Family Vacation Destinations – Italy – 1 Country 3 Itineraries

italy itinerary

Hi! How is your day? Well, I’m about to make it even better. You and I are about to take embark on the quest for your perfect itinerary of one of the world’s most beautiful and family friendly European vacation destinations.That’s right. We’re planning for Italy!

Italy is one of the best international destinations for a getaway with little ones, teens, or just the adults. This beautiful country has so much to offer visitors. From the rolling hills of Tuscany to some of the world’s finest art museums, Italy has it all.  Oh, and gelato! Don’t forget the gelato.

Ok, now that we have the important stuff out of the way (dessert), I have three separate itineraries for you. Simply choose the one that best suites your needs!

Itinerary 1 – Explore Italy With Your Children

Your Italian getaway begins in the Assisi area of the Umbria region. I suggest this area because it is somewhat centrally located. This will be your home base throughout your trip. Assisi is a beautiful small hillside town that gives visitors a great sense of real Italian culture. This tiny town was once home to Saint Francis, one of the most widely known saints of the Catholic faith. With its beautiful Basilica ,quaint cobblestone roads, and its ancient Temple to Minerva , Assisi will make a lasting impression.  While the area does have its fair share of tourists during the day, the early mornings and evenings are abuzz with locals. So, have a seat at the town square and get to know the locals. There’s no better way to experience a new culture.

  • Lodging – I highly recommend staying in an agriturismo when vacationing with kids. Agriturismos are generally family-run working farms that have opened their homes to visitors. Think of them like a bed and breakfast. This type of lodging is great when traveling with little ones. The large outdoor spaces and farm activities offer kids plenty of space to run and play.
  • A quick internet search will reveal some great bargains on agriturismos in the area.
  • Transportation – Rental cars are a great way to tour the small towns in Italy. However, if you are planning to venture into the larger cities, you might consider taking one of the many buses or trains. Driving in these areas can be umm…interesting…if you are not familiar with the rules of the road and how to navigate the unique traffic.

***Funny side note – While we were visiting Rome, via tour bus, several small cars bumped our bus and vise versa. Bicyclists were weaving between vehicles. While all of the passengers on our bus seemed a little unnerved by the situation, our driver was not. In fact he chuckled and said, “Big bus – little car. No worries.” Apparently hectic traffic is part of everyday life in Rome.

Day 1

temple of minerva assisi umbria italy

Your first day will be busy, but not exhausting. Your body will still be dealing with jet lag. Today the most important factor is to get your little ones on a schedule.

  • 7:00 – 8:00 a.m. –     Breakfast – A lot of Italian breakfasts consist of pastries, bread or rolls, and coffee. Indulge yourself in the country’s culinary culture. Be sure to ask if your agriturismo or hotel offers any type of breakfast.
  • 8:00 – 12:00 noon –     Explore Assisi –  Begin your journey with the city’s Basilica. Stroll your way through the ancient city streets. Browse the tiny shops along the way.
  • 12:00 – 1:30 p.m. –     Lunch – Take some time to enjoy the ambiance as well as the local food in Assisi’s town center. Try one of the restaurants that offer outdoor seating. You can’t ask for a better view than the Temple of Minerva.
  • 1:30 – 5:00 p.m. –     Nap and play time – A good nap and some outdoor play time will help to keep your kids happy.
  • 5:00 – 8:00 p.m. –     Dinner – If your hotel or agriturismo doesn’t offer dinner options, head back into town to enjoy some of the authentic Italian offerings.
  • 8:00 p.m. –     Bed time – Get a good night’s rest. There’s a lot of exploring on tomorrow’s agenda.

Day 2

  • 7:00 – 8:00 a.m. –     Breakfast
  • 8:00 – 12:00 noon –     Explore Rocca Maggiore – Have you ever been in a  castle? I’m not talking about Cinderella’s Castle. I mean a real castle. You know, walls around the exterior to keep out intruders, towers for look-out, tunnels, the whole medieval design deal. Well, now’s your chance! While there is not a lot to see inside the castle, the building will be enough to get the kids excited. Kids will love exploring this beautiful piece of history. Learn more about it here.

Just a little tidbit of information before you embark on your journey, it is not an easy trek. If you are traveling with infants or toddlers, you may want to consider a carrier, or find another activity to share with them while the someone else visits the castle with the older children.

