North Italy and Tuscany - too late to book for late June? should we squeeze in Bologna?

Too late to book what? Flights? Hotels?

Pretty sure you can find flights and lodging for those dates

In the above itinerary you would likely want a car for the Chianti region
If you’re not willing to drive then go to Bologna instead

Did your “agent” come up with this itinerary?
I suspect the agent wants to book you lodging where he/ she gets a cut.

You can look yourself on Booking.com

I’ve booked air tickets to Italy from California less than 24 hours before leaving (and always in the peak of summer months). They were family emergencies of course, but you can always find flights. Obviously if you plan to fly to Europe today or tomorrow you will pay through the nose, but it will never be too late. Generally however you should try to buy tickets 1 to 7 months ahead to pay less than an arm and a leg. And for June/July it is better to buy sooner rather than later. For accommodations you can also find accommodations on the spot. Some places may have no vacancies left but there will be always some that do.

You could make time for Florence by skipping S. Casciano (Chianti area will already check the Tuscan countryside box), shortening Chianti to 3 nights and spending 3 nights in Florence at the end. You would drop the car just as you get to Florence.

I like both Lake Como and Lake Maggiore enough to think that yes, visiting both makes sense, but I would not choose expensive Ascona as a base for Lake Maggiore. Stresa, Baveno or Verbania are much cheaper (being in Italy), closer to Milan airport (safe distance to drive on arrival), and right where you want to be. Also, 2 nights are enough - I would rather spend 3 in lake Como instead.

As for timing, late June is in 3 months: that's still plenty of time. Accommodation is not scarce in those parts, and June is not peak season yet.

I agree with balso^.
Don't push off until next year!!
For food, I would add Bologna.
For cost savings, I would eliminate Switzerland, but I have not been to Ascona.
Varenna is just the best!
Have a great trip!!

Thinking back on this, you could skip Lake Maggiore altogether, spend three nights in Varenna, then 2 in Bologna on your way to Tuscany. No car needed for that first part: you could rent the car in Bologna to drive to Tuscany, or even take the train to Florence, and rent there, saving a bit of driving time over the Appenines.

Ascona is pretty but hell of expensive, and so is Locarno.
Stay on the Italian side of the lake (Cannobio or Stresa), and visit both from there.
Whether you want to visit Florence (or Bologna) is up to you. It depends on your tastes and aspirations.
If you decide to visit Bologna and rent a car later for Tuscany, do so in Bologna and drive from there. No need to incur into the extra expense of taking the train+taxi to reach the rental office in Florence and dealing with the hassle of driving inside Florence. Getting out of Bologna is more car friendly.

It sounds like you are working with a travel agent? Maybe the hotels they use are getting booked up, but not everything.

I checked the popular Albergo Milano in Varenna and found rooms or apartments available for a 2-night stay on most late June dates. That includes the room we always book, on the top floor of the annex named Casa Rossa. It is large, bright, and has a huge lakefront terrace and a kitchen corner. Lots of stairs to climb to reach it, but the view over the lake makes it worthwhile.

https://www.albergomilanovarenna.com/it/casa-rossa/

Maybe consider finding and booking places yourself, rather than use the agent who seems to be discouraging you. Build your itinerary and book your hotels before you purchase flights, so you can be a bit flexible with dates.

I think I'd pick either lake but not both lakes. Stresa is a great location and the train in pretty convenient to town. Easy to get to from Milan. We have stayed up in Locarno - it's nice but it is expensive.

Can I ask why San Casciano di Bagni is on your list? I would cut a night off Chianti and take that bight and the 2 in San Casciano di Bagni and either stay in Florence or Bologna. You could fly home from either airport.

First, a HUGE THANKS to all of you for your helpful input!! The Ascona stay is due to a leftover credit from hotel group in Switzerland . Two years ago we left ski trip earlier than expected due to a knee injury, for the lost days they would only give credit to their hotel chain that has property in Ascona.

I think the San Casciano di Bagni and one night in Tuscany is getting cut for some time in Bolonga. We like to leisure e-bike thinking they will have what we're looking for..

Bologna is a nice choice; we just spent 4 nights there, in an apartment is a great location right in the center.

If you put Bologna at the end, you can fly out from there. Marconi airport is a nice small airport, very easy to reach from the city.

If it is biking you want, also consider nearby Ferrara ( half-hour from Bologna by train). The city is very bike-friendly (more so than Bologna), and since it is totally flat, you don’t need an e-bike. We stayed there at Hotel Annunziata, across a piazza from the castle. They offer bike rentals on-site —-check that section of their website.

https://www.annunziata.it/en/