The ultimate two-week summer trip through Italy with tweens and teens
Buongiorno, adventure seekers! Ready to embark on an unforgettable journey through Italy with your tweens and teens? This itinerary takes you from North to South with stops in Venice, Florence, Rome and Puglia. It promises to keep everyone entertained, enlightened, and well-fed as you explore the best of Italy’s vibrant cities, stunning landscapes, and rich cultural heritage.
Day One: Fly into Venice, stay in Padua
I recommend taking your arrival day pretty easy. Use day one to settle into the time zone, and just enjoy the fact that you made it! Staying in Padua for the first part of your trip is perfect for that, especially if you’re foodies! The best quality produce from all over the country heads to their market first- because the locals can pay top dollar! For tourists it’s still affordable, often cheaper than in the tourist cities.
Padua is also just a short train ride over to Venice each day and a fraction of the price for hotels of better quality making it the perfect base for exploring Venice.
Being a walkable city, look for an Airbnb on the same side as the train station to make it easy to go over to Venice each day. I’d suggest somewhere between Piazza Garibaldi and Via Trieste. After check in, simply explore the city until dinner time which should be spent at the under-cover market of Padua, Sotto Il Salone.
Day Two: Learn to Row experience in Venice
Grab breakfast to-go and head to the train station, it’s time to visit Venice! Allow time to ohh and ahh as you walk to your meeting point for today’s adventure. After yesterdays flight, you’ll all be keen for some movement, and what better way than to learn to row a traditional Venetian boat in the canal?
Once you’ve worked up your appetite I recommend trying the typical street food, Scartosso, which is fried fish served in a paper cone! You can enjoy it as you continue to walk around Venice, hopefully getting lost just enough to enjoy the uniqueness of Venice.
If getting lost sends your anxiety into a spin, you could consider booking a walking tour of the Venetian Ghetto to learn the Jewish history in Venice.
A day in Venice wouldn’t be complete without a plate, or two, of Cicchetti. The small plates are served like Spanish tapas and can be found in bars all over Venice. The beauty with these is not only that they’re a local thing, but they’re also perfect for sharing so you can all try a bit of everything.
Once you get back to Padua, I recommend heading back to the market to pick up supplies for a picnic lunch tomorrow.
Note: Venice’s New Entry Fee
The new entry fee for Venice came into effect from April 25th, 2024. The €5 fee will be required for peak days and weekends during high season for all visitors over 14 years old entering between 8.30 am and 4 pm. Tickets can be purchased here.
Day Three: Murano and Burano
Since you have a packed lunch, today is the perfect day to visit two of Venice’s islands. You can join a guided tour, or simply take the Vaporetto which is like a public water bus. You can see the Vaporetto timetable here, and you’re looking for line 12.
This day out is not only fun because of the unique public transport, but in Murano you can watch glass blowing or even by a custom piece. Burano is home to lace-making but maybe more exciting for your teens is the Instagram worthy backdrop of the colourful homes that line the canals.
Note: Avoid going to Murano on a Sunday which is the glassblowers rest day. Switch days two and three if needed!
Related: If you have more than two weeks, see my other recommendations for places to visit in Northern Italy
Day four: (Travel/Rest Day)
You’ve fit a lot into two days. If you’re go-go type people, you could spend another day in Venice, or make a stop in Verona on your way down, but I recommend you take it easy instead- you’re in Italy after all! Have an Italian-stlye breakfast (coffee and cake!) in Padua at the famous Pedrocchi Café, or at least step inside for a look.
If you’re happy to drive in Italy, and you want to make some stops today, pick up your hire car from Padua, otherwise, catch the fast train to Bologna (see alternate options below).
Day five: Emilia-Romagna
I’m giving you a few options for today so you can choose the one that suits your family best.
Option one: Fast cars
You’re in Emilia Romagna, aka “The Motor Valley” and if that takes the interest of your family, a day trip to Modena should be on the itinerary to visit the Enzo Ferrari museum, Maserati and Lamborghini factories. If you don’t have a hire car, there are plenty of tours that leave from Bologna, or you could go with a private driver.
Note: If you are hiring a car you might prefer to pick it up in Padua and then stay in Modena instead of Bologna.
Option two: Food lovers-paradise
If fast cars couldn’t be further from your idea of a dream vacation, then spend today in Parma comparing different ages of Parmigiano Reggiano, and tasting the finest Prosciutto di Parma. If you’re on a self-driving tour, you can also stop by Modena for a balsamic tasting! You can get to Parma by train and then join a tour if you aren’t driving.
