Hope to take our 30th Anniversary trip to Italy end of May to mid June.

You don't need a rail pass, buying a series of individual tickets is cheaper. You can also take trains most places and get a car for short stints. Here's an idea:

Arrive Rome, train to Venice.
Visit Venice
Train to Florence
visit Florence
get car? or train to Pisa (car will let you visit towns on the way).
Return car, train to Sorrento.
visit Sorrento, train to Rome
End in Rome.

There are 1000 different ways to order this trip, the point is you don't have to do just car or just train, and a train pass will be more expensive than just getting tickets.

My #1 tip for order of a trip is to END in the city you leave from. If your flight home is from Rome, end your trip in Rome. If you fly into Rome as well, immediately leave it for your first city, by train or bus. That way your jet lag day is spent traveling, not "wasting" a day in a place you want to see, and you don't have one of those messy end-of-trip one night near the airport hotel nights.
If you can arrange it, fly into Venice (or Milan and then go to Venice) and home from Rome. It's usually not much more expensive, often less than the train cost, making it very worth it.

You do NOT want to drive in Rome or in the city of Florence (traffic, lots of restricted zones, no parking). I have heard that driving in the Amalfi coast/Sorrento area is rough, too. If Naples is a consideration, driving there is even worse than Rome. And obviously you can't drive in Venice. Driving is best in the countryside between cities, returning the car on the outskirts or parking it somewhere on the outskirts and taking a cab in to a centrally located hotel.

I am just offering my humble opinion but I would recommend doing the train unless you really enjoy figuring out directions (be sure to get a car with GPS/NAV), finding parking, deciphering road signs, and the potential problems you mentioned. Also, don't forget to add gas (which is expensive), insurance as well as the cost of parking to rental car cost. You don't mention how long you are staying but if it were my husband and I on our anniversary, we would find the train much more relaxing. Obviously, there are many tradeoffs but we have found the trains to be our time to catch up between cities and plan for the next stop. You do have a busy itinerary and would be covering a lot of territory and time on the road. I would think that the trains would get you to places much faster but the downside is that you have to find ways to your accommodations from the train stations with luggage (don't know how central your accommodations are). Last year I did a family driving trip from coast of France, thru Stresa in Italy, to Zermatt and eventually flying out of Frankfurt. Cost was cheaper for group of 5 but sometimes directions were tricky even with our car NAV system and parking was the other problem. Just my take.....hope all goes well and it's unclear how COVID will affect everything. Best wishes! I can't get enough of Italy myself!

I think the first response you got is very sensible; i.e. do a mixture of train and car. A gps (your own or built in) should take care of most of the getting lost problem. European cars get excellent mileage, so if you don’t let your tank go below 1/4 - 1/3 full, you should be fine. As in the U.S., rental cars are pretty new, so breakdowns shouldn’t happen.
For reasons I won’t go into, I have driven a couple of times in both Rome and Florence. It can be done, but I sure don’t recommend it. With the places you’ve listed, there would be no need to pick up a car until you are leaving those cities.
A few more thoughts: if you use the autostrade as much as possible, you will minimize your chances of getting lost or running out of gas. Just keep a supply of cash handy for tolls and payment, in case your American cc won’t work. It’s also true that it’s much easier to find any kind of help you need on an autostrada than on a secondary road.

The length of your trip will dictate how many locations you can comfortably visit. Venice and Sorrento are the outliers, and you will need to plan carefully to visit them both.

I would budget at least 2 weeks for a trip with this many locations. Have you been to Italy before? I would use Venice as your starting city, flying there from the US. Then, I would suggest an open jaws departure from Rome, meaning that your last city to visit would be Rome.

Venice can easily entertain you for 3 nights (2 days) with Florence eating up another 4 nights (3 days). Pisa is a quick 1 hour train trip from Florence, so you don't have to budget an evening there. An early train going and a later train returning to Florence is more than sufficient time to see the Tower and the.....and the......well, the truth is, the Tower is really the premium sight in Pisa. It's a university town.

