How could our itinerary be improved?

Using a multi-destination search function, you can connect your trans-Atlantic eastbound flight through to Venice. Then fly home from Rome. It shouldn't cost any more money and it will probably save both time and hassles. Nice if you could find a non-stop to Venice but that depends on your departure city. Even then, fly home from a different city. All on the same itinerary.

First trip? You may be overestimating some times and underestimating others. First, any chance you could fly into Venice and out of Rome? That would save your first day in Italy from being a travel day and turning it into a vacation day. From Rome to Venice by train is going to be a long commute although the Freccia high speed trains are very comfortable and the scenery is beautiful. Depending on the schedule you could be looking at about 6 hours commuting time.

What do you want to see/do/experience? Venice certainly deserves, for most people, more than a one night visit. 3 or 4 might be more in line with what Venice has to offer. Read your RS guidebooks. Leaving Venice in the evening for Cinque Terre? Have you looked at the train schedules? Would not be my idea of how to spend a vacation day on my first trip to Italy. 4 nights in Cinque Terre? Why? Yes, it's a beautiful area but 4 nights? I might suggest adding a night or two to Florence, which you could use as a base and take a day trip to Siena.

4 nights in Rome is a good start. Rome is over 2500 years old. That's a lot of centuries and cultures to explore. If you get tired of one, all you have to do is turn the corner!

Read your RS books, sit with the family and set your priorities. Check train schedules on trenitalia.it to get a more realistic time you'll be spending on trains. It takes longer than you think to check-in an check-out of hotels, deal with luggage, and get to/from train stations. On your plane ride home you can start planning your next trip to Italy!

The direct 13:53 FCO-Venice Freccia train takes 4 hours and 40 minutes: If you have to change in Rome it's always less than 5 hours.

Nevertheless I agree about flying open jaw to have one day more in Venice. You have only one full day there compared to 3 in the Cinque Terre: it seems a little odd, you have already visited the French Riviera whereas Venice is unique.

5/12 - Tuscany (Siena & Val d’Orcia)

You'll need a car to see both in a day without rushing too much.

Anyway, be aware that The bus from Florence stops on the top of the hill in Siena; the train station is at the bottom and the escalators take ages.

Would it be worth eliminating a day from CT and adding it on to Rome to do a day trip to Pompeii and/or the Amalfi Coast?

It would be worth to actually see Florence!

Appreciate your comments and suggestions! I’ve updated the post to reflect that our flights cannot be changed since we’ve already purchased them. Only one of the four travelers visited the French Riviera, hence the extra days added on to CT. Will definitely consider adding another day to Venice!

Alexandra, this worries me:

5/7 - day in Venice, depart for Cinque Terre in the evening

You are looking at a long train journey between these two locations - no less than 5 hours, and probably more - and many accommodations in the CT do not have 24/7 desk services. If you left Venice in the evening, you would arrive at whichever of the 5 villages you chose very late at night, and may not be able to get into your accommodation, plus it could be difficult to find in the dark. If you keep this plan, you'd need to pre-arrange with your hotel/rental for late-night access.

This bothers me too:

5/12 - Tuscany (Siena & Val d’Orcia)
5/13 - Tuscany (Florence)

These are both PARTIAL days, as pieces of them would be consumed with transport from points A to B checking in and out of accommodations, etc. Not enough time, IMHO, for all of this, and yes, you'd need a car for 5/12: read up on driving in Italy. A partial day for Florence? Not nearly enough for getting acclimated and your head around that one.

If I was to readjust your schedule and couldn't change your flights, it would look like this:

5/5 - arrive to Rome, travel from Rome to Venice (3 nights/2 full days)
5/6 - Venice
5/7 - Venice
5/8 - depart for CT in the AM (3 nights/2 full days)
5/9 - CT
5/10 - CT
5/11 - Depart for Florence in the morning (3 nights/2 full days) Stop at Pisa along the way.
5/12 - Florence
5/13 - Florence. (you could day-trip to Siena on this day, although that still cuts Florence too short, IMHO)
5/14 - depart for Rome (4 nights/3 full days)
5/15 - Rome
5/16 - Rome
5/17 - Rome
5/18 - Depart from Rome FCO

In addition to your first long day of travel from Rome to Venice, you would have 3 other transfer days which will only be partials, as far as sightseeing goes.