Note: If you are hiring a car you might prefer to pick it up in Padua and then stay in Parma instead of Bologna.
Option three: Add a day to Florence!
Note: You could go to Florence tonight, but since accommodation is crazy expensive, and you're in foodie heaven- I’d recommend staying in Bologna again to enjoy another great dinner.
These clients adore Florence- so what better backdrop for their family portraits than under the Tuscan sun?
Day Six: Florence
Arrive in Florence early, this is a big day! Leave your bags at your hotel or in a locker at the station and beat the crowds and the heat! Spend the morning walking around Florence, you’ll go by the leather market, Cathedral Santa Maria del Fiore (Duomo)- a perfect place for your selfies, pop your head into Palazzo Vecchio, and don’t forget to keep an eye out for the “Wine Windows” as you stroll through the city! If your teens are interested in perfume, check out the 16th century pharmacy- Officina Profumo Farmaceutica di Santa Maria Novella.
Lunchtime will be near so grab a panino alla porchette at one of the many panino bars (and no, I don’t recommend the Instagram-famous “All’Antico Vinaio” which has a huge queue for a very non-traditional style sandwich), and enjoy it as you walk along the Arno River before queuing for Uffizi.
Uffizi Gallery is the perfect place to escape the afternoon heat. It’s really huge so if you’re art lovers, the afternoon alone won’t be enough, but otherwise you can prioritse the famous masterpieces like Botticelli’s “La Primavera” and “birth fo Venus” (both of which brought tears to my eyes!), Leonardo Da Vinci’s “Annunciazione” and pieces by Tiziano and Raffaello.
The balcony overlooking The Duomo is absolutely stunning so do allow time to pop up- or better yet, use it as a break during your gallery visit.
After Uffizi, you can inspect the windows of the jewellery stores along Ponte Vecchio before heading back to your hotel for a rest before dinner, or if it’s not too hot, spend the late afternoon relaxing in Boboli Gardens (be sure to check the closing times depending on the month you’re visiting).
HINT: You’ll want to book all your attraction tickets for Italy pretty far in advance, and that is especially true for Uffizi to ensure the timeslot you want is available.
If you’re interested in seeing Michaelangeo’s “David”, then visit Galleria dell’Accademia today too. If you want to see more of the Accademia, I’d suggest going tomorrow instead so you’re not rushed.
I photographed this family on the Funicular in Certaldo during their family portraits. It was their first time ever on a Funicular so it was a perfect photo as part of their album to tell the story of their Italy vacation.
Day Seven: More Florence, or the Tuscan countryside
Option One: Tuscan Countryside
Art lovers will appreciate another day (or week!) in Florence’s galleries- but if you’ve hit your limit of artworks and cathedrals, maybe a day in the countryside is more suitable for you? For food lovers, you can join a truffle hunt followed by a cooking class at an agriturismo. Or how about cycling through the hills of Chianti? Ideally you’ll have a hire car for that- or, you can join a day tour.
Option Two: Florence
If you’re spending today in Florence too, you may like to spend it back at Uffizi. You can also climb the 463 stairs to the Top of Florence's Duomo. If you’re interested in fashion, go by the leather school or consider sending your teenagers on a fashion tour while you enjoy a glass of wine! There are also plenty of art and cooking classes if that suits your family best.
Have longer than 2 weeks this trip? Consider extending your time in Tuscany. Base yourself at my favourite agriturismo in Tuscany and add a day trip to Pienza and Montepulciano, and spend another day in Siena.
Siblings play in front of the Leaning Tower of Pisa, a moment these clients want to remind them of forever so we printed and framed it for their home.
Day Eight: Tuscan hilltop Villages OR Lucca and Pisa
Option One: Tuscan Villages
If yesterday you went to Chianti with your hire car, it would be best to stay there the night, and tonight too. That will allow you to really explore the area further, and today you can visit San Gimignano (and taste “The world’s best gelato”) and Monteriggioni. I also love Certaldo which is lesser known but jaw-dropping nonetheless. You can catch the funicular up to the historical centre, admire the tops of the “sand-castle style” walls and enjoy a gelato or a glass of wine. If you do this trip you’ll fly tomorrow morning from Florence to Bari so it would be best to stay in Florence tonight.
