Looking for advice on itinerary

Think hard about flying home from Venice - flights heading west often leave early in the morning. You might want to fly into Venice and out of Rome.
Train from Cinque Terre to Venice is about five hours and twenty minutes. Driving is four hours and a bit, plus the time taken to hire and dehire the car, so train would be better and much more relaxing. Plus the train deposits you in Venice right on the Grand Canal.

include Pisa & Verona

My first suggestion is to reverse the order, starting in Venice and departing from Rome. There are two main reasons. First, it's easy to get to the Rome airport at any time of day or night; many flights leave Venice very early and it can be either difficult and time-consuming or very expensive to get to the airport for an early flight. Second, Rome is a big, bustling city with major sights. Getting oriented and trying to absorb the significance is more difficult when you're jetlagged and sleep-deprived. Venice, on the other hand, is slow and quiet with no major sights. It's a great place to relax and soak up the atmosphere while you adjust.

It's possible to visit Pompeii on the way to Sorrento. You can store luggage on site. That being said, it's a fairly unrelaxing day. Rome hotel to train, train to Naples, train to Pompeii, visit 2-4 hours (some spend much longer), train to Sorrento, get to hotel. If you are packing light, it shouldn't be too taxing. Otherwise, all that changing with luggage - ugh. Sorrento is perched on a cliff. The train/bus station is a few minutes' walk uphill from the center. The ferries are way down at the shore. That means up and down a lot of stairs, or taking the €2 elevator (maybe waiting in line), or a bus (time-consuming) or an expensive taxi. For your plan, Sorrento is the best base.

Going from Sorrento to San Gimignano: hotel > train to Naples > train to Florence > bus to SG > hotel. Are you packing light? Others can chime in on the merits of staying in SG compared to other Tuscan towns. Have you looked at bus schedules to see frequency for your day trips?

Overall, I don't see anything very relaxing in this plan, with travel every day when you include the full day excursions. If your style is "always on the go" that's fine. Also, with 3 and 4 night stays, you do have the option to just stay put for a day or two by abandoning some of the optional day trips.

Oh yeah - the Dolomites are too far for a day trip.

Posted above : Venice, on the other hand, is slow and quiet with no major sights. It's a great place to relax and soak up the atmosphere while you adjust.

I think I might disagree with the “no major sights” part of that comment.

You have 14 full days to play with---Day one you will still be jet lagged. I would skip Cinque Terre and add a night to Rome or Venice and one night to the Amalfi Coast. If your wife likes a bit more relaxed itinerary she will love you even more.

As far as the flow--I haven't been to Venice yet---getting ready for our 4th trip to Italy---everyone says to end in Rome instead of Venice? Because of flight times? So maybe reverse your itinerary starting in Venice, Tuscany/Florence, Amalfi and ending in Rome.

As far as where to sleep in Amalfi we stayed in Ravella for one trip and Positano for our last. My vote is definitely to sleep in one of those smaller towns or even in the town of Amalfi. If this is your first and only trip it's not to be missed.

Sounds like a great trip! Anywhere you end up will be lovely!

Going from Sorrento to San Gimignano: hotel > train to Naples > train
to Florence > bus to SG > hotel. Are you packing light? Others can
chime in on the merits of staying in SG compared to other Tuscan
towns. Have you looked at bus schedules to see frequency for your day
trips?

I'll question S.G. as a base for day trips as well unless you'll have a car? Where else in Tuscany do you plan to go from there?

Day 10 - Day trip to Florence, sleep in SG...

Arg. Florence, in my mind, is not a day trip: it's a fascinating small city requiring at least 3 nights/2 full days to explore properly. It also makes a good base for exploring some smaller towns in the region as it's a major transport hub. Travel between the CT and Sorrento would be easier to/from there. I know, I know, you would rather do countryside but, well, your wife may not be happy doing this one as a day trip: WAY too much there to try and do in a day.

I am worried that I am trying to pack too much into this trip.

I would have to say that this isn't a 'relaxing' itinerary by any stretch of the word: you have scheduled a LOT of travel from Day 5 - Day 14 (yes, day trips count as travel). It's difficult to critique itineraries for someone else as we all have different travel styles and interests but IMHO, it's definitely more than I'd want to take on.

As you will get a lot of water-view stuff in Sorrento/A.C., I'd skip the C.T. and use those 2 nights elsewhere. You might even consider skipping Sorrento/A.C because THAT one is really your outlier - sort of a pain to get to/from and requires backtracking. - and divide those nights between Rome, the C.T. and Florence/Tuscany.

Three comments/ideas:

1. I would skip CT both because it is crowded and because you can use the days somewhere else. I think you are traveling too much and will regret it.

