First-Time Visit to Italy – Advice on a Two-Week Itinerary

Your first option (Venice and Florence) would be best for your first trip to Italy. You can easily take a train to travel from V to F and it will take as little as 2h15. Visit the Trenitalia website for schedules and tickets.

Naples and Palermo would involve a bit more planning to travel from one city to the other.

I’d choose option 1 for your first visit to Italy as I think Venice and Florence will give you the vibe you are looking for more than Naples and Palermo which I consider two of the grittier cities in Italy, interesting to visit but not so easy for a first timer.

Start in Venice and spend your time wandering through the city exploring the many piazzas, side streets and just absorbing the city. Learn to use the vaporetto system and take trips to some of the outlying islands. Piazza San Marco is one of the world’s greatest people watching spots, and it’s worth a splurge for a light lunch to sit and watch the world go by for a couple of hours! And of course, at night Venice is magic. Verona and Padua are both easy train rides away if you wanted a break from the busyness of Venice.

Can’t help with Florence as I’ve not made it there yet but again train service makes it easy for visits outside the town. I enjoyed Lucca a lot and would recommend a day trip there. Siena is also a popular day trip from Florence as well.

The thing about pairing Naples and Palermo is that they are both rather large and very hectic cities. I really liked them, and I hope to return to them, but seeing them on the same trip, as your only stops in Italy, doesn't provide the sort of contrast I would want. (i don't mean the cities are the same.) I'd go for a combo of Venice + Naples or Venice + Palermo, or you could substitute Florence for Venice in either of those combinations.

Logistically speaking, there's no great advantage to pairing Naples and Palermo, because the train trip is quite long. I tried to get around that impediment in 2015 when I needed to move from Orvieto, north of Rome, to Catania, Sicily's second city. I booked a berth in a couchette car from Rome to Catania. It was a nightmare--not a wink of sleep because the railcar jerked constantly from side to side. It was utterly miserable, I crashed at my Catania B&B as soon as I could and slept the rest of the day, messing up my sleep schedule for several days. I think at least one person here book a sleeper-car berth on that train and found it OK, so maybe that's a workable solution if you want to avoid flying. Me, I wouldn't risk it.

I don't think you understand how different are north and southern Italy. There's nothing dangerous about them, but it's as if you are choosing between a week in the grittiest and sketchiest area of Antwerp, and a week in a luxury B&B in Bruges. (This is unfair to Naples and Sicily, but the CONTRAST is, at least, correct.)

https://community.ricksteves.com/travel-forum/trip-reports/surviving-naples

Venice is good for a week, and there are a few nearby important cities if you should tire of Venice. We "saw" Florence in four nights, so I would only point out that transportation to the broader areas of Tuscany can be difficult without a car. I simply mean that your choices, and the number of towns you can visit in one day would be greatly limited. Most posters on this newsboard say that Tuscany (meaning multiple hill towns, wineries, and so on) is one of the places where a car is highly desirable. A car is unnecessary in Florence or Venice.

https://weatherspark.com/m/72429/4/Average-Weather-in-April-in-Venice-Italy

https://weatherspark.com/m/76575/4/Average-Weather-in-April-in-Naples-Italy

I don’t think you have to choose Venice and Florence just because it’s your first trip to Italy. If you like cities, Naples and Palermo could be more up your alley, and they are just as authentically Italian as anywhere else. Choose the places you are interested in.
I typically don’t pair two places I have to fly between, but otherwise I would choose what you think balances your time in Greece well.

If you like things slower, Venice and Florence are perfect. Naples is crowded and busy, but fun, too. Haven't been to Palermo yet.

Venice and Florence are likely to have a lot more tourists than Naples or Palermo in April, if that matters.

Florence and Venice will indeed have more tourists, however, given your interests and your non-interests, you will be able to mostly avoid the crowded areas in both cities. In Venice, we are the most fond of the eastern Castello area and of Cannaregio, but there are other parts of Venice for good local food and few daytrippers. Early morning and the evening and night are your friends. In Florence, we like the Sant'Ambrogio area and the western and eastern edges of the Oltrarno --- we've just happily spent 5 weeks in San Frediano and also enjoy visiting San Niccolo. Also, all of Venice and the center of Florence are easily walkable from one end to the other.

If one's interests are mostly culinary, I'd select Bologna and somewhere in Liguria or Umbria. In my opinion those are the most important food areas in Italy. (Others likely disagree.)

Thank you all so much for your contributions. Your input has made everything much clearer in my mind regarding where I want to go and what I want to experience. After considering everything, I've decided that I'll choose just one place to stay and make it my base for the trip. I really want to relax, enjoy the experience of being in one location, and immerse myself in the daily life of that place without feeling rushed or pressured. I have about two to three weeks, and I think I’ve made my decision—Sicily.

Sicily is a huge island, about the size of Belgium, and I think it has everything I'm looking for. It's far less expensive than places like Venice and Florence, and much less crowded. I live in Brussels, and when it's crowded, it makes me feel really anxious and agitated with all the tourists. I’m hoping in Sicily, I can avoid that feeling of being overwhelmed by the crowds. As for Palermo, I'm not concerned about it being gritty. I’ve visited places like that before and honestly, I think it adds to the charm and character of the place.

So, my plan is to stay in Sicily for two weeks, explore the island, and enjoy the simple pleasures of daily life. I’ll be cooking my own meals, enjoying local produce from the fish and vegetable markets, and soaking in the atmosphere of the place. I don’t plan on eating out every day; I just want to relax and cook my own food, but I may try some small Sicilian street food or snacks, especially those that the island is famous for. Some of these include arancini (fried rice balls filled with a variety of fillings like meat or cheese), cannoli (sweet pastry tubes filled with ricotta cheese), sfincione (a type of pizza), panelle (chickpea fritters), and granita (a refreshing shaved ice dessert, often flavored with citrus or almonds).

I don't feel the need to travel all over the island—Sicily is massive, and I’ll be focusing on exploring the nearby towns and enjoying the slower pace of life. I’m not making this a tight plan or itinerary—I just want to go with the flow and not rush through it. From Palermo, I’ll be able to visit surrounding towns easily by public transport, without the need to see everything in one go.

As for accommodation, when I checked the prices in Venice and Florence, they were significantly higher—almost two to three times more than what I would pay in Sicily or Naples. For instance, on Airbnb, what costs around 50–55 euros a night for an entire apartment in Sicily is priced around 100–150 euros a night in Venice or Florence. I prefer staying in my own apartment when I travel for longer periods, as I don’t like the feeling of being in a hotel where I can’t cook my own meals and just relax in my space.

So, to sum it up, I’m excited to experience Sicily, take my time, and enjoy the simplicity of daily life without the pressure of following a strict plan. I’m looking forward to the slower pace and everything it has to offer.

Sounds marvelous--I think you'll enjoy just being on the island versus flying back and forth--enjoy!