If you’re up for a little exercise, the stone stairways, tunnels and breathtaking views make the trek to the castle worth every                bit of effort.

  • 12:00 – 1:30 p.m. –     Lunch
  • 1:30 – 3:30 p.m. –     Nap time
  • 3:30 – 5:00 -.p.m. –     Roman Forum and Archaeological Collection- This piece of history is well hidden below the Temple of Minerva. Kids will enjoy seeing the ancient Roman relics, especially if you help them understand that the Forum was where important decisions were made.

Children don’t always understand the importance of the artifacts. Museum tour directors are not always kid friendly. So, it’s                  always a good idea to provide fun commentary for your kids. Helping your child engage in the new culture will help them                        become aware of the world around them, it will encourage a lifelong love of learning. Just remember, don’t tell them they’re learning!

  • 5:00 – 8:00 –      Dinner – Choose a local restaurant, not a touristy eatery, and enjoy dinner. Afterward treat the family to gelato!
  • 8:00 p.m. –     Bedtime –  Get lots of sleep. You have a big day tomorrow!

Day 3

  • 7:00 – 8:00 a.m. –      Breakfast
  • 8:00 – 1 0:30 a.m. –     Drive to Florence – The actual drive only takes just over two hours, but I’m allowing a little extra time for any necessary breaks.
  • 10:30 – 12:00 noon –     Museo Galileo – Time for a little scientific fun! Who doesn’t love science? Gadgets and gizmos are fun,  especially when they’re hands-on, or maybe  hands off (or fingers in this case)  would be more accurate. A couple of the famous scientist’s fingers are on display! Learn more here.
  • 12:00 1:30 p.m. –     Lunch
  • 1:30 – 3:00 p.m. –     Tour Florence – Use this time to stroll the streets of Florence. Grab a gelato and enjoy this beautiful city. If your child is up to the venture, you may choose to visit an art museum, Boboli Gardens (The maze there is a blast for little ones.) or the Duomo.
  • 3:00 – 5:30 p.m. –     Home – Travel back to  your Umbrian home base. The travel time will allow for a good nap before dinner.
  • 5:30 – 8:00 p.m. –     Dinner – Enjoy a meal and some outdoor playtime, if time allows.
  • 8:00 p.m. –     Bedtime

Day 4

  • 7:00 – 8:00 a.m. –     Breakfast
  • 8:00 – 9:30 a.m. –     Drive to school – No worries! The assignments will be delicious.
  • 9:30 – 2:00 p.m. –   Cooking Lesson – You will learn to cook authentic Italian food. Even the kids can get in on the fun! There are several places that offer this type of experience. Make sure to do your research and choose the one that best suits you.
  • 2:00 – 3:30 p.m. –      Home – Depending on the cooking school’s location, there may be ample time for your little one to have a car nap. If not, wait until you are back at home base.
  • 3:30 – 5:30 p.m. –     Down time – enjoy some down time in the beautiful Umbrian farm land.
  • 5:30 – 8:00 p.m. –     Dinner and packing – Now is a great time to sort your laundry and start preparing for your final day in Italy. Getting things done now will allow you more time to enjoy Italy tomorrow.
  • 8:00 –     Bedtime

Day 5

  • 7:00 – 8:00 a.m. –     Breakfast
  • 8:00 – 10:00 a.m. –     Drive to Cugusi Pienza – Time has been allowed for a short stop along the way.
  • 9:45 – 1:00 p.m. –     Say cheese! – Visit the dairy farm to see exactly how this amazing cheese is created. Children will enjoy meting the sheep and learning how they contribute to the cheese making process. Enjoy a picnic while you’re there. The views are spectacular. You can find more information here.
  • 1:00 – 4:00 p.m. –     Home – drive back to home base. Extra time has been allotted for souvenir stops along the way. Enjoy the beautiful countryside and all of the tiny villages along the way.
  • 4:00 p.m. –     Prepare for dinner and next day departure.