2. We stayed in Amalfi town on the Amalfi coast and I would not have wanted to just do a day trip from Sorrento. But it all depends what you want to do. We started in Naples but if I were starting in Rome (or Florence if you reverse itinerary like some have suggested) I would take train to Salerno and then a ferry to Amalfi town. You could stay there 3 nights and use bus and ferry to get around the coast. Ravello is a charming day trip (about 1/2 hour bus ride) from Amalfi as is Positano (I would take the ferry here). If you can skip Sorrento (I liked Amalfi coast better and used Sorrento as base to get to Pompeii), you could go back to Salerno and take train from there. Much more efficient.

3. You can't easily get to San Gimignano and surrounding area by public transportation. You are going to have to go to Florence from Amalfi Coast (or Venice if reverse itinerary) and then rent a car and drive there. You might consider staying in Florence and taking day trips from there, renting a car for the days necessary. You can go, for example, easily by bus to Sienna which we did many years ago.

Thanks very much for all of your comments! They are very helpful. Here are some of my replies to your comments.

1) I live in Seattle and I have found that if I fly out of Vancouver, BC rather than Seattle, I can save nearly $500 per person on airfare. Even with factoring in travel to Vancouver and perhaps a couple of extra hotel nights, that is a significant savings. Plus, the flights to Vancouver from either Rome or Venice leave around noon rather than 6AM, lol.

2) Florence. Yes, I know that a single day trip into Florence is not going to do it justice however, although a couple of my friends would kill me for saying this, Florence is the least interesting location on my itinerary, but I feel like I should at least see the highlights. I will ponder this a little more.

3) Rome to Sorrento doesn't seem to be too bad. Highspeed train to Naples, taxi to the Naples Ferry Terminal and then Ferry to Sorrento. I have a hotel picked out that is not far from the Ferry terminal. Alternatively, I am considering hiring a car w/guide that would take us to Pompeii along the way to Sorrento. A little pricey, but it might be worth it for safety reasons as well, as I have heard bad things about storing luggage at Pompeii. Once in Sorrento, I was planning to take the bus and/or ferry to visit the coastal towns. Rome to Amalfi might be a different prospect. I will have to ponder this a little more as well.

4) San Gimignano as a base - I do plan to pick up a car in Florence for our time in Tuscany. I have heard that San Gimignano gets very crowded during the day and that it is best after the tour busses have left. For that reason, I am looking at a Farmhouse stay that is within a 20 minute walk from SG, but not in SG. If I have a car, does that change the opinion of those that think that SG is not the best base for touring Tuscany? If it isn't the best place, what is? I haven't decided all that we want to see in Tuscany yet, but just planned to head out in different directions from SG each day.

5) Dolomites - Thanks, I wondered if that might be too far, although I would dearly love to see them in person.

Thanks again! Much appreciated.

I would skip Cinque Terre and get that fix on the Amalfi coast instead. If you are going to see Pompeii en route with a driver, then you can skip Sorrento and stay on the coast instead. That complicates the Procida day trip, but up you you!
I choose villages and country over big cities--if you don't feel drawn to Florence, I see no reason to go.

We took the ferry from Naples to sorrento. The hotel we stayed in Naples was closer to ferry dock than train station and we mistakenly thought it would be a very pleasant event. It is just transportation. It is a fast ferry and you are inside like an airplane and there is no view. The windows are steamed up so you can’t see a thing.

You arrive on the dock which is below the town of Sorrento. If you are indeed staying close to ferry dock (I recall some hotels), you then need to take a bus or walk a very steep road up, you want to see the town or take a bus or train from sorrento. There also may be an elevator. We took a bus as it seemed like the simplest option with luggage.

We stayed in town close to train station. I would not have wanted to stay near the ferry.

Thanks Val and Beth,

Yes, you are right, Procida could be an issue if we stayed on the coast. I will have to check with the car hire I was looking at to see if they would take us out to one of the coastal towns.

Beth, what are your objections to staying near the ferry? Is it the fact that we would have to climb to get into the city? Or views? Or Noise? Or?

Thanks again for your comments. My itinerary is still very much in development.

At a glance, you’re packing in a lot. I think taking CT off the table is appropriate, and I’d probably put those days to Amalfi Coast because you can’t have too much time there. You’ll want more time in the Amalfi Coast area, not only because it’s incredibly beautiful but also because it EATS time. Getting anywhere takes more time than you think.

