Italy - August 2023 with the family

UA is a Lufthansa partner and I’m sure you can fly from EWR to either FRA or MUC. Lufthansa or Air Dolomiti (which is part of the Lufthansa group) have multiple daily flights to Florence from both FRA and MUC. Therefore there are many options to get to FLR without spending an overnight. I often do fly from SFO to FLR via FRA or MUC using either Lufthansa or United. I haven’t checked from your home airport, but another option is to fly via Zurich to Florence. Swiss is also part of Lufthansa Group.

Regarding the rest of your plan on the ground, that is up to you. The choices are endless. However if you plan to go from Florence to Monterosso, there is no need to rent a car. A car is useless at the Cinque Terre. Just take a train from Florence. It’s just as fast and you don’t have to incur rental charges to keep your rental car in a garage.

I would discourage splitting your limited before-rental time between Venice and the Dolomites. You wouldn't have time to do either of them justice. Although I love Venice (just spent 9 nights there), for a family visit in August--when Venice might be quite hot and humid--I think heading straight to the Dolomites would be a good idea. In addition to the outdoor possibilities up in the mountains (and there are some very easy hikes, basically high-altitude strolls), there are some lovely towns/small cities down in the valley. The South Tyrol Archaeological Museum in Bolzano has an excellent exhibition about the Otzi, the Iceman. Note that the valley towns in the area are likely to be hot at that time of year, and many lodgings don't have air conditioning, so proceed with caution if you decide you want to spend a night or two down in the flatlands.

I agree with the advice regarding the Dolomiti region. Even in the mountains (this past end of July) it was very hot (we left right before the extreme heat arrived) and I saw that it lasted several weeks. There are places with AC if you look - and hiking can be done in the morning, but just be prepared for potential August heat in mountains as well as flatlands. Alpe di suisi (and surrounding) is a wonderful place to go as a family.
We fly LH into Munich but most of our travels in Italy are in the north.

Another option is to go to Lake Garda upon arrival in Venice. If you arrive on Tuesday that will give you 3.5 days before you head to your villa. It's a great place to start your vacation and get over jet lag.

I just visited the Alpi di Suisi for the first time and I vote with the others for that! I’m not sure where you are from and therefore not sure what your heat tolerance is but I was stifling in Venice last week.

The archeological museum in Bolzano was wonderful.

As to the “beaches” in CT…. If you are familiar with good US beaches these may disappoint.

Venice is fine in August. I have been there several times and it was at most in the 80s.
If you arrive on Tuesday morning and depart for your villa on Saturday, You have only three full days, two of which you said you wanted to spend in Venice. You have to recover from jet lag on Tuesday. With one day extra, suggest staying in Venice or visiting somewhere on your way to Florence.
Consider taking the train to Florence it is fast and comfortable.

Using these threads or TripAdvisor, I can tell you many persons that rent cars in Italy wind up getting expensive tickets many months after their trip. Also, parking is a royal pain in these old cities with narrow streets.
Definitely would not want a car while in Venice.

Hi temperatures in Venice:

Sept 1, 2022: 88F
Sept 2, 2022: 88F
Sept 3, 2022: 90F
Sept 4, 2022: 93F
Sept 5, 2022: 91F
Sept 6, 2022: 95F

I'm a nearly-lifelong resident of the Washington DC and points south. I'm more heat-tolerant than average. I wouldn't consider those high temperatures fine. There were only four days that entire month when the temperature didn't reach at least 82F; the coolest day had a high of 79F. August 2021 looks like it was a bit cooler, but there were still five days in a row when it got up to 90 or 91F.

When I think weather at my destination may be something I have to tolerate (or overcome), I like to look at the actual, historical, day-by-day weather statistics available on the website timeanddate.com. I check 3 to 5 years' worth of data. That way I have a decent idea of the range of conditions I might run into. Here's August 2020: https://www.timeanddate.com/weather/italy/venice/historic?month=8&year=2020. You can use the pull-down menu on the right, just above the graph, to find info for other years.

Thank you all for the responses!

Regarding the flights to Florence, I have rechecked and I do see some flights with layovers that are between 4-5 hours in Munich, this more bearable than an overnight, and less stressful than an 80 min layover. So this could certainly be an option, so that we can start our trip in close proximity to the villa.

Comments on the heat in Venice and in the Dolomite region are well noted. We thought we had good heat tolerance, but being in Croatia this past August in the middle of the day simply destroyed us and the kids. So we know that we need a mid-day siesta somewhere during the height of the heat on most days. Also for us, A/C in our lodging is an absolute requirement. So that will require some careful research on lodging in the Dolomite area, if we decide to venture there.

For AFTER our week at the villa, I am back to considering my original idea of heading to Cinque Terra for a few days to a hotel in Monterosso. Ideally some hikes early in the day, followed by the beach around lunchtime and through the afternoon to cool off. (If anyone knows of any places with a pool, let me know). I also would consider the suggestion above of ditching our car in Florence and taking the train to CT, however it would depend on how much luggage we end up with, if many train connections are involved, and the walk from the train to hotel. The convenience of driving to, and parking at the hotel might win out- even if we don't touch the car for 3 days.

To end the trip, from CT I would consider taking the train (or driving) to Milan and flying home from there after a day or 2.

I am wide open to omitting CT and Milan, heading elsewhere and flying home from elsewhere too, assuming I can get flights with my United Miles. So I am open to other suggestions for after our time at the villa. The food in the Parma, Bologna, Reggio Emilia region is very appealing to us as well.

Yes. Depending on luggage, number of people, itinerary after CT, it might be more convenient to keep the car.

Regarding the flights, there will be way more choices than you listed for your flight to FLR during the summer. However it is probably too early to check now for Aug 2023. If you prefer to fly with United or another Star Alliance member these are the one stop choices from EWR to FLR (flight operator to Florence) with airlines that are UA partners:
Frankfurt (Lufthansa)
Munich (Air Dolomiti)
Zurich (Swiss)
Copenhagen (SAS)
Lisbon (TAP)
The above are all airlines part of the Star Alliance, like United. And I checked for June 2023 and they all are available options with layovers of just a couple of hours in their respective hubs. Be aware that if you fly home from FLR, then SAS may require an overnight stay in Copenhagen because the flight from FLR to CPH departs too late. But going to Florence it's not a problem as the layover in CPH is just a few hours.

Check on Kayak. If you plan to fly on an open jaw flight, select Multi-City in the drop down menu (instead of round trip), however you might have to wait till next month to see all available options.