The Perfect 14-Day Italy Trip Itinerary


14-Day Italy Trip Itinerary

Our honeymoon to Italy in September was, without a doubt, some of the best days of my life so far. I actually remember eating dinner overlooking Positano and thinking – what if I just lived the best day of my life? And I knew it was so possible. It was just that good.

We did all of the trip planning ourselves with some help from a few friends and the internet. We wanted to see as much as we could but also not be too rushed. I looked over dozens of itineraries from travel bloggers and countless reviews of museums, tours, and restaurants.

With that in mind, we opted to forgo heading to Venice. I know! Heartbreaking. But a lot of people in our lives mentioned that they were disappointed by Venice and it’s fairly far from the rest of the places we wanted to visit. We didn’t know if the day of travel to get there and back would be worth it. I don’t regret skipping it (though I still want to see it someday).

So the simple version of our Italy trip itinerary looked like this:

Rome > Amalfi Coast > Florence > Cinque Terre > Rome > Home

Perfect Italy Trip Itinerary

You might think, Nadine, you’re sure bouncing around a lot there. And we did! But here was my thought process on that: Rome and Florence are both tour heavy, museums, lots of walking, busy, go-go-go, type stops. The Amalfi Coast and Cinque Terre were both fairly chill and relaxing. I guessed that after a few days in Rome, it might be nice to have a few days to chill by the sea before heading to Florence to have a few more busy days.

I was right. If we had done Rome and Florence back to back, I think I would have been too exhausted to enjoy whichever came second.

So our vacation wound up looking something like this:

Explore > Chill/Recover > Explore > Chill/Recover

It was perfection. Nav and I marveled a couple times at how nicely the timing of this trip worked out. We never felt like we were in one place for too long but we also never felt rushed.

Since we got back, I’ve had lots of friends ask us for our Italy trip itinerary. This post actually started as an email to a friend back in January. I figure if they benefitted from it, you might too. So here it is:

Day 1 – Arrive in Rome

We arrived in Rome in the evening and thus, we had some pizza, checked into our AirBnB, and went to bed. We’d been traveling for about 15 hours at this point so that in addition to my airplane meds, I was zonked.

Our AirBnB was near the Pantheon (as recommended by a friend) and we thought it was the perfect central location.

Day 2 – Rome

We really went for it on our first full day in Rome.

Pantheon – Piazza Navona – Trevi Fountain – Piazza Venezia – Capitoline Hill – Roman Forum – Colosseum (buy your tickets ahead of time to skip the line)

A big part of the appeal of Italy for us was the food (and wine, duh). We decided that the best way to make sure we got the most out of our food experience was to do a food tour as soon as we got to Rome and Florence. I think it was a huge help in making sure we chose quality food and restaurants and avoided super touristy places.

We did a 6-10pm Jewish Ghetto and Campo dè Fiori Food Tour with guide Marta. It was fantastic and we left completely stuffed (and a little buzzed). The food tours were awesome because the guides shared history of the neighborhoods as we walked from place to place. They also are called food tours but had an absurd amount of wine as well.

Again, if you’re heading to Italy for the food, I’d highly suggest doing food tours early in your trip. Our guide was super helpful in sharing restaurants with us that she frequented and helping us learn what to look for in a restaurant.

Honeymoon in Rome

Day 3 – Rome

The Vatican! Nav and I are not Catholic but we definitely felt like the Vatican was something we wanted to see.

Let me share this most important advice with you: buy your tickets online (the skip the line tickets) ahead of time. The line to get in without tickets was absurd. Hours long. We bought our tickets online and waltzed right in at our designated time. We started fairly early and got our tickets for 9:30am.

We opted for an audio tour instead of a guided tour. The audio tour was not that great and in retrospect, I think I’d pay for a guided tour from an outside person. It takes quite a while to go through the whole Vatican Museum and to be honest, I was pretty museumed out by the time we left Rome (or um, halfway through the Vatican tour).

My husband was pretty amusing during the tour because, having only been in a Christian church maybe twice in his life (both times with me for family events), his commentary was priceless.

We then wandered down to Trastevere, a neighborhood we’d heard great things about. It was lovely and we just tried to get a little lost and enjoy a less tourist heavy part of Rome.

Dinner that night was at Roma Sparita (make a reservation). We’ve since gone back and forth many times about what our favorite meal was in Italy and we’ve both decided that this is it. The Cacio e Pepe was heaven. I read that it’s gotten a little touristy in recent years (after Anthony Bourdain raved about it) but I don’t care. It was that good.