Itinerary 2 – Explore Italy With Teens

  • Lodging – Teenagers like to feel connected to the world and being in the middle of the hustle and bustle helps them feel that bond. This itinerary is based on staying in two different cities – Florence and Rome. We will begin the stay in Florence. Choose a hotel in a central area of the city to make touring more convenient. For the best deals, check Priceline or other reputable hotel booking sites.
  • Transportation – Consider taking a train from Florence to Rome. Driving in the larger Italian cities can be a bit intimidating. While many of the sites are within walking distance, consider a taxi for those a little out of the way. Be sure to do a little research beforehand on taxi prices. You don’t want to take a chance on paying more for a ride just because you are a tourist.

Scientific research has proven that teens function better later in the day. As a high school teacher, I am also speaking from experience. Trust me, the later you wake them, the better your odds of traveling with a happy teenager.

Day 1

  • 9:00 – 10:00 a.m. –     Breakfast – Much like the need for extra sleep, the immediate need for food ranks high on most teenagers’ lists. Feed them. Feed them a lot! Feed them often! Trust me, it’s in everyone’s best interest.
  • 10:00 – 12:00 noon –      Basilica of Santa Croce – This stop simply can’t be missed. This Basilica is the burial ground of Michelangelo, Machiavelli, and Galileo, as well as a fresco by Giotto, and a relief by none other than Donatello. So much history in one place!
  • 12:00 – 1:30 p.m. –      Lunch – Ask a local for a recommendation for the best local pizza. Follow up with a gelato. After all, you can’t visit Italy without having at least one (per day).
  • 1:30 – 4:00 p.m. –      Duomo and Baptistry- Florence’s architectural masterpiece stands tall above the city. If you wish to climb to the top of the dome, make sure to allow plenty of time. It’s quite a trek, but well worth the effort. The view is amazing!
  • 4:00 – 7:00 p.m. –     Palazzo Vecchio / Piazza della Signoria – These two sites are within the same area. At Palazzo Vecchio you will find everything from the remains of a 1st Century theater of the Roman Colony of Florentia to the royal residence of Duke Cosimo I de’ Medici. There are even secret passageways! For more information visit the official website here. While you are there, simply walk outside the doors of Palazzo Vecchio to see Piazza della Signoria. It is a town square and home to a variety of historical events, as well as home to an open air museum. Two of the most notable works featured in the museum are Cellini’s Perseo and Giambologna’s Rape of the Sabines. There is a lot to take in when visiting this area.
  • 7:00 p.m. –     Dinner and bed – Enjoy a delicious Italian dinner at a table service restaurant. Opt for something other than pizza. Take time to enjoy Florentine culture. After dinner, head to bed.

Day 2

  • 9:00 – 10:00 a.m. –     Breakfast
  • 10:00 – 12:00 noon –     Palazzo Pitti and Boboli Gardens – Spend the morning entrenched in art and beautiful gardens. This palace was one home to some of Italy’s noble families.
  • 12:00 – 1:30 p.m. –     Lunch
  • 1:30 – 5:00 p.m. –     Uffizzi Galery – After lunch, head across the Arno River, via Ponte Vecchio, to the famed Uffizzi Gallery. This museum is famous because of its inhabitants. Works by some of the greatest artists of all time are housed here – Carrivagio, Raphael, Da Vinci, and Michelangelo, just to name a few. Take your time and explore the museum. This is a once-in-a-lifetime opportunity to see works of this caliber in one stop. This is a great opportunity to give your teen some freedom. Let them explore the museum and gardens on their own. Designate a meeting point and time.
  • 5:00 – 9:00 p.m. – Dinner and bed – Enjoy a nice dinner on your last night in Florence. Stroll the streets. Take in the atmosphere. Don’t stay out too late, though. Your heading to Rome tomorrow!

Day 3

  • 7:00 – 8:00 a.m. –     Breakfast – grab a quick bite to eat before boarding the train to Rome.
  • 9:00 – 12:00 noon –      Train to Rome – While the journey will take less than 1 1/2 hours, extra time has been allowed for delays, etc.
  • 12:00 – 2:00 p.m. –     Locate hotel – Locate your home base for the duration of your trip. Inquire about leaving your bags until your return later in the day. Do NOT leave valuables!
  • 2:00 – 5:00 p.m. –     Palantine Hill – Not only will you find amazing Roman ruins, you will have spectacular views of some of the city’s other notable sites such as Cirus Maximus, the Colosseum, and the Arc of Trajan.
  • 5:00 – 9:00 p.m. –     Dinner – It’s time to compare pizza’s! See if you can tell a difference between the pizzas in Florence and Rome. Oh! Don’t forget the gelato. Give your teen a little freedom to wander in and out of some of the shops. Just be sure to keep an eye on them and make them aware of pickpockets. Theft, especially among tourists, is a big business in Italy. This is a great time to teach your teen while still letting them have some independence.
  • 9:00 –     Bed – You have an action-packed day tomorrow. Get a good night’s sleep!

