Milan, Cinque T., Tuscany, Venice - What to book in advance?

Long story short, I had two other trips in planning that my teen daughter eventually vetoed :)

She has requested a culture/sightseeing/city trip over the 'nature' and 'beach' options. She's had a really tough year and with all the anxiety about heading into high school, I would love to make this happen for her. I have about a month to plan this trip, so here's my first attempt at an itinerary. We will be flying in and out of Rome (only option for a direct flight), which we'll be skipping as we have previously visited:

Day 0: overnight flight into Rome, arrive 7:30 am

Day 1: Rome to Naples via high speed train, Napoli, Overnight in Napoli

Day 2: Pompeii tour, Overnight in Napoli

Day 3: Amalfi coast tour (bus tour or private driver), Overnight in Napoli

Day 4: Napoli in the morning, leave for Florence via high speed train, Overnight in Florence

Day 5: Florence, Overnight in Florence

Day 6: Tuscany day trip (bus tour or private driver), Overnight in Florence

Day 7: Train to Cinque Terre w/ stopover in Pisa, Overnight in CT

Day 8: Cinque Terre, Overnight in Cinque Terre

Day 9: Train to Milan, Overnight in Milan

Day 10: Milan in the morning, train to Venice, Overnight in Venice

Day 11: Venice, Overnight in Venice

Day 12: Venice in the morning, Venice to Rome via high speed train or flight, Overnight Rome near airport

Day 13: fly home

Would love to hear your thoughts:

- We like fast paced, but is it too fast paced? Any suggestions?

- I feel like Milan is a bit of a 'detour' and I wonder if it's worth just for one day?

- Should we get TrainItalia passes? Which one?

- I would love to have some flexibility and not prebook hotels in case we want to linger in one area more - is this too much of a risk? (I wouldn't have considered it but i feel like we could 'wing it' this year?)

- Is there anything else I need to pre-book? (ie. tours, transportation, admission tickets, etc).

Thanks all in advance!

My wife and I had an a trip planned from Oct 17-25, flying into Florence, traveling up through Cinque Terre, and ending in Lake Como, then flying out of Milan.

But due to airline issues we now have to begin our trip in Milan. I thought "who cares, we'll just reverse the trip" and rebooked our lodgings with that in mind, but (silly me), I've just realized flying out of Florence back to our US-based airport will be a significant headache based on the airline we're locked in with (multiple flights with really tight layovers, so any delay along the chain of flights would completely screw us. That's my nightmare!)

That's causing me to re-evaluate the whole trip! We're already locked into our Como stay from Oct 17-20 because we can't get a refund. But I started thinking, instead of going south maybe we head west from Como into the Dolomites and end our trip in Venice/fly out of Venice?

My wife and I love mountains, hiking, historic architecture, and great coffee/wine. The westward trip ticks those boxes but our travel dates might be a really bad time to visit the Dolomite range, as it looks like most things are closed. Anyone have any experience or insight about those areas at that time of year?

Hey there. We are planning a trip to Italy (and Paris) next June. We are bringing our DDs, first timers to Europe, ages 21 and 16. I’ve been reading through itineraries, guide books, youtube videos of Italy and getting so excited. We have limited time (only 10 nights in Italy) and we are packing in A LOT I know. We are considering using Zicasso or another company to make the most of our time, especially since we are trying to do so much...Here’s our latest itinerary so far. (we like to see as much as possible/get a taste so we know where to spend more time the next time:)

. Summary. 2 nights, 1 1/2 full days in Venice,

4 nights in Florence with day trip to Cinque Terre, 5 nights in Rome with day trip to Pompeii and Amalfi

*We already bought our tickets flying into Venice

Day 1. Arrive Venice from Paris on the 13th. Half day in Venice

Day 2. Venice

Day 3. Take a late train from Venice to Florence.

Day 4. Florence

Day 5. Florence. (Day trip to Cinque Terre)

Day 6 Florence

Day 7. Train to Rome by 7pm. Stay near Piazza Novana

Day 8. Rome

Day 9 Rome

Day 10. LONG day with private guide to Pompeii/Amalfi

Day 11. Rome

Day 12. Departure day

Grazie!

We are traveling to Italy for our 25th Wedding Anniversary - we will be going from Rome, to Cinque Terre, to Florence, to Venice and Milan. We plan on traveling exclusively by train. Is there a need to buy any/all tickets in advance? Is a pass worth considering or do we by individual tickets for each journey?

Thanks in advance!

Hi there!

I have traveled to Italy a few times, but have always stuck to the major touristy cities and relied heavily on the Italian train system to get me to and from the cities. I am planning a family trip to Italy and my family loves drinking wine and I would love to treat them to one or two nice tuscan vineyards.