Day 4 – Rome

Bright and early we headed to the Galleria Borghese. The guided tour was wonderful and I’d highly recommend paying the extra for the guide.

We visited the Spanish Steps (which were closed due to construction). Then we headed to Vittorio Emanuele II Monument and took the glass elevator to the roof. This attraction is fairly hard to find (the signage is poor) but it is so so so worth it. Definitely the best view of Rome from above.

Day 5 – Travel from Rome – Praiano

We knew we wanted to see the Amalfi Coast but were unsure which town to stay in. Positano is fairly tourist heavy these days (thanks, Under the Tuscan Sun) and therefore pretty expensive. After lots of research we decided on Praiano, a smaller seaside town about 5 miles away from Positano. It is less expensive but getting to Praiano looks intimidating (on paper) but it isn’t, I swear. We had very little plan and had our fingers crossed that the travel would work out. It did.

Here’s how the travel worked:

Short version

Direct train from Rome to Salerno > Ferry from Salerno to Positano > Water taxi from Positano to Praiano

Long version

Train from Rome to Salerno – This was a direct train that we pre-purchased. After we arrived in Salerno, we had to wing it. We knew there was a ferry to Positano (you cannot buy tickets online ahead of time) so we did the obvious thing once we got to the train station – walked toward the water (very serious planning right there). The ferry was easy to find once we were by the water.

Ferry from Salerno to Positano – Stunning views the whole way. Honestly we were using this as a mode of transportation but WOW, those views. The ferry stops in Amalfi and Positano. On this ferry ride we happened to see the road that we’d have to take to get from Positano to Praiano via taxi. It was high up, 1000 years old (not an exaggeration), and on the edge of a cliff. NBD, I’ll just have a panic attack now.

View of Amalfi from the Water

Water Taxi from Positano to Praiano – We got off the ferry in Positano, suitcases in tow. There are mobs of tourists. We needed to find a taxi to take us to Praiano and I knew that the taxi ride would be the most terrifying 15 minutes of my life. Nav has years of experience dealing with me so he brought me directly to a restaurant and ordered me a glass or Rose. GOOD MAN. Three glasses later, I decide maybe I can handle it.

We still weren’t sure where to find a taxi (because the road is super high and we were next to the beach) so we wander down to the water where low and behold – there are water taxis. SIGN ME UP. For 30 Euro we hire a guy to take us by water taxi to Praiano and I successfully avoided ever having to go on that super terrifying road.

If you’re thinking of doing the Amalfi Coast, don’t be intimidated by all the travel connections needed to get there. It sounds rough on paper but it was pretty easy. Plus, it might have been my favorite part of Italy.

We stayed at Locanda Costa Diva, a beautiful family run place that hangs on the side of a cliff in Praiano. Shockingly affordable. We had a small room and our own balcony with two lounge chairs. Very walkable to all of Praiano via the many pathways and stairways that snake through the town. Be ready to drag your suitcase up and down hills and stairs to get there.

Day 6 – Praiano

Praiano is actual heaven and when I daydream about Italy, this is what I dream about. We sat on the dock and read books and jumped in the sea. We took 400 stairs or so (getting around this town is not for the faint of heart) to get to an absurdly fresh seafood dinner overlooking the sea.

Day 7 – Praiano and Positano

We took a water taxi back to Positano to check it out. We wandered all through the little shops and drank wine by the beach. Positano is very touristy and while I’m glad we saw it, it was nice to get back to Praiano and feel like we were in our own little world again.

You guys, the Amalfi Coast is the place to honeymoon. It’s also the place I learned that I like anchovies.

Overlooking Positano

Day 8 – Travel from Amalfi Coast to Florence

Return travel: Water Taxi to Amalfi > Ferry from Amalfi to Salerno > Train from Salerno to Florence

Once we arrived in Florence, we checked in to AirBnB and relaxed. Our AirBnB host gave us so much awesome insight about where the locals go and what restaurants and gelato were the best. We headed straight for the gelato, obviously.

Day 9 – Florence

8:45am – 2:30pm Nude and Food Tour

This food tour was amazing. First we visited the David where our tour guide gave us a brief history lesson and had lots of fun (and funny) tidbits. The tour continued to some of the most awesome food spots in Florence. The folks on this food tour with us were a riot and we had a freaking blast. We ended our tour with a private wine tasting with Italy’s Sommelier of the Year 2014 and then fresh handmade gelato. If you go to Florence, do this tour.

We spent the rest of the day wandering around Florence and hiked up one of the hills to check out the view.

Day 10 – Florence

This was the only touristy bus tour we did while in Italy. I’m glad we did it because we saw a lot but it’s hard to fully appreciate each location when you’re only there for an hour or two.

