Traveling through Italy

TravelTrip
Written By Gabrielle Severiano

Italy…

It is the perfect European destination, an amazing fall or summer getaway, and one of my favorite vacations I’ve ever had. 

If you spent any time on social media in ‘Summer 22’ then you probably saw that Americans returned to Italy… in the thousands.

After two years of living in the global pandemic, Italy opened its borders again to travelers last year but many were still hesitant to make vacation plans. This summer that changed! And it made me properly jealous and ready to return again!

When I went to Italy in 2017 it was for the first time, so I had a lot of ground to cover! I needed to see the main sites in Rome and Florence, but also the beautiful landscapes of Tuscany and the Amalfi Coast.

My travel to Italy spanned 17 days in total, and I tried to make the most of the opportunity of being there. I knew I couldn’t go to every destination on my Italian bucket list, so we focused mostly on the South in the hopes that one day we would go back to some of the areas in the North.

But I left feeling like I truly saw the best of what Italy had to offer, and I’m so excited to continue exploring it when I go back next summer! 

What I loved about Italy is what a range of experiences and activities it offered….

Wine tasting in the vineyards of Tuscany

Sailing through the lovers arches in Capri

Gazing at Michelangelo’s ceiling of the Sistine Chapel

…. and all while experiencing the most delicious fresh food and wine imaginable. 

There are many different ways to do it, but I think I mastered a first timers trip to Italy pretty perfectly.

So how did we cover over 10 different places in one vacation?

I’ll share my full two week itinerary, with all the locations, accommodations, and transportations you’ll need to reference to plan this trip on your own! You give me two weeks, and I’ll get you to all the best spots.

When To Go

Best time to travel is anywhere from May through October. Keep in mind that the busiest and most expensive time to go is at the end of the summer, since most Europeans go on holiday during the month of August. 

I traveled at the end of May over Memorial Day Weekend through the middle of June. I flew Al Italia, which is not a comfortable airline or experience but we found really affordable flights for under $530 roundtrip.

Italy Itinerary

Here is the full shebang:

Fly overnight into Rome! 

Rome - 4 Nights

Florence - 2 Nights

Tuscany - 3 nights 

Sorrento - 5 nights *with boat days to Amalfi Coast and Capri

Positano - 1 night

Fiumicino, Rome - 1 night (close to airport for early flight the next morning)

Rome

We began our trip in the eternal city of Rome.

Many people who travel to Rome claim to like other cities, like Florence, better. On the contrary, it was my favorite of the bigger cities that we traveled to in Italy. I LOVED it.

Maybe it’s the nerd in me who loved learning Italian history, but I felt intrigued by all the sites, the museums, and of course the restaurants. It’s a big city full of some of my favorite stories from history, an amazing culture, and the most beautiful Roman architecture. Best of all - you can begin your journey of eating through Italy here with some incredible restaurants.

My biggest recommendation for traveling through Rome for the first time is to purchase a ROMA PASS right when you get to the airport. It’s an affordable upfront fee that looks like a metro card, which is administered by the cities tourism office. It allows you to take a bus around to all the city and skip the lines at the major sites! So worth it if you will be there for over 2 days.

Things to do in Rome

Day 1: Here are some things to do in the center of the city

  • Walk the Spanish Steps 

  • Make a wish at the Trevi Fountain

  • Tour the Pantheon

  • Shop around at the best Italian designers

  • Dinner at Ristorante Abruzzi or Armando Al Pantheon (where you can eat outside while listening to live music)

  • See the Colosseum at dusk/night

Trevi Fountain

Day 2: Seeing the Colosseum - One of the 7 world wonders

  • Tour the Colosseum first thing in the morning

  • See the Roman Forum 

  • Lunch at Osteria da nerone (by colosseum)

  • See Santa Maria Maggiaore church

  • Visit Piazza Navona

  • See St Ignazio Cathedral

In Rome we stayed in a quaint Airbnb in the center of the city, right by the Spanish Steps and Trevi fountain. It was nice to be so central to these bustling areas where there is a lot to do. I’d also recommend staying by Campo de Fiore or Piazza Navona. Great restaurants and entertainment nearby!

