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Need Help with Italy Itinerary- Planning a Trip to Italy

Need Help with Italy Itinerary- Planning a Trip to Italy

Dec 4th, 2019, 12:14 AM
Original Poster
Join Date: Apr 2003
Posts: 42
Need Help with Italy Itinerary- Planning a Trip to Italy

We will be traveling to Italy and plan to be there about a month.
We have been talking to people and doing some research but still need some help in figuring out some of the details.

Here is what we are thinking:

Milan (flying into and spending 3N with 2 full days of touring) taking the train down to the

Cinque Terre (3 nights or more ?). We heard it is a nightmare to drive in the Cinque Terre - so no car at this point. Do we pick up a car in La Spezia and then head to Lucca? But if we are heading to Florence I don't think we want a car there - dilemma?

We will need a car at some point in order to tour the surrounding areas of Siena, San Gimignano, and Montepulciano. We would like to do a cooking class while in the area..

Do we go to Florence first or San Gimignano? I don't believe a car would be a good idea in Florence (2 full days there). We want to see Lucca, Siena, San Gimignano, Montepulciano (and some of the surrounding area). Do we do this first and then head to Florence or vice versa? How much time in the surrounding area? Will we have enough time? Driving time? Suggestions are welcomed

From Florence we thought about taking the high speed train and heading to Naples bypassing Rome to see the Amalfi coast, Mt Vesuvius, Pompeii. We also have read and heard about issues with having a car. Many people have suggested to stay in Positano. We were thinking of using it for a base to the see the Amalfi coast area (4 days??). Suggestions are welcomed.

We have seen all the major attractions in Rome so we were thinking of bypassing it but was such a long time ago.

I realize there are more advantages to flying out of the same airport you flew into. Then there is the traveling time getting back to that airport. Should we fly out of Naples or take the high speed back to one of the major cities?????

Possibilities of what to see....

Thank you so much.

CherB is offline  
Dec 4th, 2019, 12:34 AM
Join Date: Jan 2008
Posts: 72,184
Any combination that works for you is the "right" combination.
This is what we did -
Flew into Florence and took a cab into the city. (Spend as many nights as you want).
Cab back to the train station to pick up a rental car.
Drove to Tuscany and stayed here for a week - LOVED it! Vacation Rentals in Tuscany Villa Le Torri,Holiday Apartments in Chianti,Tuscany
Spent that week driving around and exploring. Took 2 days of that week to drive to pick up the train (pre-paid garage) to the CT. One overnight there. Took a small boat tour that we LOVED. On the way back from the CT, stopped in Pisa. A fabulous 2 days, again, not checking out of the villa.
Drove back to Florence to return the car and take the train to Venice.
Flew from Venice to Naples. Took the ferry from Naples to Capri. LOVED Capri.
Took the ferry over to Sorrento. Had a private driver pick us up for the day around the Amalfi coast. Very glad I was not driving those very curvy roads. At the end of the day, he took us to our hotel in Naples. Highly recommend the private driver. Let me know if you want his contact info.
Train from Naples to Rome.
Flight out of Rome.
It was a wonderful trip.
But again, any combination that works for you is great. We flew in and out of different cities. We rented a car for the Tuscan countryside. Took trains and flights between the cities.
Enjoy your planning!
starrs is offline  
Dec 4th, 2019, 02:50 AM
Join Date: Feb 2003
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There is no need to rent a car before you leave Florence. You can easily train between the Cinque Terre and Lucca. Train between Lucca and Florence then get your car after Florence.
Dayle is offline  
Dec 4th, 2019, 03:08 AM
Join Date: Jun 2017
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Naples is a major city. You might have more flight options out of Rome or Milan but if you see a flight you like out of Naples why wouldn't you?
Traveler_Nick is online now  
Dec 4th, 2019, 05:23 AM
Join Date: Dec 2019
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You could solve one of your problems by visiting a region of Italy that is very close to Tuscany rather than transporting yourself all the way to the other end of the country. I recommend Umbria - some highlights are Orvieto, Perugia, Assisi, Civita di Bagnoregio but there are dozens of atmospheric and historic mountain towns worth visiting. You might be surprised how enjoyable it is to spend time in Italy without constantly being enveloped in a cloud of tourists moving from one internationally acclaimed attraction to the next.
zzlangerhans is offline  
Dec 4th, 2019, 06:14 AM
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When are you going? If possible, fly home from Naples. The airport is right in the edge of the city and very easy to get to.
Sassafrass is online now  
Dec 4th, 2019, 06:21 AM
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my general rules of thumb for flights is this:

