Four weeks, starting mid-February in Bologna

Don't miss Ravenna. Also, Verona. Consider using Perugia as a base for 5-6 days to see Assisi and Umbria.

I would pull up the various train options first and ask for feedback on various towns with stops at a good point time-wise for you. I did a cursory glance and they look to take the same amount of time but take different routes.
Are you going to rent a car in Lecce? If not, then I would not spend the entire two weeks there.
Ascoli Piceno is a wonderful town, roughly halfway.

Ditto Ravenna. Ferrara is another fine possibility.

The Gargano peninsula might be a worthy stop for you.

It’s too soon to see what trains are available for mid-Feb, but I’m looking at next week’s schedule and it shows an overnight train departing the Bologna Centrale station at 23:52 arriving in Lecce the next morning at 8:50. You could sleep in a couchette. I’ve slept on overnight trains close to 20 times and it’s worth it. You can sleep in a private car making the experience even nicer. You’ll be awakened by the conductor 30-minutes before arrival and served coffee and helped off so you can’t miss your stop.
If you choose to break up the trip by stopping along the way, Bari and Rome are convenient stops along the Bologna – Lecce route. It will take 7h 15m to travel between Bologna and Bari, but you can take an overnight train between the two as mentioned above. If you do stop in Bari, consider visiting Alberobello (1h 15m by direct bus), Locorotondo (1h 30m by direct bus) and Monopoli (45-minutes by direct bus). Lecce is another 1h 30m by direct train from Bari.
If stopping in Rome, it’s 2h 30m from Bologna by direct train. Lecce is another 5h 30m from Rome but there no direct overnight trains.
If neither Bari or Rome appeal to you, consider stopping in Ravenna (1h 15m). The downside here is there are no direct trains between Ravenna and Lecce so you would have to change in Rimini taking 7h 30m. However, Rimini could be a another stop that would make a good spring board if going to San Marino. You can take a direct bus from Rimini to San Marino (45-minutes).

Ravenna is an easy daytrip from Bologna. Ascoli Piceno would make a nice stop on the way to Lecce.

Ravenna is an easy daytrip from Bologna

Definitely!

Ferrara is also less than an hour away. Hardly halfway and in the wrong direction!

I would just note the bullet for 7 hours and get to Lecce.

I was suggesting Ferrara as one of the day trips during your two weeks in Bologna, not as a stop between Bologna and Lecce.

Carnevale in Venice is from Feb. 19 to Mar 1. Looks like it's going to happen. In past years, Rome has had events during the last week as well. It's probably celebrated in other places as well, but maybe not so much.

Along the Adriatic coast there are several cities where you cn stop along the route Bologna-Bari. Le Marche and Abruzzi are two wonderful regions, but the most of nice towns and villages are inland. Anyway Ancora and Pescara could be two cities where to stop. Aren't plenty of monuments like Bologna or Ravenna, but for a full day stop they offer a view over a less known (by foreign tourists) part of Italy.

Thanks for all the great replies. I'm thinking we'd be better off sticking to the Adriatic Coast.

We'll plan to daytrip to Ferrara from Bologna. And we'd visited Ravenna and Verona on a previous trip. Ditto for Venice and Rome. Gargano peninsula sounds like a good possibility as do Ancora and Pescara. So, my homework is to do a little reading on the last three.

Pescara and Ancona are two port cities and there is not much to do or to see, but near Ancona there are many beautiful hill towns: check out the towns of Sirolo, Loreto, Osimo, Torre di Palme. Another interesting natural site that you can explore nearby is the Monte Conero regional park, that reminds a bit of the ligurian riviera, with several trails for hiking.

Near Ancona, there are several pleasant towns along the coast. Senigallia is tops, little Fano is very cute and pleasant. I only drove past Pesaro (as opposed to Pescara), but it has potential. I considered San Benedetto del Tronto but ultimately had to cut if from my list. I don't think Ascoli Piceno would be too long a haul from the coast, even by train--don't count that one out yet.

@ SamA

Ricky’s use of the superlative wonderful to describe Le Marche and Abruzzi is understated. He is privileged to live close to the region. His observation that one needs to leave the coast and venture in land is right on the money. The train network in this mountainous Apennine landscape is limiting. I have great affinity for the people of this area, having collected via my daughter-in-law many relatives. Also, friends from my many mates whose parents and Nona’s and Nono’s immigrated to Perth after WW2.
I read you report about your time in Stresa and Bergamo. A couple of my favourites. It was good and true. Perhaps the following may be useful. I find a car is the most useful for this region.

