Ultimate Italy Travel Guide: The Best 4-Week Italy Itinerary
Have you ever wanted to spend the summer in the Tuscan countryside, see the Venice canals by gondola, or sunbathe on the Amalfi Coast? Italy has amazing food, ancient history, and a rich culture that needs to be experienced over weeks, not days. This Italy travel guide puts together the best 4-week Italy itinerary to help you do just that!
In June 2023, my family set off on the trip of our lifetime. I want to share with you the journey that me, my husband, and our 2 kids (8 & 10 years old) took through Italy. We could have stayed for 4 MONTHS and still wouldn’t have seen everything. I guess that gives us a good reason to go back!
If you follow our family friendly 4-week Italy itinerary, you can visit 19 different Italian destinations during your trip. This will be your ultimate Italy travel guide! I will give recommendations for the easiest travel logistics for your vacation and look out for great tips along the way.
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Italy Travel Guide Itinerary Destinations:
*Click on a topic below to learn more*
Milan (2 nights)
This is the perfect place to start your Italy travel guide. The Milan Malpensa Airport (MXP) is the largest international airport in Northern Italy. From the airport take the Malpensa Express train to Milano Centrale train station in the heart of Milan. Then proceed by taxi to your accommodations.
Duomo
- Milan is known for its bustling metropolis and fashion icons, such as Armani, Versace, and Prada. Milan’s must-see historical landmarks include the Duomo di Milano, Galleria Vittorio Emanuele II, Castello Sforzesco, and the Teatro alla Scala.
- Tip: Don’t forget to cover your shoulders and knees for entry into the cathedral.
- Tip: Buy in advance through Get Your Guide: Duomo entry ticket with terrace access. Choose the terraces by elevator option if available. Otherwise, be prepared to climb some stairs.
“The Last Supper”
- One of the most famous paintings of the Renaissance is in Milan. Leonard Da Vinci’s “The Last Supper” is located in the Church of Santa Maria delle Grazie!
- Tip: As soon as you have your Milan travel dates buy your tickets to “The Last Supper”. They release tickets online every 3 months. So, determine when your dates will be released and book directly through their website: Vivaticket: biglietti online, prevendita concerti, biglietti spettacoli
- Tip: If traveling with kids, I recommend booking tickets that include the workshop. The bilingual visit (ITA/ENG) with the workshop activity is provided in the following time slots:
From Tuesday to Sunday at 11.45 am and 3.30 pm
Venice (3 nights)
The next stop on our Italy itinerary is Venice. Take a high-speed train from Milano Centrale to Venezia Santa Lucia which takes about 2.5 hours. We booked all our train tickets through the app Trainline. This makes it easy to keep all train tickets in one place, and you can also save your tickets to your Apple Wallet. From the train station, options are walking, Vaporetto (water bus), or private water taxi (most expensive option).
- Tip: Talk directly to your Venice accommodations to determine the best route from the train station to your hotel/rental.
Realto Bridge
Venice is the perfect place to drop your bags off, leave your hotel, and walk aimlessly for hours on end. Check out the Realto Bridge while out. Walking down empty, dark alleyways in Venice is actually a must-do activity (even with kids). Get lost in the history, stunning architecture, and kitschy shops. *Don’t forget to grab a gelato during your strolls.
Gondola
You can’t come to Venice and not take a Gondola ride! During your walkabout, be on the lookout for a Gondolier (wearing the striped shirts). The pricing is a set standard. The rate when we went was 80 euros for about 30-40 minutes.
Doge’s Palace & St. Marks Basilica
- Take a single tour that includes the most famous sites, Doge’s Palace, Bridge of Sighs, and St. Mark’s Basilica. We booked through Get Your Guide.
- Tip: Buy in advance: Early Entrance Doge’s Palace & St. Mark’s Basilica. I always recommend early morning site visits in Italy to avoid crowds.
Murano & Burano Islands
Take a day trip to Murano & Burano by boat. We booked this trip through Viator. We really enjoyed the small group vibe and loved that we had time to go off and explore each place on our own too. I have to say that Burano had the best gelato in all of Italy (in my opinion). I recommend Bacaro del Gelato!
- Tip: Buy in advance: Murano & Burano Islands Guided Small-Group Tour by Private Boat. We booked the 2:30p time for a chance to catch the sunset on the boat ride back to Venice.
Florence (5 nights)
Florence was my favorite city during our trip. It is quintessential Italy. You will take the train from Venezia Santa Lucia to Firenze Santa Maria Novella (about 2 hours). From the S.M.N train station, you can walk or take a taxi to your rental/hotel.
Golf Cart Tour
- Take either a guided walking tour or a golf cart tour. I recommend doing this on your first day in town, that way you get a good lay of the land on day 1. We chose a golf cart tour so our kids could rest their legs.
