Travel to Italy

It is doable, maybe not for $5,000, depending on whether that includes fights or not. Five cities may be too much for a first trip since each change of location essentially eats half a day or more and that cuts into your allotted two weeks a lot. But since you have lots of time now I suggest you pick a route from North to South or South to North, for example: Bologna-Florence-Rome-Sulmona-Villarosa. Then figure out your possible flights. Where can you depart from in the US and where you need land in Europe. You probably need to plan to fly into one city and fly out of another to avoid backtracking that takes time and money. There are direct flights from some east coast cities to Rome for example, but not Florence. Then if you want to end up in Sicily figure out the flights needed to get home including connecting cities. Since you name five cities go to Booking.com and investigate hotel prices in each desired location to understand prices/neighborhoods. Of course you can't book most things this far out but pick a two week window 3 months from now and investigate what you find. And watch Ricks' three "Travel Skills" shows, and the shows that cover the cities/areas of your interest. All are available for free on YouTube. Have fun planning. I usually don't really book anything until 3-4 months out from the trip unless there is a great deal on airfare. But I skulk on Booking anyway.

Hi pittjoe, Welcome to the Forum. So, you want to start in northern Italy with Bologna and travel all the way to Sicily— about as far south as you can be in Italia. It is doable, although adding more time to the trip would probably make it more relaxing.
Sulmona is about 2.5 hours from Rome on the fastest trains available for that route. Bologna is just 40 minutes by high-speed train from Florence. From Florence, Rome is about 90 minutes away.
The really long train journey is from Rome to Sicily— more than 10 hours. You can also fly from Rome to Palermo, Catania or Syracuse.
Check www.Skyscanner.com for flights. Generally, 6 to 9 months in advance of your departure date is the time to buy airline tickets for the best airfares. There is no predictable algorithm for that, however. You might want to fly into Venice or Milan for your first city of Bologna ( a little more than one hour from either Milano’s central train station or Venezia’s Santa Lucia train station) and return home from Rome with what is called a “multi-city” ticket. That is when you arrive by plane into one city and fly home from a different city. The advantage is you don’t need to return to Milan or Venice from Sicily. From Sicily, most flights are going to be routed back through Rome. You can check out your options on Skyscanner.com

For high-speed train tix check www.Italotreno.com and www.Trenitalia.com for train fares and schedules.

Have a great trip!

You can fly to Bologna (via some European hub, like Paris or Frankfurt or London etc.) then take the trains down to Florence and Rome. Florence is between Bologna and Rome approx. 35 min south of Bologna via high speed rail. Then you can fly back home from Rome.
Using Kayak or Google Flights enter a multicity flight
Going:
From YOUR HOME AIRPORT
To BOLOGNA (BLQ)
Returning:
From ROME FIUMICINO (FCO)
To YOUR HOME AIRPORT
I don't know how much the flight cost would be, it depends from where you fly from etc.

The train from Bologna to Florence is about $35 full fare in standard class.
The train from Florence to Rome is about $75 full fare in standard class.
If you purchase tickets in advance (if you know the exact dates and times, since discounted tickets are not refundable/changeable) you can save up to 50% and more.

Cities like Florence, Rome, Bologna can be expensive, but you can definitely find a hotel room for under $200/night in a nice 3-star (or maybe even 4-star) hotel even in those expensive cities. That generally includes breakfast, which is often buffet, therefore you can easily skip lunch if you load up at the hotel in the morning. For dinner at a regular sit down restaurant, you can budget about $35-40 per person, inclusive of multi course dinner, dessert and wine. Of course during the day you will have gelato, snacks, drinks, bus tickets and I imagine museum tickets, but it shouldn't be more than $30 a day for all of the above. So you can comfortably survive with $250-$300 day (or less if you downgrade your hotel accommodations). So $5000 will be more than abundant for 2 weeks (exclusive of airfare).

The challenge is to get to those smaller towns. Sulmona and Castel di Sangro, are both in Abruzzo and relatively close to Rome via train. The train would be inexpensive, since it's regional commuter trains. The two towns are not far from each other and connected by bus, although not frequent. The hotels would certainly be under $150/night. The most efficient way to reach those localities would be a rental car, but that would increase your cost since rental cars in Italy are $40-50 a day. Gasoline is expensive (about $7 a gallon), but the distance wouldn't be too big and freeway tolls would be minor also.

