Revised 2-week Italy itinerary: Venice, Florence, Rome, Pompeii, Sorrento/Amalfi, Tuscany/hill towns

How many nights will you be in IT? Don’t expect to do much sight-seeing on arrival day. Venice alone deserves three nights, Florence three nights, Tuscan hill towns two nights, Amalfi Coast/Pompeii three nights and Rome four nights that equals 15 nights. The Amalfi Coast/Pompeii is the outlier so it would be best to remove it. Assume you will return when you can include Sicily.
If you fly out of Venice, make sure it’s not an early morning flight or else you’ll pay in the triple digits for an early morning water taxi.

Why not simply move from north to south? No backtracking.

You have a fairly fast paced 2 week trip with Venice and Florence and Tuscany and Rome and Sorrento/Pompeii/Amalfi Coast. That allows only 2 or 3 nights at each of 5 locales. I am not sure of your exact plan and it has changed from what you posted a few weeks ago - a plan that included the Dolomites, but not “relaxed time” in Tuscany.

Your proposed backtracking adds a lengthy travel day, It’s not like you really have time for a relaxed multiple day visit in Tuscany at the end.

So, I suggest you relax in the middle and depart from Naples. Fly from Naples to Germany, Switzerland or London and then straight home to Portland OR, depending on best ticketing and shortest layover.

Sorry, but back tracking to end in Tuscany and then flying out of Rome makes no logistical sense. With such a jam packed, hectic trip, you don't have the luxury of long transits between places. Start in Venice and head south. Visit Tuscany after Florence and before Rome. If you must include the places south of Rome on this trip, fly home from Naples, even though that may require connecting flights.

How many nights are you in Italy?

Ending in Venice has the issue of getting to the airport at a really early hour for flights that connect to the US west coast.

For flight logistics it is easier to fly into Venice, rather than out.

Unless the point of the trip is to ride trains, the plan you lay out is , how to say this nicely, 'not ideal'. ( The word that first popped into my head was 'awful')

Advice on this itinerary?

Toss it and start over with a clean sheet.

When do you plan to do this trip?

From your other post this would be your first trip and it is understandable that you are trying to hit so many places, but you will enjoy the trip more if have less time 'transiting' and more time 'there'

How many NIGHTS do you have in Italy?
Could up post exactly how you will allot those nights to all the places you’ve listed in your subject line?
At a glance it’s at least one location too many and your order makes no sense.

Venice, Florence and Rome will be busy. Slotting Tuscany between Florence and Rome is a good idea, gives you a bit of a break from the crowds.

Be brutally honest about how long each transition takes. Look up length of train trips, add an hour for getting to/ from station/ hotel each end, etc.
Traveling in a straight line will almost always be most efficient

Don’t know what your priorities are but here is a suggestion based on 14 NIGHTS:

Fly info Venice
Venice 3 nights
train to Florence
Florence 3 nights
Pick up car
Tuscany hill town, one base for 3/nights
Drop car
Train to Rome
Rome 5 nights with 1 day trip to Pompeii ( not usually recommended but it CAN be done if Pompeii is a top priority)
Fly home from Rome

Thank you all for the honest, as well as brutal, feedback, lol! Tickets are booked, we will fly into Venice, and leave from Rome. We will skip destinations south of Rome, unless we are feeling peppy enough for a long day trip to Pompeii. And we will enjoy every unhurried stop in between. Already feeling better about fewer stops...
More questions. How best to plan our time in Tuscany and the hill towns? Which town makes the best base? We're interested in wine tasting/tours, agriturismo stay, and spouse wants to go Dario Cecchini restaurant in Panzano for dinner one night, anyone have feedback on this?

From Florence take a direct bus to Siena (1h 15m) and make Siena your base for two nights. The next day rent a car for the day and drive through Val d’Orcia: https://lovefromtuscany.com/scenic-drives-in-tuscany/ to Montepulciano. The next day take a direct bus from Siena to Rome (3h).

We were lucky enough to have lunch at Dario Chechini's restaurant in Panzano a few years ago. Sadly Dario wasn't there that day, but it was still a very enjoyable lunch and great fun being seated with all sorts of different people at a long table in the garden.

We had a private driver for the day and went to the restaurant after our stop in Siena.

We were there in October and it was packed, I presume our driver made a reservation but you will certainly need one.

We will skip destinations south of Rome, unless we are feeling peppy enough for a long day trip to Pompeii.

If you do this, i think I would do it the day before flying home. That way if you are 'worn out' it won't matter as all you have to do is sit on the plane the next day..

Ostia Antica is an easy commuter rail trip from Rome and can satisfy the ' un-buried ancient city' experience, with a lot less wear and tear.

Happy travels

We have a final itinerary, yay! Venice, Florence, Siena, and Rome, 3 nights in each city. Thanks again to all who gave advice. But...one last question:
I've made many reservations and bought lots of tickets. Except for Siena! I expect we'll want to spend at least one day exploring Siena, but would love suggestions for the second full day. We will have been on one Chianti wine excursion on our last day in Florence, so I'm wondering if there is a day trip from Siena for a different part of Tuscany. We aren't currently planning on getting a car, suggestions please? Some places we've considered are Volterra, Luca, or Orvieto...

This is a much more realistic itinerary. Are you still failing to say what month of the year you are going? These are high-traffic areas, and seasonal activity can vary with the part of the year. Also traffic and parking lot space, if you do rent a car.

Do you know that Lucca or Orvieto are each good for a full, solid day out? You don't have to rent a car to do either of those. But it's a matter of desire, or travel style. You could visit four neat LITTLE Tuscan towns in one day if you had a car. But I am not urging you to do that; it depends on what YOU want to do with the day. I am inclined to choose Orvieto simply because the Renaissance came later to Siena and maybe Lucca. Orvieto is a different kind of Tuscan city than Siena, if equally worth visiting.

Both Lucca and Orvieto would be too far as day trips from Siena-IMO- both will take well over 2 hours each way

Volterra ban be reached by bus-no train- and bus will take close to 2 hours I think with at least one change

ToursbyRoberto.com is highly recommended here
His tours mostly leave from Siena but he books up early

You could train to the little town of Buonconvento in less than an hour

You could rent a car for a day and explore a bit of Tuscany on your own

However nothing wrong with just slowing down for your 3 nights in Siena -plenty to see and do right there << that’s what I would suggest. Get away from the tourists around the Duomo and Campo and explore the contradas

Thanks for this additional info.
Dates: Our trip is mid-September, coming up!

Roberto is mostly booked up, unfortunately, but we might tour/taste at Madonna Bella (the estate his sister runs?) which is a short taxi ride from the center of Siena.
I'm kind of liking the idea to otherwise hang out and relax here. We have many scheduled stops before and after Siena...and one of my original goals was to just chill and enjoy Tuscany.
Thanks again for all the great input--this forum is such a helpful resource!