Best of Italy in 2.5 Weeks


I had just decided to toss out my attempt at emigrating to Ireland, and I was contemplating my next adventure. Italy was close. It was also the last of the seven wonders of the world I hadn’t seen. Originally I had been planning to save it for marriage as it’s one of the most spectacularly gorgeous and romantic countries in Europe. But, temptation overtook me and I booked a spontaneous flight anyway.

Usually when I travel, I micromanage my trips, maximizing every hour of every day at the expense of my sanity. For Italy, I decided to finally take my friends advice and roll with the adventure one day at a time. Or, at least… that’s how it started.



About an hour and a half south of Palermo are the 7th century ruins at Selinunte Archaeological Park. It features a temple and marketplace, and would make for a very majestic viewpoint to spend a sunrise or sunset, but I wound up being there in the heat of day. I was definitely dying! 

I spent a good couple hours there hopping around the ruins as if it were an adventure park. I was surprised they didn’t have everything cordoned off and let visitors climb on virtually anything they wanted.

Stair of the Turks

The real gem of the south coast is the Stair of the Turks. This rigid and gleaming white mudstone descent to the ocean is a popular spot for sunbathers. I wish I could say I spent the rest of the afternoon here, but I had my Indiana Jones spirit at maximum after doing the last ruins, and was craving more.

Valley of the Templates

The Valley of the Templates is highly geared for tourists and has the best photo ops for ruins in Sicily. Especially if you wind up there around sunset like I did. While you’ll be contending with crowds, it’ll become pretty clear as to why it’s one of the islands top rated attractions. To “step into the shoes” of the energy of the place, I took mine off and wandered for and hour and a half right until closing time.

Siracusa to Catania

Driving from Siracusa to Catania on the east coast of Sicily it’s hard not to stop for constant photos of the coastline, and some more unique attractions like the unique Ear of Dionysius, the Arethusa Spring and all the little beachside cafes. This is where you should begin building your immunity to Cappuccinos if you want to survive.

Mt. Etna

Okay, it was time for some adventure! I tempted fate and and joined my crew for a trek to the crater rim at the Mt. Etna volcano! The volcano is still very active and doing this traverse can be potentially dangerous – just don’t take off your helmet! Guided tours are required, and our guide yelled at a bunch of stray tourists to get off the hill!

The climb itself was actually very easy for pretty much everyone in our group. When we finally did reach the top, it was a whole different experience with smoking yellow vents with volcanic gasses oozing out all over the place, and vapour clouds casting shadow and mystery all around us. It felt like an ideal spot for a super villain to have his final battle.

We had a chance to meander through some of the crevices before we were told we had to pick up pace and get down the volcano quickly as it was starting to become more active. We let our imaginations run wild, as if escaping a fatal blast over at Pompeii thousands of years ago.

South Italy

Sassi di Matera

Don’t do what I did next — take time after the hike to relax! I immediately hopped back in my car, drove for two hours, crossed the ferry to the mainland, and bee-lined it for Matera — four hours east. Tomorrow would be one of the most important days of the trip and I didn’t want to risk anything getting the way.

Arriving in Sassi di Matera, likely one of the first human settlements in Italy over 9,000 years ago, you’ll immediately feel like you’re stepping into a scene of Lord of the Rings. The houses are dug right into the rock cliffsides. Many of the homes are in such poor condition that they’re uninhabitable, but there is a huge regeneration effort with the aid of the EU under way.

Grotta Palazzese

Probably what is the single-handed most romantic restaurant in the entire country, Ristorante Grotta Palazzese was nothing more than a photo hiding away in my bucket list folder for years and years. I had dreams of visiting here with a future wife, and who knows, maybe will some day.

But today, after making a quick pit-stop at the local mall for something that would pass for dress clothes, I enjoyed an afternoon appie and Prosecco while finally, truly, relaxing and watching the ocean waves crash against the cave, twenty-five meters below.

This cave restaurant has been host to parties since the 1700s, and still to this day would make the perfect wedding venue. It was well worth the massive detour to the far east coast of Italy, as the next stop would be the Amalfi coast!

