Our Italy Itinerary: The Best Places to Stay, See & Eat in Italy!

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Buongiorno, friends!

We just got back from a whirlwind trip in Italy and let me tell you, it was incredible! The art, architecture, the natural beauty, the fashion and food and history – all of it was just dreamy. I spent a long time planning our trip and today I’m sharing with you our complete itinerary, plus tons of travel tips for your next adventure.

Boston > Lisbon > Milan > Florence > Cinque Terre > Florence > Rome

We started our trip in Milan by way of Lisbon. Our flight was a red-eye, so we caught some sleep on the way over, and by the time we made it to Milan, it was the late morning. I loved starting in Milan, because it was less tourist-y than our other destinations and eased us into the busyness that is Italy.

From the Milan Malpensa airport, we took the Malpensa Express train to Cadorna Station, and from there, we took the M2 green line to St. Ambrogio. From there, it was a quick 10 minute walk to our Airbnb.

We booked all of our apartments for the trip on Airbnb. I chose all Airbnb plus locations, because they all have an in-person review before being approved, and are the top-tier of stays on Airbnb while still being affordable. They have self-check-in, reliable wifi, great amenities, and lots of charm.


We stayed at the most chic little Airbnb right near the Milan Cathedral. The location was excellent, and it was the perfect amount of space for a couple – a super comfortable, luxe bedroom, a sleek modern bathroom, and a mini kitchen to die for (not that we used it). The Italian courtyard entrance didn’t hurt, either.


Once we settled in Milan and freshened up, we ventured into the city for lunch and some exploring. First stop was the Milan Cathedral – a towering monument of Gothic beauty. It was SO stunning and the spacious piazza (city square) in front was a great place to hang out, take in views, and people watch. If you want to enter, you can buy a combined ticket with rooftop terrace access ahead of time or at the ticket office – I’d recommend getting a fast pass ticket to skip the line and lessen your waiting time. The views from the top are incredible, and if you have a bit of time in the city, I’d totally recommend the trek to the top.

Next, we headed right next door (literally, right next door in the same piazza) to Galleria Vittorio Emanuel – Milan’s gigantic and gorgeous luxury shopping center. Even if you don’t plan to do any shopping, it’s a must-see.

Milan is home to The Last Supper by Leonardo Da Vinci – but if you want to see it, you better plan in advance. Tickets are extremely limited, and when I checked for our trip, they were sold out six months in advance. You can buy tickets online to The Church of Santa Maria delle Grazie and the Refectory with the Last Supper – just be sure to snatch them up quick!

The Theatro Ala Scalla – Milan’s premiere opera house is a gorgeous building to visit if you have a bit more time to spend in the city, and you should also hop over to the Navigli Grande – Milan’s very own canals. Best viewed at sunset, it’s a location to just slow down and take in the beauty.



Obica is located at Via Santa Radegonda 1 in Milan, adjacent to the cathedral. It can be a little tricky to find – once you locate ‘The Space Cinema’ enter the glass doors directly across and take the elevators up to the restaurant terrace. We showed up without a reservation but got in easily because it was before prime dinner time (7-10). If you want to ensure you’ll get a spot with a view of the Dumo, it’s worth a call ahead of time. OH, and order the cacio e pepe. Just trust me on this.

Spotini was the most recommended spot to me in Milan for pizza. It’s cheesy, soft, and oh-so-gooey. By the way, Italians eat their pizza with a fork and knife and this pizza can only be eaten this way or with a very New-York-esque fold.


Panini Durini was our favorite breakfast stop. Lots of locals milling around, and no cover charge for sitting with breakfast (sometimes you’ll need to pay a small fee to sit and eat, even just for breakfast). I highly recommend the chocolate croissant, it was so good!

Getting from Milan to Florence

Our Milan Airbnb was a quick metro ride to Milan Central Station – a massive train station, one of the biggest in Europe. From there, we took a two hour train ride to Firenze Santa Maria Novella Station.