1. i prefer non-stop over connection, even for an added price. So if you can fly non-stop into Milan and perhaps out of Rome then that may be a good option. Getting from Naples to Rome airport is not hard, but it will take a few hours hotel to gate. You could do that the morning of your departure, or if you have an early departure or you are risk averse, get to Rome the night before your flight and stay near the train station for a quick 30min ride to the airport that morning.
2. if you cant to #1, then if you can fly non-stop to then connect at a European hub (frankfurt, munich, amsterdam, paris, etc) then open jaw/multi city flight into Milan out of Naples would be best.
3. If you can mix non-stop into milan then 1-connection out of Naples for a reasonable price, then go for it.
J62 is offline  
Dec 4th, 2019, 06:28 AM
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If you have a month to travel, what is the overall plan for your trip? So far, you've identified about 2 weeks worth of travel. I would first plot an overall plan, trying to determine what areas you are interested in seeing and then figure out where and when you might want a car. When will you be traveling?

My husband and I returned from a 5-week trip to Italy a little over a month ago. We flew into Milan and out of Rome. We've been to Italy before, but went to a few places in central and northern Italy we hadn't been to before, then traveled to Naples and the Amalfi Coast area, ending in Rome. Here's what we did:

Arrive Milan - train to Vicenza (4); train to Bologna (4). Picked up car, drove to Spello (3); drove to Orvieto (1), dropped off car. Train to Naples (4). Ferry to Capri (2). Ferry to Sorrento (4). Bus to Atrani (3). Ferry to Salerno, pick up car (2nd time), drove to Paestum (2). Drove back to Paestum, returned car, then train back to Rome (6). Fly home from Rome.

How I planned: my initial focus was on the Amalfi coast. Then I added the stops in Vicenza (to see the Palladio's work); then Bologna. I had always wanted a few nights in the Umbrian region, so added in a few nights in Spello. For this, I knew we'd be better off with a car. I looked for a place where I could drop the car and still get a direct train to Naples -- Orvieto fit the bill perfectly. And so, one night there! After that, there was no need for a car until we visited Paestum. So, all in all, we rented a car twice - 3 days from Bologna to Orvieto, and 2 days r/t from Salerno. Both were easy, but it wasn't until I got an overall plan that I figured out where I needed the car.

I found traveling between regions - north to south! - not nearly as difficult as it sounds, but I plotted it in such a way that the transitions worked very smoothly. I know it sounds crazy going from Vicenza to Paestum, but it worked well and it wasn't hectic - then again, we had 5 weeks. But I still eliminated places I'd love to see, so there's another trip to Italy sometime in the future!

In your trip so far, it looks like the only place you'll want a car is in Tuscany, so I would also go to Florence first, then pick up a car. I wouldn't want a car on the Amalfi coast. You could get a driver or even take buses for day trips, which is what we did. If you stay in Naples or Sorrento, the local train, the Circumvesiana, is good for travel to Pompeii and other archeological sites. We didn't stay in Positano so I can't speak to that.

Another small point - as Lucca is located between La Spezia and Florence, you might want to consider taking the train there and then on to Florence, so you don't need a car yet.
progol is offline  
Dec 4th, 2019, 08:15 AM
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Cher, you have to tell us which month, please?
bilboburgler is online now  
Dec 4th, 2019, 08:20 AM
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You have left out probably the most important piece of information - WHEN are you traveling?

It's kind of funny to read that it's a "nightmare" to drive in Le Cinque Terre because it's practically IMPOSSIBLE to drive there. I think you need a map.

I love everything that zzlangerhans said - my idea of a trip to Italy, and I've made many of them.
StCirq is offline  
Dec 4th, 2019, 09:44 AM
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I also buy into the idea of avoiding the crowds and just visiting beautiful ancient city centres and lovely countryside without the masses. It is how I do Italy.
bilboburgler is online now  
Dec 6th, 2019, 12:18 PM
Original Poster
Join Date: Apr 2003
Posts: 42
Need Help with Italy Itinerary- Planning a Trip to Italy

I'm sorry I couldn't post sooner - too much going on with an upcoming birthday and Christmas. Thank you for all the comments.
We hope to leave at the end of April or beginning of May. I have been doing a lot of research (Fodor's & Rick Steves). We don't have flights yet but hope to accomplish that today.We were looking at flight arrangements a couple of weeks ago, the price was not so bad. The price jumped a lot in the last couple of days. This may affect our timing of eitther leaving earlier or later than expected. Since we are both retired, we usually adjust our schedule either way. The overall plan has changed slightly. The main goal for the trip was to go the Cinque Terre (M wanted to go there) and the Amalfi coast (opposite ends). Here is what we decided late last night. Question is do we go to Florence before the Cinque Terre???? We have decided not to do Lucca. Before we added Venice getting to the Cinque Terre wasn't so difficult.

