— How to See A Big Chunk of Italy in Two Weeks

On August 18, 2014 by travelogueblog

Arno River in Pisa
The idea of seeing a big chunk of a whole country like Italy in just fourteen days seems overwhelming and daunting. Wouldn’t it be better to rent a little villa in Umbria or Tuscany and just plop there for two weeks, savoring the lengthy meals and adapting to the slower pace of life until, sadly, it’s time to go home?

Well, that depends. If you’re looking for a relaxing spot with a unique culture and don’t want to worry about seeing or doing much, then, yes. Sure. Plopping sounds great. But most people reading this blog only get to take one or two big trips per year — and even that’s with a lot of travel prioritization. Realistically, with the rest of that great big world out there to see, if you stuck around in one spot for two whole weeks, you might not get a chance to see the rest of Italy… ever.

We opted for a broad sightseeing tour over a deeper, more rustic and intimate getaway. If my wife and I ever get to go back, maybe we’ll spend time in a spot we’ve grown to love. Until then, here’s how we saw a really big chunk of Italy in just two weeks.

(1) We based the trip around Florence

Michelangelo's David
Florence is a major city with a lot of history going directly back to the Italian Renaissance. In fact, it was pretty much the center of the 16th century “re-birth” of math, science, medicine, art, and politics. This was largely thanks to the ruling Medici family, founders of modern finance and fanatic patrons of the arts for a couple of hundred years. Florence is a destination in itself, with plenty to see and do, and yet it’s situated centrally enough within the country to be close to other spots. With trains and highways connecting to other important regions and big cities, it’s the perfect place to start.

Ponte Vecchio over Arno
For our most recent vacation, there was a group of six of us: me, my wife Sarah, and four of my in-laws. It sounds like the set up to some kind of punch line, but this was no joke! We all chipped in to rent an apartment for 10 days through VRBO, right on the edge of the Santa Croce neighborhood in Firenze. It was a fairly long stroll to the major tourist attractions, but any slice of Italy we wanted or needed could be found right in our little neighborhood, from 150 year old cafes, to crazy good local restaurants, to late night gelaterias. Rather than travel as a lumbering pack the whole time, we agreed to “do our own thing” during the days, share stories and tips over dinner and ice cream at night, and group back up for out-of-town excursions when it made sense to do so.

In the first couple of days, we managed to tour the Uffizi art gallery, climb to the top of both the Duomo Cathedral and the nearby bell tower, admire the touring Jackson Pollock exhibit in the Palazzo Vecchio, and window shop along the Ponte Vecchio, the oldest surviving bridge in the city that dates way back to the middle ages. All of that was in addition to the great meals we enjoyed every day: a standard lunch and dinner were usually two hour commitments, each. It’s a totally different experience from the in-and-out culture back home in the US. Stuffing our faces for hours and then walking off the calories was a lot of fun, but soon we were ready to see another part of Italy.

(2) We utilized the regional trains

Leaning Tower
Our overnight trip to Pisa and Cinque Terre was probably my favorite part of the whole vacation, and if I ever did get to go back to Italy, I’d stay in C.T. for two weeks. The train from Florence to Pisa runs regularly during the summer, and since it goes along a regional line, the “seat reservations” that are required on some of the bullet trains to other major cities aren’t necessary for this trip. You can purchase a plain ticket, or if you’re like us, simply have a seat with your Eurail pass in hand. When you arrive in Pisa, it’s a short amble to the leaning tower. We’d bought our tickets to go up the stairs inside before we arrived in Europe, so we had an appointment to keep, but the rush we felt trying to get from the train to the tower on time didn’t match the rush of seeing the whole city from the top of its tallest, most famous, and slightly diagonal building. After taking the obligatory “holding up the tower” shot and scarfing down some good sandwiches from a nearby shop, we made our way back to the train and continued onward to the first village of the “Cinque Terre.”

Cinque Terre
Cinque Terre, which literally translates to “five lands,” is a cluster of five villages, each carved into the towering cliffs along the coast of the Ligurian Sea, part of the Mediterranean. The picturesque pastel houses of each community descend steeply downhill to the marinas below, where bobbing boats and swimmers compete for space in the placid waters. Each town is connected by train tracks and walking trails that lead hikers through designated National Park space. We stayed just one night, but we were able to get a feel for each town after spending a couple of hours there. These tiny beach spots all cater to vacationing Italians and internationally curious tourists alike. The short break from the hustle of city life in the laid back shore-town atmosphere added a healthy dose of relaxation to our trip.

(3) We took a road-trip through Tuscany

Castello Montefioralle
Back in Florence — the capitol city of the Tuscan region — Sarah and I spent another day finishing up our checklist of sites and sights, starting with the marble David statue in the Galleria Accademia and culminating with a picnic we purchased at the Central Market and enjoyed with a view of the whole city from the top of Piazzale Michelangelo. The next day, our group all met back up and four of our gang hopped into a car that we rented from the airport. I’ll be honest: renting the car was easy enough, but it was already expensive, even before taxes and fees were tacked on. If we hadn’t split the cost of the rental, it wouldn’t have been feasible for us to take a drive through the Tuscan countryside, though a bus or train would be more affordable. With that said, I’m still really glad we ended up taking the car.