For Metro tickets, buy a ticket at the kiosk immediately before you board and validate as you go through the gates to the platform. We booked our major train rides online ahead of time to plan the cheapest & quickest train rides. It’s pretty simple to book online – just be sure to have your ticket on your phone pulled up when you are ready to enter the platform. You may be asked to show your ticket on the train and the code on your phone will work for this.


Boston > Lisbon > Milan > Florence > Cinque Terre > Florence > Rome


Our Florence Airbnb was a classic Tuscan apartment and our largest apartment of the trip. Terra cotta floors and wood beam ceilings gave it authentic flair, and the washing machine was a major plus. Right near Santa Maria Novella Basillica, it’s a perfect central location for all of the best attractions in Florence.


We used a Firenze Card while in Florence. If you plan on doing some museum-hopping, it’s probably worth the cost: when I priced out three of our top spots + skip the line access, the cost of the Firenze Card was cheaper. So if you figure you plan on seeing at least three major stops and want to skip the gargantuan lines, just go for it.

One of our favorite parts of the Firenze card is the flexibility: no need to get to each attraction as soon as it opens. We would pick one or two big attractions a day: the Piazza del Duomo, the Uffizi, Gallerica Academia, Pitti Palace, and then fill in the rest of our time with smaller piazzas, monuments and galleries. You can look up nearby attractions on the app, or mark them as favorites in your favorite map app before your trip.

On our first (half) day, we stopped at the Piazza della Signoria and Palazzo Vecchio before visiting the Uffizi Gallery (Botticelli! Leonardo Da Vinci! Michelangel! Giotto!) Everywhere you looked, there were masterpieces and hidden treasures, and the museum wound around in a never-ending maze of art. You’ll find famous works like Botticelli’s Birth of Venus as well as Primavera in the Uffizi, but don’t miss lesser-known works like Botticelli’s 7 Virtues and Judith Slaying Holfernes by female artist Artemisia Gentileschi.

We spent two and a half hours in the Uffizi, and then crossed the Ponte Vecchio to the other side of the river. Ponte Vecchio has great cultural and historical significance, but it’s hard to appreciate in the midst of so many tourists and souvenir shops. We crossed over to the next bridge, Ponte Santa Trinita on our way back and preferred the views and shops from this spot.

After an afternoon gelato, we appreciated our neighborhood in Piazza Santa Maria Novella. The basilica is quiet, uncrowded, and beautiful. A nice change of pace from the crowds before dinner.

On our second day, we started at the Galleria dell’Accademia which houses Michelangelo’s ‘David’. Even after reading books, taking art history courses, and countless documentaries, it’s hard to appreciate the scale and detail of David until you are at his feet. We spent the bulk of our time here admiring the work of Michelangelo, including ‘Prisoners’ or ‘Slaves’ – unfinished sculptures intended for the tomb of Pope Julius II della Rovere, After visiting the work of Michelangelo, we took a quick jaunt through the rest of the museum – don’t plan on spending hours at this spot.

The Florence Cathedral (Basilica of Santa Maria del Fiore) took up much of the rest of our day. It’s incredible to view from the outside and even more spectacular from the vantage point of the cupola (dome/duomo) or campanile (bell tower). The cupola was designed by Brunelleschi and is a major feat of art and engineering. Worth admiring from inside, despite the lines. Even with a Firenze card, you’ll need to make a reservation to climb the cupola at the ticket counter in advance, because it fills up very quickly.

We loved the views from the bell tower, which was designed by Giotto. The narrow stone staircases were not for the faint of heart, but the view from the top was beautiful. The interior of the basilica was beautiful, but did not take long to view. We also viewed the crypt, an unexpected but interesting detour. Make sure to tour the inside of the Baptistery of Saint John, and especially make time to admire ‘The Gates of Heaven’ – the famous golden doors of the baptistery crafted by Ghiberti.

