two week itinerary in italy

Long Read: Two Weeks In Italy

I wrote this piece in 2015 and it was published in The Irish Independent.

It is a longer read than the usual quick-hit “must do” list we’ve become accustomed to online, but I think it paints a lovely picture of a perfect two week itinerary in Italy.

One of my favourite things about living on the little island of Ireland is our proximity to so many diverse countries. A short flight, sometimes the same price as a decent night on the town, can get you to the Mediterranean, Scandinavia, Eastern Europe, Northern Africa and even Asia if you fly to Istanbul and get a day trip boat across the continental boarder. It’s something I take advantage of as often as possible. Some places I know I’ll only visit once, while others get under my skin and leave me eager for the day I’ll be back. Italy is one of those places. I think it’s the most beautiful country in Europe, possibly the world, if you take into consideration the food, the people, the arts, the style and the history as well as the scenery and weather.

I’d visited Italy a handful of times before this trip. Explored Rome, Pompeii, Carpi, Bologna and Milan. The longest I’d stayed in any one place was 4 days. On this trip I wanted to give Italy more attention, my main aim being to experience the country like a local. Minimal exposure to tourist trap restaurants, business hotels or tour buses, this time I wanted to frequent the supermarkets, picking up local produce to cook in our apartment. My boyfriend Dara and I decided on two weeks in the north of the country, as usual I insisted on organising our itinerary. Honestly I think I’ve forgotten how to holiday like a normal person because he seemed pretty overwhelmed when I presented him with our jam-packed to-do list. Fly into Milan, head east towards Portofino, down the coast to Cinque Terre, further south to Pisa, then inland to Florence and finally north to Venice with a pit stop in Bologna in case I’d missed anything there the last time. He drew the line when I suggested trying to squeeze in Lake Como as well, and even I had to agree I was being a little ambitious!

We boarded our AerLingus flight on a drizzly Friday morning with that holiday anticipation in the air. Italy’s industrial fashion capital greeted us with clear blue skies just two and a half hours later. We spent only a few hours in Milan to wind down after an early morning and the general disruption of flying. A bite to eat, sat on the Duomo Square with that iconic, gothic cathedral filling the backdrop before catching a bus headed for Portofino. It took just under two hours of winding mountain roads and one stomach settling tablet before we could disembark, to compensate we hugged the coast for the entire journey and the views were nothing short of spectacular!

We stayed in Santa Margherita Ligure, a couple of kilometres outside of the small fishing village of Portofino, renowned for its wealthy visitors and impressive collection of docked yachts, so it’s easy to guess why. But Santa Margherita is beautiful in its own right, quaint and rustic with a long sandy beach recognisable for its rows of colourful, stripped umbrellas. It takes 15 minutes in a car or just over an hour walk to get from Santa Margherita to Portofino. We were warned many times that as standard, taxi’s way over charge for the short journey along the Italian Rivera, so we decided to take the popular walking route for our first trip into the village. The route was so breathtaking and leisurely that we never ended up getting a taxi for our entire stay, morning or night we walked and it never got tiring. Portofino is small and centred around the iconic harbour, I was immediately surprised by how peaceful the area was despite its acclaim. I had expected to find lots of hustle and bustle especially during summer months but instead if felt like we’d happened upon a hidden gem.

two week itinerary in italy

Portofino Harbour

On our first day there we ambled to the Portofino lighthouse, which sits on top of a high, vertical cliff face with nothing but infinite blue in every direction. There is a rough and ready outdoor café here serving aperol spritz and snacks so you can sit to take it all in. It’s one of those places that makes you feel very tiny. On our way back we noticed the bird’s eye views of Portofino that we had missed on our way up, the area is fittingly called “the view from the church on the hilltop” and it is postcard perfect. We snapped some photos and headed to the harbour for dinner. Portofino is heaven if you’re looking for R&R, there’s market stalls to browse, scenic trails to walk, no shortage of delicious cafes and restaurants serving that wonderful authentic Italian cuisine we all love but live like a local you cannot, unless a local millionaire was what you had in mind. So after three incredible nights we took a train south to our little apartment in Cinque Terre.

two week itinerary in italy

The view from the church on the hilltop

two week itinerary in italy

Italian dinner overlooking the harbour

Cinque Terre or The Five Lands is made up of Monterosso al Mare, Vernazza, Corniglia, Manarola and Riomaggiore. Five crazily constructed villages set amid some of the most dramatic coastal scenery on the planet. This area is a favourite for travel bloggers, hiking enthusiasts and unfortunately throngs of tourists. No longer the undiscovered utopia it once was but frankly, who cares? People flock here because it’s worth flocking too. The entire area is a UNESCO world heritage site with cars banned over a decade ago. The only way to reach Cinque Terre is a 19th century railway line that cuts through a series of coastal tunnels to ferry visitors from village to village, or the more energetic among us have the option to walk the meandering pathways that traverse cliff sides taking you from Monterosso, the most northerly village, all the way to Riomaggiore, the most southerly in about four and a half hours. We stayed in Riomaggiore for convenience as we were travelling further south to Pisa in a few days. There really is no best village to stay in, it comes down to preference and price because they are all staggeringly beautiful and worth a visit.

