Heart of Italy in late May questions/input

Hi Lisa and welcome to the forum!

When I took this tour in 2019, I stayed an extra day in Florence then went to Bologna for four days. I had planned 2-3 day trips from Bologna. But I liked Bologna so much that I only took one day trip - Ravenna to see the mosaics. I was very happy with that decision.

I did not do any food tours. But I would note that May is peak travel season and food tours may get booked up.

Both seem so casual and I worry about looking under dressed.

Don't. be worried.

Keep your feet happy. No one will care or say anything about your footwear.

....is the weather nice enough this time of year to warrant adding in the travel days and heading to the water?

You want beach time or swimming? Whether the water will be warm enough for you is impossible to answer. Probably not 'polar plunge' cold , but not summer in Florida warm.

From where do you fly home? Knowing that will help in making suggestions of what do to with your '6 additional days'

Thank you both the replying :)
We haven't booked our flight home yet- waiting until we decide where we want to travel. So if there is a gotta go to location we can make it happen. I guess Im wondering if it will be warm enough to even lay out in the sun, knowing that the actual water is not going to be enjoyable for swimming yet this time of year. Thanks again for the help!

I don’t know about the water temperature in May, but the air will be warm if not hot by the end of May. When we took this tour a few years ago, we spent 3 days in Milan and 3 days in Varenna on Lake Como. Both are easily accessible by train from Florence.

Bologna then Venice
3 nights each

Late May is almost always fantastic weather-wise. We have swam as part of long hikes, but it wouldn’t be swimming temps for me otherwise. A refreshing dip if sitting on the sea would not be out of the question.
Where on the sea were you thinking of?

I agree not to worry about your footwear looking too casual. Your Brooks and your Chacos will work really well if you can walk a long distance in both of them, lol!! This will not be too casual for the RS tour and any place you have group meals. IF you guys are going to high end restaurants on your own, then maybe slip in a pr of ballet flats although I would not be able to walk on cobbles in them! Maybe your feet are a lot younger than mine, lol!

I do recommend you bring a waterproof rain jacket with a hood. My first RS tour was Heart of Italy in May and we got drenched in Cinque Terre and in Florence. I had shoved in a rain jacket at the last minute so was good buy SIL had to buy herself an umbrella in Florence, lol. Some of the tour members went into the Med in Monterosso but I'm not really a water person so didn't even dip my toe in.

Do try to get to Rome a day or 2 ahead of the tour start, both to give yourselves flex time in case of travel hiccups but also because there is so much to see and do in Rome. Yes to adding at least one more day in Florence. I'd add time in Venice if you can unless you feel strongly about Bologna. I have not been to Bologna so no real opinion there.

Bologna is great for food - there’s a reason they call it “Bologna la Grassa”! But if you can spend a few days in Venice I recommend doing that - there is no other place in the world like it. Good luck with the trip!