re: A two-week travel get-away to Italy.

Venice is a straight up tourist trap, I spent more money over 3 days in Venice than I did during my 18 days anywhere else

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Definitely rent a car so you can travel around. We did that, had zero issues.

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Really? I’ve heard Italy is a bitch to drive in. And my experience suggest trains are the way to go.

Where did you go?

Outside of major cities you can find host houses (think B&Bs) practically everywhere. We would spend spend all day out and then come back for dinner before heading out for late evening drinks.

Outside of Rome we spent a couple days in the Ferentino area, where I've had some of the best food I've had in life.

Visited Pisa on a day trip from Florence. Arrived by train and walked to the Cathedral and tower. I didn't feel entirely comfortable on the walk. There were a lot of immigrants on the streets.

It would not stop me from going back but it just did not feel right.

Best day trips if youre staying in Montalcino for say 5 nights? Obviously that includes Pienza and Montep

We also enjoyed Lucca which is a short drive from Pisa. The town is surrounded by medieval rampart walls with a bike path on top. We rented bikes and cycled around the walls a few times. The scenery is nice with the town on one side and the mountains on the other.

Bumping thread as to not start a new thread on Italy, and I've already asked a few questions here.

Booked to in/out of Rome for Thanksgiving week.

What are the best areas to stay in both Rome and Florence to get an authentic stay and be close enough to walk everywhere, but not be in the super touristy/busy areas.

i.e., in Paris we stayed in Saint German de Pres and loved being close enough to everything but having more of a low key neighborhood with lots of food/drink options close. Have two teenagers to entertain as well.

Thinking 3 nights in Rome, 5 in Florence, or should we do 2 Rome/3 Florence/3 Tuscany?

How would you rank the following to visit: Siena, Chianti, Orvieto, San Gimignano, Pisa, Lucca, Montelcino?

Is Naples/Pompeii worth taking the day trip?

Thanks!

San Giamigano, Volterra, Lucca, Orvieto are all fantastic and you can flip a coin as to which one is best.
Spent two nights in a BnB on the cistern square in San Gimigano and it was absolutely fantastic!!
Volterra has a great collection of small museum and great Etruscan sites.

As many said, there is a lot to Italy, so the mission shouldn't be two hit as many spots as possible from the Dolomites to Sicily, but I recommend picking two broader regions and spending about a week in each, examples:

1.Tuscany - Florence, Sienna and countryside.

2.Veneto - Venice, Verona, Vicenza, Lake Garda (Sirmione)

3. Dolomites - Belluno, Bolzano, Trento, various scenic Nature routes

4. Northwestern Italy - Torino, Milan, Cinque Terre

5. Puglia - Polignano a Mare, Lecce, Ostuni, Alberobello

6. Campagnia - Naples & Amalfi Coast

6. Lazio - Rome

7. Sardegna

8. Sicily

These aren't ranked but I would say pick 2 and aim for about a week's worth of time in each.

Edit: upon further review I'd so one of these two itineraries:

A.) The North: fly into Venice (1 nights/2 days max), drive up to former (Austrian Tirol) Bolzano and/or Trento for some Alpine and German-speaking culture in Italy, base out of these towns and do some Dolomite hiking (2 nights), then head down to Lake Garda and stay in Medieval Sirmione 1-2 nights, head to Verona 1 night spend one day seeing the city the next touring the surrounding Valpolicella wine region. Then head over to Cinque Terre, spend 3 nights there, then to Torino for 2 days, then Milan, fly home.

B.) South-Central:

Fly into Rome spend 3-4 days there, then take the train to Polignano a Mare, gorgeous seaside town, with nice beach (bring water shoes though) and great eats, do day trips from there to Ostuni, Alberobello and Lecce (4 days), train to Siena, spend 1 night there, then to Florence 3 nights there - fly home

Both are probably a bit ambitious and require some cutting of stops (i.e. Torino for option A and probably Rome for option B, IMHO) but they'd both give you a taste of the diversity of cultures, lascapes and cuisines in Italy.