We stopped at the Medici Chapel before heading across the bridge to Pitti Palace and Boboli Gardens. This could be considered the Medici portion of our tours: worship places, trailing gardens and a vast palace all once owned by the Medici family. They were breathtaking and had so much to see. Most of it is self-guided: just walk around until you get bored, then find your way out.

View from the top of Boboli Gardens

If you have some time before a meal, take a bit of time to wander through Florence’s central market or the leather district, both located near excellent restaurants. If your idea of shopping is more along the lines of H&M and Zara, stop near the Piazza del Mercato Nuovo – lots of great stores you’ve heard of, plus an open-air plaza including replicas of great Italian works of art. The Piazza della Repubblica is another fantastic bi-way to cross off your list while on your way to other major attractions. Here you’ll find something unexpected: a giant carousel in the center of historic square. Piazzale Michelangelo is the best place to catch a colorful sunset.



We loved Pasticceria Nenicioni for breakfast pastries in Florence in the midst of all the big attractions. Before heading to the train station, we stopped by Deanna, a small little cafe adjacent to the station. Ordering was quick and the selection was huge.


Trattiorio Mario was one of the most recommended lunch stops and for good reason – the line is always out the door but the food is incredible. Panino Mondiale is another hole-in-the-wall spot for a good meal.

Our host recommended Osteria dei Centopoveri to us and we loved the atmosphere and menu. The staff was especially nice, which was greatly appreciated. Down to earth and delicious. For pizza, you NEED TO GO to Simbiosi. The pizza is made in a stone oven right before your eyes, and the pretty brick interior is a nice place to relax at the end of a long, adventurous day. This is the only place in Italy that we went twice: it was so good, we got a take-out pizza on our last night in Florence.

La Giostra was an oft-recommended and beautiful dinner spot for a more elegant night out. It’s pricier, but if your aim is beautiful food in a beautiful setting, this is your spot.


Our favorite gelato stop in Florence was Gelateria Santa Trinita, located right on the end of the Ponte Santa Trinita bridge. This was the most delicious gelato in all of Italy. Gelateria dei Neri was another favorite.

Getting from Florence to Cinque Terre

We used the speed train to get from Florence Santa Maria Novella Station to La Spezia Centrale, the central train station of Cinque Terre. It had a lot of stops and took a few hours – the most fatiguing of our train rides – but it’s definitely worth it for a day or weekend stay in Cinque Terre. From La Spezia, you take a quick train ride between the individual cities. We went to Rio Maggiore first – it was the first of the city stops and took only 10 minutes to reach.


Boston > Lisbon > Milan > Florence > Cinque Terre > Florence > Rome

Cinque Terre (which translates to ‘five lands’) is a series of five colorful cliff side cities on the coast of Italy. It’s a short enough train ride to be a day trip from Florence, but there’s enough to see to spend a few days between the towns. The five towns are Riomaggiore,  ManarolaCornigliaVernazza  and Monterosso. We started our trip in Riomaggiore and ended in Vernazza, seeing the rest of the towns from the water by ferry.

I’d recommend starting in Riomaggiore and grabbing a bite to eat for lunch – the town has lots of fresh fried seafood served in cones for easy snacking while you walk. Take in the views and meander along the narrow passageways while admiring the locals hanging laundry from clotheslines outside their shuttered windows.

If it’s warm, it’s possible to climb onto the rocks and sunbathe or even take a dip. If we had more time, we would have opted to take a boat ride over to a small cove, where you can swim under a waterfall and snorkel.

I’d highly recommend admiring the cities from the water somehow – even if it’s just a ferry ride between the cities. The ferry ride from Riomaggiore to Vernazza was cheap, easy, and so completely unplanned – a small man hawking paintings told me to talk to his daughter, who spoke better English, who told me to come back in five minutes to buy my ticket, and when I asked “Do you need to reserve a spot?” She waved a hand at me.

Pretty much, ask anyone in the city “FERRY?” They’ll point you to a tiny ticket booth built into the side of a cliff, where you’ll pay 11 euros for a small slip of paper. From there, wait at the cliffs for your ferry to arrive. You’ll be shepherded in by bored looking Italians who won’t check your ticket and you and the rest of the giddy tourists will “ooh” and “ahh” at the views for 25 minutes while you bob along the coast.

