Should you plan your own Italy trip or book a tour?

The topic of whether to plan and book your own Italy trip vs. going with a package tour has come up a few times recently, both on the WhyGo Italy Facebook page and in the comments of some of the articles here on the site, so I thought I’d take a moment to post my thoughts here.

So, should you book your own Italy trip or go with a tour? My short answer is: it depends.

Those of you who have poked around on the site probably won’t be surprised to hear me say that. On certain topics, I’m happy to take a stand – but most of the time, I don’t feel like it’s my place to lay down some kind of travel law everyone must live by. I’m just happy y’all are traveling, y’know?

And now, yes, here’s my longer answer.




I genuinely believe that planning and booking your own trips, no matter where you’re going, results in more rewarding travel experiences. This is partly because you, as the traveler, get to see the process through the whole way, from sowing the seeds right up to harvest. It’s extremely gratifying to do your research to find, say, a secret ticket window in Florence that lets you get reservations to bypass the line in front of the Uffizi – I give you permission to feel a bit smug when it works just like you heard it would.

Besides the personal satisfaction of a job well done, however, there is the simple fact that when you’re on an organized tour you don’t have the leeway that’s required for spontaneity. If you’re lucky, you’ll get a few hours of free time each day, but asking serendipity to adhere to a schedule sort of defeats the purpose. Making your own agenda (or making up your mind not to have one) gives you the freedom to explore whatever strikes your fancy. Spend longer in a cafe because you’re having a great conversation with a stranger, seek out a suburban flea market to look for treasures, or take a wrong turn on purpose just to see where it goes. In my own experience, it’s these unexpected detours that have led to some of my most cherished travel memories – and most would have been impossible if I were being shepherded around on a tour.

All of this waxing on about the merits of planning your own trip, and I still think “it depends?” Absolutely.

Planning your own trip to Italy does require more work than booking a package trip, there’s no getting around that. If you’re one of the many over-worked people who barely has time to do the grocery shopping, let alone research hotels in Venice, you might feel a panic attack coming on at the very thought of figuring out all the details involved in trip planning. Folks, travel is supposed to be fun. The best kinds of trips include challenges, I firmly believe that, but the overall feeling shouldn’t be one of dread, obligation, or discomfort.


The bottom line is that you need to listen to your gut – what are you comfortable doing? Do you get excited about planning your own trip, or does the very idea make you want to stay home? The answer to that question will tell you whether you should go DIY or book a tour. Either way, so long as you’re getting out and seeing the world, that’s a good thing.

photo by pmorgan67

18 thoughts on “Should you plan your own Italy trip or book a tour?

  • Melissa

    I totally agree. I think I did both. We booked through a travel agent, and though she tried to get us to do 3 days in each city, I insisted on a week, booked a few tours through her, and left the rest of our days to wander around each city, get lost and go where the locals go.
    We did get to bypass everyone at the Uffizi and the Vatican, with a bonus at the Vatican-it was only my husband and myself on a guided tour! So we did spend more than a few hours there, Francesca was also out guide at the Forum, and she was an rcheologist student! Our wine tour was great too, only one other couple!
    In each city we found some oout of the way places we really enjoyed. If you have the time, blend both.

  • jennice evans

    Hi myself and 2 friends are currently trying to plan our first trip to italy and have 4 weeks. When you work full time it is hard researching, finding the best accommodation deals and panicking wondering if you will get it to come together. For us doing our own trip means all the confusion and wrong steps will lead us to find and experience people and places we would never have had the opportunity to enjoy if we did tours. That doesnt mean some day tours wont be happening, just that we want to embrace all that we can from being accidental tourists in a way. Flying into rome we have booked 4 days in a b & b, then train to sorrento where we have 5 nights booked. The decision to then book as we go i hope will be the right one as we have a friends family in brindisi to stay with before we head to venice, florence and pisa. We hope to go from pia to sardinia and then back to rome to fly home to Australia. All sounds good in theory but i cant help wonder where we will really end up on our travels. Living in a country where travel distances are huge our biggest challenge is understanding that in Italy distances between places is quite small. Ciao

    • Jessica Post author

      Distances may seem short, Jennice, but be sure to look up transportation times in advance to give yourself an idea of how long it takes to get from city to city – sometimes, it’s much longer than you’d expect!

  • Nancy

    Interesting blog post. About 10 years ago I promised myself I would go to Italy before I turn 65. I will be 65 the end of February. For the past year I’ve agonized over planning this trip — completely planning it on my own, opting for an independent package, or an escorted tour. Since I’m traveling alone, don’t speak the language, and am getting a bit lazy in my old age, I finally decided on a nine day escorted tour with some free time in the afternoons. I’m not a follower so it will be interesting to see how I fare. Whatever happens, the highlight will be waking up in Venice on my 65th birthday!