Amalfi Coast

The scenery turns from vast open vineyards with rolling hills to tight narrow winding mountain passageways, which will make you feel like you’re about to scrape the paint off of your rental car. Even more painful are all the viewpoints you’ll have to skip because there’s nowhere to pull over, so make sure any passengers you have are queued to jump into action on a moment’s notice.

Aside from its rich cultural heritage, the towns on the Amalfi coast are known for their limoncello liqueur production. You’ll literally find it everywhere!

My timing to arrive here on this particular day wasn’t by accident. I admit, my OCD-like planning instincts started to nag at me and it worked in my favour. Today was the celebration of the Byzantine Empire’s new year: September 1st. While not quite as gaudy or wild as Mardi Gras in New Orleans, the day was still chalked full of parades.

On the church steps that evening was a phenomenal spectacle of dance, music, fire and pyrotechnic effects after the sun had set. This was a complete surprise to me and I was in the right place at the right time. It was a sign that I had to make sure I didn’t accidentally miss something important along the way.

In the next few days that followed, I had booked and planned out the rest of the trip, hour by hour. Perhaps the “relaxation” vacation would have to wait until the next trip. And, thankfully I had planned out the rest of the trip, as even at warp-speed I would only just narrowly made my flight home and gotten everything off my bucket list. Going at a day-by-day pace, I would’ve easily doubled my trip length, not to mention cost.

But, tonight’s light show was also a cue to sit back take it all in and just breathe.


Pompeii, just south of Naples on the Mediterranean, is well known for its immaculately preserved ruins from the eruption in 79 AD. The volcanic gasses immediately killed the towns occupants, and the six meters of ash helped keep it in pristine condition until modern day.

The volcano had been sputtering for days before the eruption, but few of the townspeople took the threat seriously, and ultimately to their own demise.

The archeological park will easily take a full day to explore. It’s even easy to get lost in the immense network of buildings and streets. Admire rich frescos, an antiquities shop, the forum, temple of isis, baths, theatres, amphitheaters, and more. While most of the buildings are empty, a few artifacts have been placed for demonstration.

With the ample documentation on placards, it was pretty easy for my imagination to run wild with envisioning what life must’ve been like there. But the source of destruction called to me, and I headed to the trailhead of Mt Vesuvius.

Mount Vesuvius

I’m not going to sugar coat this one. While seeing the source of Pompeii’s destruction was nice to get off of the list, it was a super easy walk and a definite skip for anyone who’s already done the more impressive active crater at Mt. Etna.

It was, however, fun to imagine if you were a volcano god, that this would be your viewpoint over the valley where you’d be hurtling your reign of destruction from.

Capella Sansevero

Cappella Sansevero is chalked full with almost thirty impressive marble sculptures from the Rococo period. It might sound weird, but despite it previously being a chapel, it reminded me of the room in one of the final scenes from the Devil’s Advocate!

They are super strict with their no-photos policy, so dip in to take photos with your mind.

Naples National Archaeological Museum

The Naples National Archaeological Museum is a massive archive of relics, statues, frescoes, and even some of the most legendarily gorgeous mosaics. They even have an Egyptian section!

In grade school, I remember learning about Hercules carrying the world on his shoulders and it made my day to see a huge statue of him doing just that. It also made me laugh how explicit some of the artwork was… from a sculpture of an afternoon orgy with prostitutes to incredibly phallic paintings.

To truly appreciate this venue, I’d highly recommend a proper guided tour.


Armed with my new best friend: Prosecco I struck out to the coastal island of Capri to let my mind breathe a little after all the education of the last few days. On the boat, I made some new friends who were celebrating a wedding anniversary. Then, kicked back for the short ride to numerous swimming holes such as Blue Grotto and eventually to our island destination.

Most tours are pretty limited on time once arriving. You’ll have to make a choice for what strikes your fancy the most. For me, it was hands-down the gondola ride to the peak of Monte Solaro. Atop there is a cute little bar where you can sit back and enjoy the breathtaking views. I felt like a god of my own little mini Mount Olympus.

I made friends with two sisters, who turned out to be news anchors for some sports channel, and taught them the ways of Fact or Fiction. A little bit of home abroad… ahh…


The most serendipitous moment of the trip, or perhaps my entire life, was when I was wandering around Sorrento late one night and stumbled across the patio restaurant at the Excelsior Hotel. While I wasn’t staying there, I felt sneaky as I crept onto the balcony and ordered up a late evening beverage. The cost to stay there that particular night? Over five-hundred euros.

