Planning a first time trip to Italy

Most of us here plan our own trips.

Have you looked at the RS tours?
https://www.ricksteves.com/tours/italy/best-italy-tour

My Way Tour might be what you want
https://www.ricksteves.com/tours/italy/my-way-italy-vacation

Christine is right, the My Way tour sounds like just the ticket for you.

We travel independently for the most part, though we have taken three guided tours, one of which was a Rick Steves tour (Sicily 2024)

The Rick Steves website has a wealth of information. Look under the Explore Europe and Our Tours and Travel Tips tabs. https://www.ricksteves.com/. That’s a great resource. Explore!

The Rick Steves tours are relatively less expensive than others out there and they are nice sized groups. 24 max. They simplify much of your planning, though they move quickly and may not allow you the time to linger where you choose and explore on your own. Since this is a first time trip for you, their experience and mastery of logistics will serve you well.

Some people link their trips. Since you also want to see Switzerland or Austria, per you one other forum post, maybe take two tours. RS has ten different Italian tours to choose from and three alpine tours, plus some longer Europe trips that include both alpine countries, Italy and other places.

You’re only 70 per your one other forum post, so don’t lock yourself into the idea that this is your first and last trip to Europe.

Planning your own independent travel can be tedious and enlightening and rewarding. All of the above. Independent travel can be cheaper, since you’re not paying for a tour guide or other, specialty guides that a tour offers. Yet those guides do provide value in terms of knowledge, experience, information and interest.

Enjoy your future adventure.

LATE NOTE. I am not on the same page as others (below) about how much $8-10,000 for a 3 week trip is. To me, that’s not a high end travel budget. Rick Steves 10 day classic Italy tour, Venice-Florence-Rome, is $4595 for late Sept 2027, not including airfare. Plus you’ll spend a few hundred dollars just for the meals that are not included, snacks, souvenirs etc. so that is half your budget for half the trip, not including airfare. (Village Italy is a cheaper trip, likely because accommodations are cheaper)

As I mentioned above, tours are a bit more expensive than independent travel - I believe 15 to 20% to 45% more - because of what the tour gives in terms of guides and logistic support. I broke this down in our 2024 Trip Report: https://community.ricksteves.com/travel-forum/trip-reports/southern-italy-30-days-three-ways-to-travel

In 2024, our southern Italy travel costs averaged, $250 per day per person, but inflation and higher energy prices might increase that to 300 or more by Sept 2027. That would be 6,000 plus airfare, so 7,500 to 8,000. Northern Italy and Switzerland (your other post) are pricier per diem. Again, more if you do mostly tours - and RS are relatively inexpensive. For Sept 2027, it looks like the RS tours will run you $450 to 500 per person, per day, after you add in your extra incidentals but not airfare. Travel will cost less if you can comfortably travel independently.

Your budget is $8000-$10,000 PER PERSON???

If you are into higher-end travel style, I have always thought this company had nice offerings https://italybeyondtheobvious.com/. Seems very personalized.

Your budget is $8000-$10,000 PER PERSON???

LOL I was hoping that was a typo.
We barely spend that much for 2 people/3 weeks all inclusive.

Definitely a high end budget if accurate

Google lists Tauck, Kensington, Abercrombie & Kent, Luxury Gold as luxury tours of Italy

Perillo is a well known tour company but maybe not as high end as you might be looking for.

Your budget is $8000-$10,000 PER PERSON???

You can certainly spend that much money for 3 weeks in Italy, very easily. You can also spend half that, if it's done right, and save the other half for a trip a couple years down the road. If you're 70 and in decent shape, you should have 4-5 more trips in you at least while you're still ambulatory.

Also, you have to realize that if an agency plans it and something goes awry, they won't take responsible for the screw-up. At least if you do it you can blame yourself! :)

I would take a month or two and really study the posts and response on this forum before deciding which way to go--either DIY or through an agency. And then decide. But don't take too long--a year out is when to start planning. It's what I did 15 years ago when I was a-skeered of doing it myself--I came to this forum and was helped out immensely. These folks here are pros, and are eager to help out new European travelers that want to learn. Some folks on this forum look for the best prices, some just want the best experiences, but the common thread is that we all know value. And between this group, we've got the logistics down in real time.

One mantra--assume this will not be your last or only trip to Italy. If you feel like this is 'it', the only time ever, you'll cram too much into it and be on the road all the time. Ten days? 2 destinations. Two weeks? Three destinations, four would be too many. Three weeks allows you to do a deep dive in one or two places, and visit a couple others. Research and find out where you really want to go. Using the Rome2Rio website, get a cursory knowledge on how long it takes to get from Point A to Point B. Don't book anything through there, but it's useful for time management.

Good luck with your planning!

Your budget is $8000-$10,000 PER PERSON???

You can certainly spend that much money for 3 weeks in Italy, very
easily. You can also spend half that, if it's done right, and save the
other half for a trip a couple years down the road.

