Need help with what to see on our first trip to Italy

Sound like the Best of Italy in 17 days tour on this very sight would be perfect for you. Good mixture of group activities and free time, and a good group of places. Since you are planning for 2019, you've got plenty of time to prepare financially. Rick usually announces the next year's tour dates in mid-summer or so. Prices don't change much.

My husband and I are taking the Berlin, Prague and Vienna tour this September, but have been planning it since Spring of last year. Trip planning is so much fun!

Your instincts are correct in that it's best to spend some time in each city. A group tour would be fun, I'm sure, and it takes care of a lot of the planning. But, you have plenty of time to plan. Use guide books, like Rick Steves' of course and one or two others. Rick has tons of good info for planning your own trip on his website. Watch some of his TV shows online, too. He has some episodes that explain how to plan for your trip.
I like the "home base" approach where I stay at least 3-4 nights in each city, perhaps even more if you want to take a day trip or two. For Italy, Rome and Florence are must-sees on my list. Sorrento and Naples are great too. There's a lot of good info on this forum. The hardest part is deciding and prioritizing where you want to go! Assume you will return.
Italy is wonderful, good luck!

Very broadly speaking, I think there are three possible advantages to non-specialized European tours:

• A great deal of the planning burden is off your shoulders with transportation and hotels taken care of. You still need to do research to decide which tour best fits your needs, and you need to make plans for your free time.

• Dedicated transportation from city to city can be quite a bit more efficient than finding your own way. This, however, depends on where you are going. If the tour is Venice-Florence-Rome, you can do that much faster on the Frecce trains than any tour bus can go. So this advantage doesn't really come into play unless you choose a tour that includes some smaller places. Those are typically a bit more difficult to get to.

• Some tours (including the Rick Steves tours) teach you how to be an efficient traveler by introducing you to things like city subways, buses, and vaporetti. This will make it easier for you to travel independently in the future. I would not assume that all tours take this extra step, especially not the more budget-oriented tours.

You can probably tell that my bias is toward tours that get you to places that go beyond Venice-Florence-Rome, yet I recognize that those are called The Big Three for a good reason.

Most tours move much, much faster than I like to go, so I'd suggest looking for a tour that doesn't fill your entire available time period. It's good to have a couple of days (one is sort of a minimum) in Italy before your tour starts. There will nearly always be plenty to keep you busy at the starting point of the tour that will not be covered by the tour itself. Then you could use the rest of your remaining time after the tour. By that time you'll be comfortable moving around Italy, so you wouldn't necessarily need to spend the extra time at the final tour stop.

Definitely push the length of the tour out as much as you can. As you've already discovered, there is more to see in Italy than most of us manage to cover in a lifetime. You may as well get a good start!

We are leaning towards a pre-planned group tour, as we don't want to
be concerned with coordinating our own reservations for hotel,
transportation and entrance to specific tours. (I have heard that
group tours avoid the long lines getting into some attractions)

OK, so you're looking at an escorted or pre-packaged tour. That will largely eliminate the "what do we want to see" question as a tour will include popular attractions chosen for you. However, It is not true that group tours are the only way to avoid long lines: we are independent travelers and have been able to skip long ticket lines by purchasing tickets in advance. How to do that depends on what you want to see...but that's a completely different subject.

I have no idea if I should focus on trying to see as many cities as
possible (I don't really want to be changing hotels every day to get
to the next city) or if we should limit the number of cities so that
we can spend more time in each one and really explore. (actually this
sounds better to me)

IMHO? Less is more. If you are going with an escorted tour, choose one which limits the number of cities it will cover. It's too exhausting to get your head around one city over a few hours in a day only to have to do it again the next day, the one after that, etc. Also make sure your tour offers some free exploration time, and doesn't include any mandated shopping stops.

We don't take tours but it sounds like one of the RS offerings for Italy might be a good choice for you.

https://www.ricksteves.com/tours/italy

I will mention that May and Sept fall within high season in the tourist centers of Italy,, and October can be plenty busy.

We've been to Italy four times, and I'll be returning late August. Our first experience in Italy was the Rick Steve's Best of Italy trip, and I highly recommend that trip because each place was a "wow" moment, the tour guides gave us so many insights into Italy, the art in the museums, etc. And, we were able to travel to several places with the tour that aren't as handy when traveling by train. The trip hits the Big 3 - Venice, Florence & Rome and also several smaller towns that I really enjoyed. In fact, my trip this year will be focused just on smaller towns.