We plugged Sienna into the GPS. Hugging mountain curves along scenic route 222 and stopping on the side of the road for incredible views of the rolling green hills, we spent the morning and afternoon hopping stop to stop. From a cured cold cut and cheese lunch at a local wine shop, to trying to find the historic Castello Montefioralle; from sipping ruby red Chianti in Chianti, to souvenir shopping under the towers of San Gimignano. We finally ended up in the UNESCO historic center of Sienna with just enough time to go inside the cathedral and to grab some (admittedly bad) tourist grub before hitting the road again back to Florence.

Siena Cathedral
As I said earlier in this post, we sacrificed “depth” for “breadth” on the whole trip, but no one can say that we didn’t experience what Tuscany has to offer that day.

(4) We made time to see Venice

Grand Canal
The canals of Venice are amazing, and you should go just to see them. It’s a novel experience to walk around a fully functioning city with no cars. Your whole mode of movement is subtly, yet quickly, transformed.

Despite having purchased our Eurail tickets ahead of time, we still had to pay for a reserved seat on the bullet train from Florence to Venice — an extra €10 each. We reached the sunken city, though, in record time. Jumping from the train to the vaporetto, the water bus that scoots along the canals to pick up and drop people off, we made our way to San Marco plaza for a great meal at Pensione Wildner.

Grilled Octopus

Grilled octopus was actually not the weirdest thing I ate in Venice.

Unlike our other stops, we had no “plans” in Venice except to aimlessly wander, eat at a few of the restaurants we’d picked out in a food guide before we arrived (recommended, or else you’ll probably end up eating at a restaurant with a picture menu), and maybe take a gondola ride if we could negotiate a good rate. And that’s exactly what we did. After checking out the golden ceilings at St. Mark’s Cathedral (holy expensive namesake!), we grabbed aperitifs alongside the Rialto Bridge, then toured the Grand Canal and a few of the back waterways with a private gondolier: it was after 7:00 PM and the cost should have been €100, but he knocked off ten minutes and brought the price back down to €80 for us. Afterward, we wandered the streets, shopping until we happened upon our pizza dinner at Antica Sacrestia.

Gondola Ride
The next day, we circled through the city, stopping for gelato, one last big Italian meal, and to sniff through the costume and perfume museum. Finally, we took the last train out of town back to our “home” base, Florence.

(5) You should leave from Rome

Getting home to the US was a little messy for us, and I’m going to give advice based on what my brother-in-law and his wife did for the last few days, as opposed to my own experience. You see, Sarah had to leave a few days before I did. She had to return to work on Monday, but I could only use my frequent flier miles for a free flight on Wednesday. We decided to save money and go separately instead of taking the same flight home. She would fly out of Florence, and after dropping her off at the security gate I took the train to Fano, a quaint beach town on the Adriatic Sea where my ancestors have some roots.

Fano Summer Carnevale
There, I was able to find a street named after my family, and I met a few distant cousins, plus spent some more time at the shore reading and catching some rays. The summer seafood Carnevale was happening, too: it was a small-town parade with some really big floats, and tasty food served out of trucks. Wednesday rolled around, and traveling backward, I flew out of Florence, too. It was a satisfying conclusion to my trip, but I don’t know how much of it resonates with an audience that’s trying to see a big chunk of Italy in two weeks.

Sarah’s brother and sister-in-law did what you should do, too. They took a bullet train to Rome, checked into a new hotel, and spent the next couple of days sightseeing and living “La Dolce Vita” on their own. I’m sure it was super romantic, and they had a great time. They flew out of Rome back to New Jersey when their two weeks were up.

I don’t mean to cut out all the things to see and do in Rome, but I intend to write about that city in a separate entry, and I’ll link to it from here when I do. Until then…

In the end..

If you follow most of our itinerary, but then go to Rome for the last few days, you will see a lot of the country in a very brief window of time. More than anything, there was quite a lot of traveling around. We felt rushed a couple of times when trying to keep appointments or catch trains, but the culture in this country forced us otherwise to slow down. Things happen at a slower pace, and once we got where we were going, it was a shift in paradigm to realize that we didn’t have to run anymore, be anywhere, or do anything besides think about the next place to eat. While you may feel like doing that in just one spot (and more power to you if you do decide to do that!), we felt that seeing more of the country was essential to our understanding of the people, the places, and the culture across Italy.

What do you think?

Is it better to have a broad trip, or a deep one?

What spots would you add to this itinerary?

Does anyone else have a good itinerary for Southern Italy?


Oh yeah… cuttlefish over spaghetti in a sauce made of its own ink was the weirdest thing I ate in Venice.

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