- Tip: Buy in advance: Florence: Old Town Golf Cart Excursion. We booked the 5:30p tour. Tour sites/stops vary, but our guide took us up to Piazzale Michelangelo and it was the highlight of the tour.
Uffizi Gallery
- If you only visit one museum in Florence, make sure it’s the Uffizi Gallery. Famous artworks include Birth of Venus, Medusa, Annunciation, Venus of Urbino, Musician Angel, and a lot more. You can book a guided tour through Viator or Get Your Guide. Or buy your timed entry tickets directly: Tickets | Uffizi Galleries
- Tip: Buy in advance: Whether you want a simple entry ticket or a more expensive private tour, you must purchase months in advance. Otherwise, you will be waiting in long lines.
- Tip: If traveling with 2 adults, multiple kids, and no planned museum tours, I recommend purchasing the Passepartout. Annual Subscriptions | Uffizi Galleries. For 100 euros it gives a family unlimited priority admission to Uffizi, Pitti Palace, and Boboli Gardens. It’s cost-effective even if you only visit each place once.
- As a family with young kids, we opted out of taking museum tours. My kids would have been bored to death. With the annual pass, we went to Uffizi as a family once, then I returned without my husband and kids. I spent hours alone doing a “self-guided” tour with the rented headsets they offer. It was lovely!!
Pitti Palace & Boboli Gardens
Pitti Palace and Boboli Gardens can be visited at the same time. The gardens have a separate entrance, but it is all in one place. I recommend visiting in the morning to avoid crowds. We went through the palace right at opening and basically had the place to ourselves.
Pasta Cooking Class
A Pasta Cooking Class is so much fun, especially if you have kids who are older than 5 years old and have an interest in learning to cook. We booked an amazing experience through Viator: Pasta Making Class. We took our class between 4-7pm. It was a great family activity and we ate our delicious pasta dishes as our dinner.
Michelangelo’s David
- If Michelangelo’s David is a must-see, book tickets to Galleria dell’Accademia well in advance. Again, you must choose a guided tour or a simple timed entry ticket. We booked an early morning timed entry ticket to avoid the crazy crowds. We were basically the 1st people in for the day! Book direct here: Tickets – Galleria dell’Accademia di Firenze (galleriaaccademiafirenze.it)
- Tip: When you arrive, you will probably see a very long queue even in the morning. If you have bought your timed ticket in advance, skip this line, and go straight to the entrance. Look for your timed line or ask an employee if unsure.
Street Food Tour
- Food tours were some of our most memorable experiences in Italy. When I ask my kids about their favorite parts of the trip, they first say “GELATO!”, but then they talk about the amazing tour guides we met on our food tours. In our tours, the guides were locals who personally knew all the street vendors and restaurant owners. They introduced us to “what the locals eat”. If you see a food tour that interests you, do it!! We booked: Florence Morning Street Food Tour – Streaty and it was beyond amazing!
Pisa
The Leaning Tower of Pisa. If you want a break from Florence during your 5-night stay, take a day trip to Pisa. It takes about an hour by train from Firenze Santa Maria Novella to Pisa Centrale. Book your train tickets through the Trainline app. Check out Get Your Guide for Pisa tickets and tours.
Siena (3 nights)
Siena must be reached by car (1.5 hours). So, I recommend renting a car in Florence and driving yourself. We used Europcar: Car Rental – Rent a Car & Van Worldwide. They were inexpensive, and we had a good experience with them. You must get an international driver’s license (about $20 from AAA) before your trip.
Walking Tour & Duomo
I recommend starting with a walking tour. We booked the Siena 2-hour Walking Tour & Skip-the-Line Duomo Tickets. Our guide was entertaining and informative. It was a rain or shine event, and of course we got rain. It would have been a better experience if we had sunny weather. I don’t feel that this tour must be booked way in advance. Therefore, you might wait until a few days out to check on the weather. Also, by this point in the trip you will know if you (and maybe your kids) are enjoying all the guided tours. But don’t miss seeing the Duomo!
Tip: By this part of your 4-week Italy itinerary, you may need a day off. If vacationing in the summer, Siena is the perfect place to book a hotel/rental with a pool. Take a full day to relax poolside and rest.
Pienza
- Make a day out of traveling the Tuscan countryside. Start early in Montalcino, then do lunch at Podere il Casale in Pienza and end the day in Montepulciano. Or just keep it lowkey and enjoy a slow morning in the town of Pienza, then make your way to Podere il Casale for lunch, then head back to Siena. We really enjoyed slowing down in Siena and taking in the scenery.
