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Top 14 Things To Do In Italy (That Travel Guides Don’t Tell You!)

#1 When you’re in Italy, ogle the gorgeous men. They are one of Italy’s most salient points-of-interest.

Whether you’re a married straight man or a twenty-year-old Kappa Phi Beta Epsalon Theta Omega (as my friends and I were in the photos below) you really owe it to yourself to take in the grandeur of the Italian male, as they are some of the most wildly attractive in the world.

14 things to do in Italy

1986: Left: Me (with an alluring bush on my head) fondling an embarrassed waiter in St. Marks Square. Center: my damned friend Kristen got to sit next to the gondolier. Right: My wily friend AC managed to “fall” into his arms as she exited the gondola.

Yes, yes I know. Daniel Craig, British. Sam Heughan. Scottish. And my dashing husband, Henry. American. But really, who can argue with this?

14 things to do in Italy

#2 When in Italy don’t worry about redundancy. There’s no such thing.

I spent my honeymoon in Italy in 2001 and thought my sweetheart and I should conquer new terrain and not revisit the past.

But we really wanted our children to see the locations where they began.

So we took our girls to many of the lovely spots we’d already visited and realized, the thing about Italy is this; you can never truly get tired of seeing the same places over and over again.

Because the country has layers of history and beauty that must be peeled like an onion.

The people are so vibrant, the food so delicious, the leather so affordable, the pizza and wine and cheese so delectable, that revisiting the past imbues it with a deeper resonance and a greater richness than before.

14 things to do in Italy

2001: Left, Me with a lovely shopkeeper, indulging in a favorite past time, buying shoes in Castellina en Chianti. Top Right, Henry and me on the roof of the Siena Cathedral. Bottom Right, In my bathing suit at the Santa Catarina in Amalfi where Liz and Dick carried on their illicit affair after meeting on the set of Cleopatra. Back then I could eat whatever I wanted and look like that. #DamnYouMenopause!

We took our girls back to our honeymoon lodgings at the Villa Vignamaggio, supposed birthplace of the Mona Lisa, site of Kenneth Branagh’s 1993 film adaptation of Much Ado About Nothing and now so popular you have to book a tour to walk its grounds.

I played my we-want-to-show-our-daughters-where-we-honeymooned violin and they let us roam (briskly) about.

14 things to do in Italy

Upper Left, Henry showing a rather disinterested Bridget the pole he drove our rental car into back in the day. Upper right, Villa Vignamaggio facade. Center Left, a chair overlooking the view from the pool. Center, Center, Henry and me looking a wee bit more mature than our last visit. Center Right: me mum at the Villa. Bottom Left, the piscine. Bottom Right, yet another building on the grounds.

#3 Share Italy with your family. Even if there are moments you want to throttle each other.

My mother is the person who first took me abroad when I was thirteen.

In doing so she opened up my world.

It was a chore for her, as I hated getting out of bed before eleven a.m. during the summer at that age, despised tours, museums, monuments or anything reeking of “history” and was only interested in taking furtive snapshots of Italian boys and putting as much gelato as I could into my hollow leg.

My mother swore, up and down that, despite the past, she wanted to take me and my family to Italy for my 50th birthday, which happened on June 27th (please put this in your calendars so you will remember to send me macaroons and diamonds on my 51st next year. We may proceed.)

My mom and I had our moments, on this trip, when we both wanted to be the alpha. There was a brief moment in Lucca where we each had our hands around each other’s necks and were strangling each other, without actually cutting off any airways.

Even so, my mother yet again provided a lifetime experience for me, and now my girls. An experience that I hope will open the world up for them in the way it did for me.

Traveling alone is certainly less stressful than managing many different personalities and agendas on a trip (there were ten of us on this one), but it’s also somehow less impactful.

As we look back we’ll polish not just the perfect moments, but also the tense, human, stressful ones, like diamonds made brilliant under pressure.

14 things to do in Italy

Mom, without you I’d never have this wanderlust that constantly pushes me outside of my comfort zone. xoxo

#4 Make your kids go on tours to museums and ruins and dungeons and towers even if they mope, whine and gripe. (Accompanied by as much gelato and Coca Cola as they want.)

They don’t know it yet, but they’re taking everything in.

Yes, their feet are tired. Yes, they’re hungry and have to go to the bathroom. Yes, this stuff was created a kajillion years ago by a bunch of people who are currently dead.

But it’s going to sneak up on them, especially if you spring for a young, handsome Italian tour guide. They might spend more time photographing him than the Coliseum.

14 things to do in Italy

This was our first day after landing and we were jet-lagged. But we spent three hours at the Coliseum and the Forum with an incredible tour guide, Giovanni, who made history live for us.

And when my girls are 50-years-old and I take them back to Italy they are going to wonder about what it must have been like to be a senator living in the viper’s nest that was the Forum, plotting Julius Caesar’s demise.

Or what it was about Cleopatra that bewitched Marc Antony to the point he transformed from the hero of his people to their much-maligned deserter.

