First time in Italy!

"I think we will have a personal driver take us directly to the Hilton on Lake Como" - that is the expensive option. Where are you going to on Lake Como (which town / village)? Depending on destination most people take a train.

"Could we take a train from Lake Como to another city" - probably, depends where on Lake Como. I assume you want the car while you are in Greve for touring, if so you need to check your hotel has parking.

Greve doesn't have a station, probably best to pick up and return the car in Florence, then train to Venice.

I have some thoughts. First, why the Hilton at Lake Como? I'm a Hilton Gold Member and use them exclusively for business travel, but I wouldn't stay in an "Americanized" hotel in Europe if I could help it. There should be plenty of places in the area for the same money that would have more character.

Do you have plans on where to stay in Greve? We stayed at Castello di Verrazzano and loved it! It is a very convenient place to explore Chianti. You might also check to see if there are any harvest festivals nearby the weekend you are in Greve.

I think your best bet is to return to Milan, train to Florence and rent a car there. With the rest of your itinerary, I'd skip Venice and spend a few days in Florence. You could rent a car immediately and go to Greve, or spend a few days in Florence before heading to Greve. If you stayed in Florence first, you could get the lay of the land regarding car rental and how to drive out and back in. We rented from Hertz at the Rome FCO and recommend Hertz.

We also took a good Michelin map and also our Garmin with the Italy/Greece SD card. The Garmin was a big help. Once you get into Tuscany, you'll find ZTLs well marked in the hill towns. Also, Greve doesn't have a ZTL. They have a large lot with free parking and you walk across a small river into the town square. It's a charming town with plenty of places to eat and shop.

If you feel you must see Venice, you could return the car to Florence, train to Venice, stay two days and train back to Milan.

Here's a suggested itinerary:

September 30 - Day 1 - Travel to Lake Como (Night 1) Sunday
October 1 - Day 2 - Lake Como (Night 2) Monday
October 2 - Day 3 - Lake Como (Night 3) Tuesday
October 3 - Day 4 - Lake Como (Night 4) Wednesday
October 4 - Day 5 - Travel to Florence Thursday
October 5 - Day 6 - Florence Friday
October 6 - Day 7 - Florence Saturday
October 7 - Day 8 - Rent car, drive to Greve, have food and wine tasting for lunch at Castillo di Verrazzano Sunday
October 8 - Day 9 - Explore Tuscan countryside Monday
October 9 - Day 10 - Explore Tuscan countryside Tuesday
October 10 - Day 9 - Return car to Florence, train to Milan Wednesday
October 11 - Day 10 - Fly home

Trenitalia and Italo are the train operators in Italy. Use these websites to research availability of trains for different parts of your trip.

Avoiding the cruise ships in Venice will likely be impossible, they come in numbers every day. Maybe you won't find as many in early October as in midsummer, but I saw at least two or three every day in late October last year. If you want to see this magical city (which I highly recommend), stay on the island itself, preferably in Cannareggio or Dorsoduro outside the main routes between the cruise terminal and San Marco. Enjoy the mornings and late afternoons/evenings when the day trippers are on board, and spend middays in less central areas, including nearby islands if they interest you. A vaporetto pass for however many days you have will get you around cheaply and (mostly) enjoyably.

This will give you an overview of possible choices for getting from place to place

https://www.rome2rio.com/map/Greve-in-Chianti/Como

From Terminal 2 at Malpensa, you can take the Malpensa Express to Saronno and then take a Regionale train to Como Nord station. It takes about an hour and a quarter and costs €10.90. From the station you can take a taxi to the Hilton.

Easy to get to Florence by train on Trenitalia from Como’s other RR station - Como S Giovanni. You’ll have to take it to Milan and change trains and you can rent a car near the depot in Firenze. The car rental offices seem to be grouped together on Borgo Ognissanti. They should be able to guide you out of the city without violating a ZTL and give you a map showing how to return it.

If you fear the ZTL on returning the car, from Greve you can drive to Venice in about 3 hours. I looked up rentals on AutoEurope. Avis and Europcar have locations in both cities with no drop fee. Another option would be to drop the car in Padua and take the train to Venice - rental offices are centered in the large piazza in front of the RR station outside the ZTL.

You can learn about train travel in Italy from The Man in Seat 61. Buy your tickets in advance (about 90 days out) for best discounted prices. I always purchase my tickets at the TrenItalia website or the easy to use TrenItalia app. Remember to use the Italian city names while searching for tickets and make sure you’re going to the correct station:

• From Malpensa - Saronno, Como Nord
• To Florence - Como S. Giovanni, Firenze S. M. Novella
• To Venice - Venezia S. Lucia
• To Milan - Milano Centrale

I would not recommend staying in Como for the Lake Como experience primarily because you are a long ferry ride to the upper (more interesting IMO) portion of the lake. Train to Varenna should be just as quick as a train to Como and there is a ferry stop there with quick passage to all upper lake sites.

Have a great trip!

As Doug has pointed out, unless you have an early afternoon flight ( after 14:00) you need to be in Milan the night before your flight. Trying to leave Venice or Florence in the early morning hours can be expensive and exhausting.

Remember that Como can refer either to the lake or to one specific town on the lake. The directions from Como to Greve are for the town of Como. Most Rick Steves travelers stay in Varenna on Lake Como, not the town of Como.

We have traveled to Italy many times, Lake Como four times, and the Chianti region at least four times too.
I would never ever stay at the southern end of Lake Como. The beauty and the most activities to enjoy are mid lake, Bellagio, Varenna, Cenobbio, Mennagio.
And I would never stay in a US chain hotel if I could avoid it. I use Hiltons to stay at airports in Europe, the only location.
When leaving Lake Como get a rental car and easily drive south to Greve. Why would you combine the hassle of getting on and off trains with luggage, then switching to a the car? When leaving Greve, drop off car in Florence and take a train to Venice or keep car and turn it in at Venice Piazzale Roma. If you prefer to leave Lake Como by train( Varenna or city of Como are the stations) , take train to Florence, pick up car at places I mentioned, drive all over Chianti region, return car to Florence, city or airport, and train to Venice.Rental car agencies in Florence located on Borgo Ognosanti have easy access out of the city to the Autoroute. Or, if you prefer, pick up car at the Florence airport.
Your itinerary is one of the most common and easiest itineraries for travellers to Italy so relax. It is not difficult.

Thank you so much for your replies so far. I am now definitely planning on taking a look at Varenna and scrapping the Hilton on Lake Como. That was a departure from an original plan and truthfully I clearly did not research it enough. Was thinking of doing an AirBnb in Varenna - there seems to be places available right in Varenna but also many that refer to the surrounding hillsides. Should we stay right "in town" or venture a bit outside of town? Also, will there be a place we could get a few groceries for our apartment? We would probably (new plan) go via train right into Varenna from Milan and will need a few supplies.

I am so excited I can't stand it!!! Thank you!!!

Since it is your first trip to Europe, a hotel staff would be very helpful for you to have, making dinner reservations, ferry and train times. Save an apartment for a return visit.

I don’t know if you have a guidebook to Italy yet. It sounds like you might not have one. I’d suggest you get the Rick Steves Italy guide (either paper or ebook). It will have information about what to see a d also restaurant and lodging recommendations as well as logistics and transportation. Study about your destinations and it will make your experience less stressful and more enjoyable. A little knowledge goes a long way.

Stay in a hotel IN Varenna, not outside. It is a very small village full of charms.