Day 4

roman colosseum

  • 9:00 – 10:00 a.m. –     Breakfast
  • 10:00 – 12:30 p.m. –     Colosseum / Roman Forum – You haven’t been to Rome until you’ve visited these two iconic sites. At the Colosseum, make sure you see the areas where the gladiators were held until they fought. Take in the vast expanse of the sports arena that started the trend that influences stadiums today. From the Colosseum, move across the road (literally) to the Roman Forum. Walk in the footsteps of some of history’s greatest figures. Your journey will follow that of Julius Caesar.
  • 12:30 – 2:00 p.m. –     Lunch
  • 2:00 – 3:30 p.m. –     Pantheon – When you step into the latest version of this magnificent building, and by latest I mean built circa 118 – 125 A.D., you will be amazed.  Be sure to take a moment to stand directly in the enter of the dome and admire the forethought and craftsmanship that went into planning this amazing structure. Don’t forget to take a picture! Renaissance art fans will also be interested to know that Raphael’s tomb  is located in the Pantheon.
  • 3:30 – 5:00 p.m. –     Trevi Fountain – This iconic Roman site is a must do for any tourist. Don’t forget to toss a coin into the fountain to ensure you will visit Rome again someday. You must throw the coin over your left shoulder using your right hand.
  • 5:00 – 9:00 p.m. –     Dinner and a stroll – A lot of time has been allowed for dinner. Meals in Italy are not quick. They are a time meant to be shared with friends and family. After dinner take a stroll and soak in the atmosphere of Rome.
  • 9:00 p.m. –     Home – Head back to your home base. Get plenty of rest. Tomorrow is a big day!

Day 5

  • 9:00 – 10:00 a.m. –     Breakfast
  • 10:00 – 1:00 p.m. –     The Vatican Museums, St. Peter’s Basilica, and the Sistine Chapel – There is so much to see! Seriously, it’s almost impossible to describe the vastness of the art collections, the awe-inspiring architecture, and the magnitude of standing beneath one of Michelangelo’s greatest masterpieces.
  • 1:00 – 2:30 p.m. –     Lunch – There are several restaurants in the immediate vicinity of Vatican City.
  • 2:30 – 5:-00 p.m. –     Explore the city- Stroll the streets. Take in the ambiance of Rome.
  • 5:00 –     Dinner and bed – Have a nice dinner to honor your last night in the Eternal City. Be sure to get back to your hotel early enough to pack for tomorrow’s departure.

Itinerary 3 – Adults Exploring Italy

  • Lodging – A hotel in a central location within each city is highly recommended.
  • Transportation –  Driving is not necessary during your vacation. You will take a train between the major cities. Most sightseeing can be done on foot. Otherwise, a short ride in a taxi is an inexpensive way to get from Point A to Point B.

Day 1


  • 8:00 – 9:00 a.m. –     Breakfast
  • 9:00 – 11:00 a.m. –      Basilica of Santa Croce –This site is often overlooked by tourists. Visitors are often rushing from one museum to another and the Basilica goes unnoticed. Please don’t let the opportunity to see the tombs of some of the most influential people in history – Michelangelo, Galileo, and Machiavelli. Of course there will be beautiful art to see as well. After all, Florence was the birthplace of the Renaissance.
  • 11:00 – 12:30 p.m. –     Lunch –
  • 12:30 – 2:00 p.m. –     Duomo and Baptistry – Don’t miss this architectural masterpiece! The dome was a massive feat of design and engineering, long before technology and cranes existed!
  • 2:00 – 4:00 p.m. –     Palazzo Vecchio and Piazza Signoria – With its secret passageways and Medici heritage, this venue will delight any visitor. Whether you’re an art aficionado or a Renaissance royal wannabe, Palazzo Vecchio  is a must-see. Just outsides the doors of this elaborate building, you will find Piazza Signoria’s outdoor sculpture display. Don’t miss it!
  • 4:00 – until –     Free time – Enjoy a leisurely Italian dinner and stroll the streets of Florence. Soak in the atmosphere of this beautiful city. Make sure you get to bed early. You have a big day tomorrow.