I organize our trips now and enjoy the planning process, but for that first Italy trip, it was so nice to just fly to Italy and not have a worry since everything is planned for you for hotels, transportation, plus "fast-pass" entrance reservations to the busiest museums, etc.

We arrived 2-3 days ahead of the RS tour - flew into Milan and took the train to Verona. Verona was a fun town to acclimate to Italy and easy as a tourist's first days in Italy.

On our 1st trip to Italy, we did the Rick Steves Venice, Florence, Rome tour and then extended 4 days in Sorrento to see Herculaneum & the Amalfi Coast. We then went back to Florence for 4 more nights and did some WALKABOUT FLORENCE tours into Tuscany. It was one of our BEST European trips. We spent a total of 3weeks.

I highly recommend a guided tour like RS. There is just SO MUCH TO LEARN, SEE AND DO and I don't think you can do it justice on your own. We flew into Venice (which is where the tour started) 3 days early and did many things on our own. Definitely download the RS app before you go and bring earbuds. Take the #1 Vaporetto with the RS app tour- it takes you around the whole canal and he points out all the highlights. Get the guidebook!! Get lost in Venice. Have a coffee at one of Europe's oldest coffee houses in St.Marks Square, Caffe Florian - it is in his book. The tour will take you to the big places like St.Marks Cathedral, museums, Burano.

The bus ride Venice to Florence was fantastic. Florence has so much to see, I can't imagine doing it on your own - THE DAVID!!

Rome - they take you and teach you about the highlights - the Pantheon, Colosseum, Forum, Vatican. We stayed another 2 days on our own after the tour ended and did 2 EATING ITALY walking tours that were amazing.

We took a train to Sorrento, stayed at a B&B - went to Herculaneum (liked better than Pompeii) - again get the RS Italy guidebook, he walks you right thru it. Took a day trip with a RS recommended guide (Mondo - sharedtours.com) to the Amalfi Coast. Spend another 2 days in Sorrento (which is spectacularly gorgeous with amazing food).

We took train back to Florence -(which has become one of our favorite cities) = did 2 days trips into Tuscany with WALKABOUT FLORENCE - we loved them both - BEST OF TUSCANY and CHIANI WINE & FOOD SAFARI.

We are going to Sicily with RS next year!! You will LOVE Italy.

For '2-3 weeks' the 17 day Best of Italy by RS would be a very good choice. You could then add some additional days in Rome at the end if you have a full 3 weeks to use.

Our 1st trip to Europe was the RS Best of Italy and we added 10 days, and by then felt reasonably comfrotable with doing things on our own. Used the time to visit ancestral villages

"We are leaning towards a pre-planned group tour, as we don't want to be concerned with coordinating our own reservations for hotel, transportation and entrance to specific tours. (I have heard that group tours avoid the long lines getting into some attractions)"

As this will be your first trip to Italy, taking a guided tour would be a really good idea for a number of reasons. IMO, you'll learn more about the country, culture and foods and traveling with a group is often a lot of fun. It will also provide you with some travel skills that you can use on your next trip. Rick Steves has a number of Italy tours of varying lengths and costs, so have a look at the tours page to begin with.

If you'd prefer a more independent tour but with all hotels and transportation taken care of, have a look at the RS My Way Italy tour. Tour members are responsible for planning their own sightseeing, but the My Way tours are accompanied by a tour manager, who helps tour members with sightseeing, etc. in each stop. IMO, you'd get more out of one of the fully guided tours.

With many tours you'll have to book your own flights. I'd suggest arriving a day or two prior to the start of the tour, in order to get over jet lag, etc. You could also stay a night or two after the tour ends and do some sightseeing on your own.

You might want to check your local Library to see if you can find a copy of the RS Italy guidebook. There's an enormous amount of information in the book, and that may help you with touring ideas.

You may also enjoy watching this - https://www.youtube.com/watch?v=g_OrVr4_yP0 .

OMG thank you so much to all of you that responded to our post! I will definitely take the advice from all of you and look into the suggestions you each made.
I am excited again and ready to do more research for what we hope will be a trip to remember. I forgot to mention that this will be the year of our 40th wedding anniversary and so we want it to be really special.
Thanks again everyone!
:)