If you train from Florence to Naples, you can pick up the Circumvesuviano (or hire a private car) to take you to Sorrento. Sorrento is lovely, worth 3 nights or maybe 4, but Rome is worth as much time as you can budget for it. That's a two week trip.

You are all awesome and believe me EVERYTHING will be written down. We will be there for 21 days 4 in Rome, then 4 in Sorrento, 3 in Venice and the rest in Rome where we will drive or train ride to Florence and Pisa on 2 days and possibly go somewhere else to visit

Hi anaroy68 and welcome to the forums!

Just out of curiosity, would you mind sharing your complete plan? By "complete" I mean a place-to-place itinerary with actual dates? (Editing to add: oops, I see you sort of did that while I was banging away. Thank you!)

Aside from that, rail passes aren't usually recommended for Italy: you can usually do better booking train tickets for each individual leg of the trip. If your travel dates are firm, which allows you to buy in advance, you can often land VERY nice price breaks on super economy tickets for Trentialia or Italo "fast train" journeys.

For your particular itinerary, I'd absolutely travel by rail. As the others before me have stated, you do not want to drive in Rome or Florence, cannot drive at ALL in Venice, don't want to leave a car with anything at all of value in it in Pisa (break-ins are common enough for concern) and the Amalfi Coast roads can be real zoo in high season. That's not to mention scarcity of parking. You can get on a train in the middle of all of the cities listed and be dumped off right in the middle of the next: no ZTLs or speed cameras or bus lanes to dodge, no parking fees, etc. and they'll get you there more quickly than by road. You can sit back and enjoy watching the world fly by from the windows of your carriages.

The one city you might NOT take rail into/out of is Sorrento. We have taken the no-frills, beat-up Circumvesuviana commuter train to there from Naples without incident - "fast" trains don't service Sorrento - but you can get around it if desired by taking a ferry from Naples' docks or splurging for a private driver from Napoli Centrale train station. There is also the Marozzi bus from Rome Tiburtina train station >Sorrento, although it operates on a limited schedule. It's a little unfortunate that you'll have two journeys (Rome> Sorrento, and Sorrento>Venice) that can't be done by direct trains but no matter; in both cases you'll be switching transport in Naples and it's no big deal.

https://www.marozzivt.it/home

Florence is a terrific base for any number of day trips by public transit so I hope you can give that one plenty of time! Favorites amongst the RS posters are Fiesole (by city bus), Lucca (by rail), Pisa (by rail), Siena (by bus or rail) plus some others. Some folks are OK with renting a car for a day to tool around the countryside so that's an option too.

Traveling Italy by train, getting around the way many Italians do themselves, has been one of the experiences that has had us feeling like we're on a real adventure! :O)

I'm a little confused.

In your post your question is

"Rome to Sorrento to Venice to Rome to Florence".

Then just now you replied:

21 days 4 in Rome, then 4 in Sorrento, 3 in Venice and the rest in
Rome where we will drive or train ride to Florence and Pisa on 2 days
and possibly go somewhere else to visit

They are pretty similar but I see Pisa and somewhere else added in.

If you have 21 days (most find it easier to count nights so you don't double count a day when you are moving, and 3 nights for example gets you 2 full sightseeing days), Then I see you have
4 days in Rome
4 days in Sorrento
3 days in Venice
which is 11 days.
Then the rest in Rome again.... That must be a second visit to Rome of 10 days from where you will take 2 day trips, one to Florence and one to Pisa?

Is that right?

It sounds like you have rebooked all your hotels so that isn't a potential plan but a cast in stone plan. Is that right?

I ask because Florence is midway between Venice and Rome and most people would stop there on the way back and visit Florence and Pisa (quite close to Florence) and then continue back south, or do multi-city and arrive at Venice and depart from Rome to avoid all the backtracking.

Rome to Florence and Florence to Venice is a pretty decent length of journey.

To do two long day trips after you have just gone through Florence will include a LOT of backtracking.