Day 3: The Vatican & Trastevere

  • Cross the River Tiber to Castel Sant’Angelo (an easy subway ride away) Tour the castle and sip a cappuccino at the cafe on the top of the while overlooking the Vatican!

  • Vatican Museum Tour 2pm of St Peters Basilica, explore Vatican City (schedule and purchase in advance!)

  • Stop by 200 GRADI or Trapazzino for lunch

  • Explore the neighborhood!

  • Dinner at La Fraschetta di Castel Sant’Angelo

Day 4: Villa Borghese

  • Your the Borghese Museum and bike around the Gardens (purchase tickets in advance)

  • Visit Campo de Fiore

  • Dinner at Trattoria Der Pallor 

Rent bikes to tour the park around Villa Borghese!

Eating through Rome!

Firstly, one of my favorite meals or experiences in Italy was our dinner at Trattoria Der Pallor! It’s basically an old Nonna cooking traditional Italian food where no menu exists. She just cooks you whatever she’s in the mood to make, some pasta, some vegetables, some meat. The dishes were phenomenal.

Here are some top dinner recommendations in Rome:

Casual Food

Amazing Pizza

Italian meats & sandwiches

Best Pastries and Gelato in Rome

Florence

On our 5th morning in Rome we checked out of our Airbnb and headed to the Termini train station to make our way to Florence. The experience was so simple and the ride itself was comfortable and easy. I would highly recommend using it! You can reserve tickets online in advance.

Again my biggest tip to see all the museums in Florence stress free is to immediately buy the FIRENZE pass when your train arrives to Florence. You’ll be skipping all the lines

Where we stayed:

In Florence we decided to stay in the Santa Maria Novella area, which we picked because it was close to the train station (Firenze Santa Maria Novella) where we would be arriving with all our luggage.

We stayed at Hotel Alba Palace for two nights, which was a very unique hotel. Our family liked that the ‘superior quadruple room’ was spacious enough for 4 adults, with a loft with the second bedroom on its own floor. It also had like a massive hot tub jacuzzi with a whole painted sky which was interesting… but I would recommend it for the convenient location where we could walk to everything, and the solid breakfast buffet that was included.

Here are some other hotels I would recommend in Florence:

All of these hotels have great locations and stunning rooms, some with outdoor spaces overlooking the Duomo.

Day 5: Exploring the highlights of Florence

  • Lunch at iL Desco (healthier/fresh ingredients, but great food and has a Michelin star)

  • Tour the Duomo (need tickets to enter - buy in advance!)

  • See the Statue of David at Ufizi Gallery

  • Visit the Academia Gallery

  • Dinner at La Giostra (recommend!)

  • Walking the Ponte Vecchio in the evening which usually has live music!

I will say, for me Florence got a little boring. But I think that was because we crammed a lot of museums into one day. But there is so much world famous art in this city, and it would be a shame not to see it if you’re a first timer!

Day 6: Tour the Boboli Gardens

  • Do a morning tour of the Piti Palace and Boboli Gardens

  • Get lunch at Gusta pizza nearby

  • Tour the Cathedral of Santa Maria del Fiore

  • Amazing shopping for leather goods!! I bought a jacket at Massimo Leather (he has good deals for students and referrals so say that I recommended you!)

  • Dinner at Acqua Al Due (2)

  • Before you go, make sure to see the amazing views of Florence from Piazzale Michelangelo

If you aren’t planning on spending a few days in Tuscany, then I would at least recommend a day trip from Florence to Chianti!

The Best Food in Florence

  • Eat the most delicious sandwiches at All’antico Vinaio (prepare for a line, but its worth it)

  • Enjoy the best pizza in Florence at Gusta Pizza

  • The most flavorful blueberry steak at Aqua al 2

  • Dine at La Giostra for the delicious pastas and the famous Florentine steak. This was one of the most amazing meals of my life, and we adored the staff!