Arriving at Vernazza, you’ll be greeted by a spectacular view of colorful homes, an old stone chapel and bell tower, terraces of lemon trees on the cliff side, and dozens of striped umbrellas. Here, there is a small sandy beach to dip your toes or go for a little swim.

Stop into Santa Margherita di Antiochia, the stone church right in the center of town for a quick tour. Then, venture up the hill in the narrow alleyways to Doria Castle (Castello Doria). Admission is just two euros, and the climb isn’t arduous. You’ll enjoy panoramic views of the city and the water from the top.

If you want a sit-down meal with a view, stop over at Belforte Tower. The views are breathtaking, and the experience is truly once in a lifetime. For more casual fare, we loved Pippo a Vernazza – a small, tucked away gem with the best pasta we had while in Italy. It’s a type of pasta unique to Cinque Terre, and we loved the pesto which is a specialty of the region. Don’t pass up the seafood cream pasta either, if it’s a special. The meals come in small, take-out containers that can be taken with you while you walk around the city.

Spend the rest of your time taking in views, stopping to admire the local shops, and of course taking your fair share of photos. To get back to Florence, take the local train to La Spezia, and then hop on the speed train to Firenze Santa Maria Novella.


Boston > Lisbon > Milan > Florence > Cinque Terre > Florence > Rome

Getting from Florence to Rome

From Santa Maria Novella station in Florence, we took a speed train to Roma Termini Station. The trip took about an hour and a half, and the views of the Tuscan hillside were a bonus. We liked using ItaliaRail to book our long train rides in advance and the process of boarding was seamless.

From Termini, you can switch to a metro to get to other parts of the city or go on foot. We walked to our Airbnb, and it was only about a 15 minute walk.


Our Rome Airbnb might just have been my favorites. It was so close to the Colosseum, and nestled in the small, non-touristy neighborhood of Rione Monti. Every morning and evening you’ll find locals milling about in the Piazza, where you can fill your water bottle and enjoy a morning pastry on the steps of the central fountain. We expected Rome to be our most tourist-laden destination, but this Airbnb made all the difference: we felt truly immersed in Italian culture.


On our first day in Rome, we were ambitious: we checked into the apartment and then headed straight back out to catch our reservations at The Vatican. The seat of power of the Catholic church, the Vatican it’s own small nation.

Of all the experiences in Italy, I think the Vatican is most worthy of a guided tour. It’s crowded, it’s huge, there’s a lot to see, and getting in between the many destinations is trickier than it looks: some are closed off to tourists without a guide, others require guests to stand in long lines outside. We booked our tour online with Headout.

Booking was easy, and all we had to do was show our QR code to staff outside so that we could skip the line and meet with our guide. You’ll be given a headphone to listen to your guide, and keep up with your group. Be warned, it’s notoriously busy with numerous tours in a million different languages, so you need to work to stay with your group.

Choose the major three tour: The Vatican Museums, Sistine Chapel, and Saint Peter’s Basilica. The Vatican museum doesn’t just hold Christian art: there were many ancient sculptures and Roman works. The Sistine Chapel is a must-see in Rome. Silence is required in this place of worship, and you can no longer take pictures of the interior. Michelangelo’s frescoes are incredible – particularly The Creation of Adam and of course The Last Judgement.

From the Sistine Chapel, you can enter Saint Peter’s Basilica with your guide. However, without a guide, you would have to exist the chapel and stand in another line to enter the basilica.

Saint Peter’s was stunning – our favorite of the day. It was much more massive than I anticipated – enormous, with so much to see. If you want a quiet moment, certain areas are closed off for worship, and you can enter to pray – just don’t chat or take photos in those areas. Here, you’ll find Michelangelo’s Pieta – a true masterpiece. As the name implies, Saint Peter is alleged to be buried on the site, underneath Bernini’s Baldacchino. Beyond the Baldacchino, you’ll see Saint Peter’s golden throne. The whole of the basilica has been touched by so many legendary saints, popes, and artists, it’s enough history to fill a day.