Day 2

  • 8:00 – 9:00 – Breakfast
  • 9:00 –  11:00 – Uffizzi  Gallery – This is your opportunity to see works by some of the world’s most famous artists. Enjoy your time in the presence of art greatness.
  • 11:00 – 12:00 noon –      Tuscany – Head to your departure point for your pre-booked Tuscan vineyard excursion. Be sure to grab a snack along the way. It might be a bit before you get to enjoy the tasty Italian foods and wines that await you.
  • 7:30 – 8:00 p.m. – Arrive back in Florence – Prepare for your trip to Rome tomorrow. Your train will leave early. You might consider packing tonight.

Day 3

  • 8:00 – 9:00 a.m. –      Breakfast
  • 9:00 – 12:00 noon –      Train to Rome- While the actual train ride will not take three hours, this will be enough time to locate your hotel and inquire about checking your bags until you return later.
  • 12:00 – 1:30 p.m. –     Lunch – Ask one of the employees at the hotel for a restaurant recommendation.
  • 1:30 – 3:00 p.m. –     Palentine Hill- Enjoy an amazing view of some of Rome’s most notable sights, including the Colosseum and Circus Maximus, all while touring beautiful Roman ruins.
  • 3:00 – 6:00 p.m. –      Colosseum / Arch of Constantine / Roman Forum – Explore one of history’s greatest architectural feats. When you exit the Colosseum, be sure to take notice of the arch that commemorates one of Rome’s most notable leaders, Emperor Constantine. From the Colosseum, walk a short distance to the Roman Forum where you can walk on  the same grounds that Julius Caesar once stood.
  • 6:00 – 8:00 p.m. –     Dinner
  • 8:00 p.m. –      Bedtime!

Day 4

vernini's four rivers fountain piazza navona rome italy

  • 8:00 – 9:00 a.m. –     Breakfast
  • 9:00 – 10:00 a.m. –    Piazza Navona – See the works of Borromini and Bernini in one beautiful outdoor location.
  • 10:00 – 11:00 a.m. –     Pantheon –  Just a short distance away from Piazza Navona is the Pantheon – a true architectural masterpiece. Sand under the center of the dome and admire the dome. It’s hard to believe that the building was built so long ago.
  • 11:00 – 12:30 p.m. –     Lunch
  • 12:30 – 2:30 p.m. –     Trevi Fountain – Take a leisurely stroll to Trevi Fountain. Be sure to toss a coin in this iconic Roman landmark!
  • 2:30 – 4:00 p.m. –     Castel Sant’angelo – Your day has been filled with a lot of walking. For this trek, I suggest catching a bus or taxi to this venue. This magnificent structure houses Hadrian’s tomb.
  • 4:00 – until –      Free time – use this time to shop for souvenirs or soak in the ambiance of Rome. Enjoy a  table service meal and then head back to your home base for the evening. You have a big day tomorrow!

Day 5

  • 8:00 – 9:00 a.m. –      Breakfast – eat a substantial breakfast. You will have a later lunch today.
  • 9:00 – 1:00 p.m. –      Vatican  – This may sound like a lot of time, but it really isn’t enough to see everything. The Vatican Museums are vast, and filled to the brim with priceless works of some of history’s most beautiful pieces. Your tour will begin with the museums. It will then progress to the Sistine Chapel . Oh, are there are absolutely no cameras allowed in the chapel!!!. Finally, you will see St. Peter’s Basilica and St. Peter’s Square.
  • 1:00 – 2:30 p.m. –     Lunch
  • 2:30 – until –     Prepare to leave Italy – Enjoy one last gelato. Pick up any last minute souvenir. Enjoy one last authentic Italian meal. Then, pack your bags to depart for home in the morning.

There you have it- one country, three itineraries.

If you have any questions or comments I would love to hear from you. Please feel free to drop me a line in the comment box.

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Happy travels!


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