  • Grab a glass of vino from one of the Renaissance wine windows at Babae

  • For fancy pastries thats as pretty as the art of Florence itself go to Dolci E Dolcezzi

  • The best gelato in Italy is Gelateria La Carraia and we also loved Gelateria dei Neri

  • And though I’ve tasted all the deliciousness mentioned above and can attest to it’s goodness myself, I’ll also drop in one of Stanley Tucci’s favorites (because he’s the best). Enjoy the simple delights from Osteria Cinghale Bianco like Tuscan white bean soup.

At the end of our time in Florence we picked up the car in the city and headed out to Tuscany. Once you have a car, it’s easy to do trips from Florence, and there are so many options. We decided there was too much to see all at once. But here are some of the places at the top of my list!

To the west there is Pisa where you can see the leaning tower, Genoa, Portofino, or Cinque Terre.

In the north you can go to Bologna, Milan area and the lakes, like Garda and Como.

Or head to the east towards Venice!

Tuscany

Next up on our trip was the beautiful region of Tuscany, south of Florence. We spent a few days there exploring different towns including San Gimignano and Montepulciano, both which were spectacular!

San Gimignano

Day 7 - Begin the drive south from Florence to Tuscany

  • Soon enough we pulled off the highway and onto country roads, with beautiful green rolling hills of Tuscany, as far as the eye could see. Eventually we found ourselves in the region of San Gimignano, and turned onto the winding dirt road towards our home for the next few days, Fattoria Poggio Alloro

  • We spent some time relaxing by the pool

  • Enjoyed an afternoon wine tasting, including some of the most delicious varieties of wine in the world. My favorite was their Vernaccia, which is famous from this region!

  • End the night with a fun group dinner at Fattoria Poggio Alloro with the other guests

Fattoria Poggio Alloro was recommended to us by our family friends who stayed their before us, and spoke highly of the experience. Our favorite part was that it’s a family owned business passed down from generation to generation.

Though it was a small and simple bedroom, the property itself was idyllic. I’ll never forget getting out of the car the first day and seeing the view of San Gimignano reflecting off the sparkling waters of the in ground swimming pool, and cows and horses grazed in the distance.

Looking to stay in San Gimignano? Here are some other hotel options in the area?

Day 8 - San Gimignano

  • Start the day with a fresh breakfast on the farm

  • Explore the beautiful town of San Gimignano, with shopping around town and tasting some of the country’s best gelato

  • Highlight of the day was a pasta making class at Fattoria Poggio Alloro, taught by the family who own the property. After learning how to create the fettuccini we sipped wine and tasted fresh tomato crostini’s in the courtyard overlooking the landscape of San Gimignano

  • In the evening we gathered with the other guests and enjoyed a delicious homemade meal including the fresh pasta we made together earlier that day.

Top Vineyards in Tuscany

If you are looking to sample even more vineyards, I highly suggest taking either a group or private wine tour through the region! There are so many amazing DOCG wine’s in the area like Brunello, Chianti, Vino Nobile etc to sample across a number of incredible vineyards. Here are some of the best options in the area!

Montepulicano

Day 9 - Drive to Montepulciano with a stop in Siena

  • On the way to our destination we stopped in Siena for a little detour

  • Arrive in Montepulciano and explore this quintessential Tuscan town!

  • Visit the Sanctuary of the Madonna di San Biagio

  • Take a tour of the underground cellar at Cantina de' Ricci

Where to stay in Montepulciano

We found a great hotel called Palazzo Carletti which I would highly recommend. It was located right in town, and used to be the private residence of Montepulciano’s nobility in the 18th century. When restored in the 1900’s, the walls behind the sheetrock revealed beautiful fresco paintings still in tact. Though it’s a small luxury boutique hotel, I would definitely book here! If you need any more convincing, the view was great from the main lobby, the hotel rooms were beautiful, and there was an amazing bathtub in the bathroom.