After admiring the basilica, we strolled in St. Peter’s Square – stopping for a minute to notice the Swiss Guard before leaving the Vatican city and going back to the main areas of Rome.

On Sunday, we went to church in Rome. We belong to the Church of Jesus Christ of Latter-day Saints, and there are meetinghouses all over the world. Since Rome is such a big tourist destination, the meeting was translated into many languages via headset. After our meetings, we spent an hour touring the Rome Temple and Visitor’s Center. The temple grounds are stunning and quiet and the visitor’s center welcomes all guests with free tours.

The rest of our day was spent touring the Colosseum, the Arch of Constantine, the Roman Forum and Palantine Hill in quick succession. These ancient ruins were awe-inspiring simply for their enormity. I would suggest doing an in-depth tour of one, and seeing the rest from the outside, unless you have several days to spend in Rome.

It’s a quick metro ride to other main tourist sites. I suggest getting a 24 hour metro ticket, which is only 7 euros, that will get you unlimited metro rides for a full day. This comes in handy when slinging across the city of Rome to major tourist sites without exhausting all of your energy. The metro is quick, clean, and super easy to navigate.

The Pantheon is well-worth a trip, and you’ll see many other small monuments along the way. It is free to enter and the line moves very quickly. The massive room is a major feat of engineering: the hole in the dome opens to the sky to allow in light and even rain, and there is a drainage system below it’s sloped floors. We only spent 15 minutes inside, but got a good feel for it.

You’ll also want to stop at Piazza Navona, a large public plaza featuring an Egyptian obelisk and The Fiumi Fountain. The Trevi Fountain and Spanish Steps are a short walk away and can also be admired from the outside – no tour needed. Be prepared for well-meaning crowds: everyone just wants to say they’ve seen it.



The best breakfast we had in Italy was served up at La Licata (Vei dei Serpenti, 165). It’s a tiny, hole in the wall neighborhood place in the same little square as our Rome airbnb. You could almost miss it, if you just walked by, as it doesn’t look like much. When you walk in, you’re greeted by fast-talking waitstaff at the counter, a la Eat, Pray, Love. Order a pastry (quickly!) and then enjoy in the piazza or en route to one of your destinations (you can see the Colosseum from it’s corner).


We loved getting a flatbread sandwich at La Piadineria ro eat on the go. The menu is large and simple and the prices are very good. It’s the perfect meal to eat in the middle of a busy day when you don’t want to spend a lot of time in one place.

Chicco di Grano was another favorite from our trip. The best pizza in Rome and wonderful pasta, too. Brett got the carbonara and said it was incredible. It’s a small place with beautiful outdoor seating. Service is slow and wasn’t the friendliest, but if you’re content to eat slowly and savor, it’s a good option for dinner.


We got our daily gelato (yes, daily) from Gelateria dell Angeletto right in our neighborhood. I realize all of our favorite restaurants in Rome are in the same block as our Airbnb, but it really was the best place to eat! The selection was huge and prices were very reasonable. It’s a small counter to order at, and then eat as you walk.

Venchi is a chain that has locations all over Italy, but we only stopped in when we were in Rome. Half chocolatier, half gelateria, this place is fun to explore and worth the hype.


To get from our Airbnb to the Rome Fiumincio airport, it was a quick metro ride to Roma Termini station, and then a direct line to the airport.

Rome Fiumincio is crowded, and it’s easy to get swept into the wrong line. Be sure to look for your airline when checking in, rather than your destination. The security & customs process was easy and quick – we only bought a few things while traveling, so we did not have to declare anything.

Our trip was a whirlwind week of museums, gardens, castles, dotted with pizza and gelato. I can’t wait to go back. Are you planning a trip to Italy? Which of these stops are on your list?

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