In the history of the classic “Grand Tour” of Europe, Italy was a must for any traveler’s itinerary. For many, it was the top destination, with several months spent exploring the peninsula from north to south. Today’s travelers might not have several months to spare, but with a well-organized itinerary and knowledgeable guides, it’s still possible to fully experience Italy’s history, culture and food.

Most first-timers to Italy will surely include Italy’s greatest hits: Rome, Florence and Venice, but a Grand Tour doesn’t stop there. Between those cultural powerhouse cities, there is the idyllic countryside of Tuscany, the medieval villages of Umbria and the romantic towns of Veneto, for example.

Of course if you take part of our Grand Tour of Italy we’ll take care of all the details for you, but first-time visitors can read our guide with everything you can expect while touring through Italy.

The Grand Tour of Italy Destinations

Where to go and what to see on your first-ever grand tour trip to Italy.

The colosseum in Rome, a perfect destination on a grand tour of Italy
The tradition of a Grand Tour in Italy always calls for a stop in Rome! Image by Alexander Naumann from Pixabay

The best trips to Italy have the perfect mix of culture and relaxation, culinary experiences and outdoor activities, and they all have a full immersion into the beauty of the Bel Paese!

Ciao Andiamo has launched its Grand Tour of Italy with the best of what Italy offers, from the big hits to the smaller town charm of Padua, Orvieto, Assisi and Verona. 


The Top 3 Destinations for First-Time Visitors to Italy

The Duomo of Florence is a must-see for a first time visitor to Italy!
Along with the Colosseum in Rome and the canals of Venice, The Duomo of Florence is a must-see for a first time visitor to Italy! Image by Andrea Spallanzani from Pixabay

The capital of Italy, the birthplace of the Renaissance, and the most famous city on water in the world. There’s a reason that Rome, Florence, and Venice are must-see destinations, and they should be for first-time visitors to Italy as well! These big hitters are filled with 2,000 years of history and culture to explore and experience.

Read more about what to see and do in these classic cities at our Guide of Italy’s Greatest Hits for First Time Visitors.

What to Do in Tuscany

The Tuscan countryside is filled with gems to explore, like beautiful Siena. Image by BÙI VĂN HỒNG PHÚC from Pixabay

There’s plenty to see between Florence and Siena, but a trip to Tuscany is hardly complete without a vineyard tour!

Visit the UNESCO World Heritage city center of Siena. Home of the infamous Palio race, the massive Torre di Mangia with spectacular views over the Tuscan countryside and the beautiful Duomo complex, tiny Siena packs a big punch.

After, get into the Tuscan countryside to taste your way through the super Tuscans at ground zero. The long history of winemaking and beautiful rolling hillsides of Chianti and the valleys surrounding Siena are the perfect location to learn about the history of Tuscany’s wine culture and taste some local snacks!

What to See in Umbria

a close up of the cathedral of Orvieto to show it's beauty
The Cathedral of Orvieto is a masterpiece that merits a visit on a tour of Italy. Image by Peter H from Pixabay

Filled with unique, medieval towns to explore, the scenery, food and lifestyle combine to make the perfect vacation atmosphere. Here’s what to see while you’re there:

Visit Orvieto. The entire town is built atop a volcanic tuff cliff, with the 14th-century cathedral towering above while the wine cellars and infamous double-helix well of St. Patrick are dug into the soft rock below. 

Travel to Perugia, Umbria’s largest city and the capital of the region. Home to the oldest university in the region, Perugia’s small city center packs a big personality.

Deep dive into Italy’s religious roots in Assisi, birthplace of St. Francis of Assisi and home to the massive two-level basilica dedicated to the patron saint. One of the best-preserved medieval cities in Italy, the entire city center is a UNESCO World Heritage site. Between these towns and even smaller hamlets, like beautiful Spello, there’s a wealth of charm to explore in verdant Umbria.

