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Tipsy Tour of Rome: Sightseeing, Storytelling & Spritz

Posted on November 20th, 2022

by Expat Living in Rome

Italy is a country rooted in tradition.

Socialising over a spritz; parking in the middle of the road; enjoying an aperitivo with a view; sporting sunglasses after dark—such traditions are the glue that binds the nation together.

Parking in Rome is a thankless task; and your choice of eyewear is yours and yours alone. But if you’re visiting the capital and want to immerse yourself in Italy’s other traditions, a Tipsy Tour should be top of your list.

Boasting over a thousand rave reviews left by tipsy clients from around the world, the Tipsy Tour is one of the most unique experiences in the Eternal City.

This is not your usual tour. It’s neither a bar crawl nor a city walk but a combination of both—a heady blend of scandalous stories and traditional drinks, enjoyed slowly, in good company, over the course of three hours.

So what exactly can you expect from a Tipsy Tour?

Here’s what I remember from going on mine.

Our Tipsy Tour started on a terrace overlooking the Colosseum

I met my guide and group just before sunset on a terrace above the Colosseum. Our guide, Chiara, broke the ice, getting our group chatting while our hostess, Georgie, poured our drinks—glasses of red or white wine and beer.

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When everyone had arrived, we sat on the stone stairs overlooking the city and sipped our drinks while Chiara took us on a whirlwind tour through Roman history. Starting with Romulus’ and Remus’ fratricidal squabble that led to the founding of the city, she took us on Rome’s journey from a kingdom to a republic to an empire, finishing with the chaotic demise of the emperor Nero.

Telling Rome’s story against the backdrop of its birthplace, the Palatine Hill, made the start of the Tipsy Tour extra special. And this was just a taste of what was to come.

After finishing our drinks, we moved on to a nearby bar

But this was no normal coffee; it was a caffè corretto—a corrected coffee.

Corrected’ **cracks whip** with a shot of Baileys.

Chiara told us where the tradition of the caffè corretto comes from while we relaxed at the bar and chatted to the others in our group. After 15 minutes we made our way outside and walked the short but scenic route towards the ancient district of Monti.


We then made our way into the underbelly of ancient Rome

As we made our way down towards Monti, Chiara gave us the area’s backstory. Monti was once called Suburra. It was a grimy, dangerous district—walled off from Augustus’ pristine forum; home to roving gangs, criminals and prostitutes.

Oh, and the birthplace of a certain Julius Caesar.

We were treated to a story set in Suburra’s ancient brothels involving Messalina, the wife of the emperor Claudius. Messalina was a woman of insatiable libido – and her decrepit, ageing husband was unable to satisfy her lusts. Because of this, Messalina would often escape the prying eyes of the palace to pass her evening among Suburra’s brothels.

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Chiara told us that Messalina once competed with the Suburra’s most prolific prostitute over the most men they could please in 24 hours. Messalina came first, finishing with a total headcount of 25 to her adversary’s 24. But the real loser was the cleaner, who had one of the worst jobs in the ancient world.

Messalina met a suitably sticky end (and you’ll have to join the Tipsy Tour to enjoy all its grisly details). Suffice to say that after her story we needed a drink. So we ducked into a local-looking bar on Monti’s cobbled street.

Georgie ordered our spritzes—some aperol, some campari—while Chiara filled us in on where they get their names from. My aperol spritz was perfect; deliciously sweet, as golden as a Roman sunset, and as cold as an Italian border official.

We stayed here for about 45 minutes, spilling out onto the streets and chatting away, before making our way through the imperial fora towards the statue of Caesar.

Our tour finished against the backdrop of Julius Caesar’s Forum

Chiara reeled off the highlights of Caesar’s eventful life, including his close brush with a gang of pirates, his sexual escapades with Queen Cleopatra, and his pretensions to become king.

She finished with the story of his assassination on the Ides of March 44 BC, when he was stabbed 23 times by his senatorial colleagues as he went about his business in the Senate House built by his rival. This story was made all the more moving as we stood beneath his statue.

We sipped limoncello under Caesar’s statue—it’s what he would have wanted

Our Tipsy Tour ended beneath a statue of Caesar, against the background of his forum. But this wasn’t the end of the night. We followed Chiara past Piazza Venezia to a lively local bar where we kept drinking and dancing until around 3 in the morning.

So what’s the verdict on the Tipsy Tour of Rome?

Let’s be honest, who doesn’t like binging on stories of sex, scandal, and assassination with a traditional Italian drink in hand?

Okay, teetotallers—but they probably won’t have read this far. And if you have, the Tipsy Tour also serves a strong selection of soft drinks, so come along as well!

Taking the Tipsy Tour of Rome is the most fun, light-hearted way of getting to know the Italian capital. It’s a great way to get some context for the city’s ancient attractions while making friends you’ll want to stay in touch with—while you’re both in Rome and after. When in Rome… be sure to check it out!

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