two week itinerary in italy

The balcony of our little apartment in Riomaggiore

We rented a charming top floor apartment that hung from the packed cliff face overlooking the sea. Riomaggiore is famous for its fried seafood in a cone and the only place in town to get it is Il Pescato Cucinato, we grabbed one and ate it by the boat ramp on the seafront, watching fishermen ease their crafts out to sea. Afterwards, a twenty-minute walk along the coastal trail brought us to Vernazza for dessert. Gelateria Vernazza is often named the best place for gelato in all of Italy, now I can’t confirm this because I haven’t tasted every other option, but I can tell you it’s pretty damn good. Plus eating it while soaked in sunlight on the steps of an adjacent shop front made it all the more delicious. I’m sure you’ve gathered by now that the views around Cinque Terre are pretty incredible, well Nessun Dorma eatery in Manarola boasts arguably the best views of all. We took the train here on our second morning in Cinque Terre. The village’s stacked and brightly coloured buildings attract photographers and artist from around the world to capture its rare allure. Plus the area is well known for its wine, behind Nessun Dorma we found a dirt path that led us up the hills to vineyards that grow in the fields above the town. We sunbathed here for a few hours watching people’s day unfold on the streets below us.

two week itinerary in italy

Eating my Il Pescato Cucinato seafood cone on the boat ramp

two week itinerary in italy

Gelateria Vernazza goodness

two week itinerary in italy

Nessun Dorma eatery in Manarola

two week itinerary in italy

Lazing in the vineyards overlooking Manarola

Our last notable stop in Cinque Terre was in Monterosso al Mare, the largest and least charismatic of the five villages as well as the only one with a beach, meaning it’s also the busiest. We stopped by for one main reason, to eat at Da Eraldo, a tiny gem nestled away on one of the village side streets. With only eight tables and an impressive reputation as the home of Europe’s best antipasti platter I was surprised when we were seated and served straight away. Either tourists aren’t doing their research or we got incredibly lucky, regardless this is a must visit! After a final homemade breakfast on our little apartment balcony, we packed up our air-dried washing and took another train south to Pisa. Travelling by rail in Italy is fast and cheap with tickets ranging in price from €2 to €15. Waiting for us in Pisa was a grand, old Italian house on the river Arno which we found for a steal on Airbnb, all high ceilings, creaky floors and mahogany four poster bed with beautiful views of the city. Arriving just before noon with plans to stay for two nights, we dropped off our bags and headed straight for, of course, the Leaning Tower of Pisa. When I see famous landmarks like this in real life, I feel the same as I assume a mega fan feels when they finally meet Kim Kardashian or Taylor Swift or whoever. We climbed the tower, all 294 lopsided steps and sat at the top for an hour or so with 360 degrees of Pisa around us. I didn’t want to come down but hunger finally got the better of me, so we broke the ‘living like a local’ rule this once to sit outside a pizzeria called Trattoria La Buca which had a full view of the tower. Bellies full and obligatory cheesy photos captured we had Keith Haring’s famous mural ‘Tuttomondo’ next on our list. A bright and instantly recognisable painting covering the entire sidewall of a church, completed in 1989 it is the last public work of his life and it’s free for anyone passing to appreciate.

two week itinerary in italy

Europe’s best antipasti platter at Da Eraldo

two week itinerary in italy

The last breakfast on our quaint little balcony in Riomaggiore

two week itinerary in italy

Sitting on top of The Leaning Tower of Pisa

two week itinerary in italy

I’ll see myself out for this bad tourist joke

two week itinerary in italy

Keith Haring’s famous mural ‘Tuttomondo’

It turned out one night in Pisa was enough and the more I read about Florence the more I wanted to get there. Cue another train and another rented apartment, this time a sprawling, modern Airbnb penthouse called “across the Arno” in Florence’s chic Oltrarno neighbourhood, a place like this on the south is less than half the price of a standard hotel room on the touristy north side. It was just off Piazza Santo Spirito, a local favourite with better prices and arguably a better atmosphere than traditionally popular spots. There’s a handful of restaurants on this square, one of which is called Osteria Santo Spirito, they serve the greatest spaghetti bolognaise I have ever tasted. Also, the church of Santo Spirito is where Michelanglo carried out his anatomical studies on the corpses of the church’s hospital in his early teens. Now, where to begin with the whirlwind of things we managed to see and do in Florence, first up I took a selfie with one of the oldest bridges in the world, the Ponte Vecchio, built in the year 996. It’s so beautiful rumour has it Hitler himself directed his men to bomb around it during WWII. Then it was onto the Galleria Dell Accademia, home to Michelanglo’s Statue of David, who’s actually much, much taller in person and has a grossly under appreciated backside. We followed that excitement with a lunch break in front of the Florence Cathedral, a gothic masterpiece topped by Brunelleschi’s dome, a feat of engineering still revered and studied to this day. That evening we walked down the river to the Piazzale Michelangelo, on this square you’ll find panoramic views of Florence and the best spot to watch the sunset. I’m old before my time I know, but I love a good sunset!