Or they’ll simply gape in awe at the resplendent ubiquity of masterpieces from the Renaissance. A time that is actually only a blink of an eyelash behind ours in the evolution of mother earth.

14 things to do in Italy

My eldest had to miss two softball games in the All-Stars tournament to visit the Pantheon in the Piazza Navona. But she was sure to wear her jersey while visiting there.

#5 Be open to whimsy.

Before leaving on our vacation we’d exposed our youngest daughter, Bridget, to another masterful Renaissance man. Wes Anderson, of course.

He doesn’t quite have the body of work that Michelangelo and Da Vinci racked up. Yet.

But with films like Bottle Rocket, Rushmore, Fantastic Mister Fox, The Royal Tennenbaums, Moonrise Kingdom and The Budapest Hotel (we’ll overlook The Life Aquatic with Steve Zissou and The Darjeeling Limited) under his belt, I’d say he’s well on his way (if you’ll forgive him for not being biblically inclined.)

Somehow, no matter where we traveled in Italy, Bridget seemed hellbent on bringing a Wes Anderson vibe with her. The images her father captured of her throughout our trip gave it a somewhat iconic feel.

14 things to do in Italy

#6 When in Italy, no matter how overwhelmed you might be by the plethora of sights at hand, take a moment to sit down and look up.

Below you will see nothing but the ceilings which are found in the Vatican and the Pantheon.

The photograph in the upper right-center is an illegal photo I stole of the Sistene Chapel before we entered the room.

I could have spent an entire day just sitting on a bench looking up in the Vatican and I would have learned all I, or anyone, ever need know about symmetry, harmony, excellence and sacrifice for beauty as an inherent value, than I could learn in a lifetime.

14 things to do in Italy

7. One word. Michelangelo.

Below you’ll see the photographs I took while in the Galleria dell’Accademia in Florence, most of which were chiseled by Michelangelo.

For me, the most striking after David are Michelangelo’s Slaves and also his evocative Palestrina Pieta. 

Despite the fact my mind kept straying to the Central Mercado and all of the leather I’d like to pillage there; even this shopaholic had to sit and absorb the raw emotion a 26-year-old man poured into being 456 years ago.

And one more bit of advice.

If you plan to go to either the Accademia or the Uffizi (home of Boticelli’s Venus on the Half Shell), you must arrive 45 minutes before the museum opens or you will find yourself at the end of a never-ending line in sweltering, humid heat.

(You have to pick one; which is almost as difficult as Sophie’s Choice).

If you do this, even at the height of tourist season in July, you’ll be able to get in within fifteen minutes and will have at least an hour to see everything you want without being pushed, crowded or prodded.

14 things to do in Italy

8. Rent a villa in Tuscany. But make sure it has air-conditioning on the second floor if you go in the summer.

We rented the stunning Podere San Carlo villa just outside of Florence which was incredibly affordable considering there were ten of us staying there.

There were five bedrooms and four bathrooms. A refreshing, picturesque swimming pool overlooking lush vineyards and sunflower fields as far as the eye could see.

A pool table. A ping pong table (which became a hot-bed of sharking, betting, vituperation, victory, defeat and cock-of-the-walking) and a fantastic farmhouse kitchen.

It would have been absolute perfection except for the fact that Tuscany had a heatwave our last two days that sent me into tsunami-like hot flashes in our bedroom above the kitchen facing the fading sun.

I don’t know if there’s such a thing as 100-year-old villas with AC, but if they exist you should definitely spring for the extra cost.

14 things to do in Italy

9. Take day trips to nearby medieval villages. BUT USE GPS!

Have a map of Italy, just to see the region you inhabit. But don’t use it for actual navigation.

If you plan to drive around the country you absolutely must use GPS. Because it is impossible NOT TO GET LOST no matter where you drive in Italy.

You will get lost in Rome. You will get lost in Florence. You will get lost in San Gimignano and Lucca and Pisa and anywhere there is a paved road or a goat trail.

And it won’t be charming.

You will be at each other’s throats and you will probably run over someone on a Vespa. You may not kill them, but you will definitely maim them and you will get lost trying to transport them to the hospital and will run over six more people inexplicably having an on-foot Saint Parade in the middle of the Amalfi Coast Highway during rush hour.

USE GPS!

Also your rental will be a stick shift. And the only way you can get it into reverse is to pull the stick shift up (not push it down).

Below is a lovely day in San Gimignano we were able to find due to Google Maps.

14 things to do in Italy

Upper Left, Henry buys Claire, Bridget and my friend’s daughters, Haley and Lexi, gelato at the “Best Gelateria in the World!” Upper Right, Collegiate Church. Lower Left, view from the Torre Gross. Bottom right, me with my buds since 4th grade, Kelly and Viv.

10. If you go to Lucca, take the bike tour.

Like many of the medieval villages in Tuscany, Lucca is surrounded by a thick wall which served to keep marauding Fireze-ans at bay.