I count 13 nights. Right now you have 2 Venice, 4 CT, 3 Florence (and Tuscany) and 4 Rome. I would switch one CT to Venice. We were 4 nights in Venice this past August and barely scratched the surface. We were there with young adult children as well and we all loved Venice. Also, if you are into the beach, some of our party went to Lido to swim. But I am not sure that the water will be swimable in May anywhere in Northern Italy. So consider that in your plans.

I also think it would make more sense to go from Venice to Florence and then from Florence to CT.

You cannot take an evening train from Venice to the Cinque Terre; there simply isn't one. The current schedule for May 7 shows the latest departure time to be 4:40 PM. That trip (with four transfers required for Monterosso; Vernazza requires three transfers) takes almost seven hours, arriving at 11:29 PM. I agree that your time in Venice seems very short. It would be surprising if all of you were fully recovered from jetlag on May 6.

I haven't been to the Cinque Terre since it became a zoo, but I enjoyed my earlier visits. A major difference between the Cinque Terre and the French Riviera is that the CT's attractions are primarily outdoors--hiking, walking around the cute villages and swimming (though I don't know about beach conditions or temperatures in May). The French Riviera has many, many museums as well as nice gardens and some interesting homes to visit (including the Villa Ephrussi de Rothschild and the Villa Kerylos.

Where are you planning to sleep on the nights of May 11-13? I would be very unhappy with three one-night stops in a row.

IMHO you have too many locations for a 13 night trip.

Have not been to CT but have been to Amalfi and French Riviera and can say Amalfi is nothing like the French Riviera. Don’t believe CT is either.

Venice needs more time than you are giving it, especially since you are spending so much time getting to and from. Leaving in the evening for CT is probably not going to work out.

It’s not clear how you will travel around Tuscany. Will you rent a car? Will you base in 1 place or move every night? UGH

Amalfi/Pompeii is too far as a day trip from Rome. A good alternative to Pompeii is Ostia Antica- easily done from Rome.

As much as we love Venice, I’d say drop it from this itinerary. You don’t have enough time to enjoy it anyway. (looks like you haven't prioritized it?)

Go straight to Florence on arrival- 3 nights- first night hardly counts as it is jet lag day-add a night for every day trip. (1 for Pisa, maybe visit Lucca as well, 1 for Siena, you will need a car to visit Val d’Orcia - or move to Siena and day trip from there)
Then CT- 3 nights is plenty
Then finish in Rome- 4 nights minimum

ETA: if you can't give up Venice OR CT- then Kathy's suggestion is great

OK so if going Venice> Florence> CT> Rome, this could would work too:

5/5 - arrive to Rome, travel from Rome to Venice (3 nights/2 full days)
5/6 - Venice
5/7 - Venice
5/8 - depart for Florence in the AM (3 nights/2 full days)
5/9 - Florence
5/10 - Florence
5/11 - Depart for CT in the morning; see Pisa along the way (3 nights/2 full days)
5/12 - CT
5/13 - CT
5/14 - depart for Rome (4 nights/3 full days)
5/15 - Rome
5/16 - Rome
5/17 - Rome
5/18 - Depart from Rome FCO

That said, yes, I'd consider dropping Venice as it's the outlier, and you haven't allocated enough time for it to begin with so it must not be all that high on the family's interest list? Going directly to Florence instead is a good idea. If not wishing to deal with a car, there are any number of easy day trips in the Tuscan region by bus or train from that one. Swimming in the CT: every season is different but people were swimming the year we were there about 3/4 way through the month of May.

Editing to add: I'm not personally a fan of day trips from Rome to Pompeii/Amalfi. I think you could very easily spend the time you have just covering ground in Rome...and you'll only scratch the surface. The Naples/Sorrento/Amalfi region deserves far more than just a partial day. If taking any of the escorted bus tours to do that, they also tend to be VERY long days with at least half of it spent sitting on the bus to/from Rome + Pompeii to the coast. That one day you planned for it could also be the day the weather doesn't cooperate so save it for another trip when you can give that region the time/attention it deserves?

