Day Trips vs. Overnight Trips in Italy: How to Choose

Going into an Italy trip knowing you can’t possibly see everything is a good place to start, but of course that won’t stop you from trying to cram more places and sights into the trip. We all do this. I do it every time I travel. And as part of this process, one of the inevitable questions is whether you can fit a day trip or two in to expand your travel horizons a bit more.

I’m a big fan of day trips, and I often advocate them in my suggested Italy itineraries. Recently, however, I’ve gotten questions about day trips that made me think I ought to consider the options more thoroughly – for me and for you.

Day trip or overnight trip? That is the question.

Venice || creative commons photos by Turinboy (left) & halbag (right)

Venice || creative commons photos by Turinboy (left) & halbag (right)

A few readers have written to ask whether they should, as part of the Italy trip they’ve got almost entirely planned already, include City X as a day trip or if they should spend a night there instead. My replies have felt like gut-level reactions based on the rest of the existing itinerary and the city in question, but the truth is there are some factors I take into consideration when answering – I just hadn’t articulated them before, even to myself.

Keep in mind that some places are really only good as day trips, so they’re easy to plug into your itinerary without considering the question any further. Attractions like Pompeii or Tivoli, for instance, aren’t exactly places you can spend the night, after all. No, this question is really about cities, places that can be (and often are) considered day trip destinations, but can also easily become home base for a night or two.

My goal with Italy Explained is always to give you the tools you need to make more informed decisions about your own trip. I’m less inclined to tell you definitively to do one thing over another, since we all travel differently. Here, too, I’m going to offer my suggestions about what to consider when you’re figuring out whether to spend a night (or more) in a place or treat it as a day trip.

The choice, as always, is yours.

The Case for Day Trips

Pisa || creative commons photos by Ryan Raffa (left) & Steve Slater (right)

Pisa || creative commons photos by Ryan Raffa (left) & Steve Slater (right)

Hotel Changes

My rule of thumb when sketching out an itinerary is that I want at least two nights everywhere I stay. This is largely because I hate packing and unpacking during a trip (it eats up too much time, and if you’re doing it every day that’s a lot of wasted time, in my opinion) and also because the whole checking out/checking in process can take a big chunk out of what should be sightseeing or relaxing vacation time.

I’m stingy with how I spend my travel time, in other words. And that means sometimes I’m not interested in turning a day trip into an overnight trip if it’s only going to be for one night. This might not be a big deal to you, but it’s worth mentioning because it’s easy to forget the time it takes to move cities and hotels every day.


Sometimes a city’s lodging options are expensive enough that it makes an overnight trip more of a challenge for budget travelers. Venice is a good example of this for many people, and one of the reasons why it’s such a popular day trip city. I love Venice to bits, and I’ll splurge on a night or two there, but not everyone shares my affection for that crazy city.

When you’re weighing the options and you feel an overnight trip is just too expensive for your budget, I’d suggest still doing the day trip if you’ll regret not seeing the place in question. A day trip is, in most cases, better than no trip at all.


Deciding not just to take a day trip but to book an organized tour day trip means that not only is transportation often taken care of for you, you won’t meander around aimlessly trying to find a museum or figure out where to eat. You know in advance what’s covered in a tour, and can choose one that hits all the highlights of a place on an efficient schedule.

Taking an organized day tour can be an especially good idea if the destination has a long list of things to do or see (meaning you’ll be overwhelmed with options without some guidance) or it’s difficult to reach on public transportation (meaning you’d otherwise spend a lot of time in transit or need to rent a car).

Not Much to Do

This is where some advance research on the destination is important, because you’ll probably be able to tell pretty early on whether the list of things you want to do or see there is long or short. And I don’t mean the list of all the things to do or see – I mean the list of things that interest you.

If there are two museums you’d love to see and that’s it, then spending more than a day is probably not worth it – you might get bored. If it’s a small town where there isn’t necessarily anything to do other than stroll through the historic center, think about how long you can realistically enjoy doing that before you’ll want to move on.

