Taking our first trip to Europe end of August/ first part of September. In the planning stages. Sibling vacation and interested in seeing Paris, Rome, Florence and Venice. Possibly rent a car and drive to Portofino (if time allows). How many days should we realistically consider in order to see the sights (1st timer). Also, is it best to consider a "tour" vacation package? Any initial information you're able to provide would be helpful. Thank you!

Most of the forum regulars are Do-It-Yourself travelers, so unlikely to recommend tours. September would be better than August, outside the peak tourist traffic.

Personally, I'd focus on one country/region and explore in-depth (i.e. beyond just the big cities). Without the benefit of your specific interests or priorities, as a first-time traveler to Europe you would probably need 3-4 nights in each of the cities you mention. I'd fly open-jaw i.e. into Paris and out of Venice or Rome or the other way around, so you don't retrace. Such a trip would involve at least one European flight connecting between Paris and Rome or Venice.

Rome, Venice and Florence are well-connected by the rail network - book on www.trenitalia.com/tcom-en or trainline.eu upto 3 months in advance to get best fares.

Of your bases, Florence is closest to Portofino, yet 200+ kms away, at least 3-4 hours by train or car - so its not exactly a daytrip. Renting a car for a very short duration can be expensive.

Considering
- that you are a first timer,
- that you give no relevant info (where you fly from, total duration of stay, budget, interests, age etc
- that you obviously didn't open many guide books
- that you cite the 4 most known cities in Europe

I would indeed recommend a tour. Go see a travel agent let him organize it for you and sign the itinerary he will propose.

You are imo not ripe to do it by yourself.
Enjoy Europe or the way US think Europe is.

There is also a middle ground: a do-it-yourself tour with a guide. Do your own research and bookings, but hire a local guide for a day in each city. Rome, Florence, and Venice have great ones but also their share of duds. I have seen good reviews for Walksofitaly.com

I would also recommend spending 3 or 4 nights in a small hill town or an agriturismo to break up the Rome-Florence-Venice route. Italian hill towns have an entirely difference feel than its great but clogged and noisy cities. Montepulciano and San Gimignano are good options.

An agriturismo is a farm house locals rent to supplement their income and they are great bases for exploring the countryside. There are lots of these in Tuscany and Umbria to use as a base to explore Siena, Assisi, and countless tiny towns. www.agriturismo.it is a good place to start.

I would fly into Rome and spend 5 nights there. Then I would rent a car and spend 4 nights in a hill town such as San Gimignano or stay at a farm house in Tuscany or Umbria. Then I would drop the car off and take the train to Florence for 4 nights. I'd finish the trip by taking the train to Venice for 4 nights. I'd fly home from there.

That's 17 total nights, but you can add or subtract a few days to fit your time allowance.

I certainly would not drive from Florence to see Portofino, you'd be very disappointed. Unfortunately, Woin's tongue was firmly in his cheek when he posted above, so if you don't share a sense of humour, move on.

Let's look at your four choices; Paris, Florence, Rome , Venice. To see all of them and to allow for travel, you really need at least 3 weeks to scratch the surface. You say that you have "end of August/ first part of September". Is that a week, 10 days or two weeks? In any case, you cannot do all four destinations in 10 days. Choose two or three maximum and that would possibly be the classic triangle of Rome, Florence and Venice. Fly into Rome and home from Venice or vice versa.

You don't need a tour, just get a good guidebook for the one's you choose.

Right back to you on "any initial information you're able to provide would be helpful" such as:

How old are you?

What's your budget?

What do you wish to see and do?

How much time to you have?

Where are you coming from?

People here don't tend to sign up for tours, so you're probably on your own there. Buy some guide books and maps and study them and go online to the official Tourist Office websites of the cities/towns you want to visit.

Forget about renting a car until you actually know what you're doing. Car rentals are a horrible deal unless you rent for at least 3 days in a single country and absolutely a non-starter if you rent in one country and drop off in another.