Best Food in Montepulciano

This is one of the highlights of this region - it’s delicious produce! The cheese, the bead, the meats, and that INSANE wine. Be sure to sample the Vino Nobile while you’re here. Plus I love all the outdoor dining in the street you see as you walk through the narrow roads of the walled city. It’s so romantic!

There is nothing like those views of the Val d’Orcia

Here are some of the other areas in Tuscany worth Exploring!

We didn’t make it to everywhere on our long list of vineyards or towns to explore. But there is always next time!

  • Montalcino

  • Orvieto

  • Chianti

  • Pienza

Villa d’Este

Day 10: Drive to Sorrento, stopping in Tivoli

It’s a long drive, so you might as well have something to look forward to. For us that meant stopping in Tivoli at the beautiful Villa d’Este. Do those fountains look familiar? Probably because this was featured in the Lizzie McGuire movie when Paolo takes Lizzie to the gardens to impress her.

I’m just saying, I was impressed! Beautiful gardens - could you imagine being the lucky bastards who lived here? And on top of that, it sits on the top of a hill overlooking the most magnificent views of Tivoli. It’s also one of many UNESCO world heritage sites you’ll see on this trip.

Arrive in Sorrento!

Day 10 continued - arrive in Sorrento

  • Arrive in Sorrento by the late afternoon and check into your accommodations

  • Watch the sunset at Bellevue Serene

  • Dinner at one of the restaurants along Marina Grande or Marina Piccola

We decided to stay in Sorrento for several reasons. First, it’s easy to see that it’s a gorgeous city on the water with fantastic views of Naples and Mount Vesuvius. It also has the most amazing food, and our neighbor Massimo grew up here so we had a ton of recommendations from them going into the trip! We were able to spend a day with his friend who drove us all around Naples and Sorrento to provide a unique experience, from a locals point of view.

Where to stay in Sorrento

There are some gorgeous hotel options in Sorrento, but also some fantastic Airbnb’s. We did the latter, and rented a beautiful home from an Airbnb Superhost - Giuseppe. I would highly recommend his properties! We loved how the space was affordable, large, clean, and prepared for our arrival. Plus Giuseppe was available to assist us with check in and check out, and offered help and recommendations along the way! Here are just a few of his great options.

And here are some of the most luxury hotels nearby if you are planning a Honeymoon or special trip. My #1 choice the next time would be the Bellevue… add it to your bucket list too!

Day 11: Boat day in Capri

  • Start the day at the harbor in Sorrento, boarding the tour from Luca’s Boat Tour at 9am

  • The full day Capri tour will not only take you to the island but it’s the best way to enjoy the journey there and back. There’s snorkeling, swimming, sunbathing and drinking on the boat

  • Take the chair lift in Mount Solaro to see Ana Capri

  • Highlights for me included boating thru the lovers arch and Faraglioni rocks, and seeing the Blue Grotto!

What to Expect on Luca’s Capri Island Boat Tour

This day was absolutely incredible. It’s perfect if you’re planning on exploring a lot of Italy in one trip and don’t have the time to extend a few days in Capri. Even if you’re staying, I’d still recommend a boat tour around the island as it’s the best way to see it and they are really fun!

  • The tour starts from Marina Piccola in Sorrento. You then go along the peninsula’s rocky coastline, Massa Lubrense and Mitigliano Bay and enjoy an aperitif on the boat.

  • Then you have lunch at a restaurant when you arrive at Marina Piccola in Capri, followed by 3 hours to yourselves to explore the island. We took a ride around town, did some shopping and then took the chair lift.

  • Once you’re back on the boat Luca will take you to all the main grottos around Capri - white, green, and blue!

  • Back on the boat you will slowly return in Sorrento at the sunset time! There will be free time to swim and snorkel before heading back

Capri is great, and I would recommend staying a night if possible! If you do here are some additional stops I would recommend!

Where to stay:

Day 12: Day trip to Naples

  • Day trip to Naples and tour Pompeii with a private driver. As mentioned, we had my neighbors friend as a driver who rocked!

