Did the 2nd visit not seem as magical?

it may be magical in a completely different way, but I predict the magic will still be there. even if you re-visit places you have been, in the intervening years you have grown and experienced new things, and will see everything with "new" eyes. one strategy I have when visiting cities for the 2nd or 3rd time is to find a theme -- for example on my 3rd visit to Florence and 2nd visit to Rome (same trip) I decided to focus on Michelangelo and look for his work in various churches, chapels, etc. I love art and art history so that's what I focus us, but it could be anything, for example focusing on gelato and seeking out various gelateria and learning about the different styles, maybe finding a class on making gelato. keeps things fresh!

I have been to Italy 8 or 9 times now, and I still love it. Granted, it has all that I love....art, music, history, ancestral links, etc.
However, as relates to your specific question, I think your son will be awestruck. We took our adult children to Rome for a week, in 2016. We stayed in Trastevere. They really enjoyed it all! (one disappointment...the Sistine Chapel was terribly crowded, and we were shuttled through like cattle, and this was in April) But, aside from that, it was all wonderful and YOU will enjoy watching HIM enjoying Italy. So much so, that in 2018, our son accompanied us to Sorrento for another week, and was hooked.

Massachusetts had a fun suggestion on looking for specific themes or pieces of art work. (I actually did that very thing in Paris last fall....hiked around the Louvre looking for a specific painting, and found it)

And Florence/Tuscany will be new to all of you, so you can be awestruck together!

Buon viaggio!

Don't worry a bit! Your son will love it.

It will be magical. Italy always is. Whenever I travel I always revisit places I have already been and loved as well as new places I have never been. I had been to Italy several times before my adult daughter joined me for a visit. It was magical just to see her reactions and what she was enjoying.

I've been to Italy several times - on a high school art history educational trip, for a semester study abroad program, summer solo visit before I graduated college, with my then-fiancé (his first trip), back with my now-husband and toddler (toddler's first trip), and we're going again this summer with our now-five year old. On each trip, I've done a mix of repeats (I always visit Florence) and new (this summer we're going up to the lakes for the first time).

It's every bit as magical as it was when I was an awe-struck high-schooler traveling to Europe for the first time back in 2004. There are still new things I discover in Florence, much less in the rest of the country. Everyone is different, but for me, Italy is my favorite, and I can't imagine the day when it won't be completely enchanting.

I've felt this about European travel in general, not about specific destinations I revisit. I remember how excited I was when I got my first passport and I had never even flown domestically before. When I was growing up in Georgia, there were no regularly scheduled international flights from Hartsfield! I don't get that excited now ( yeah I'm going to Europe again, it's what we do) , but I actually find revisiting a specific place better because I know my way around and I'm not trying to see everything on one trip. And to paraphrase a movie "Florence is always a good idea". I've been there 4 times and hope to go again in 2023, rather than going to some places on my bucket list that I've never visited. I feel comfortably "at home" when I visit Florence now, rather than it being a new location to be conquered.

I am currently on the Amalfi Coast for the 8th time, and I hate to say it but the magic is gone for me. It has become so incredibly crowded and has lost much of its charm, and it’s only April. I hopped on the bus today (which was 25 minutes late) and it was completely packed. Four of us couldn’t even stand in the aisle but we’re stuck on the stairs of the bus. Hanging on around the twisty turns was difficult so I sat on the floor with my back against the bus driver’s gate. I have never experienced this before and it is all very much like what has happened to the Cinque Terre over the years. I am traveling with someone who has never been here and is absolutely giddy and talking about “next time” but I don’t think that I will be back. At least probably not the AC. Or the CT for sure.

I'm on seven (eight)?--all magical! I think it gets better actually, as you become accustomed to life's flow there. I always say I could just go to Italy forever because there is so much variety and so much to see/do. I have rarely repeated the same place, but you could spend months in Rome and not see it all, plus you'll be seeing it through others' eyes.

I lived in Rome for 2 years in my 20s and have been back & forth many times over the intervening 25 (!) years. A piece of me will always be in Italy; my experiences there changed me forever. There's always more to see & more to learn. And now, going back with my kids puts a new spin on it. I love seeing it through their eyes.

This all helps! I’m getting excited!

I’ll answer generally since I’ve traveled to France way more than Italy. The magic never goes away. I step off the plane and it’s a thrill just to know I am back.

It was sad last October when some of my regular cafes were closed but more things have reopened and they are eager to have visitors back.

It gets better and better!!

"The magic never goes away. I step off the plane and it’s a thrill just to know I am back."

Happy to read that, because I was thinking along the same theme. I'm more Italy, but I land, get a taxi to my hotel, check-in, and then run a few errands that I need to do to position myself for the remainder of the trip and then, just start enjoying yet another 3-week foray.