On our trip to Italy last year, my husband and I spent about $500/day for the TWO of us. That included lodging, meals, transportation, and tickets to whatever sights or excursions we did.

But for three people it would be even less per person because the accommodations and some of the transportation (like car rental, ride share, or private transport) is split three ways instead of two.

Yeah, I guess you could spend any amount of money if you wanted to, but we traveled quite comfortably - spending whatever it took to make our trip enjoyable - and we only spent about $5000/person for three weeks. If you add in the airfare, that was another $2500/person, but that still only brought it up to $7500 each.

How old are your children? I think children 8 or older can go on some Rick Steves tours.

In 2024, our southern Italy travel costs averaged, $250 per day per
person, but inflation and higher energy prices might increase that to
300 or more by Sept 2027. That would be 6,000 plus airfare, so 7,500
to 8,000. Northern Italy and Switzerland (your other post) are pricier
per diem. Again, more if you do mostly tours - and RS are relatively
inexpensive. For Sept 2027, it looks like the RS tours will run you
$450 to 500 per person, per day, after you add in your extra
incidentals but not airfare. Travel will cost less if you can
comfortably travel independently.

Fred, you're pretty much spot-on, and I even think that $300/day per person can be improved upon. We're starting a 16-day trip next March with a week in Rome, and with AirBnB lodging at $100/day per person (nice 2 BR, 2 bath), and with food, public trans with the occasional FreeNow Uber-like app, I can't see us going over another $100/day, maybe $125 max. Seeing we really only eat dinner out, and with the great competition in Rome for tourist dinner business, that definitely keeps prices in line, even for GREAT ristorantes. 70 Euro as an average for two. And I also think the longer you stay in one place, the cheaper it is per day. We'll be heading to northern Italy, Switzerland & Germany for the other week plus, so I guarantee my pricing structure will probably be shot all to heck!

Rick Steves tours are great, but can be very active. You also make your own air arrangements, arrange your own airport to hotel transfers (you are given instructions on how to get to the first tour hotel, and the tour guide can assist you in making transfer plans at the end of the tour), and get your own travel insurance.

Some other tour companies that include a bit more (as optional add ons) such as air and airport transfers and travel insurance, include Overseas Adventure Travel and Road Scholar.

Most tours don't offer "triples". I'm assuming with you being 70 that your children are adults. One of you may need to pay a single tour supplement. OAT has an advantage of offering "no single supplements" on their land tours (assuming you sign up while the singles spots are available.)
Other well regarded tour companies include Odysseys Unlimited, Tauck, and even Gate 1 (make sure you're looking at the small group tours for some of these companies.).

Check out the trip planning info on this website or Rick's "Europe through the Back Door" and "Italy" guides (get them at the library first.) Check out the websites for other suggested tour companies in these replies, and order their brochures if you like. Whether you use any tour company or do a bespoke tour, you can get itinerary ideas from all of them. If a tour has most of what you want to do but is missing a few, then add some independent days to your tour at the beginning and/or end (staying in the major cities that you fly in and out of may be easiest for you.)
There are plenty of good options for you; don't let FOMO or decision paralysis interfere with you just picking one that sounds good to your group, sign up, and look forward to your trip!

How old will your children be then? What kind of experience are you after? What do you want to see in those three weeks?

This October we will take our fourth trip to Italy, the first being I. 1966 when we were in high school. We have done both packaged tours and independent travel. We planned this upcoming trip all on our own.

I imagine you are planning to visit the big three of Rome/Florence/Venice. That is certainly understandable, but it is also just a small portion of Italy. For us the small villages in Tuscany, Umbria and other regions are the true heat of the country.

There’s always the tension of going wide or going deep. Most first timers way overbook, running themselves ragged and the trip ends up an exhausting blur. Consider doing the biggies in two weeks, the spend a week in the country.

Finally, we travel close to the ground, staying at small inexpensive hotels and Agri Turismos. The more money you spend on accommodations, the more insulated you are from an authentic experience. We are spending ~$120 a night for our rooms. For 5 days we will be at an Agri Turismo in Umbria helping with the olive harvest and taking cooking classes from a “nonna” (Italian grandmother).

I would like to find a travel agency that would plan our itinerary for
the entire time, from hotel bookings, train tickets/schedules, bus
schedules, tour guides, etc - everything planned out in advance to
make the most of the little time I have without wasting any time.

I would prefer a small group of tourists, to make it more
personalized...There are zillions of tour companies out there and it is so confusing which one
would be the absolute best.

Okay, I'm not sure exactly what you're looking for here. First you say you want a travel agency to plan your itinerary for the entire time - hotels, trains, buses, etc.

Then you are saying you want a "small group of tourists" and you ask about tour groups.

So to clarify, are you looking to do your own personal trip with the assistance of a travel agent to help you with the bookings? Or are you looking to join a tour where everything is already done for you?

Those are two entire different ways of trip planning, and I'm not sure from what you're saying which one you want to do.