As I watched the thunderstorm over the Mediterranean cast bolts of lightning across the sky, a warm breeze grazed my cheeks. The fire-lit torches accenting the already serene sunset. To my right, a grand piano with Elton John’s “Your Song” being pumped out live. At the time, I had never heard the song before. Now, it’s one of my favourites. It brought the whole scene together. I’ve never felt more at peace as when I sat there, undistracted, for hours.

Showbiz Napoli

I shocked when I showed up at Showbiz Napoli for my pizza making class and was the only one there! I got the royal VIP treatment, and a gut fit to burst after pounding back a marinara and margarita pizza. Though, my imagination wanted me to believe they gave me a private class because they thought that I might be some world-class travel influencer. hah.

Apparently the margarita pizza was designed after the Red, White, and Green Italian flag: tomatoes for the red, mozzarella for the white, and basil for the green!

The marinara pizza, was, you guess it, for fishermen! It was popularized in 1735 because of its low cost for poor sailors, and that it could be easily made with preservable ingredients.

Central Italy

Gardens of Ninfa

Before arriving in Italy, I polled my friends for their best recommendations. My friend Anna’s family is from Sicily, so that was a huge resource. My friend Jen, despite a few other suggestions, ensured me the Gardens of Ninfa was a romantic spectacle that I’d be a fool to miss.

About an hour and a half or so south of Rome, the gardens are manicured around ancient ruins. It’s a magical Jane Austin-esque venue that belongs in the best of romance novels. However, no trip is complete without a few glitches along the way.

When I arrived it was closed for the season! I was so excited to get there that I neglected to check not just the hours of operation, but the dates as well. Thoughts raced through my mind about sneaking around through the gates or hedges. Whatever it would take to ensure that I didn’t miss out. But, I didn’t want to get a criminal record in a foreign country if I got caught. FOMO was getting the best of me.

Then, a caretaker appeared from the side of one of the buildings, and told me the only way to get in was via private tour. I offered him one-hundred euros, but he declined and told me I had to schedule with an agency. He made some calls for me, but couldn’t find an English guide.

He saw the look of desperation in my eyes, and took pity. “How many euros did you say you had on you again?” And it was just as quickly that he let me in to wander around solo for a whole hour. This is a place that is normally packed with tourists! I was so lucky.

Vatican City

The Vatican, and most of the other attractions as you head farther north in Italy are such hot-spots that you’ll have to buy timed entry tickets well in advance. The incredible paintings by Michelangelo in the Sistine Chapel were just as amazing as I had imagined. While no photos are permitted here, there are numerous other photo-friendly rooms with art cascading from every ceiling and wall. You won’t be disappointed.

One of my favourites was the Gallery of Maps. Commissioned in 1580 by Pope Gregory XIII, it was complete in three years. It contains numerous topographical maps of Italy. Until being here, in this moment, at this time, I had no idea that Narnia was a real place!

Outside there is a giant bronze globe called “Sphere Within Sphere” which looks like it is cracking apart and has gears on the inside. The artist states the inner ball represents a fragile and complex Earth, and the outer hard shell: Christianity.


Rome is so saturated with culture, history and amazing architecture that it would be easy to spend most of your vacation there! Spend a day and just wander around on foot, making sure not to miss the Pantheon, the Spanish Steps and the Trevi fountain.

There are numerous legends around throwing various numbers of coins into the fountain: from guaranteeing a return visit to finding true love. Over 1.5 million euros are collected every year and given to Catholic charities to help the poor and homeless.

The Roman Forum was the heart of ancient Rome. From gladiator matches, elections, and public speeches to trials, temples, and even the prison where St. Peter was held prior to his execution. This is one place not to be cheap. Take a guided tour. There is so much history here, you don’t want to miss any of the details.

Just behind the forum was the whole reason I came to Italy: the Colosseum! One of the biggest goals in my life was to complete all seven wonders of the world. And now, here I was, standing on top of my goal. The feeling of victory rushed through my head and I couldn’t stop smiling. Plus, I beat my ex to seeing all seven!