Option Two: Lucca/Pisa
Alternatively, you can catch a train from Florence to Lucca. Lucca is a small city that has quite an “authentic” feel. You’ll effortlessly find great food, and enjoy your time just walking the city. The city walls are completely intact and you can either walk along the top or hire bikes to ride! Always a hit with tweens! From Lucca you can train to Pisa which I recommend during in the early evening once the tourists have gone. Piazza dei Miracoli is even more beautiful when it’s lit up at night! If you decide to do that, you could stay in Pisa tonight before catching your flight tomorrow morning to Brindisi/Bari. If your flight is in the afternoon, consider staying in Lucca instead and visiting Pisa before you fly. There is luggage storage at the station.
Day Nine: Getting to Puglia
The heel of Italy’s boot has become extremely popular in recent years, and for good reason. The beaches are gorgeous, the villages are like something from a film, and the food is next level. The region is served by two airports; Bari and Brindisi which have direct connections to most cities in Italy and throughout Europe. You can fly into either, and stay anywhere on the East Coast.
To truly see Puglia you need a hire car or private driver, but if you prefer not to drive and you’re on a budget, I’d recommend staying in Monopoli or if you want the town only as a base, maybe Bari. You’ll need a private transfer to get there, but then it is on the train line so you can visit Lecce and Bari easily. If you’re driving, it’ll be best to base yourself at a Masseria/agriturismo near Ostuni which is quite central. The most amazing family-friendly place is Borgo Egnazio.
Two teenage sisters learn to sail during their time in Puglia
Day Ten: Sailing/Boat Hire from Brindisi
Puglia is all about the sea, but the beaches are packed all summer long so the best way to enjoy the water, is on it! You and your teens can learn to sail, or relax while the pro’s do it for you! Alternatively, you can hire a small boat (no licence required). Don’t forget to take a picnic lunch with supplies you picked up yesterday. Almost all the coastal towns have boat hire, but I recommend this sail boat in Brindisi.
Day Eleven: Ceramics, Archaeology and a Fairytale Village
About 30 minutes from Ostuni is an inland town called Grottaglie. Famous for its ceramics, almost every store in the historical centre is a ceramics workshop, with artisans at work. I recommend heading their in the morning. You can watch them at work and purchase finished pieces.
After Grottaglie, drive to the port city of Taranto. The old town is split by a bridge, and I recommend you go for a walk on both sides- especially with teenagers. It’s quite shocking to see the disparity betwen the side which has been renewed, and the side which has been all but abandoned by the commune- the area lived by the local people. If you’re into ancient history, the National Archaeological Museum of Taranto showcases a fantastic display into the history of Southern Italy.
Taranto is a great place to grab lunch. It’s one of the least visited towns in Puglia, so the restaurants are authentic, and of great value.
From Taranto head up to Alberbello to see the magical Trulli town at sunset. The unique white wash houses are made of stone with a cone-type roof. The story goes that the locals built them this way to avoid paying land tax! Apparently when the inspector was on the way, they’d tie rope around the top of the cone, and with a few pulls (I’m guessing by an Ox!) the whole house would come tumbling down. Once the inspector left, they were quick to rebuild- taxes avoided!
In contrast to Taranto, Alberobello has seen a huge tourism boom so I’d avoid having dinner in town. Instead, stop by Locorotondo on your way back. Although it’s also become popular, you can still find authentic restaurants down side-streets! Just be sure to read the menu because you can still find horse on the menu
Note: This plan won’t be achievable with public transport. You could join a tour to Alberbello though! Alternatively, you can look for a private day tour.
Capturing the in-between moments in Puglia for this couple during their photoshoot
Day Twelve: Salento
The southern half of Puglia is called Salento. There you will find the stunning baroque town of Lecce about an hour’s drive from Ostuni. Most of the big cities in Puglia are harbours, clearly reflected in the way of life, but Lecce is inland and was a city for academics and poets, perhaps another reason beyond its beauty that it’s often called “the Florence of the South”.
The architecture alone is a reason to visit Lecce, but nowadays the boutique shops in the old city offer wonderful (high-end) shopping too.
You can reach Lecce by train from Bari, Brindisi or Monopoli, but if you have a car, I recommend driving because then you can continue your day trip further south. Just be sure to park outside the city walls to avoid a ZTL fine!
If you arrive in Lecce early which I recommend, you can start your day local style with “Caffe in Ghiaccio”, or what has become known throughout Italy as “Caffe Leccese”. It’s coffee on ice with a splash of “almond milk” which is actually a syrup.
With a car, you can also get to my favourite gelateria in all of Italy, in the suburbs of Lecce. It’s called Le Mucche Volanti and absolutely worth the detour. You can also purchase fresh mozzarella and burrata from them (go early to watch them literally pull it out of the water for you!) and delicious fresh bread next door. There’s often an Ape (an Italian tuk-tuk) parked around the corner too which is full of fresh, seasonal vegetables- including tomatoes for the sandwich you could make for lunch from all these fresh goods.