- Tip: Make lunch reservations in advance: Reservation – Podere il Casale, Tuscany. Organic Garden Restaurant, services, products.
Podere il Casale is a working farm in Pienza that offers tours, cooking classes, and an amazing farm-to-table restaurant with spectacular views. Our kids loved seeing the farm animals and playing with the resident cats!
San Gimignano
If lounging by the pool isn’t your jam, then do another day trip to San Gimignano (45-minute drive). Spend the day exploring the town known for its medieval towers. Have a nice lunch, and maybe even take a gelato-making class at Gelateria Dondoli. Gelato Class – Dondoli Gelato Class.
Naples (2 nights)
Next, your Italy travel guide brings you to Naples, you must first drive back to Florence and drop off the rental car. When choosing a rental company, pick one that’s close to the Firenze S.M.N train station so it’s an easy walk with your luggage. Then, take a train from there to Napoli Centrale station (about 3 hours). Once you arrive in Naples, take a taxi to your destination.
- Naples’ historic city center (Centro Storico) is a very busy place. The streets are narrow and congested with people, cars, and motorbikes. I found it hard to traverse with small children.
- Tip: Stay in the Chiaia neighborhood if visiting with young kids. This area is also where the pizza class is that I will be sharing.
Pizza-making Class
Learn to make pizza from the people who invented it! A Pizza-making class in Naples is an activity you can’t pass up! We booked the 6p class and made some delicious pizzas. Save room for the “fried pizza!”
- Tip: Book this Premium Pizza-Making Class at a Pizzeria. If staying in Centro Storico, schedule a taxi in advance to get there in time. It can be a 20-30 minute taxi ride with traffic.
Naples Underground Tour
Stay in Centro Storico if you only plan on doing activities that are located here. In that case, make plans for Museo Cappella Sansevero, a Street Food Tour, and Naples Underground Tour. The Underground tour is a unique look at the history of Naples. It’s unlike anything I’ve ever seen.
Tip: Tickets to see the “Veiled Christ” must be purchased in advance. Buy direct at Sansevero Chapel Museum – Online Tickets (museosansevero.it)
Pompeii
Now, we will be heading toward the Amalfi Coast. But first, we will make a stop in the ancient ruins of Pompeii for a guided tour. Getting from Naples to the Amalfi Coast will require a car, but I do NOT recommend renting a car and driving yourself. Leave the driving in this part of Italy to the professionals. You can easily schedule car transfers through Daytrip: Sightseeing Transfers with Local Drivers. Daytrip was recommended to us, but ultimately we used a different company. See below.
Grand Tour Experience
We went with Grand Tour Experience who came highly recommended to us. They are full service with multiple tours and drivers. We had 3 different car transfers during our trip, and they scheduled the same driver for each transfer. This helped tremendously since we knew who and what to expect each time. During our 2-hour Pompeii tour, our driver kept our luggage with him, so we were free to enjoy our visit without worrying about our bags.
- Tip: Book a private Pompeii tour with Raffaele Romano, Ph.D. He is the founder of Grand Tour Experience as well as an archaeologist. He has so much passion for and knowledge of Pompeii’s history, and that made our visit to this site an unforgettable experience.
- Tip: Reach them at info@grandtourexperience.com for any questions about tours, car services, and all Italy travel needs.
Sorrento (3 Nights)
Once you complete your tour of Pompeii, your driver will bring you straight to your accommodations in Sorrento. I would use the remainder of the day to settle in and rest. You can also explore the town, which is very walkable. Everywhere you look in Sorrento you will find a cute shop or a quaint place to eat.
Walking Tour
The next morning, book a walking tour so you can learn about Sorrento. We took an awesome tour that we found on Viator. Our guide was very sweet and knowledgeable. She took us to a new café/bar with spectacular views. Our group was their 1st customers! I can’t wait to go back and see how that café is doing!
Tip: Book in advance: Secret Walks of Sorrento with Locals.
Beach Clubs
Beach Day!! Our family loves the water, so we spent most of our time at the beach while in Sorrento. We visited 2 different beach clubs, and both were great.
- Leonelli’s Beach club
- We liked that this place had a sandy beach area that didn’t have a lot of rocks. So, when reserving your umbrella and chairs, request the sandy beach spot.
- Peter’s Beach Club
- We really enjoyed the restaurant at this club. Great food and great beach vibes.
Praiano (4 nights)
Traveling from Sorrento to Praiano is done by car or bus. We used Grand Tour Experience for all our private car transfers. Like I mentioned before, with each transfer we had the same driver. This made everything so easy. The drive to Praiano took about an hour, along winding cliff roads. Me and my kids did have a bit of car sickness on the ride, so you might want to take Dramamine for the trip.