Many people assume the Colosseum looks the way it does because it has decayed over the centuries. In reality, various leaders actually harvested building materials from the site. It was cheaper and more effective than digging up fresh stone.

If you have the time, by all means check it out in the day. But, try to get in for the night show. The way they light it up makes it look absolutely magical. And, you’ll learn a few of the insider details about what used to happen there.

Northern Italy


In my eyes, Pisa only really had one major attraction: the tower! It’s impressive that it is still standing to this day, but that’s not just by chance. Engineers dug a series of tunnels on the north side of the tower to remove small amounts of soil, and then used metal cables to pull it back into place. At this current time, they believe it should be secure for another two hundred years.

The winding narrow staircases will definitely give you a feeling of claustrophobia, not to mention the irrational fears that you could get trapped if it were to spontaneously collapse. The view at the top which features the city and Pisa Cathedral was well worth any sort of mental anguish.


Florence was an absolute nightmare to drive through. With all of the ZTL zones, which are areas that prohibit traffic at certain times of day, you’ll be lucky if you don’t wind up with multiple fines unless you have a very keen eye for signage or have a permit. Don’t be fooled by other cars going ahead of you. Many tourists believe it’s a cash grab, but it’s always important to well verse yourself with local laws before travelling anywhere. Find somewhere safe to park, and walk into the city’s core instead.

I’m not much of a shopper, so all the Gucci, Prada and Tiffany stores went to waste on me. I was more interested in seeing the real life original of the Birth of Venus, and other works, at the Uffizi Gallery and the Statue of David.

Ponte Vecchio is a medieval strip of stores along a bridge that connects two segments of the city. More shopping opportunities, ugh! Gelato, of which the city is bursting with, piqued my interest a bit more!

At this point I was getting pretty fatigued with all of the churches and cathedrals, but still made time to do another tour around the Florence Cathedral. It’s an impressive double-layed dome structure which has helped keep the frescoes free of damage. At the time, it was an engineering marvel.

Two quirky and unique attractions that I loved — now these are the sorts of things I live for — were the Leonardo Da Vinci Museum which had tons of bizarre creations of his that you could actually play with. I was there for well over an hour! Then, there is also the Santa Maria Novella pharmacy.

It’s credited as being the oldest pharmacy in the world, being built around 1612. Today, they sell everything from toiletries and liqueurs to medicinal balms and foods.

Cinque Terre

Cinque Terre is very similar to the Amalfi coast, with the big exception, and be it novelty, that you have to commute town to town via train. There’s five towns in total, so that’s a big day! Tours are usually about a solid twelve hours round-trip from Florence (it’s a two hour drive each way).

Some of the most legendary photos of Italy come from here. You’ll, again, be saturated with cafes, fishing harbours, gorgeous coastal scenery, a full spectrum of colorful buildings, and tons of idyllic places to sit down and read.

Be prepared for a lot of well-earned downtime.


Ham and parmesan are two of the country’s staples. I took a big detour and headed to Parma to get that “how it’s made” experience. The Parmesan part was fun to watch, and not to mention, sample all the delicious variations. It felt like being back home in wine country, Canada.

However, by the time we hit the ham portion of the tour, I wanted to plug my nose and fast forward. The smell of rotting, err… curing, meat was so overwhelming that I almost threw up. The large metal elevators taking us between levels felt like something out of a horror movie. The long dark hallways of pork strung up to age helped add to this effect.

By the end of the tour, it was time to sample. Do you actually think I did? Yeah, about that… not so much!


Verona is famous for Shakespeare’s Romeo and Juliet. Tradition has it that if you cup the right breast of the bronze Juliet statue, it will bring you luck. The verdict is still out on that one, and this attraction has no end to controversy for people who overly sexualize her and the ritual, and cite her age of thirteen in the play. But, both men and women, too numerous to count, are still seen trying their best hand at better future.

It’s also possible to visit Juliet’s balcony, and lover’s lane.

To this day, the Verona arena is still a venue for performing arts, notably opera. While I was there, there was a huge concert with multiple local artists!


Taking a ferry to Venice, my first stops were the outlying islands of Murano, Torcello and Burano. These colourful islands are famous for their handicrafts, such as glassblowing. I had a chance to check out a live demonstration of a glass blower at work. Then, wandered the city streets for the remainder of the afternoon.