No matter where you go in the region, visit Umbria in style with our Guide to the Green Heart of Italy


Where to Go in Veneto

First-timers to Italy should include Verona to their itinerary to add even more romance to their Grand Tour of Italy itinerary

Moving north, visit the romance and long-lost power of Verona. The setting of Romeo and Juliet, travelers can still visit Juliet’s balcony and take a picture with her much-frequented statue, but that’s not all Verona has to offer. Admire the impressive frescoes of the houses in Piazza delle Erbe and the 1st-century Arena, a predecessor to Rome’s Colosseum that is still used for operas and concerts today. Read on to learn about how to see an opera in the Verona Arena.

Traveling from Verona to Venice, stop in small Padua, a university town and home to the Scrovegni Chapel, a UNESCO World Heritage Site famous for its 14th-century frescoes by Giotto, in particular the Last Judgement and its vibrant blue sky.


How to Travel in Italy

When in Rome, do as the Romans do! Here are the top tips you need to know if you want to travel in Italy with ease.


Order Coffee like an Italian

coffee in Italy

No matter where you go in Italy, authentic Italian coffee is just around the corner. A glimpse into Italy’s culture and identity, Caffè Italiano revolves solely around espresso and the different ways it can be served.

Be prepared at the bar with our in-depth Italian Coffee guide.


Navigate Like a Local

Though a first-time visitor rarely feels like a local, there are some ways that a visitor can look and act more like a local. After all, when in Rome….

From eating to language to tipping, here are some pro tips to help you feel right at home when traveling in Italy.


What to Pack for Your First Time to Italy

Italians have a reputation for good style. And though it might feel intimidating, with a bit of attention, anyone can make a bella figura when traveling in Italy.

Packing for Italy means a simple but elegant style. We suggest you use light fabrics for the summer, dress in layers for the shoulder seasons and bring smart, but polished footwear. And when in doubt, a comfortable sundress, linen pants and sunglasses will get you far.

Get the full list of what to pack for your Italian vacation here.

Summer in the Mediterranean is hot! Pack accordingly to feel cool, calm and collected on your Italy tour. Image by LUM3N from Pixabay

Relax knowing every detail of travel is taken care of while you experience the best of what Italy has to offer on Ciao Andiamo’s Grand Tour of Italy. Click here to book!

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Our guest blogger is Michelle Damiani, a best-selling author who has written extensively about her own travels in Italy and is co-leading our new small group Insider Journey through the Riviera this October 2024. If you’d like to explore beautiful coastal Italy while practicing travel journaling with Michelle, reserve your spot today.

Preparing for a stay in Ghent, I pulled out an old journal to read about my experience in the Belgian city during my college backing trip. I hadn’t opened that faded velvet cover in a decade or two, so I never connected the dots between my fledgling venture into travel journaling and the travel journal I turned into a memoir about my year in Italy with my husband, three kids, and two cats.

That memoir has subsumed so much of my life that, truth be told, I’d forgotten about my early travel journaling. Leafing through those pages that told stories of having my clothes stolen from a Dublin laundromat and twirling pesto pasta with new friends in the apricot light over Cinque Terre, I realized anew the importance of travel journaling to document experiences that would otherwise be lost to the chaos of memory.

Comparing that early work to the memoir that came so much later, I realized something more… good travel journaling makes travel better.

1. Increased sense awareness

Most travelers only pay attention to what they see, and maybe what they taste. When you set out to create a meaningful travel journal, you notice so much more. You notice the smell of woodsmoke beckoning you to dinner. You notice the easy cadence of the banter around an Italian bar. You notice the taste of forest floor in a glass of Sagrantino wine. You notice the worn cobblestones under your feet. You notice swallows inscribing love notes into the evening sky.

In short, good travel journaling tunes you into your senses, which creates the opportunity to celebrate the moment. What a contrast to having those moments slip past, unnoticed and unrecognized.

By grounding through senses into the present, travel seems to stretch out longer. It unfolds and envelops you, like a hug from the universe.

2. Learn your travel values

Writing about your travels allows you to find your themes. Do you give most column inches to meals? You are probably a food-centric traveler (welcome to our table). Do you focus on moments when you get lost and found again? You are likely a traveler happiest with a loose docket. Do you write with the greatest gusto about watching rugby matches in pubs? I recommend seeking out sport wherever you land.

