Day trip from Florence opinion: private boat tour of Cinque Terre or Venice?

Either way, you are looking at spending a minimum of 5 hours sitting on a train. Then add the time needed to get to and from the train stations. Subtract that from the time you have available that day.

The CT villages will be crammed with day trippers, and you are assuming that the weather on that particular day will be condusive to a boat tour. Venice will also be jammed with day trippers just like you, and all trying to see all the same famous sites in the few hours available to them. To me this seems like a coin toss between 2 less than ideal choices.

Meanwhile, you have only allowed a partial arrival day, with its attendant jet lag and fatigue, and another half day to see the many world class sites of Florence. But it's your vacation, and you know your group's interests better than strangers on a forum.

I agree with CJean. I personally would not day trip to either of those locations from Florence. My family and I went to Florence, the Cinque Terra and Venice last summer (late June/early July.) Venice was our favorite place in Italy and a day trip would not do it justice. Also, to Cjean’s point about the cinque Terra boat tour….even that time of year the waters can be rough and boat tours cancelled. Our boat tour from Santa Margherita Ligure to the cinque terra villages got canceled due to rough seas and it was a beautiful day that didn’t seem overly windy. I also agree that you could take that extra day and give it to Florence as you may find that the time you have allotted for Florence isn’t enough.Hope you have a wonderful family trip!

Oh gosh- I don't think I would do either for all the reasons Cjean lists above but if I had to choose I think the boat tour would be most enjoyable.
You are not giving Florence enough time.

late afternoon train to Montepulciano. 3 nights at Terra Antica
resort, explore area (will have rental car Sat-Tue), train to Rome

This is confusing. The train from Florence to Montepulciano takes a lot of time- over 3 hours with a change in Chiusi- station is well outside the town of Montepulciano. Where and when will you pick up and drop off car? Montepulciano doesn't have any car rental agencies.
Best plan would be to pick up car in Florence and drive to your villa. You could drop it in Chiusi then train to Rome

( the agencies in Chiusi close at noon on Saturday otherwise I would have suggested picking up car there)

Are these your only options?

How did you choose Florence as a base? Why not skip Florence altogether and spend that time in Venice?

I know all travelers have different wants and needs. Here's my experiences with Florence going back over 30 years ago. A friend and I did the typical Rome-Florence-Venice trip. Loved Rome and Venice, hated Florence. The crowds back them were miserable. The sidewalks were packed, it was loud even late into the night, Vespas everywhere. The only thing that was enjoyable was seeing the art and discovering the beautiful leather gloves at a small shop.

10 years later and I was back in Italy. I wanted to go back to the shop and explore some more art. But knew there was no way I would stay in Florence. I booked a week in Lucca (this was before Rick Steves started promoting it) and day tripped into Florence not once, but twice. It was great to return to my quiet town in the evening when all the residents were out enjoying their passeggiata. Best decision ever. I also day tripped to the Cinque Terre from Lucca.

I guess what I'm trying to say is don't force yourselves to go somewhere if it's not offering what you want. But, as mentioned, you know you. Do what gives you joy.

Florence is an impressive city, but it way over-touristed, and there is not much natural charm to take in. Its crowded everywhere, I was just there last October in low season. Venice is the same. I have been to Cinque Terra 3-4 times and I have not seen it that over crowded and touristy but it essentially some villages on the rocky hillsides. There are equally interesting and beautiful places all the way to Genoa - I just took that train and stayed in some of the coastal towns.

If you want a more reasonable day trip, maybe rent a car and see Siena, Montepulciano, Cortona, Arezzo, etc. I didn't really know you can take a train to Montepulciano because all the times I went, I drove, and its up on a hill, and I did not see any train stations anywhere nearby, nor a bus station.

You're trying to do too much, too fast, at the worst time. I can't imagine it being enjoyable at all.

Less is more. Do not try to visit too many places. They will still be there when you return to Europe.

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This is confusing. The train from Florence to Montepulciano takes a lot of time- over 3 hours with a change in Chiusi- station is well outside the town of Montepulciano. Where and when will you pick up and drop off car? Montepulciano doesn't have any car rental agencies.
Best plan would be to pick up car in Florence and drive to your villa. You could drop it in Chiusi then train to Rome

( the agencies in Chiusi close at noon on Saturday otherwise I would have suggested picking up car there)

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Sorry I was just writing out a vague version of plans, but we are taking the direct train from Florence to Chiusi and getting the rental car from there, then driving to the hotel in Montepulciano. I had the times incorrect earlier, as we are picking up and dropping off the rental at Avis in Chiusi as it was cheaper than picking up in Florence and doing a different drop off return location

Ok good. That works.

Have you considered going to Venice on arrival rather than Florence? It’s a longer train ride but take lunch, nap.

It will be crowded mid day with day trippers but when you stay there 3 nights you’ve got the quiet mornings and evenings. Find an apartment on a back canal. Take the vaporetto to Burano, Torcello or Lido one day. Look into Row Venice for your kids. Visit fish market early am. Venice is so unique.

Your post doesn’t sound like you are all that into what Florence has to offer- just using it as a base.
Unless your mom wants Florence more than Venice?
You’d probably want to pick up car as you leave Venice- drive to Montepulciano.
You can day trip to Siena from Montepulciano.

Looks like choosing what color rope you want the hangman to use

Hope your choice works out for you