Venice is a veritable maze of homes, shops, and passageways. Without Google Maps I would’ve been incredibly lost. Ticking off the Bridge of Sighs, which was the last view of the outside world convicts would see before being imprisoned, I did a quick prison tour and headed to something a little more light hearted.

For contrast, another church couldn’t hurt, right? Saint Mark’s Basilica had a treasure room filled with artifacts that would make Indiana Jones scream.

Having that penchant for unique attractions, the Libreria Acqua Alta (or High Water Book Shop) appeased my nearly insatiable lust for such places. Room after room of stacked books, wall-to-wall magazines, and maps, it feels like you’ve stepped into a scene from Harry Potter. Water-proof bins, bathtubs, and even gondolas store many of the items on the ground level, as thus to haphazardly protect them the numerous annual floods of the city.

Venice isn’t Venice without the obligatory ride down the Grand Canal in a gondola while being serenaded by song and accordion. It was packed. Apparently everyone loves this one cliché a little too much. But, who was I to talk? There was one performer for every four gondolas, and we were on a boat with other random tourists they matched us up with. The ride was short and only mildly satisfying. If you’re looking for a romantic moment like the movies, you won’t find it there!

I made some new friends from South Africa, and had a double date right on the edge of the canal over sunset. Now that was romantic!

Dolomites – Alps – Tre Cime

At 3000 meters above sea level, almost the same as Cusco, Peru, the hike through the Italian Alps at Tre Cime di Lavaredo is breathtaking. Long stretches of Canadian-esque mountains, and rest stops along the way with tea houses and more. Now these guys know how to make hiking a luxury sport. 

The villages surrounding the mountain ranges are quaint and something that made me think medieval Germany meets ski resort. But, perhaps that’s my lack of cultural awareness showing. 

Either way, this was a place that’s been etched permanently in my revisit list should I ever return. The hikes are endless and you could spend months here.

Lake Como

If I hadn’t planned so well, I would have missed Lake Como. The entire lake is dotted with tiny little communities, rich with their own personalities. They’re connected by a tiny, but fast, ferry system. Each destination felt like stepping onto a different resort, and I couldn’t believe more poeple didn’t live here. It was calm, quiet, and far less touristy than I expected.

I strolled around the quaint city streets, admired the gardens, and climbed the haunted stairs to the Vezio castle in Varenna. The birds-eye view it gives you of Lake Como will make you want to stick around for a while. And if you’re particularly lucky, perhaps the ghost of the Lombard queen Teodolinda will come pay you a visit.


To me, Milan was just another big city. I wasn’t too sure what to see, even with all of the Trip Advisor recommendations and blogs I read. I booked myself into a guided tour. Now, that’s something I usually avoid at all cost because they’re often way too slow for the RPM of my life as well as overpriced. But, it was the only way to make sure I didn’t miss access to the Last Supper painting by Leonardo da Vinci. So, I humored the tour and hit the other attractions on their list.

We got carted around the cathedral. Apparently it took six centuries to complete! It is quite elaborate, I suppose. It is covered with statues, and has your typical impressive stained glass windows. Afterwhich we hit up the market at Galleria Vittorio. Tradition has it that if you grind your heel into the mosaic of the bull in the center of the complex, it will bring you great financial success. I’m still waiting…

It was all pretty run of the mill and, a calmer end to a whirlwind of a trip. That’s until, at least, I met Dalia. I like ending every trip with a little bit of luxury, and splurged on having dinner atop the Ceresio 7 Bar in Milan. Before that, I was settling in with more Prosecco and amping up for a relaxing sunset view of the city.

We started chatting because she, like myself, was chronically low on battery power and needed to juice up with my power bank. We both come from very different worlds. She is a high energy fashion designer living in Vancouver – back in Canada. Not so far from my home city. She took me into her world for the night, and scored us VIP access to some Vogue party next to the Milan Cathedral. It was like hanging out with a celebrity for a few hours. We did a couple photo ops nearby, and called it a night.

Without question, Italy was the absolute most photogenic country I’ve ever visited, with the greatest diversity in cultural attractions and such intense rich history. But now, it was time to head onto my next adventure…

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