Travel is intense, with all that radio static in the form of figuring out bus routes and museum hours and how to ask for the bathroom. By writing about your travels, you cut through the clutter. You discover what matters to you, which helps you shape your travels to ensure better traveling experiences.

There are other ways to do this, of course. For instance, in this travel story, Sarah and Paul discover that by having Ciao Andiamo manage their travels, they found themselves relishing meeting locals. It’s something I’m realizing through my own travel journaling—creating connections makes travel an intimate thing, soft and human.

This is why I’m so excited to co-lead a travel journaling course in Liguria—if writing helps us discover what we want from travel, and Ciao Andiamo cuts through the travel clutter, what new values might we discover?

I can hardly wait to find out.

3. Decreased travel anxiety

This is another area, as you might imagine, that traveling with Ciao Andiamo excels—with someone managing the details, travelers are free from worry.

It’s less obvious how travel writing works to decrease travel anxiety.

I call it curating a “gather content mentality.”

This is something that barely glimmered in my early journaling but came to full force while writing my journal-turned-memoir. When your goal is chronicling your travels, low moments become plot points. What that translates to is learning to consider those inevitable challenges as CONTENT. Material for the pages of your story. This creates the kind of psychological distance required to soften your fear reaction and increase your trust in yourself. The instinct to brace for impact evaporates, replaced with a more open worldview.

Plus, once you don’t fear hardships, they become the anecdotes you trot out at cocktail parties. I can’t tell you how many times I’ve told the story of having my laundry stolen in Dublin (twice in this one article! You may spot a third!) when no one really wants to hear about pretty green hillsides.

I remember during our family gap year in Umbria when I pushed my language ability by asking our shopkeeper what kind of marinated fish he had on display. He hesitated and pointed to the tomatoes. “These?” he asked, his face creased with concern. “No, those,” I answered. “Anchovies,” he responded, though it sounded more like a question than an answer.

It was only walking home that I realized I’d asked, “What kind of peaches are these?” (pesche) rather than, “What kind of fish are these?” (pesce). I flushed with embarrassment the whole walk home, but then remembered…THIS IS CONTENT. Rather than allowing that fish shame to coil up and fester, I wrote about it with glee.

Thus emboldened, I later asked the barista at Bar Tullia what cocktail everyone was drinking on the patio. Which is how I learned about Aperol spritzes. Which changed my life. There can be no greater testament to the importance of cultivating a “gather content mentality.”

Now, this is a process, not a light switch. But with time and practice, I’ve learned to push myself further, creating experiences absent while I was busy hiding in the shadows, hoping nobody would notice me.

4. Increased travel gratitude

One thing I’ve learned is that nothing kills travel joy as quickly as “must sees”. You know what I mean: “What are the must sees in Rome?” Or, worse, “You can’t go to Rome without going to the Vatican! The Sistine Chapel is a must see!”


Listen, I’ve been to Rome more times than I can count, and I’ve never seen the Sistine Chapel. Even though I love art and I carry an especial fondness for Michelangelo, I have never seen his ceiling work, yet somehow my arms and legs stay attached to my body.

What I’ve noticed is that as soon as someone gets locked into “must sees” they stop seeing what they see. They become so busy checking off their infernal list or hand-wringing about what they’re missing, they race through the Rialto market and miss the shades of silver in the piles of tiny fish.

Journaling keeps you focused on YOUR experience, so it becomes easier to inhabit the belief that, sure, there are loads of possible experiences. But the most important ride is the one that you’re on.

With all the blog posts I’ve written (as a blogger, my travel journaling is in the public domain—a perfectly valid lifestyle choice if it floats your ferryboat!) and never once in the writing did I stop to worry, “Would Paris have been BETTER with a Seine cruise???”

In writing, I’m focused on chronicling MY story, not what could have been.

I have to tell you, this hasn’t just changed how I travel, it’s changed how I live. Imagine life without FOMO.