I have not travelled on the train system in this area, but have seen the many tracks, and at times regional passenger and freight trains. Mostly hugging the Adriatic coast. About 20 Km’s inland from Pescara is the Abruzzi hilltop town of Chieti, which is close to halfway on your proposed journey. A railway line runs close by. Have yet to go into the town only seeing it from the passing autostrada. A search through YouTube video’s reveals a town with Palladio pediment style renaissance and baroque history, neo classical and no doubt all the way back to the times of the Roman Empire.

A little to the north is the already mentioned Le Marche town of Ascoli. About 35 Kms inland and with what appears to me to be a branch railway line breaking from Porto d’Ascoli. Plenty of YouTube videos. I recommend Alex Polizzi’s Secret Italy episode 2 video on YouTube. She gushes about the town and her memorable times of her youth spent there. It’s about halfway through the video.No additional words needed. Long may I and others have this secret to ourselves.

Further north still is the le Marche Town of Macerata, about 25Km’s inland, and with a train track passing through. Not that easy to get to. Facades from Palladio renaissance, baroque and neo classical. Most of Le Marche and Abruzzi was controlled be the Kingdom of Naples, and influences of the de Medici and Venetians. (Napoleon briefly ruled the region, installing his stepson. Thankfully left little trace of his presence. Apparently did loot some artifacts though.) To my eyes an east coast version of Siena. A university campus with a renown Academy of Fine Arts, and my now favourite open air opera theatre, Arena Sferisterio. (Previous equal was Bregenz Festival on Lake Constance, until Bond franchise used it in Quantum of Solace and made the world aware of its lakeside beauty.) A magnificent neoclassical theatre where one is close to the stage. Bizet’s Carmen, with a young voluptuous soprano can make one feel as though she is inviting you into her net. And an invitation for my wife to give me a sharp elbowing in the ribs. Try YouTube, though many are in Italian. This town takes one back to the Italian era as it was during the time of filming of Roman Holiday and Three Coins in the Fountain. Do you get the impression I really like this area?

Multitude of other hilltop towns but one needs a car to inhale the sweet aromas of Le Marche and Abruzzi. For the ladies. I am told that the LVMH group has its top of the range shoes and accessories made along the coastal strip in this area of Le Marche. Alex Polizzi’s video, mentioned above, has a tour of the rather exclusive Loriblu factory outlet. The women in my family have an addiction for these. Shoes, handbags and coiffure are not the first things my mates and I notice. Of course, my mates and I spend hours discussing our Florshiem styles.

The Mille Miglia often tour through these hill towns. Sounds of early Italian V12’s and post WW2 British and German straight sixes vibrating and shaking the foundations. Testification to renaissance building techniques.

Make sure you quiz Ricky about Emilia-Romagna. He is a wonderful resource. And is free.

Regards Ron

Folks, we have a plan!

Fly into Bologna Feb. 15, two weeks.
Train down to Lecce, five days.
Ostuni, three nights.
Monopoli, four nights.
Bari, three nights, and we'll fly home to D.C. from here March 15.

We'll fill in with day trips from each location - as time and interest allow. We plan to use trains and local transit options for the whole trip.

Sounds great, and you have plenty of time to scope out the transit (highly recommend--it is not as simple as in other regions) and look into occasional drivers/day tours. good luck!

The train stops in Pescara on the coast- very pleasant city. From Pecara, you can do a side trip by bus to Urbino, a wonderful hill town. We also went by train to Macerata, inland from Ancona.

I love your itinerary! We have visited all of those places and would happily return to all of them.
One suggestion I have is to rent a car when you arrive in Puglia.

I'm hoping this is a good balance of big and small-ish, go-go and go-slow. At any rate, this area of Italy will be all new to us. Susan is booking the last of our hotels/B&Bs/apartments today. Now, we need to start back on learning (and remembering) some Italian!

Alas, Delta/KLM cancelled our February flights - Washington, D.C. to Bologna via Amsterdam, so there goes the month-long visit we'd planned for Bologna and down the coast to Lecce. It's the second time in two years our planned trips met the big kibosh! We'll have the Delta/KLM flights credit and, perhaps, we'll get a shot at going in March or April.

Now, to cancel the land reservations. The couple we booked through Booking.com are easy-squeasy. The couple we booked direct through the hotel or through VRBO may take a little more work to get refunds.

A bummer, for sure.

Why can't you rebook flights? There must be others.

We'll certainly rebook flights later when things may be calmer/more certain. Maybe March or April. For this trip, though, the flights kept changing. In one iteration, the Amsterdam to Bologna leg was rescheduled to leave before the first leg from Washington to Amsterdam even left the U.S.! Once that was sorted out, both legs were cancelled.