Just checked, ITA, the replacement airline for Alitalia, offers one way tickets FCO to Venice for $68, might be worth considering…you can take the bus from Marco Polo airport into Venice (a few Euro). Just make sure that if you have checked bags you allow lots of time for off-loading in Rome…I waited 1.5 hours on occasion!

The big problem is the lack of accommodations in the Cinque Terre where the "reception" is open in the late evening, but there is a way to depart later than 16:40.

the current schedule for May 7

That's what trenitaia.com displays, but You'd better not search the train schedules that far in avance during a pandemic.

The actual timetable will be uploaded on March 31 on trenitalia.com, or earlier.

The last train departs from Venice at 18:26, but it takes 6 hours and 2 changes to arrive at Monterosso.

I'd ignore the solutions displayed by trenitalia. com , the site is programmed to minimize the time of travel. I'd rather minimize the number of changes and have reserved seats all the way from Venice to Monterosso.

You could take one of the many 2h and 15 direct bullet train from Venezia S. Lucia to Milano Centrale (either trenitalia's or italotreno's). Then I'd get on the direct IC 687 that leaves Milan at 21:10 and that calls at Monterosso 1 minute past midnight. As I wrote the problem will be entering the room in Monterosso!

You do not have the time to attempt a trip to Amalfi Coast/ Pompeii.

I agree with others that Venice should have at least one more night

You can easily see Ostia Antica while in Rome to satisfy your 'ancient Roman city' yen.

Kathy’s second itinerary works best.

Yes Kathy is an ace at this. The best train from Florence to any CT village is from the Campo di Marte station at 7:54AM arriving at 10:26.

Right: that 7:54 train out of Firenze Campo di Marte is the fastest way into the CT (you'd change at La Spezia for your train to your chosen CT village) but I'd look at trains out of Firenze Centrale if intending to get off at Pisa en route, check your bags, and have a look around. You'd buy separate tickets: Florence>Pisa, and Pisa > CT village.

(Open to correction here so please chime in if I'm in error!)

Here’s one more option.

5/5. Arrive Rome. Train to Florence. 2 possibilities, direct from FCO at 13:50, 2H13m
or Fco-Termini and direct Termini to Florence.
The two tickets can be purchased at FCO.
Arrive Florence.

5/6. Florence, Day trip to Siena by bus. 1H17m.

5/7. Florence.

5/8. Florence, Day trip to Venice 9:30, 2H14m. Return 19:26. 2H13m. While not ideal, it would give you a taste without changing lodging.

5/9. Florence. Day trip to the Val d’Orcia. By tour or rent a car.

5/10. Train, Florence -Monterosso ( best beach) that leaves @7:54 2H25m leaves from Campo di Marte, but from SMN at 7:34, 3H04m w/change at the above. Just depends on which station is closer to your lodging. Make sure you can drop your luggage at lodging, check in is normally around 14:00.

5/11. CT.

5/12. CT.

5/13. Train, Monterosso-Pisa. 9:07 1H10m
Luggage storage@ Pisa Centrale, bus to field of Miracles. You can also catch a bus from Pisa Centrale to get to Piazza dei Miracoli. From in front of the station, catch the LAM "ROSSA" bus heading toward "Park Pietrasantina" (not toward "Ospedale Cisanello" as it is in the opposite direction). Get off at the "Torre" stop, you'll see it as it is right after you've passed the gate into Piazza dei Miracoli at Piazza Manin. It is likely the bus will always make the stop there in any case, considering how popular the stop is.

Make sure to buy your bus ticket before getting on the bus directly at the Pisa Centrale station from the automatic machines. You can always buy a ticket from the bus driver but it costs more and you need exact change to buy it. Cost at the machines is €1,70 and the ticket is valid for 70 minutes from the time you first use it. You need to stamp the date and time on the ticket as soon as you get on the bus the first time (yellow machines for this are right by the door of the bus as you get on).

Train, Pisa to Rome. 2H52m at 13:32 & 14:32.

5/14. Rome.

5/15. Rome.

5//16. Rome.

5/17. Rome.

5/18. Travel.

I’ve been to the French Riviera, CT and the Amalfi Coast. None are similar. If you want something like the Riviera try the area near Santa Margherita Ligure about an hour north of CT.

Edit: there are earlier trains to Venice @ 7:20 &
8:20. Giving you 10-12 hours in this beautiful city
Depending on departure time.

