing the moment of listening with a respectful crowd. The Boboli gardens—the official gardens of the Palazzo Pitti—still one of the most serene, heavenly places in the world with so many statues that many dub it an ‘outdoor museum’. There’s an entrance fee, but it’s relatively budget-friendly compared to many of Florence’s sites and well-worth paying for the abundant space you get even in the busy season.

Noi non potremo avere perfetta vita senza amici: ’We cannot have a perfect life without friends’

The ironic thing about solo travel, at least in my experience, is that you actually end up meeting so many more people than you would, typically, day-to-day. In fact, sometimes I struggle to spend much time alone at all.  As my experience the previous night illustrated, you’re more open-facing and therefore more approachable, in a way you wouldn’t be in a couple of with a group of friends. 

In that vein, let me talk you through a meet-cute with a friend I ended up spending an afternoon with. On my third day in Italy, I visited Piazza Santo Spirito—an area popular among the city’s local artists that is aesthetically much more stripped-back than the equivalent squares of Piazza Signoria and Piazza Republica. The plan was to visit the church of Santo Spirito, which has a basic plaster facade, allegedly because Brunelleschi, the architect behind it, died before executing his designs and so it was simply left bare. The church is free, so one I’d highly recommend to visitors (it’s much more ornate inside). Yet, as I approached, I saw a sign requesting shoulders and legs be covered—in my crop top and shorts, I didn’t qualify. ‘If I’m not getting in, you have no chance,’ joked a fellow solo female traveller, who was wearing a similar outfit—and we decided to get a coffee to enjoy in the square, instead. 

Next on my itinerary was to hike up to Piazzale Michelangelo—a hill overlooking the city, which had yet another copy of the David statue on it. I’d spent the trip almost entirely solo at this point, three days in. And so when Pran, my new friend, asked if she could join me for the afternoon, I thought, ‘Why not?’ After climbing to see the 360 views (another memory to revisit and as breathtaking as ever) we went to have a well-deserved lunch together at Spaccio Alimentare, a delicious pizzeria at the foot of the hill, taking a scenic detour on our way back down at the Giardino delle Rose (literal translation, the rose gardens), a free public garden filled with artists painting at their easels in vibrant shades of acrylic. While we parted ways afterwards to go on our separate travels, I really enjoyed sharing some of the trip with another person, and trading experiences, before returning to myself. It was a pleasant reminder that, if you do want company when holidaying alone (and that’s absolutely OK), it’s easily found in friendly strangers—us solo travellers know how to spot each other!

Venni, vidi, vinsi: ‘I came, I saw, I conquered’

I was gazing out at the Ponte Vecchio, colloquially known as the ‘jewellery bridge’, where everyone gets engaged (where I once hoped that someday, via a drip feed of hints to a significant other, I might too), when I had an unexpected thought. Right now, there is no one I’d rather be here with than myself. Unlike my first time in Florence ten years previous, I no longer felt like half a person. I felt whole. 

Solo travellers, women particularly, are so often pitied for travelling and it’s easy to internalise that pity—which is, ultimately, just ignorance—and to forget to give yourself permission to enjoy it. But take it from me, once you can, it’s liberating. I spent years wanting to return for the trip of a lifetime with a partner, but instead I managed to have it by myself—and the trip was no lesser for it. Sitting there on the river Arno, I realised: I am my own plan A.

Francesca Specter

Francesca Specter is a freelance journalist and the author of Alonement: How to be alone and absolutely own it. Based in north London, she's previously worked for Yahoo Lifestyle, Express.co.uk and Healthy magazine, and has written for the Telegraph, Red and Huffington Post.