We spent three hours pleasantly pedaling around the entire city from the elevated walls. This was rated the “best tour ever” by the kids because it was as much play as learning.

And because there were ten of us the price was very manageable. Everything in Italy is less expensive when purchased in bulk.

14 things to do in Italy

Upper Left, Entering the Piazza Anfiteatro. Upper right, in the square of the Piazza Anfiteatro. Bottom Left, biking to Giacomo Puccini’s statue where he once lived and composed his operas. Bottom Right, San Michele in Foro

11. When in Italy forget about not gaining weight. Eat everything and anything you see.

You will be walking so much that you might even lose weight. But it doesn’t matter if you gain weight. Because every pound will be worth it.

True Italian food doesn’t have hormones or nitrates or preservatives or anything that will congeal in your heart.

It is fresh from the earth, the well and the cow and the Italian cooks I’ve come across seem to know how to make even the simplest fare into a Puccini opera.

We walked most nights down the road from our villa to what appeared to be another two-story home that someone converted into one of the best restaurants in northern Tuscany called Podere (which stands for “farm”) Toricella. It only seats 40 people per night and you must book in advance.

Sometimes there will be towns that only have one building in them and it’s usually a restaurant that people drive from miles away to dine in.

Some of our favorite restaurants were found in Lamole, Panzano and Castellina in Chianti.

So for the Love of God, people, mangiare! (And don’t forget to drink your wine as well. Preferably chianti.)

14 things to do in Italy

Upper Left, celebrating my 50th birthday with my friends Viv and Kel who will be turning 50 this year too. I will always be just a bit older (and wiser?). Upper Right, our four girls. Bottom Left, wine tour and tasting at Castello Sonnino. Bottom Right, walking to dinner.

#12 Don’t worry about speaking Italian, go out and make new friends anyway. 

It’s great if you can find the time to brush up on your Italian prior to your trip. But if not, it’s okay.

Italians seem to be the most tourist-resilient people I’ve met. They have a great deal of patience with we-bumbling Americans and seem quite happy to share all of the things that are so wonderful about their culture.

The cats, on the other hand, simply can’t be bothered.

14 things to do in Italy

#13. This is not the time to be frugal.

There are things in Italy that you just can’t get anywhere except in Italy for the price. Also, every time you look at them in your home they will remind you of your Italian sojourn, making you feel exquisitely continental and as if you are Sophia Loren during her Two Nights With Cleopatra era.

For me these items are; shoes, purses, tablecloths and ceramic olive oil containers. For Henry they are; shoes, purses, tablecloths and ceramic olive oil containers he lets me buy so I won’t be a shrew.

14 things to do in Italy

Left, I hold in my hot little clutches a white bag which contains a deep red linen tablecloth which I will be buried in when the time comes. Upper Right, my mom in a stunning leather store in the tunnel in Castellina in Chianti. Bottom Right, Henry and me after I bought shoes and he didn’t mention it.

#14 Be grateful you get to be in Italy even when the shit hits the fan.

You will be in the Rome airport and have to take six shuttle buses on an insane loop-de-loop because one of their terminals burned down.

You will end up on a goat trail that dead ends into an olive tree in Montespertoli because you were trying to save money by not using your cellular roaming and your GPS.

If you don’t hit a Vespa, it will hit you.

Something of yours will be stolen, just make sure it isn’t your virginity. (Unless … oh never mind)

You will try to go shopping or eating between 1 and 4 p.m. and will discover that everything is closed because of siesta. Everything will also be closed on Sundays because it’s the Lord’s Day. Everything will also be closed on Monday. Just because.

You will get sick of your traveling companions at least a few times a day.

But somehow, when you get home, you’ll love each other even more, because you’ve been on an adventure and you’ve made more memories to tuck under your pillow for when you dream at night.14 Things to do in ItalyLet me know if there are any other things you’d like to know about Italy and what to do there. And remember to share if you found this article interesting. E Grazie per la lettura!! xo S



6 comments

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  1. Junebug
    Junebug 13 July, 2015, 11:15

    Thank you! Loved every photo and peeking-over-the shoulder experience! Hugs and again, Thank you! XO

    Reply this comment
  2. Shannon
    Shannon 14 July, 2015, 15:42

    Ohmygawwwd, what a great trip and such fun photos. Now I have to plan my own trip. 🙂 Thanks for sharing!

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    • Shannon
      Shannon Author 14 July, 2015, 16:13

      Hello Miss Chastaine — Let me know when you’re headed out and I can give you more info!

      Reply this comment
  3. KymberlyFunFit
    KymberlyFunFit 14 July, 2015, 16:44

    That Henry is one smart man (in reference to “his” shopping list. And you may have all my macaroons. Bu then I get all the chocolate and pasta.

    Reply this comment
  4. Amber
    Amber 14 July, 2015, 22:59

    So glad you had a wonderful time in Italy. I am heading there next week. Not sure if you got my email about things to do and see over there; I sent it to your email some months ago. (I’m the woman you met on the plane departing from Florida last year.) Happy birthday!

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