I agree with most of "Geri's" plan...for me, Venice is a day trip and you have scheduled too much time in CT...add more time in Florence and you can do some great day trips from there...even Bologna and/or Parma. You can also do Pisa and Lucca in one day as not much to see in Pisa other than the "tower". I would even dare to say break up your travel from Rome to Florence with a stop in Orvieto (about halfway in between). Rome to Venice is a very long wasted day in my opinion. I'm sure you will love your trip in any case.

5/5 - Arrive to FCO in the AM. Spend the night in CT (town TBD - and
to clarify, we’ll have one home base in CT)

have you checked train schedules for this transit? it will be a long day after that overnight flight

5/8 - Depart from CT to Florence in the AM. Stop by Pisa and/or Lucca along the way to Florence. Spend the night in Florence.
5/9 - Day in Florence. Pick up rental car and spend the night in Tuscany (town TBD)
5/10 - Day in Siena. Cooking lesson and/or food tour? Spend the night in Tuscany (town TBD)
5/11 - Do the Val d’Orcia driving tour in RS book, visit La Foce gardens. Spend the night in Florence

since you are not spending much time at all in florence i guess i'd say pick a town in tuscany for your base. you could pick up car in Pisa if timing works out- car agencies mostly close by 12-1. the agencies in florence at train station close at 4:30 IIRC
5/9 is a monday so that's not a good day for florence
no need to return florence- drop the car in Chiusi

5/13 - Spend the day in Florence. Spend the night in Venice

confusing- must be a typo?

OH

OP must have deleted her post from tonight with new itinerary

oh well

Oops, yes you were right, Christine! I accidentally deleted my previous post with the updated itinerary, but have reposted it below. Any feedback or input you have would be greatly appreciated! Your comments and suggestions on the original itinerary were super helpful and I've incorporated suggestions from RS' book. 

A few additional questions: 

• is it worth spending the night in Florence or should we make a Tuscan town our home base and travel into Florence for a day trip?
• Should we consider switching the order of CT and Florence? I know that first day (5/5) will be long, but since we'll be tired from jet lag, maybe it makes more sense to spend that time on the train getting to CT rather than trying to sightsee in Florence? On the other hand, it might be better to have a change of scenery/pase and break up the visits to Florence and Venice with CT in the middle (but that gives us 6 hours of train travel from CT to Venice).
• Does anyone have any recommendations for a food tour/cooking class and when that would be best to incorporate into our itinerary?

Updated itinerary

5/5 - arrive to FCO in the AM. Take train to La Spezia/CT. Sleep in CT (town TBD, but we will have one home base in CT)

5/6 - Spend day in CT. Sleep in CT (town TBD, see note above)

5/7 - Spend day in CT and/or Italian Riviera (town/exact plans TBD). Sleep in CT. 

5/8 - Depart for Florence in the AM, stop by Pisa and/or Lucca on the way. Sleep in Florence (or does it make more sense to have one home base and stay in a Tuscan town?)

5/9 - Spend day sightseeing in Florence, pick up rental car. Sleep in Tuscan town (town TBD)

5/10 - Spend the day in Siena (should we plan for a whole day? If not, what other additions do you recommend?) Sleep in Tuscan town (town TBD)

5/11 - Val d'Orcia RS driving tour, visit La Foce Gardens. Spend night in Tuscan town or Florence...? 

5/12 - Depart for Venice in the AM, sleep in Venice

5/13- Spend day in Venice, sleep in Venice

5/14 - Venice in the AM, depart for Rome in the early afternoon. Sleep in Rome

5/15 - Spend day in Rome. Sleep in Rome 

5/16 - Spend day in Rome. Sleep in Rome 

5/17 - Spend day in Rome. Sleep in Rome 

5/18 - Depart from FCO 

Not sure where you are flying in from. Your trip is ambitious but doable. Just remember after arriving in Rome you have a three hour train trip to CT. You will be exhausted. I would base in Florence and do day trips from there rather than be all over the place. My twenty-somethings would have been bored three nights in Venice. They saw and did everything they wanted in a day and a half. But that's their age. They loved Florence, seeing the David, the Duomo, and walking around. They also would have been bored in CT for three days. Florence and Rome both offer great day trip options, and the less you have to pack up and move constantly, the better.