You will still see amazing sites, the thrill of travel but for me, it just changes when you add in other people. When it's your adult children, your mom hat will still be on, and that can also change to dynamic of the trip, more stressful and frustrating.
We went to Europe the first time just me and husband, so wonderful, magical, romantic, exhilarating... the second trip was done with another couple within like 14 months of the first trip...totally different! We were not as in synch and as carefree, we did some excursions I would never have done had it been me and my hubby, I felt like time was wasted and I can be a baby about that kind of stuff. It was not as magical or as fun, I still had a great time but my expectations were high after that first trip.
We also plan on taking our adult sons (34) with us on our next trip to show them the ropes, get them excited about traveling but I know it will never be like just me and my husband together ( we are magic when it is just him and I).

We've been lucky that we've had an opportunity to return to a number of places in Europe we've been before. We started on a middle school trip in 1966 when Deb was 14 and I was 15. Our first kiss was in Florence! We returned 50 years later to celebrate the beginning of our lives together.

Every trip is magical. For us, we have experienced Europe in general and Italy in particular at different ages, seeing familiar places from different perspectives.

You'll find you'll see little things you've missed before, kind of like watching a favorite film again. We've also had the chance to visit familiar places in London and France with our grandson, who studied in Paris and Tours. It was a treat to introduce him to some of our favorites. It never gets old.

I've felt that it wasn't as magical when revisiting the same places, with a few exceptions. Museums like the Louvre are so big that there's always something fresh to see, as are larger cities like Paris or Rome. But I've found that revisiting places we've been before, while still enjoyable, seems a bit of a letdown from the first time.

For example on one trip we stayed in Perugia for a few nites and it was just amazing! From the first view down the hill when the bus up from the train station dropped us off at the Carducci Gardens, to walking down the wide street to the large piazza, the restaurants with outdoor tables along the street, the architecture of all the buildings in town, we were sold! We liked it so much that on a subsequent trip to Umbria we decided to use it as a base for further daytrips. And it was nice, but the magic was gone. No thrill seeing the view for the first time, for walking down that wide street, etc. This isn't to knock Perugia, and if you haven't been I highly recommend it!

People differ, of course, but to me I think the novelty of seeing someplace for the first time adds to the experience. Maybe a way to guess ones reaction to repeat travel is to ask are there favorite films you watch over and again? Or do you just enjoy the memory but find seeing them the 3rd or 4th time nowhere near as rewarding as you first remember the film?

I hope the second time is as magical. I went to Italy once in 2007 and am planning to go next year with my husband (who has never been). Knowing him well, I'm soooo excited to see his face light up when he sees things. He is a huge Caravaggio fan and I just know seeing his art will be a highlight for him.

As for me, I'm such a different person now than I was then, it'll almost be like the first time for me too.

@letizia, (my given name is Leticia BTW), My husband I and also enjoy traveling just the two of us, rimanthc and we do things exactly how we want without having to be concerned with another couple’s interests , wants, or idiosyncrasies. I prefer traveling with others on just short vacations, even then sometimes we wish we were just by ourselves. It definitely will be different with the boys, ages 28 and 25, but I do have fun with them. Not necessarily romantic, I suppose.

I do love watching my favorite movies again and again, that’s a great comparison, I also like the tip about making sure we do something different. Rome is so big, we need to explore other areas when just walking about. Great idea!

First time visitors, we just arrived in Rome having started on Amalfi Coast and Naples and we've been often underwhelmed up until our first day in Rome.
Amalfi coast was just jammed with people (over the Easter weekend). A local said there were 200,000 visitors to Sorrento! The bus terminal in Amalfi was chaos. The 17:00 bus up the hill to Bomerano was so packed that the driver refused to set off. Next bus was due at 19:00. But suddenly two additional busses were diverted to Bomerano so all three set off, crammed with people at about 17:15.
Naples was filthy with garbage and dog mess everywhere. The baths and many of the houses in Pompeii were closed. Vesuvius is now a entry ticket and parking scam with the official ticket office closed "due to covid".

But Rome yesterday was absolutely stunning. Clean buildings and pavements with lots of pedestrianised areas. Perfect weather and manageable crowds. Starting early at St. Peter's Square (and unexpectedly seeing the Pope live) we walked past the castle Sant'Angelo and over the pedestrian bridge and down the atmospheric Via dei Banchi Nuovi to start Rick's excellent Heart of Rome walk.

That’s too bad about the Amalfi Coast. It wasn’t that way in September 2015 when we were there. But we never did busses, just took the ferry from Salerno to Positano.