Private Boat Tour
Boat Trip along the Amalfi Coast, ✅! This was the biggest splurge of our entire 4-week Italy itinerary. Was it worth it?? Absolutely! We booked via Barbara Positano Boat Tours. There are many other companies to go through, but we had a great experience with this company, so I recommend them.
The 35ft luxury boat picked us up at the Marina in Praiano at about 10a, then we were off! We made port in Amalfi, Nerano, and Positano. We had multiple swimming/snorkeling excursions to beautiful places only reachable by boat. The day’s events are completely up to you. The boat had changing areas, a bathroom, and all the snacks and drinks you need for a full day.
- Tip: Ask Barbara to make a lunch reservation for you at Lo Scoglio in Nerano!
Beach Day
- We only went to one beach while here since we spent a boat day on the water. We rented an umbrella and 2 chairs at Marina di Praia Beach. The water was beautiful, but as it got closer to lunch, a lot of stinging jellyfish invaded the beach.
- Tip: It was a very rocky beach, and we found some broken glass as well. So, bring your water shoes!
Amalfi Coast Scenery
Praiano and the surrounding towns are beautiful places to relax and enjoy the views. Take it easy while here, because the final stop in our Italy travel guide is the busy, “Eternal city” of Rome.
Rome (4 nights)
Nearing the end of our 4-week Italy itinerary, you will need to take one more private car transfer to begin your journey to Rome. This will be from Praiano to Napoli Centrale train station, and it’s less than 1.5 hours away. Then take your last train ride from Napoli Centrale to Roma Termini which will take 1 hour and 10 minutes. Once in Rome, either take the Metro or a taxi from the train station to your accommodations.
Walking Tour with Gelato Tasting
- Once we arrived in Rome, we settled into our Airbnb and set out for an 5p evening walking tour. The tour was called: Welcome to Rome: City Stroll with Gelato Tasting. We booked through Walks of Italy. The tour started in Piazza Navona, walked through the Pantheon, then the Trevi Fountain, and ended at the Spanish Steps. We loved this tour (our kids loved the gelato stop) and we would probably do it again!
Colosseum
- The next major site in our Italy travel guide is none other than the Roman Forum & Colosseum. In the summer, it was very hot, even at 9am. This was a long tour, and unfortunately, our tour guide was quite boring. If I had it to do over, I would book a Colosseum by Night tour. I think this would be more enjoyable without the huge crowds and blaring sun. Please give this tour a try and let me know what you think!
Vatican and Sistine Chapel
The earliest set out time for us was Vatican day. We did Walks of Italy’s Pristine Sistine Early Entrance Small Group Tour which met at 7a. This allowed us to see the Vatican museums which included Raphael’s School of Athens before the crowds. By the time we walked through the Sistine Chapel, it was more crowded but still amazing. This tour ends at St. Peter’s Basilica, where we saw Michelangelo’s Pieta. We had a funny, light-hearted, and very knowledge tour guide.
Trastevere Street Food Tour
The Trastevere Street food tour we took was nothing short of spectacular. The food was amazing, the history was unexpected, and the tour guide and fellow tourists made for a memorable evening. My oldest daughter turned 10 years old in Rome, and our tour group sang Happy Birthday to her during our last food stop (gelato of course). We simply had the BEST time!!
Villa Borghese Park
- For our last full day in Rome, we strolled around Villa Borghese Park and rented a rickshaw bike. We walked around town, ate gelato, and stuffed our bellies full of pasta and bread. And of course, we slowly packed up and prepared for departure. The only thing left to do was schedule a taxi for an early morning flight home. And our Airbnb host was gracious enough to take care of that for us.
Family-Friendly Accommodations in Italy
In Summary…
The reason for such a grand tour of Italy was to immerse ourselves in a unique culture, meet different people, and learn a new language. It was an amazing experience, and I’m so happy we were able to bring our kids on this journey as well. Our girls still get excited about telling stories of our trip to Italy. And they are ready to keep exploring the world!
Check out my Italy Travel Essentials post to see everything we packed with us for our trip.
If you stuck around through my Ultimate Italy Travel Guide, then you have the perfect plan for the Best 4-Week Italy Itinerary! Everything included here is family-friendly but can also make for a great adults-only trip too. Please comment or contact me with any questions that you may have about your own Italy trip.
Hi would be super helpful if you had a list of accomodations you stayed at, or recommendations
Hi Priya. We stayed in an Airbnb in each city, with the exception of Siena. Airbnbs just worked better for us traveling with kids. In Siena, we stayed at Hotel Borgo Grondaie, which I definitely recommend. Email me (kelly@kellybethandbeyond.com) if you are interested in the exact Airbnbs we stayed in. I believe most of them are still actively taking reservations. Thanks!!