Back to your original question - how did you come up with $900 for the train for:
Rome-Sorrento
Sorrento-Venice
Venice-Rome
Rome-Florence-Rome
Rome-Pisa-Rome?

Most of those can be done for not much more than €29 pp each way. Because I need to go to bed, that's 7 legs x 2 people x 30 in round figures or around €420, and there are economies to be made as I said if you can rearrange.

But even at 420 that is much much less than the amount you quote.

Please help me help you....

If you are thinking of renting a car in Italy, you really need to browse the Italy forum for the many many many discussions of tickets in the mail.

The issue in Italy is the no-go travel zones (ZTL). These are in cities, and appear to be poorly marked, and subject the traveler to high post-trip tolls. In one case, a traveler got a notice 5 years after the trip:

https://community.ricksteves.com/travel-forum/italy/traffic-violation-new-scam

Another:

https://community.ricksteves.com/travel-forum/italy/rental-car-driving-fines

Another:

https://community.ricksteves.com/travel-forum/italy/italian-traffic-ticket-pay-it-or-no

For others, they got tickets for hundreds, even thousands, of dollars.

The fantasy is that "we want to visit the countryside". Well, hire a driver for a day. This is all based on the delusion that Americans have of carefree European driving.

1) When you rent a car, the car sits on a paying basis for probably 80% of the trip.
2) For 2 persons, it's far cheaper to do the train.
3) European rules about "the magic cushion" where you exceed the speed limit but are not penalized are not the same as the USA. I know that in the USA, I can go 7-8 MPH over the limit and will not be ticketed. In Europe, it is more like 1-2 which gives you little room for error. Plus there are speed cameras all over, which are rare in the USA
4) When you get a ticket, you have returned to the USA, but your card is debited, and a fee is tacked on by the rental agency for the "favor" of dunning you.
5) You will have the fun of not knowing where you are going, and where you will be parking.
6) Since this is your 30th anniversary, you got married in 1990. That puts you at 55-60. How much hassle do you want?

The only time I consider driving these days is if the party is 4 or more.

Take the train. Go to the TI and ask to rent a driver for a day.

4 days in Rome, 4 days in Sorrento, 3 days in Venice, which is 11 days.
Then the rest in Rome again.... That must be a second visit to Rome of
10 days from where you will take 2 day trips, one to Florence and one
to Pisa?

Echoing Nigel, I'm now reading your itinerary as he's laid it out above. Ouch. IMHO, Florence is not really a day trip from Rome! There's much too much to cover in that one in just a single day! Also, Pisa is an easy day trip from Florence (abt. an hour by rail) but not really from Rome: it's about 3 hours each way by rail from Rome so approx. 6 hours of sitting. Florence from Rome is a little over 90 minutes each way.

Much as I love Rome, I'd cut time from that one and add it to Florence, at least 5 days if wanting to take a day trip or two.

We did Venice, Florence, Rome, Sorrento, with 2 trips into Tuscany and NEVER rented a car. Flew into Venice for 4 nights, Train to Florence for 5 nights, did 2 day trip tours into Tuscany with WalkAbout Florence - we loved them - we did the Chianti Wine & Food Safari and the Best of Tuscany (which stopped at Pisa and Sienna and San G), Train to Rome for 4 nights, train to Sorrento for 4 nights with a day trip with RS sharedtours.com to Amalfi Coast and a day trip to Herculaneum (which we like better than Pompeii) - we followed the RS book on how to do Herculaneum from Sorrento and it was PERFECT. Then train to Naples to fly home. We wouldn't change a thing. PM me if you have questions.

I, too, am concerned about the apparent planned day-trips to Florence and Pisa from Rome. If you simply cannot shift some nights from Rome to Florence, I'll concede that for many people Florence is enough of a must-see that doing it as a day-trip from Rome is better than not seeing it at all. However, know going in that you will be sitting on trains for at least 3 hours and 12 minutes as you make that round-trip. And your hotel in Rome is unlikely to be right near Termini Station, so your total travel time will probably be closer to 4 hours--possibly more. And you may end up taking that trip twice, because Florence has a lot of things to see and enjoy.