I've been searching and trying to figure out the best vineyard itinerary and am unsure of how to get from vineyard to vineyard and where to stay / how to get to wherever we stay. The plan is to go from Milan >> Cinque Terre >> Florence (or a smaller city closer to vineyards, if I can figure out the optimal location).

If anyone could share their suggestions and if I need to rent a car, I would greatly appreciate it! Thank you in advance!!

I'm trying to not spend too much money. For example staying at Castello Banfi for the night, which is something I saw come up a few times is out of my budget.

After cancelling our 2020 Italy trip, I've just booked a trip for spring 2022. We fly into Venice in late April and will be in the country for 21 nights before leaving from Rome. I've booked accommodations online but everything is cancellable so I'd love to know you suggest any changes to my itinerary. And I have a few questions. Any input would be much appreciated as I've never been to Italy!

Here's what I've booked:

3 nights Venice - Wander, see Doge's palace & St. Mark's Square

3 nights in Sirmione, Lake Garda - explore Roman ruins, drive around lake, maybe boat trip to Isola del Garde

3 Nights in Florence - Museums & sights. Rent car when leaving & drive to Montepulciano via Chianti.

3 Nights in Montepulciano - Wine tasting, explore hill towns in Tuscany (& maybe hot springs?)

4 Nights in Sorrento (day trips to Capri & Amalfi Coast & maybe Pompeii, but that would be all the days and I want to just relax & wander in Sorrento too)

4 Nights in Rome - Colosseum, Vatican, and maybe day trip to Tivoli or Ninfa Gardens (though my husband won't be that excited about the latter so may skip it)

Does this look like a good number of days / nights in each place?

Also, I have a few other questions... From Venice to Sirmione - Would I be better off to simply take the train from Venice to Desenzano and rent a car there, meaning I could drop it at the end of my Sirmione stay and not pay one-way charge? Or rent a car in Venice and drive to Desenzano? And when we leave Montepulciano to go to Sorrento, am I better off dropping the car in Chiusi and taking train from there to Sorrento, or driving back to Florence & dropping it there, taking the high-speed traing?

Or should I re-order the whole trip, driving from Venice to Sirmione and then to Montepulciano, then take the car back to Florence, spend 3 nights there and then train to Sorrento?

I've noticed that a lot of accommodations are booking up already for next spring so if my itinerary isn't logical, I want to switch it around now while there's lots of options. I know there's plenty of time for booking cars & trains, but does the order make sense? Thanks in advance for any input!!

Hi! We have been to Italy a few times, mainly Venice and Rome with trips in Tuscany, Florence, Verona, and Naples. At this point, I'm looking to go back for a mix of adventure and relaxation, going to 2-3 destinations over the course of ~9 days. What we can't determine is where...places we are interested is: Capri, Positano (and nearby areas), Sorrento, sardegna, bari, and lake guarda. Any suggestions on where to focus or not focus would be greatly appreciated. Thank you!

Hi Everyone,

Re-planning my postponed trip from 2020 this year. I seem to have forgotten all the valuable tips I had received for my previously planned trip. Is August a bad time to travel in terms of closures and holidays? Since I have nothing book yet, would it be better to travel in September instead?

I am thinking the following itinerary for now:

Aug 5-10-Roma

Aug 10-13-Florence with day trips to Sienna, Pisa?

Aug 13-15-Venice

Aug 15-16-Train back to Rome and fly home.

Is this too ambitious?

Will be travelling on a Covid tested flight in and out from Rome from Canada

First off- thanks in advance for any advice! (first time posting)

We are planning a ~2.5-3 week trip to Italy for May 2022 with our 2 kids (6 and 8).

My idea of a dream Italy vacay is cozy farms, beautiful scenery, amazing food, space for the kids to run and explore, bike rides, horse rides, and an authentic feel.

We also like to take our time in places vs trying to rush and see it all. I feel we have to see Rome and Venice but also know our kids will easily get overwhelmed and tired by the big cities.

Based on that, I have loosely come up with the following itinerary:

Fly into Rome (found a great points flight from our city); 3 nights here

5 nights in Umbria (agriturismo)

5 nights in Tuscany (agriturismo)

? 1-2 nights in Bergamo (my hubby has been and loves Citta Alta neighbourhood)

3 nights in Venice - fly home

Any thoughts on this? I love the idea of Cinque Terre but perhaps best to save it for another time (without the kids!).

Thank you!! Cait

We're tossing around the idea of returning to Italy (late July or August) and wondered if we could get some recommendations on cities. We've done some of the 'must sees' on previous trips (Rome, Venice, Verona, Florence, Milan, Genoa, Siena, San Gimignano, Naples) and are now looking to put together a schedule that includes other biggies we've missed and perhaps less touristy hidden gems. We'll have about 2.5 weeks.

Anything recs you could throw my way would be greatly appreciated!