The Case for Overnight Trips

San Gimignano || creative commons photos by Justin Ennis (left) & Danilo Paissan (right)

San Gimignano || creative commons photos by Justin Ennis (left) & Danilo Paissan (right)

See Another Side of a Place

I’ll admit that whenever I add a day trip to a draft itinerary, I am soon scheming to see if there’s a way I can extend that into an overnight trip. It doesn’t always work, of course, but I’m usually motivated by a desire to be in a city before and after the day trippers.

Whenever you read that a place is a popular day trip destination, that means it’s an interesting candidate for an overnight trip simply because the character of that place changes (often dramatically) at night when the last train or cruise ship or tour bus leaves town. This is my favorite way to experience a place, and the only way to do that is by spending the night.

You just never know what you’ll discover about a city if you give it a little more time.


You can get a lot done in a day trip, I won’t disagree with that. Especially if (as mentioned above) you book an organized tour or you purchase tickets for popular museums or attractions ahead of time so you’re not standing in line for half the day, it’s certainly possible to tick a lot of boxes with a day trip.

The thing is, I don’t usually move at that speed. I’m not sure I ever did, even when I traveled in my 20s – and I certainly don’t now. Sure, I can hustle if I need to, but I’d rather not. I’ll take two days to see what other people can see in one, and that’s fine with me.

(You might get antsy with too much time lollygagging in between things to do, in which case this relaxed pace may sound dreadful. In any case, it’s something to keep in mind.)

Too Much to Do

On the flip side of the “Not Much to Do” item discussed above, if your pre-trip research yields a list as long as your arm of things you want to do or see in a place – well, that’s a pretty good bet that a day trip wouldn’t be long enough.

And if that small town in which the only thing to “do” is stroll sounds like your idea of heaven – you workaholic who can’t slow down unless forced, or you honeymooner who just wants to walk around with your beloved all day – then a couple days immersed in the small town vibe might be ideal. Again, it’s about what you want to do in a place, not what the guidebook says there is to do.

Reverse Day Trip

Here’s a fun twist on the whole question – why not stay the night in that potential day trip destination and take a day trip from there? This really only works if you decide to spend a few days rather than just one overnight, but it gives you a chance to explore the city you’re staying in, see another nearby place, and enjoy the evening and morning atmosphere of an otherwise busy day trip destination.

The first time I visited San Gimignano, a Tuscan hill town that’s a very popular day trip spot, I stayed 4-5 nights there in a hotel inside the old city walls. Being there after the buses left that first day was all the reason I needed to become a “stay overnight in day trip cities” convert, but it got better. There were day trips to Cortona and into the Chianti countryside to be had, plus I came back each night to a peaceful after-hours San Gimignano. It was utterly delightful.

So, how do you choose?

Siena || creative commons photos by Sergio Del Piccolo (left) & Gianni (right)

Siena || creative commons photos by Sergio Del Piccolo (left) & Gianni (right)

These are some of the things I consider when I’m making my own travel choices and, it turns out, when I’m replying to reader questions. But I’d love to know what drives your decision to stay the night somewhere or visit for a day. Let me know how you choose!

2 responses to “Day Trips vs. Overnight Trips in Italy: How to Choose”

  1. You covered it all nicely. The only other decision on doing a day trip or not for me is how long it takes to get there, what the transportation schedule is and do I want to then turn it around in a short period of time, but the packing/unpacking of a suitcase and checking in/out of hotels is time consuming and can even be stressful, not to mention rolling your bag yet another time to and from the new location, and perhaps up and down a moving staircase that just happens to only be standing still at the particular moment you arrive…

    • Jessica says:

      Exactly. It’s so easy to forget the time involved in things like transportation or packing or checking into a hotel, since they’re not the focus of a vacation. So, for me, it’s important to remind people of those time-consuming things so that they’re factored in appropriately.

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