8:30am – 8:30pm Walkabout “The Best of Tuscany” Tour

Siena > Chianti > San Gimignano > Pisa

All locations were lovely and the tour guide we had in Siena was amazing. This tour company really knows what they’re doing and they were super efficient at getting us in and out of each spot.

Pisa was the last place on the list and was wildly disappointing. It’s not at all picturesque and is mostly a college town with lots of graffiti and (shocker) a leaning tower. We were pretty over it inside of 10 minutes. I would have rather stayed in San Gimignano for longer and gotten a second cone of gelato.

Day 11 – Florence/Lucca

We started the day by climbing to the top of the Duomo, the large church in the center of Florence. We bought tickets two days before at the ticket office across the street from the Duomo. Do this or you will wait in line for hours.

You guys, what they don’t tell you about the Duomo is that it is the most claustrophobic experience you will ever have. I can feel my heart start to race just thinking about it. Just imagine being stuck in a stairwell built for a teeny tiny priest in the 1200’s. There are very few windows (like one every 8 flights of stairs). There are so many people and everyone is waiting. So you’re just stuck, standing in a tiny stairwell and once you go up, you can’t go back down. There is literally not enough room to change your mind. I was in full on panic attack mode. I’m getting worked up just writing about it. I can’t believe they let so many people in at one time.

Nav knows that what I need during times like these is a distraction so he started telling me the entire plot of the fantasy novel he was reading. So just picture me having a panic attack and Nav squeezing my waist (this helps me for some reason) as we walk up (and then down) stair and rambling about a wizard that he keeps calling “the Dumbledore of the book”. Nav, you are the best husband a girl could ask for.

I would never do this again. Never. But if you like good views and you’re way more chill than me, you should totally do it. But I think I’d rather fly on a haunted airplane dead sober while petting a tarantula than ever do this again. It was the worst combination of being high up and trapped.

This is actually not a picture of the Duomo but a picture of the bell tower across from it. Once we were done we got a lot of wine (so I could chill the eff out) and then checked out of our AirBnB and traveled to Lucca.

Travel to Lucca – 1h 19min direct train ride, not purchased ahead of time

Lucca was little town I’d read good things about. We wanted to experience something that was outside of the traditional stops. It has the most intact medieval wall around the city and you can walk around it or rent bikes and ride. This stop wasn’t necessary but was a nice change of pace and a good halfway point between Florence and Cinque Terre. That said, this is the one thing I’d remove from the itinerary if we did this again. I think I’d rather spend another day in Cinque Terre.

Day 12 – Travel to Cinque Terre

Lucca > Viareggio (20 minute train ride) > La Spezia Central (35 minute train ride) > Riomaggiore (7 minute train ride)

We did not purchase these tickets ahead of time and again, although switching trains this much intimidated me at first, it was super easy. The trains come so frequently that you don’t need much planning to make it work.

We stayed in Riomaggiore, the first village of the five at an AirBnb. It was nice and easy to get to but if I went again, I’d stay in Monterosso Al Mare.

Day 13 – Cinque Terre

Our plan was to spend the day hiking but a huge storm the night before closed all of the hiking trails. We were super bummed (so many of the awesome photos you see on pinterest are taken from the hiking trails) to miss the views.

We bought a day pass for the local train and checked out each town. The train rides between towns are short and the towns are small so you can walk through them fairly quickly.

Vernazza was stunning (pictured above). Our last stop was at Monterosso Al Mare around noon.

Since we couldn’t hike, we decided to do the exact opposite. I bought a bikini from a street vendor for 19 euros and Nav had on his workout shorts and we rented beach chairs and sat on the beach and drank wine all day. This day was exactly the opposite of what we had planned and it turned out to be absolutely perfect. The water was so warm! Warmer than the Amalfi Coast, which confused us because it’s much further north.

Day 14 – Cinque Terre/Travel to Airport

On our last day we checked out of AirBnb and took a train to Rome and then the train to the airport. We checked in to a hotel near the airport and prepared to head home.

Day 15 – Fly Home

We were up bright and early to catch our flight back to New York.

I’m so glad we took this trip to Italy. It was one of the highlights of my life so far. Experiencing another country with Nav was awesome and I can’t wait for our next adventure. At times when we were house-hunting (you know, before we decided not to buy a house yet) I wondered if we should have saved our money to put it toward a larger down payment. But not one bone in my body regrets spending the money on this trip. It was worth every penny.

Feel free to leave any questions below or add your own thoughts about trip planning. I’d love to know what else you’d add or a recommendation on where we should go next!

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