This is all about fine tuning your priorities. Sorrento is just fine, a lovely enough place but it’s real attraction is it’s sightseeing convenience. If your plans were focused on Pompeii day trip, Capri day trip, and an AC day trip then it makes sense. However, I don’t get the sense you’re super interested in that. I would find a place on the Amalfi Coast itself and play it by ear. Make it a relaxing time. Perhaps a car hire to make a day trip to Pompeii from here makes sense for you. It will be expensive, but may be a worthy splurge.

I also think Florence needs a couple days to experience its art treasures. I also did not find the city all that enjoyable (it’s a minority opinion.) So, if it doesn’t interest you... skip it! This is your trip and there’s no rules saying what you have to see. Maybe make this leg a low key exploration of Tuscan towns? With that, maybe skip Pisa too!

Haha, it's true, but I have a couple of friends that would be horrified if I left Florence completely off the itinerary.

Lot's to think about. Thanks!

We did stay in Florence during our trip to Italy, but didn't go to the Uffizi Gallery. Several people said things like 'but that's a bucket list item', and I replied 'not our bucket'. It's your trip and you and your wife know better what will be of interest to you. Good thing about day trips is that if you are tired or enjoying where you are, you don't have to go that day!

Not our bucket. I will have to remember that!

Hi Mocks.

I am so happy to find your post. I am also planning a 17 night stay April 2020 arriving Rome and leaving from Venice, newly retired couple.. 58

leaving from Montreal. you seem to have done a quite a bit of research. I am just in the beginning stage. if you want to share your final itinerary I would greatly appreciate..

Louise

As far as location by the ferry goes, I recall that there were just a few hotels there but I may be wrong. I honestly was a bit surprised to be docking not in the town but below the town. Consequently, I was quite focused on figuring out how to get to the town above.

It just doesn't seem like it would have been a good location to do anything but stay at the hotel. It would seem like you would need to get up a very steep road to do anything. But I did not stay there. I deliberately prioritized convenience to trains and buses.

And really, you just have to figure out what you want to see. Posters like me can help because we can tell you our surprises and what we did right and wrong. I did not have the benefit of this board when I planned my trip to the Amalfi Coast and made some mistakes. I have since made two trips (one to Greece and the other to the UK) with the help of this board and there is very little I would have changed.

And don't think there is anything you have to see. I am just planning to go to Venice next year almost 30 years after I first went to Italy. And honestly, Florence was crowded 30 years ago when I went so if it isn't important to you, I would not go. You can't see everything so see what you want to see most.

Thanks Beth. That is VERY good advice!

We took the train from Rome to Naples and I hired a driver to take us to Positano. We decided to stay there for that leg of our trip. On our way back I hired another driver to bring us back to Naples and we stopped at Herculean Archeological site (we didn't have time for Pompeii) but if we had time for Pompeii we would have done that if we could. And we grabbed the train after Heruclean back to Rome for our flight out the following day. We loved Positano. We did a day trip to Capri and another day trip to Amalfi and Ravello.

we stopped at Herculean Archeological site

ownedby3, I think you meant Herculaneum.

Forgot to mention...

I have heard bad things about storing luggage at Pompeii.

I don't believe I've read of any problems checking luggage at the scavi or Circumvesuviana train staton (lower level).

I have been to Italy twice and would suggest to experience Florence at least 2 nights. Its a beautiful city and has much to offer in regards to art and landscape. I was robbed on the street in Rome so I am not too fond but the Vatican is a must see. I also stayed in SG for several days its ok but nothing to write home about. The drive Val'd' orcia is a must see. We also rented a car and it was a stunning place to drive and see. I also recommend not to pack all the days < I did as well > because its tiring and its so rushed. Sienna is nice as well. Pisa was ok but really not much except the tower which we booked in advance to climb. I advise to hide your money well. Pickpocket are all around and they are very clever. Book all your tours in advance as well. We booked many tours in all different cities all recommended by this site. We will be in Germany in December and are flying while there for a few days to Italy arrive in Florence and drive to Assisi which will be our home base. Have fun you will have a blast This site has a wealth of information.

Florence is the least interesting location on my itinerary, but I feel
like I should at least see the highlights. I will ponder this a little
more.

The reason I'd give this one more time is that one of the best ways I know to get a lousy impression of it (and Rome too, for that matter) is to try to 'do' it in a hurry/as a day trip. You'll end up smack in the middle of the day-tripping hordes and everyone else trying to get a look at those highlights. I notice that people who've commented about their dislike of either city because of the the crowds (and the heat during high season) often were scrambling to stuff the Greatest Hits into a day or two. Both cities are more easily digested if given some space in which to enjoy the quieter hours (early and late) and less-visited but thoroughly interesting attractions

Otherwise, yes, maybe best to skip it altogether versus have a negative experience, especially if you're not keen on it to begin with. That's OK.