I would definitely discourage day-tripping all the way from Rome to Pisa. That will involve 5 hours and 40 minutes sitting on trains, plus the extra time to get to and from Termini Station in Rome. Although Italian rail fares are reasonable, it appears that (even buying non-refundable tickets way in advance) you'll be paying at least $45 per person for the privilege of making that trip to see--as I recall--a couple of buildings and a large green lawn.

If you really are going to have so much time in Rome, I recommend some additional research on closer potential day-trips. Orvieto is lovely and has enough to more than fill one day. There are many more possibilities.

hey hey anaroy68
have you looked at multicity flights, into one city out of another, into venice out of rome. then you are not back tracking and the time involved with train travel? i would not get rail pass. look at seat61.com that has info about train travel. buy tickets from point A to point B. you can look at rome2rio.com to check city to city and what towns are in between but do not book anything on the site. i've used trainline.com, or trenitalia/italo.com for prices and times. trainline may charge a fee but not much, compare the websites. that $900 seems so outrageous like nigel mentioned.
travel is easier by train instead of a car. look at all the signs within towns/cities, ZTL's, parking outside of city centers and the cost. you don't want a traffic ticket after you get back home that could cost you many euros! if you are renting a car, make sure you get an IDP (international driving permit) at AAA for about $25 and 2 passport photos, a requirement with many car rental agencies or if you do get stopped by the italian police. the available parking spots will be a long walk away from center.
how many days are you staying in your cities you want, may not want an apartment with airbnb. if longer than 4 days i would. look at refundable/cancellation policies, where to recieve keys, early checkin/luggage storage, which is usually after 2pm. changing hotels/apts usually takes half a day, getting to new place, acclimation to area, what does place have in case you need to shop for necessities and how close is a store. what is the cost for transfers to airport, fuel is not cheap and if their are toll roads to pay. hop on a train and relax. hire a driver/tour to take you around. what countrysides do you want to see, getting lost is always a thought with stress. let someone who knows area show you and inform you of area.
don't know what covid will bring to anyone next year, keep informed of do's and don'ts, do they charge more since they have lost money during it or do they reduce rates just happy to have tourists, who knows. so many people are looking to travel and you want to travel during busy summer season, read that what activities/sites you will have to prebook. no walking up like before. all the cities you want to go to and see are the same places other tourists want to see and do. you are spending lots of time on a train/car, changing places and the time it takes, count nights instead of days.
don't wanna be a delores downer but please research and ask questions here before booking things. the posters here will give you good bad and ugly to help you have a great vacation with as little stress as possible.
aloha

We will be there for 21 days 4 in Rome, then 4 in Sorrento, 3 in Venice and the rest in Rome where we will drive or train ride to Florence and Pisa on 2 days and possibly go somewhere else to visit

Are you able to re-book your rooms for different dates? If so, plan to spend 2 -3-4 nights in Florence to see it and Pisa and anything else in the area that may interest you. "Commuting" from Rome as day trips to Florence and Pisa is a fate I would wish only on the worst of my enemies

I see no benefit in having a rental car for your destinations

We did a similar itinerary in about 18 days back in 2009. We rented a car as we like to be on our own time and be free to drive off to a place that looks interesting that we hadn’t known about when planning our trip. We get up early so that we can see every bit of what we came to see. We are probably 15-20 years older than you.

We flew into Milan and drove to the town across from Venice where we parked our car. We stayed 3 nights in Venice.

We then got up early and drove to Pisa through beautiful Italian countryside. We spent 2 to 3 hours at most in Pisa and then drove on to Luca and spent the rest of the day there. At the end of that day we drove into Florence. Our hotel was in the restricted zone but the hotel contacted the powers that be and we were allowed to drive our car into the hotel parking lot where it stayed until we drove out with no fees. We spent 4 nights in Florence.

The day we drove out we spent the entire day on the Chianti wine trail going through sweet quaint towns along the way and stopped at the many little towns and wineries that looked interesting. We also stopped at the lovely hill town of San Gimignano a few hours before ending up in Siena around dinner time. We spent 2 nights in Siena.

