Hello - We are planning a 2 week trip to Italy in November 2025. I've been lurking here for awhile, but planning was interrupted when I tore my ACL skiing in March and thought surgery/recovery would wreck these plans. Long story short: I'm apparently a champ at PT/rehab and no surgery so the trip is back on.
As first timers, this is our rough itinerary: Day 1: Arrive in Rome > Day 2&3: Rome > Day 4: Rome + Train to Florence > Day 5&6: Florence; Day 7: Florence Day Trip > Day 8: Florence + Train to Bologna>Day 9: Bologna; Day 10: Bologna Day Trip > Day 11: Bologna + Train to Venice > Day 12& 13: Venice; Day 14: Venice + Fly Home.
We will not be renting a car and plan on taking a train for day trips. We are active and in our 60s looking to explore the culture rather than ticking the boxes of big tourist attractions. We're like good food and wine.I am looking for the following recommendations:
*Guides to hire in each city
*Ideas for a winery tour in a hilltown for our Florence day trip
*What would you do as a day trip from Bologna? Parma (by train)? Savigno (by bus) for truffle hunting? Modena (by train)? Verona (by train)?
My only recommendation is for a day trip from Bologna. I would strongly encourage you to consider Ravenna. The mosaics are simply stunning.
Although I agree with Phrank that Ravenna is well worth a day trip, let me recommend the daylong food and wine experience with Italian Days. https://www.italiandays.it/
We did this a few years ago, and it was great. You'll learn all about Parmigiano cheese, balsamic vinegar, prosciutto, and sample more wine than you could imagine. Highly recommended.
If you haven't booked flights yet- consider changing the order. It is much easier to fly IN to Venice, out of Rome.
However if your departure flight from Venice is later morning you will be ok. If it's early am it's doable but a pain. Make sure you have your transportation to VCE figured out.
Day trip from Florence- see what toursbyroberto.com offers- always gets rave reviews.
Day trip. from Bologna- Ravenna
I'll echo the Italian Days recommendation in Bologna if you're into food. If you want a food tour in Bologna, I was very happy with Taste Bologna. Another option, if you're into cars, is to go to Modena to see the Enzo Ferrari Museum, then take the bus (museum shuttle or public) to the Maranello Ferrari Museum.
In Venice, I took a private tour of Murano with Valerio from Detourist. There was no pressure to buy anything, and the tour went to a working glass shop and the showroom of one of the really fancy-pants glassmakers. There's also the opportunity to make a bead (as an add-on or you can schedule that directly). Valerio does other tours and group tours, but I went during the 'dip' season between Carnevale and Easter so only private tours were available.
“guides to hire in each city”
This can run a huge gamut and is hard to recommend unless you have specific sites or interests in mind. Do you want private tours? For Rome alone you could need more than one guide or different tours each day.
Rick Steve’s’ guidebooks always have recommended tour guides and tours, although he does not cover Bologna. We have used many Rick-recommended guides over the years as well as his many self-guided walks and tours of sites. I suggest getting a copy of his Italy book, at a minimum and read his recommendations, look at their websites.
I'd ditch the tour guides, and explore places on your own, afterall, you said you were both active.
If you hire guides in each city, you can gain a lot of knowledge, but you will also be tied in to that activity on that day. So it depends on how you feel about the structure of your days. Really consider what you might want a guide for, and why. For example, for us, we have visited Rome a number of times and visited all of the main sites that you would see in any list, and a lot of others, all without a guide. Because I am very into ancient Roman history, we did take a Context Travel small group tour of the Palatine Hill; it's even more ruinous than the Forum, so I felt that having a guide there would be very useful, which it was. For the other sites, in Rome and other cities, we use a combination of Rick Steves info, the Rome (or whatever location) Blue Guide for a huge amount of detail (honestly probably more detail than most people want), or the Michelin green guides or Cadogan guides. I'm old-school, and these trips go back over the years, hence actual books (though some are now on my kindle). Also, more recently, we took a ToursbyLocals (I think?) private tour of Trastevere, which was awesome because she explained a lot of architectural details that we weren't familiar with, and we had a lot of conversations about the politics of Italy and Rome. But on your first trip, I wouldn't really suggest a niche tour like that.
If you're going to take a Florence day trip, get a guided tour that includes a hill town or two and a winery or two. Doesn't really matter which or where because it will all be wonderful, unless you like a specific type of wine (i.e. Chianti or Brunello).
I don't know that you'll want or need to take a day trip from Bologna (which is a city that I love) given the amount of time you have there, but if you do, I also would vote for Ravenna. The mosaics, as stated, are marvelous, and it's a nice little untouristy city, as well. But that suggestion works for you only if you really like mosaics. Any of the other cities are good, too. I love Modena, and have made two 5-night stays there because we like it so much, but IMHO it's a better hang-out city than one that has specific sites that I would say are must-sees. So, Verona if you are into Romeo and Juliet, and Parma has a number of good sites to visit. The Parmesan cheese, you will see on almost every menu in any restaurant in the region, plus in every market in every city that you mentioned.
Enjoy!