  • First we stopped in Pompeii and took a tour of the UNESCO world heritage site, and the amazing preservation of this town after the eruption of Mount Vesuvius above it

  • We then toured the Castel dell'Ovo on the peninsula to take in the views of Naples

  • We stopped for lunch on the water, and picked up some pastries before heading back to Sorrento!

Naples is known for some of the best pizza in the world, so you have to try it when you’re here!

And try the fried pizza while you are there too.

Best Dining in Sorrento

The food is so good here, from the lemons to the tomato’s you truly get the most fresh produce from the soil of this region. And of course the freshest seafood!

Day 13: Sorrento & Amalfi Coast Boat Tour

To see more of the Amalfi Coast in a short time period we decided to do another boat tour. The itinerary was totally different which we loved, so that nothing felt redundant to our day in Capri!

  • Pick up from Lucas Boat at the Sorrento marina and boat around the peninsula to Amalfi and Positano

  • The trip begins with a one hour stop in Amalfi to see the Duomo and the Paradise Cloister

  • Then the second stop is about two hours to spend exploring Positano!

  • The highlight for me was boating into the beautiful Furore Fjord. Next time I would love to also stop there and have time at the beach!

  • The afternoon included trips to see the picturesque hamlet of Praiano, the small Fjord of Crapolla and the enchanting Isle of Eduardo de Filippo.

  • The boat ride itself was amazing! I loved snorkeling in the Li Galli Islands, and stopping along the private beaches to swim

It was fantastic. I would highly recommend this tour especially if you don’t plan on staying overnight in this area.

Positano

Day 14: Leave Sorrento and head to Positano

When I visited with my family I begged and pleaded that we do one day in Positano. I knew the hotels were more expensive than where we had been staying in Sorrento since it’s such a popular destination, but I didn’t think 2 hours on a tour would be nearly enough. We decided to spend our last night in the Amalfi Coast in Positano. It was absolutely worth it!

Best hotels in the Amalfi Coast

Our family stayed in a beautiful hotel, Conca d’Oro with gorgeous views! The only downfall was that it was in a more quiet and secluded area, which could be ideal depending on what you are seeking! However this meant more travel time to get into the center of Positano, where we wanted to be.

Here are some of the best luxury hotel options in the area:

Best Areas in Amalfi

Positano and Sorrento where I stayed are both amazing and I would highly recommend them! But here are a few other great towns to spend a night in nearby:

  • Ravello

  • Praiano

  • Conca dei Marini

Best food in the Amalfi Coast

In addition to the restaurants I mentioned above, if you have more time in Amalfi then check these out!

  • Lo Scoglio - This is one of Tucci’s favorites from Searching for Italy!!

  • Rada - Positano

  • Santa Croce - like da Fernando it’s accessible only by boat!

Day 15: Leave Positano for Rome

As sad as it was to leave, it was time to move onto the last and final destination. Our return to Rome was long, but we broke up the drive with a stop along the way.

  • Drive from Positano to Rome

  • Tour Ostia Antica which is one of the best preserved ancient roman civilizations

  • Check into Hotel in Fiumincino close to the Airport. We stayed in Hotel del Mare but I would recommend staying in Hotel Isola Sacra

Day 16: Head to the airport and return home

  • Travel to Termini Airport in Rome for morning flight, drop off car at the airport on the way!

La Bella Vita

And what a beautiful life it is there. You can truly relish in the simple pleasures. As CHEESY as it sounds, this place just brings it out of you. You feel fully grateful to be there.

Italy is truly an amazing vacation, and I had the best time with my family exploring it.

So then, are you tempted to start planning your trip to Italy? It’s the perfect time to book your summer vacation next year and capitalize on early flight deals. 

Next summer I’m planning a vacation to return to Italy, and bringing my husband for his first ever visit! We’re both Italian, and I know it will be amazing not only showing him what a beautiful place it is, but also experiencing our culture together! The best part is I can relive some of my favorite parts of the last trip, while planning to explore even more new areas.

I can’t wait!

Xx Gab

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