Liberating, right?

Welcome to the beautiful world of travel journaling.

5. Creating Indelible Memories

A friend recently told me that her travel journal is more precious to her than her photo album. She said that in her journal, she documents small but meaningful moments that it wouldn’t occur to her to photograph, and it’s somehow those that become the most important in her family’s story.

It made me think of those experiences made permanent in my internal landscape solely because of journaling.

My friend Concetta inexplicably breaking into “Volare” as we brushed olives onto waiting nets during the harvest. How I found myself, despite my terrible voice, joining her, our voices twining over the shimmering tree (full story here).

The moments I practically teetered into the Venetian lagoon during gondolier school, and how I righted myself by focusing on the horizon—either the distant Alps, dusted with snow, or Venice’s storied silhouette (full story here).

Walking out of a Tuscan restaurant with friends and noticing the fading light. It was the first time I realized that a good Italian lunch will take you straight through till dinner.

How could you capture any of those while having a phone so permanently in hand that it risked being plunged into a lagoon

Short answer: You can’t.

You shouldn’t.

Not only are there all those moments that are bad form to photograph—like religious observance—but as this article in the minimalists argues, photographing every moment in the moment forces you out of the moment.

A travel journal avoids all those pitfalls while creating a way to remember experiences small and large of significance to you. That journal becomes a meaningful sibling of your photo album, overstuffed with treasured memories.

Now, does simply having a written log create better travel? Not in an obvious sense, perhaps. But each time you describe a moment, that moment becomes a pearl on a string that you carry from place to place, connecting past to present to future.

I’ve long harbored designs to turn my backpacking journal into a book. After all, the story of trekking through an abandoned train tunnel while a friend sang opera, the search for a thrift store after my clothes were stolen from a Dublin laundromat, the half hour I spent sobbing so hard I made myself sick outside of the Mauthausen concentration camp, the old man who shared his bread and cheese with me between Marseille and Nice while he told me about his life and I only pretended to understand but somehow understood it all—that seems like an interesting read, no?

Well, no, not so much.

That journal, much as I love it, falls a bit flat. After years and years of writing, I’ve learned what it takes to create an indelible map of memories. More than that, I’ve learned to allow journaling to change how I travel. It’s not rocket science, actually. I wish I could go back and guide my youthful self.

I can’t, of course…but I can guide you. Even if you believe you lack the time or the ability or the discipline to keep a written record of your travels. I want to share my joy of journaling with you, to create a roadmap, and learn the tools of the trade to create a meaningful companion piece to your travels, all the while making travel, well…better. More satisfying.

If you, too, want a travel journal that sings, a collection of word photographs that evokes more than just a cerebral memory but captures the sensuousness of travel, then I encourage you to join me on my October trip to the Italian Riviera!

I want to help you document the flavors in a classic pesto. I want to show you themes in your writing to sharpen your focus on what matters to you. I want to help you curate a “gather content mentality” to create more openness and curiosity about Ligurian culture. I want to sink together in gratitude as we sip an Aperol spritz and look out over medieval rooftops to the blue beyond. And I want to show you how to etch those hillsides terraced with vineyards into your soul so that you’ll carry them wherever you go.

With the itinerary Ciao Andiamo has put together we’ll have excellent opportunities to hone our skills in travel journaling. We’ll dig deeper into real Italian food-ways with a risotto lunch at a rice farm, as well as a cooking class in the heart of medieval Genoa. After a visit to Portofino, the darling of Liguria, we’ll lunch on the beach as the sea gathers and ebbs before visiting a convent only accessible by water. We’ll visit Camogli, a jewel-box town on the water, famed for its trompe l’oeil and for being dear to Max, our fearless and fabulous guide, the co-owner of Ciao Andiamo, and a son of Liguria.

Together, we’ll meet people, taste flavors, see contrasts, and learn history in a way most tourists miss.

Contact Ciao Andiamo today to sign up and get ready to make your travels better through travel journaling. One day, one entry, at a time.

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