We got up very early on the day we left and drove through Tuscany on our way to Sorrento and eventually Positano. We stopped in Montalchino, Pienza, Montepulchiano and Orvieto along the way. We spent 4 nights in the Positano area.

The next day we got up early and drove to Pompeii and spent most of the day there before driving into Rome. We then dropped the car off at Hertz. We spent 5 nights In Rome. We flew out of Rome.

There are so many ways to travel. You have to decide what works best for you and your budget. While some of the time our rental car was parked and not being used we like having one so that we can be free to go additional places along the way that look interesting that we hadn’t known about until we saw it. We can stay longer in places we like and shorter in places we thought we would like but didn’t. We also try to never back track. We backtracked once on this trip by going past (but not into Rome) on our way to Positano. Having a rental works for us because we can find hotels that we like that don’t have to be near a train station. We don’t have to be on a schedule to get to catch a train and we don’t have to call a cab or figure out a bus route to get to a train station. We have traveled extensively in many countries using rental cars... always with GPS and have not run into any real problems getting lost. A few times we got a little off track but we also found places then that we hadn’t known about that were definitely worthy of being a little lost!!! We carry a map with us though just in case. And we found Italians will turn themselves inside out to try and help you in any way they can.

We also use Rick Steves books as our travel bible to book hotels, restaurants, how to avoid lines, as our travel guide in churches, museums, town and city tours etc. We especially like his recommendations for what to do/see given how many days you have in each area which saves a lot of planning time.

Take what you like from all the suggestions here and have a wonderful 30th anniversary trip!!!

@Ana Wed9PM

And now for something completely different.

When you are in Roma select a warm evening with a gentle breeze from the direction of the Apennines and take your beloved with you to the Spanish Steps and savour the sun as it sets. My wife and I did this late September 2010. My brother in law purchased a local pizza in the piazza and together with a super Tuscan wine I procured from Steve’s recommended wine shop in San Gimignano we ate, drank, and watched the sun go down. I believe the local council banned eating and drinking the following day. So do not try the eating and drinking bit. I think the water from the prow of Bernini’s boat fountain is alright to drink. I know you can wash your hands there.

Then slowly meander hand in hand, preferably your husband’s hand, through the streets to the Fountain of Trevi and let yourselves become absorbed in the atmosphere. Walk to the front of the fountain turn with your back to the water and throw a €2 coin over your head into the water (do not be cheap it goes to good cause) hoping you will return to the fountain. Has not worked for me yet, maybe 2022. Encourage your husband to buy you a rose from one of the young girls offering them. Make him a cheeky offer he cannot refuse, to be delivered later. Sit on the steps and relax. You may find yourself reminiscing about your wedding day and those wonderful dopamine induced feelings that took over your whole being at that time, during your courtship and early marriage years. Perhaps they have comeback. At this point, in 2010, my wife gave me a sharp elbow in the ribs. I had glazed over playing in my mind the scene from La Dolce Vita movie where the voluptuous Anita Ekberg frolicked in the water. Later that evening she reminded me, in a raunchy way, that I should have been reminiscing about her body from an earlier era.

Yes, setbacks will happen during your trip, but the memorable good times will completely overshadow them.

Congratulations on 29 years, bloody well done. Here is to 30 next year and another 30 more.

Cheers and stay safe.
Ron

Ron, you are indeed a Devil!

Your post definitely made me smile at the beginning of what is going to be a tough day.

thank you to all. our anniversary was 07/21/2020 and this trip was to celebrate it. But postponing just means we'll have an even better time when we do go. we are arriving in Rome first for 3 days, then off to Sorrento for 5 days, venice for 3 and the other 10 days in Rome to finish off our trip where we will do the normal "tourist" tours but we are also visiting some churches and several oddity stores. also we cannot miss the Papal Audience. I wish we could stay the whole month. Which we are seriously considering it

Longer is always better!