Travel to Italy May 2024

Remember that your first and last days of your trip will essentially be wasted. And every time you move to another city is essentially a wasted day. Your itinerary has more days travel that I would prefer. We've been to Italy 10+ times, and we now travel slower due to Italy having such great food, art, architecture and culture. It's easy for this country to overwhelm first time travelers.

You might want to start planning with a good travel book--Like Rick Steves' Italy. The Big 3 are Rome (4 day minimum), Florence (3 day minimum) and Venice (3 day minimum.) I would probably skip Cinque Terre and Pisa since you're wanting to visit the Amalfi Coast. Sicily is another place that you could save for a future trip.

We spent a long weekend in Florence and then moved into an agriturismo outside of San Gimignano and Certaldo for a few days with a rental car. The Tuscan countryside has some great hilltowns that are well worth slowing down to see closely--Siena, Volterra, San Gimignano, and others. We turned our rental car in at Orvieto (great hilltown) and took a 70 minute train into Rome Termini. Tuscan roads are well paved, well marked and easily traveled--if just a little crooked. No problem driving there.

You'll be traveling in the high season, and I would suggest you get prior hotel reservations. I usually go thru Booking.com or Hotels.com but there are many ways to find hotels. I often go to Google Maps and find a city or neighborhood to stay at--then click on the Hotels block on top and icons pop up everywhere for rooms.

The more tourist traffic a city has, the more English will be spoken. We have found rural Italy to have many non-English speaking people, however. But language has never been a barrier to us.

Italy is so popular of a travel destination that you will do better to plan your trip closely--and not try to wing it. Preparation is just so important to avoid any surprises. I'm not about to sleep in a rental car again--for example.

First of all, language will not be a big issue, most of the people you deal with will have a little to excellent English, learning a few polite words is all that is needed.

For most of the places you mention, and the time of year, yes, I would book ahead. Once you are comfortable with your itinerary, start looking, if you notice things getting tight, book sooner than later. Leavings a night or two here and there is not a problem if you need some flex. I like Booking.com, they have a wider range of accommodation, from hotels to apartments, so you can really compare. Payment also seems to be better on booking than Airbnb, and all costs are disclosed upfront. I tend to forgo a hotel breakfast, especially when you see the discount you can get without. Coffee and a pastry in a nice cafe is part of travel, a bigger breakfast can easily be found if needed.

As for your itinerary, yea, it is optimistic. Pisa can be done when passing through or from Florence, not worth a night. The others are fine, except for Sicily. Sicily is a long ways, even from the Naples area, and really needs quite a bit of time. I would personally drop Sicily, easily allowing 3-4 nights in each of the other towns, a bit more for Rome, Amalfi Coast, and Florence

We want to visit Milan, Venice, Bologna, Pisa, Cinque Terre, Sorrento, Amalfi Coast, Sicily and Rome.

Good for you for taking 4 weeks in one county! Still, it would be a very hurried pace to visit all of these locations and have any quality experiences. Let's say you have 28 nights on the ground in Italy and plan from there. Sightseeing, I presume, involves historical sites and perhaps some museums? Wine area abound so I have a few you can key in on for an itinerary.

I agree with David that if you visit Sorrento and the Amalfi Coast, skip the Cinque Terre. Or vice versa. One seaside location.

Perhaps arrive in Milan and assuming you land in the morning, immediately take the train to Venice for 4 nights. You can get used to Italy and recover from travel. Lots to see and do and May weather is usually lovely! There is even a winery on one of the Laguna islands, https://www.venissa.it/. We haven't made it there yet, but it is on the list for our next (14th!) visit.

From Venice, Bologna is easy to get to and a great base for day trips to Ravenna, Ferrara, Modena, and Parma, if that interests you. All great food and wine cities. Several nights in Bologna would not go amiss. A car is not necessary although you might want to set up a private tour or two. (Usually a good plan for a group of 4.)

Tuscany is notably absent from your list. Perhaps because you feel you'd need a car? You could stay in Florence and day trip to Pisa by train and also get a nice tour with Tours By Roberto (see Rick Steves' guide books and also Roberto's website.) He combines history, food and wine in one of his all-day tours and we enjoyed it very much. You can also day trip to Pisa from Florence and also set up a wine tour of Chianti whether with Roberto or another company. Lucca is another nice day trip. Easy to pass 5 to 7 nights here assuming you also want to take in some famous art museums.

If you choose the Cinque Terre getting there from Florence is a bit schlep involving two or three trains and about 3 hours. Stay at least 3 nights to make the journey worthwhile. Check out wineries in the area that make Vermentino and Sciacchetrà. Walk thorough the vineyards high above the sea. Fabulous. And once you are high up (there's a shuttle to take you so you don't have to climb all the way) you will escape some of the hordes in the villages.

Getting to Rome is easy from the Cinque Terre and a week would not be too long and at least 4 nights. Myriad day trip options.

Once you add up those nights, there really is not much time to go south. It is a schlep to make it to Sorrento and Sicily is a two-to-three week destination in itself. And it will be getting very warm by early and mid June.

Are hotels with breakfast better than Airbnb?

Each has advantages and disadvantages. First off, how close is your relationship with the other couple? Would you be comfortable living in the same space as them for four weeks in an apartment? Or would you prefer to have some private time?

I just spent two weeks with another couple in Italy, staying in three apartments and one hotel/pensione. My preference was for the hotel.

If you can find a 2 bedroom, 2 bath apartment, the advantages are more living space, a kitchen, and usually a washer/dryer [you will learn the pitfalls of a condensing dryer}. But you will then have the responsibility of shopping for food - you'll be lucky to find more than coffee and sugar already stocked - and probably learning how to brew coffee in a Moka pot.

A disadvantage of apartments can be less flexibility storing luggage - both on arrival and departure - especially important if traveling by train.

A hotel will almost always allow you to drop luggage early or store it after checking out. I very much preferred having the hotel breakfast each morning, with a wide selection of cereals, proteins, fruits and baked goods, as it was easier to stick to the high fiber, high protein, lower carb diet that I'm used to. Plus no need to venture outside to find a breakfast venue, especially if you're looking for more than caffe and a cornetto. In addition, having hotel staff available to answer questions, recommend restaurants, calling a cab to get to the train station - all advantages in my view.

You may want to consider a combination of both types of lodging, with an apartment more appropriate for longer stays in larger cities. And note that for three of the four locations, there was at least one long flight of stairs up, and in one case three flights. So mobility concerns could also be a factor.