Organised with your picnic lunch, you can now make your way to the coast. First coastal stop, Grotta della Poesia. The thrill-seekers in your family will particularly love this stop as it’s a natural sea-water pool that you can jump into and then swim in a cave. For those less adventurous, you can walk down too!
After the refreshing, perhaps exhilarating, dip make your way to Otranto. It’s beautiful like Lecce, but on the crystal clear sea. You’ll find an abundance of seafood restaurants for dinner too.
Day Thirteen: Fly or Fast Train to Rome for Ancient History
Take your hire car back and make your way to Rome (you don’t want to be driving there)!
My husband and in-laws (who are Puglian) laugh at me, but I honestly find the train the most comfortable way to travel in Italy. They’re usually city-to-city, you don’t need to arrive very early. There’s no checked baggage to get lost and unless there’s a strike, they’re efficient! There is a fast train from Lecce (also Bari) to Rome, and without the airport hassles, it’s usually quicker and less stressful than flying between those two cities. They’re also frequent so you can choose a time which suits you!
About Rome- well clearly you can’t come to Italy and not see any of Rome. This itinerary will only allow you to see the highlights, but at least it’s a start!
With that in mind, I’d recommend getting to Rome as early as possible to make the most of your time. Check in to your hotel, or at least drop your bags, and then head straight to the Roman Forum hopefully before the hottest hours of the day (which is normally from 4-6pm in high summer). From there you’re right beside the Colosseum so when the sun becomes unbearable, you can play gladiator! (As with all the sites, you’ll want to have pre-booked a ticket). By the way, if you’re looking for a family-friendly tour guide in Rome, I highly recommend Mariaclaudia so check out that link.
Next up are the Catacombs since it’s one of the few sites where you can escape the Roman heat! If that’s not your thing and you’re up for another gallery, head to Villa Borghese instead!
For dinner, please, avoid the tourist traps and go as far away from the sites as you can! If there are photos on the menu, or if it’s written in English, it’s a good sign it’s not authentic. And Roman food is so good, you really want authentic!
You’ll all be exhausted by now no doubt, but I highly recommend you go for a walk after dinner. Some how, The Eternal City becomes even more magical after dark. The monuments are lit up and the city is actually quiet making for an out of this world walk.
Family photos aren’t only about the kids! I posed this couple naturally in front of the Colosseum so they can remember how they felt about each other in this moment too
Day Fourteen: Exploring Ancient Rome with Teenagers
It’s your last day in Italy so you’ve got to make the most of it! Start your day bright and early with a stop at the Spanish steps and Trevi Fountain (as close to sunrise as you can!) and then get to The Vatican for your pre-purchased 8am time-slot tickets. Be aware that if you’re also going into the Sistine Chapel there can be a huge line after 10 am which is completely in the sun- hats and sunscreen essential! After your morning with the Pope, you can spend the rest of your time exploring the corners of Rome before heading to catch your flight home.
Have time to extend your trip? My recommendation would be to extend your time in either Tuscany or Puglia because both offer a lot more than this whirlwind itinerary! Prefer to travel slowly? Consider cutting one section to allow more time in the other regions.
Vacations gift us the rare space to spend quality time together.
Hold onto these moments through quality photographs on your walls.
Travelling with family, especially tweens and teens, can be a balancing act of interests, energy levels, and new experiences. Yet, Italy’s diverse offerings have made it easy to keep everyone entertained and engaged.
This unforgettable two-week journey through Italy is full of memories to be made and the wonders to experience- memories you’ll want to hold onto forever. From the gondola-filled canals of Venice to the rolling hills of Tuscany, the ancient ruins of Rome to the sun-kissed beaches of Puglia, this trip is designed to ensure the whole family has a wonderful time- even your teenagers! It’ll be nothing short of epic and what better time to capture your family portraits than while you’re all having the best trip of your lives, bonding as a family.
At Classico Portraits, I specialise in photographing families truly enjoying these precious, real moments. I’ll photograph that cooking class in Tuscany, the sailing trip in Puglia or the rowing experience in Venice. Or perhaps it’s your family bond captured against the Italian backdrop that would be special to you.
If you’re coming to Italy soon, I’d love to customise a photoshoot for you too. Learn more about my vacation photography in Italy.
P.S. I do not receive any commission for this blog post I just wanted to share these great experiences with you all!