Sorry, Alexandra but what you mean when you talk about Tuscan towns as if Florence wasn't one?

Is it a matter of size? Being on a hill or not? Being close to the picturesque SR222 road you see on the cover of many books about Tuscany?

Pontedera is a typical Tuscan town, but I doubt you dream of to staying close to the Vespa factory. So, if not Florence, what kind of Tuscan town are you looking for? I have the impression you mean hill villages like San Gimignano, but less touristy.

Have you actually checked with your airlines about changing flights?
I know United (and I believe other carriers) has completely done away with change fees)- I have changed our flights a few times without fees

As I said above that arrival day is going to be exhausting
that’s a 3 seat transit- FCO-Termini-La Spezia- CT town
I think you are better off going to Venice first. Yes it’s a 4 hour train but you won’t be changing trains once you board at Termini - you can sleep- Venice will be end of the line

Kathy posted the best itinerary here (and it avoids Florence on a Monday):

5/5 - arrive to Rome, travel from Rome to Venice (3 nights/2 full days)

5/6 - Venice

5/7 Venice
5/8 - depart for CT in the AM (3 nights/2 full days)
5/9 - CT
5/10 - CT
5/11 - Depart for Florence in the morning (3 nights/2 full days) Stop at Pisa along the way.
5/12 - Florence
5/13 - Florence. (you could day-trip to Siena on this day, although that still cuts Florence too short, IMHO)
5 /14 - depart forRome (4 nights/3 full days)
5/15 - Rome
5/16 - Rome
5/17 - Rome
5/18 - Depart from Rome FCO

I realize that leaves out La Foce (Only open Wed, Thurs, Sun?) and Val D'Orcia.
You really are going to have to give up somewhere or cut somewhere even shorter to fit that area. It needs a full day and a night (2 nights would be better) I suppose 1 option would be to pick up your car as you leave Florence and drive thru Val D-Orcia on your way to drop car in Rome (check car agencies closing times though-you may have to drop at airport)
Or pick up car as you leave Florence 5/14- drive Val D'Orcia and stay in Pienza or Montepulciano that night- drop car in Chiusi in the am and train to Rome early am 5/15.

ETA- oops can't do that ^^ 5/15 is a Sunday, I knew that as we will be heading to Rome next day as well. Car agencies closed in small towns on Sunday

ok- another suggestion
with above itinerary posted by Kathy- consider picking up a car in La Spezia as you leave CT on 5/11- drive to Pisa , Val D'Orcia. etc
Stay in one of towns mentioned above- 2 nights. Visit Siena as a day trip from there. (read up on parking/driving in Siena).
Return your car to Chiusi in am, train to Florence- 2 nights there then train to Rome
I think you have to drop a night somewhere else (CTor Venice?)- for that to work.

Late getting back to this one, sorry!

I'm with Christine on heading to the CT on arrival day: sort of a risky plan, IMHO. Besides being a long trip, any sort of transport snag (and they do occasionally happen) could be a real headache. I'd stick with travel from major city to major city via the fastest trains, as in Rome to Venice. That will be a long trip too but less risky on arrival day, IMHO.

Not to flog the horse but If you decide to drive, be SURE to read up on the ins-and-outs for motoring Italy. Become familiar with the signage, especially the type indicating where you, as a visitor, are not allowed to drive, and understand that practically all infractions are recorded on camera so you can acquire traffic fines without being stopped by law enforcement. Those would show up in your mail at home sometimes many months after the fact. I'll also caution about leaving anything of value in an unattended car, especially in Pisa. If you absolutely can't do that, make sure nothing - as in luggage - is left in plain sight. Not to be an alarmist -visitors can and do drive in Italy without incident - but we hear often enough from the unfortunates who didn't do their homework. OK?

Thank you for your feedback and suggestions. We’ve rearranged the itinerary and are going to go to Florence first, then CT, and then Venice. Will be mindful of the driving rules!

For comprehensive driving information, scroll down to free PDF “driving in Italy”. Print it out, take with you to refresh your memory. While some rules are similar, signage and speed limits will vary in different locations.

https://italybeyondtheobvious.com/custom-italy-vacations/itineraries/