    Thanks for the great posts. I’ve picked up some good information over the past few months.

    • Jessica Post author

      Waking up in Venice on your birthday sounds just about perfect to me, Nancy! And I think you’ll have a great time – going on the trip with a tour is better than agonizing about it for years and then not going.

  • Cameron

    Hi Jessica. Loved your tips. I will post soon my pics in Rome. Italy is really wonderful. The pasta I had near St. Angelo Castle was the best thing I ever ate in my life. I personally prefer going alone, thank booking a tour. A good choice is using the bus tour, especially if you have no time

  • Jamie

    Hello: Your site is very helpful and overwhelming at the same time. We are taking our three kids to Italy this summer for our 25 anniversary. They will be 22,19 and 14 at the time. We will probably go for at least one week, maybe a little longer. Want to see Venice, Florence, Rome and a beautiful beach with lots going on to keep kids from being bored. Any helpful hints on where to anchor oursleves, how best to travel (train), and which direction to go?

  • karen

    Hi Jessica,
    My daughter and I (she is 26 yrs old) will be traveling to Italy (from LAX) this summer. We would arrive in Italy on Sat Aug 25, 2012 and need to depart on Mon Sept 3, 2012, so 9 nights/ 8 1/2 days there. We are thinking of visiting 3 areas in that time 1.) FLORENCE (including a couple day trips from there, possibly Pisa, Chianti area wine tour, Siena, San Gimignano), 2.) CINQUE TERRE area (would like to spend at least an overnight and do some hiking and 3.) LAKE COMO area.
    Do you feel these 3 areas are doable in this amount of time and how many days/nights in each?
    Also would you suggest beginning in Lake Como ( I am assuming flying into Milan would be best?) then to Cinque Terre and end in Florence (depart form Florence airport back to LAX) or would you do the reverse? I have heard that Lake Como is crazy busy on summer weekends, so wondering if it would make sense to do that area in the middle of the trip (middle of the week). Or just skip it completely this trip and concentrate just on the other 2 areas? Thanks for your advice 🙂

    • Jessica Post author

      I think planning to stay in three places during an 8-9 day trip is fine, and your three suggestions are good ones. All three of them are popular, especially during the summer, so I’d recommend you book accommodation (& possibly train tickets/reservations) in advance so you don’t get caught out. And it really doesn’t matter which direction you travel in – the main thing on such a short trip is to fly into one airport and out of another so you don’t have to backtrack, but it looks like that’s your plan already. One note – sometimes Pisa’s airport has better/cheaper options than Florence’s airport. (Pisa’s is bigger.)

  • Julie

    I have 23 days in Italy in August 2013 so will be doing a 9day/8night tour around Tuscany/Florence region. It’s a smaller group so won’t have to have 40 people trying to fit into restaurants and such. The smaller bus gets us right into the towns and villages and goes to out of the way places that I might not have thought of (or had time to research) myself. We can also eat and stay in smaller boutique restaurants and hotels/villas. The rest is on our own (with partner). We have 3 other couples in Italy at the same time and will just make sure we have some time together in Milan and hope to meet up at a few other places as we travel around. This way, we have the first few days with our friends (fly into Milan), before going on our tour, which is still very flexible, and then another 9 days at the end to see more sites on our own (most likely Sicily). I think we have the best of both worlds!

  • Ron Greenwood

    My Wife and I are planning a tour of Italy this coming Spring over 7 days. We are starting in Rome visiting the Colosseum, Vatican Museums St. Peter’s before heading to Florence where we plan to see Michelangelo’s David and Signoria Square. We end out tour in Venice and plan to visit St. Mark’s Square and Basilica, Doges’ Palace and the Bridge of Sighs. We are spending around 2.5 days in each city before moving on, is this enough time?

  • Jake Brown

    You’re right, planning is everything to make sure that you get what you are looking for from your travels. That is never more true than when you are planning school trips to Italy. Planning is what will not only keep everyone entertained but also safe.

  • Jamie

    I agree with your thoughts about not going on tours. I spent a few days in Venice, Verona, Padova, Desenzano del Garda, and Portofino this summer and letting yourself idly wander is the best way to see these places. My method of travel is somewhat different from everyone else’s however, as I was hitchhiking everywhere and sometimes just sleeping in my tent. Despite this, I was completely free and I had a wonderful experience in all of the places that I visited.

  • Mark S

    I couldn’t agree more with planning your own trip because who knows your like better then you. You can pick what area of whatever city you are going to stay in and you can do that much better after you figure out what you want to see. Doing it this way you will be able to pic the most convenient place to get to all the places you want to sight see. However i could see if you were going as a very large group that maybe going on some kind of guided tour I know many older people like to do this and is probably ok as long as you don’t have any specific places you want to see.

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