We just returned from 14+ days in Italy w/our 3 children (ages 18, 15, 11). We flew into Venice, I was very glad we started there as the water makes it a bit more relaxing and "vacation-y" and there aren't as many must-see sites. We then spent 2 nights in Florence which we all loved dearly. Then 4 nights in Rome and 4 nights on AC. Glad we did that order as Rome has such energy and so many must-sees -- our jet lag was gone by then so we could really get around w/out fatigue. From there took train to Casserta (family connection), rented car there, drove to Pompeii where we did RS audio tour for about 2 hours, then drove the rest of the way to our wonderful AirBnB in Furore, tiny town which is b/t Positano and Amalfi town. The prettier side of the coast is not on the Sorrento side. Yes you can do day trips but it helped being able to hop on a Sita bus for a quick 20 minute drive to Amalfi town to catch ferry to Positano, or catch our boat for tour, or catch bus up to Ravello (recommend). We just left car parked most of the time on AC.

Do visit Pompeii.
The Dolomites are too far for a day trip from Venice. For an Alpine feel, you could take a train from Venice to the town of Bassano de Grappa as a day trip. But you really do not have enough time in Venice for a day trip.
I would never stay in San Gimignano. Choose another Tuscan location that is not so touristed.
We have stayed in several of the Chianti towns, Siena, Cortona and Lucca. I recommend being in or near Chianti region( Radda, Castellina, Panzano, Greve, Siena) or in or near Montalcino or Pienza. Florence is in Tuscany.

I think you should at the very least stay 1 night in Florence because going from San Gimignano to Florence and not staying there for at the night, you will not have time to see Florence, specially taking account of the bus/train schedule for the day. It is more logical to go the other way round as SG is a very very small town, I would call it a village
Also where in Tuscany do you do your day trips. Florence is a very nice starting point for visiting Tuscany and Siena not very far behind, depending which part of Tuscany, I would choose one or the other to stay. Venice to Florence by fast train takes a little more than 2 hours. If you want to go to San Gimignano from Venice, it takes 4 -5 hours to Poggibonsi, then you have a 20 minutes ride by bus to San Gimignano and you might have also to wait for another 20 min in Poggibonsi. Also you might have to change train several times before getting to Poggibonsi. If you choose to stay in Siena, it will take you 4 hours with a change in Florence, however connections between Siena and other Tuscan towns are better than from San Gimignano.

Also Florence is a middle size town and Siena a small town, big cities in Italy are Milan, Rome, Turin ( though smaller than the two first mentioned). Other cities in Italy are medium to small sized specially considering American standard.
I live in Florence part of the year and I can assure you, distances are very small and easily walkable. Florence is rather flat for its centre, Siena is hilly.
I also do not understand why you say at the age of 60, that this will be your only trip to Italy. You might have another 30 years to live ...!
Were I at your place, I would divide my trip in 3:
1) Venice (2 days) Garda Lake or Lake Maggiore -(3 days)
Dolomites ( 3 days)

2) Tuscany and Umbria
Florence (3 days)
Siena (2 days)
Lucca (1-2 days)
Montepulciano (day trip)
San Gimignano ( day trip)
Toiano ( day trip leaving early)
Arezzo ( day trip)
Assisi (1-2 days)
Perugia (2 days)
Gubbio (2 days)

3) Rome - 5 days
Naples - 3 days
Amalfi, Procida, Capri, Ischia - 6 days

Thank you Francoise,

I say that I will likely not be back because I have not to this point been much of a world traveler and there are many many places in the world that I want to visit, so at the very least, another Italy visit may not come for quite awhile.

Thanks for your suggestions!

I am the same age as you and I would think about this trip differently. I traveled to Europe several times before having children and now my husband and I are starting to travel again as our children are grown and we have more money. We are planning a trip to Italy for next May. We did go to Florence, Sienna, and Rome as part of a multi country trip 35 years ago and spent 10 days on the Amalfi Coast two years ago. We went to Greece last year and the UK this year each for the first time.

You sound like you are in the same position as we are--maybe more places you want to see than there are years to go to see them. Still, I plan as though I will go back even though I may never. I think this mind set is important because it keeps you from trying to see everything which means you will enjoy little. One time we had annual passes to Disney. What turned out to be our last time on our pass was not planned that way; we thought we would go one more time but did not. In retrospect, we were glad we did not know as we did not try to see everything as we might have other wise.

If you are planning on traveling to other countries in the coming years, the truth is you could choose to go back to Italy. You may not (and I am certainly not saying you should) but that is different than you cannot.

Go where you want to go most at a pace that allows you to enjoy it. And keep open the possibility that you might come back.