I have to agree with you about Naples. We went to Venice, Rome, Positano and Naples and hated Naples. Loved everywhere else. Hope you enjoy yourself from here on out.

I’ve been 4 times and have done same sites multiple times it is always magical. Enjoy

I was afraid I'd be disappointed in Venice, my expectations were so high. I wasn't; it was magical. I was afraid I would be disappointed in Venice on my first return visit, I wasn't. I recently returned from my 5th visit. I can't describe it as magical because it felt so comfortable. But along with the familiar, I spent a lot of time exploring new (to me) parts of the city and seeing other parts with fresh eyes. Delightful. When I left after 4 full days, I just wanted to return for 2 weeks.

I'm always torn in Italy between returning to places and sights I've been to and seeing new ones. I've rarely been disappointed by return visits to sights, never to cities.

@Lulu348 I don't know if you know about Rick's free Audio Europe app, but he has 10 narrated walks in Rome - some outside and some inside (museums etc.) We find them an excellent way to explore places.

(Also the 3 audio tours in Amsterdam are excellent).

My wife and I will be retrained Italy for the fourth time in October and every time it actually gets more magical if that’s even possible! My advice to you is go and enjoy Italy!

For the places I love, I enjoy every return trip. I have been to Zagreb 5 times, and live in expectation of the next visit. Ljubljana, Vienna, Budapest, Beograd, all these cities are better on each visit. It's like romance - the first moment of infatuation is one thing, but the true mark of a long-term relationship is the ability of the place to grow and develop.

I can’t count how many times I have been to Italy since 2006. At least 12, maybe 15. As soon as it was re- opened to the US last year my husband and I booked a flight so that we could revisit some of our favorites (Ravello, Montalcino, Bologna and Venice.) Then a few months later in October I took my sister to Venice, Dolomites, Florence, Castelnuovo Berardenga. This September I am taking my Mom and two sisters to Venice, Tuscany, Rome and Ravello. I can’t explain the magical feeling of Italy, but I know that many people here can attest to it. It’s also always so cool to see it through someone else’s eyes and to share in there awe and excitement when they are able to experience it for the first time.

You’re going to LOVE Florence and all of Tuscany.

We went to Rome several years ago, and enjoyed it immensely. Then a few years later we went to Florence and that was magical. So it didn't get worse. It actually got better.

But don't look for the magic or you won't find it. You have to let it happen. It won't happen if you look for it.

"It won't happen if you look for it"

On the contrary for me. My first time in Trieste, booked in for 5 nights, and after day 1 (albeit arrival day), I thought the place was a dud. I kept thinking, how can that be. So after many beverages and almost single handedly cleaning out the Aperitivo table, I thought man you're going to have to bear down on this place, and I did. By noon of the 2nd day, the beauty and history of Trieste started to unfold and continued for the remainder of that trip and 3 return trips.

Rome was actually better on a return visit as we could dispense with some of the acclimation stuff such as how the city is laid out, where to get euros, how public transit worked, etc. Was nice to be able to hit the ground running, sort of speak. We also stayed longer, and could skip the majority of the most overrun attractions we'd seen before, such as the Colosseum and Vatican Museums, and explore other corners. Can't wait to do it again!

Every trip is different. Just consider your own interests and those that you travel with. Enjoy.
Our first trip to Italy was in 1987 and we got food poisoning at breakfast in Interlaken which made the travel through the tunnel miserable as my wife was throwing up into plastic bags. We got a good hotel in Milan with one need: an ensuite bathroom. Then on to Venice for a couple of nights and she couldn’t eat anything except gelato while I was recovering with normal foods. I still remember eating in a small back street fish shop sitting at the counter and when asked if I would like some wine with my fish, I said yes. It was house red served in a heavy glass. Nothing fancy but good. We did the normal tourist things but we would like to return to Venice but other areas called and are calling. In Italy, we’ve done Aostra, Cinque Terra, Tuscany, Naples, Capri, Amalfi and Puglia and they were all good. This year, we are going to Rome, Umbria, Lakes district and Dolomites but we spend more money and more nights in each place as we’ve retired and more affluent than in 1987 as our children are all educated and self-supporting.
Our interests and expectations have changed over time but we still look forward to our trips, one big one each year again, post COVID.

Just returned from 8 nights in Italy and this time we brought 2 of our adult children. I can't imagine Italy not being magical, I simply love it.

We spent 3 nights in Rome and while it was quite busy, that didn't impact everyone's absolute enjoyment of everything the eternal has to offer. Our remaining nights at Agriturismo Bonellino Vecchio outside of Pienza were nothing short of amazing. Great wine and food and of course stunning views. My DW and I were just talking about how we already can't wait for our next trip to this wonderful country.