I think you might need to skip Sicily for this trip. That requires an extra flight from Rome and you definitely need a rental car to go to Villarosa. Since you are 70 years young, you have time to go again another year so that you can concentrate in Sicily alone. The island is so rich in places to visit, that it will keep you busy for another two weeks.

In my opinion $5 K would not be enough for a two week trip like this.

You can use the Italian Rail website to get an estimate of the cost of using rail. I wouldn't recommend renting a car in Italy, parking is terrible in the places you plan to visit and many come home later to get an expensive ticket in the mail.

Use TripAdvisor.com to price you lodgings.
You will likely spend a minimum of $150-$200 a night in Rome and Florence. This is for lodging that might get 2 stars.
Also, TripAdvisor can price day tours. If you do it on your own, you need to research and plan carefully.

You can check with Gate 1 Travel and see what they come up with for a portion of your trip.

We use them a lot and their group tours are very reasonable.

Regarding flights, you could do an open jaw flight booking, flying into Bologna and out of Sicily.

You might want to add a little more to your budget depending if you are including airfare into the mix as someone else pointed out. My two-cents may or may not mean anything on your itinerary. Have you thought about utilizing the train system? Do open jaw flight of course. The train can leave main land Italy and enter into Sicily with no issues via ferry. Transportation will be your key issues, however the train can help. Book early for the best deals and know you are in competition with the rest of the world. Save money by going in low season, as well as reading reviews of any hotels you are considering. Currently, Sicily is less expensive than the mainland of Italy and some places in Italy are really pricey. However, Sicily is now exploding with tourism due a few factors. At least with low seasons you will have less crowds and the hotels prices do adjust accordingly. Most places you can get around easily if your hotels are located in key areas. Know public transportation is not exactly reliable, but if you have time to burn it's not a big deal. If you can find someone to travel with you and share some of the cost that could be helpful to your budget. However, after traveling with a few friends who are no longer close to me, I can advise honestly say make sure you get along really well, and know the most their most annoying habits, e.g. smoking. When packing plan to share some things instead of double packing, e.g. shampoo. I can caution you when traveling on your own eating alone can become very lonely unless you are use to it. Rick Steves guide books are always helpful in finding interesting places to see. Also, Google map things in order to see how far away things are from a chosen hotel. There are lot of helpful apps you can install on your phone so check them out. Additionally, I like to recommend viewing Rick Steves past tour scrapbook winners. They cover their RS tours, but also overview some of the things they did before and after their tours. Rick Steves also has audio tour guides that ca be helpful. The food markets and grocery stores are great way to help save on the cost on food while traveling though Italy. Having a picnic while traveling is cost saving, but also another way to enjoy your adventure.

Have a budget of around $5000, but it is flexible.

Does that include airfare? You traveling alone?

For 'about 2 weeks', adding in Sicily really stretches you thin.

"Unrealistic"? Hard to say. Depends what your plans and expectations are.
Logistically it would be possible to go everywhere on your list; but you have to accept you will be spending a lot of time moving from place to place at the expense of 'being there'.

Would 2 1/2 - 3 weeks be better?
Thanks!

More time in Italy is always better!

Three weeks would be great for including all of those specific destinations, but more time equals more money, so first I would search the flights and see what you can get. Airfare is always my largest expenditure for any trip. Those smaller places will be cheaper, which is a plus, but you'll need to make the time investment to get to them. For example, you'll likely need to fly into Catania to get to Villarosa. I love hearing about family history trips--I don't think you will regret the extra effort!

The outlyer here is Bologna, which is a city that I love, but you're adding to the distances that you would have to travel.

I would also suggest taking the train, instead of renting a car. For your first trip internationally, and being solo, keeping track of everything would be difficult. You won't need a car in places like Florence, Bologna, and Rome, in any event. There are restricted traffic zones, though I don't know if they exist in your ancestral places. I think the signs are pretty obvious, but that's partly because there are two of us, one driver and one navigator who is looking for things like signs.

Except for Abruzzo and maybe Sicily, I would not rent a car but depend on buses and trains.
If push comes to shove, I would rather skip Florence.

Skipping Firenze ( Florence) means you can get from Bologna to Rome in 3 hours by train. From Rome. you can train to Sulmona in 2.5 hours. Then it’s off to Sicily.

I agree for this first trip that I’d just take trains and buses between destinations. Unless you know a car rental is specifically going to get you to places you definitely want to see— it’s more carefree and more pleasant to stick to the trains and buses.