two week itinerary in italy

Casual selfie with one of the oldest bridges in the world, the Ponte Vecchio!

two week itinerary in italy

The Galleria Dell Accademia, home to Michelanglo’s Statue of David

two week itinerary in italy

The Florence Cathedral

The following morning we rented bikes and cycled to the Basilica of Santa Croce, inside this church are the resting places of Michelangelo, Galileo and many other notable Italians and there is no fee to enter. The pharmacy of Santa Maria Novella also got a visit, it’s a luxurious step back in time where they’ll cook you up artisan lotions and potions from brown bottles stacked high behind the counter. We had to queue for around twenty minutes to get into the Uffizi Gallery; this is where you’ll find the Botticelli masterpiece, Birth of Venus, perfectly preserved since the mid 1480’s! You could get lost in this Gallery for days it’s enormous and wildly impressive. And the activities didn’t end there; we had a class to attend at the Food & Wine Academy of Florence that evening as an interesting substitute for a regular dinner date. Three hours spent creating the perfect pizza and gelato with a traditional Italian chef. At the end I got a diploma. Yes, I really do own a framed and mounted diploma in pizza making and I couldn’t be prouder of that fact.

two week itinerary in italy

The Botticelli masterpiece, Birth of Venus at The Uffizi Gallery

two week itinerary in italy

The mess I made in pursuit of my diploma in pizza making

There are so many things to do in Florence we could have spent a whole other day exploring the extravagant homes and secret city tunnels left behind by the Medici family, instead we settled for a morning of sunning ourselves in the impressive grounds of the Pitti Palace. Spread over 32,000 square meters, it was bought by Cosimo I de’ Medici in the 1500’s when his wife Eleonora decided their other palace on the far side of town was too small. Before moving onto Venice we wanted to get out into the Tuscan countryside, so we booked an evening of horse riding through the grasslands and vineyards of Chianti, central Tuscany. It was serene and incredibly beautiful, plus they gave us lots of wine! Then after a peaceful day came an eventful evening of trying to get to our next destination. Our train from Florence to Venice was the first trouble we encountered travelling by rail, it was almost completely sold out and our only option was to pay €50 to travel direct one way in first class, meaning our scheduled pit stop in Bologna was out of the question. As a result, I would suggest booking trains between the bigger cities a day in advance!

two week itinerary in italy

Dorsoduro neighbourhood in Venice

two week itinerary in italy

Beautiful Venetian street corners

Venice is divided into six districts with San Marco the busiest and most expensive of those. We stayed in Dorsoduro, a quiet but still central neighbourhood often referred to as ‘real Venice’, the best of both worlds. Venice is such a strange and picturesque city, when my boyfriend and I arrived we ignorantly assumed there would have to be some roads but when we surfaced from the train station straight onto a boat dock we realised this really was an entire city built on water. It’s cheesy but when in Venice you must take a gondola ride, it costs €80 as standard and you can nab one for a tour of each district, we chose San Polo because there’s less traffic and lot’s of beautiful historic buildings to drift by. After that we climbed the bell tower on San Marco Square for some great views over all of Venice. If you ever find yourself on San Marco Square there’s two things you have to do, first get a coffee at Café Florian, it is the oldest café in the world serving since 1720, Casanova drank his coffee here! Secondly grab a box of pasta to go and a baguette from Dal Moro’s famous take out spot, sit on the steps of the square and watch the world go by. Also near San Marco Square we found the Bridge of Sighs, named that because of the reaction it causes, most claim it’s the most beautiful bridge in Venice and while it’s definitely worth a visit, I preferred the iconic Rialto Bridge, not to be confused with something that could be found in Dublin, it spans Venice’s Grand Canal. We also took trips to two neighbouring islands, Murano and Lido. Murano is famous for its artisan glass and Lido is where you’ll find the only beach in Venice, it’s also got the best sunset views – I told you I like a sunset! On our last night we got a waterside table at Villa Laguna to watch it. But to tell you the truth of all the beautiful things we did in Venice, my favourite was to just walk and look around. The city in itself is an experience!

two week itinerary in italy

Boarding our gondola in San Polo

two week itinerary in italy

Cafe Florian on San Marco Square

two week itinerary in italy

The sunset at Villa Laguna in Lido

Now just to get back for that Lake Como stop I missed…

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