Milan (fly into + 2 days)
Venice (2-4 days)
Cinque Terre (2-3 days)
Florence (2-3 days)
Tuscan area (approx. 1 week driving around - Siena, Montepuliciano, etc) still working on this) Where to drop off car????
Naples area (including Naples, Capri for 1-1/2 days, Positano [hope to stay there], find a tour giuide for a coastal drive, Pompeii, mt vesuvius - not sure of rest)
Naples (fly out of)

Any suggestions greatly appreciated. Thank you

CherB is offline  
Dec 6th, 2019, 01:05 PM
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<<Tuscan area (approx. 1 week driving around - Siena, Montepuliciano, etc) still working on this) Where to drop off car????>>

The easiest would be to return the car to Florence and get a direct train to Naples from there. The trip is between 2 1/2 and 3 hours.

We took a train from Orvieto as we were in Umbria, and it was a bit longer, but still direct.

The itinerary looks much better so far.. How long are you planning to stay in Naples and the Amalfi Coast? By the way, we loved Naples and encourage people to visit the city before going on to the coast.
progol is offline  
Dec 6th, 2019, 04:01 PM
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Following on from what progol says it looks like your best bet would be to rent a car either in La Spezia or Lucca, then tour Tuscany, return your car to somewhere convenient for Florence [eg Pisa airport] then get the train to Florence, and after ? days there, get the train to Naples. If you are flying out of Naples I would put it at the end of the trip.
annhig is offline  
Dec 6th, 2019, 08:54 PM
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I had typed up a post and before I knew it - it was gone - not sure what I had done!!! Sigh!!!

Our flights were booked today and which changed our plans slightly. We are leaving mid-April flying into Milan and flying out the third week in May from Rome. The flight was actually cheaper with 2 additional days added on. We have added on Venice and have taken out Lucca. We will be there about 5 weeks (you lose about 2 days at the beginning and at the end of your trip and some traveling days as you move around).

We are planning to take the train to Milan→ Venice→ Florence→ Cinque Terre→La Spezia (car rental) →Tuscany area (approximately 1 week plus stay) - starting in San Gimignano & Voltara→Siena→ then stay somewhere near Piezna or Montepuliciano and then for the last day or two drive down to Orvieto spend the night and return the car. Take the train from Orvieto to Rome and then high speed train from Rome to Naples (approximately 1 week stay in the area) - we want to visit Naples, Sorrento, stay in Positano, Capri (1-1/2 days stay), Amalfi coast drive/tour, Mt Vesuvius, Pompeii and return to Rome the night before our flight or a day or two earlier.

Milan (3N, 2 days) We have reservations for the first 3 Nights in Milan but no where else yet.
Venice (3N, 2 days)
Florence (2-3 days) Would you recommend an extra day here?
Cinque Terre (3 days) Base either in Monterosso or Vernazza. Train or private driver to La Spezia to rent car (its the luggage thing!).
Tuscany area (approximately 1 week + - still working out details (San Gimignano & Voltara (1-1/2 days), Siena (1N) then drive to stay somewhere near Piezna or Montepuliciano area to stay the rest of the week.
Naples/Amalfi coast area (approximately 1 week stay

Any suggestions would be greatly appreciated. I want to thank everyone for their comments and suggestions.
Thank you.


Last edited by CherB; Dec 6th, 2019 at 09:17 PM.
CherB is offline  
Dec 8th, 2019, 06:56 AM
Join Date: Jan 2003
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Darn computer kicked me off after a very detailed response....

Congratulations on your tickets! It's great to have that in hand - you know the trip is real! Now comes the part that is both fun and hard -- zeroing in on your itinerary.

Overall, I think you've got a nice outline of a plan. I don't know your priorities, so it's hard to recommend where to stay specifically or for how long, but on our recent trip, most of our stops were 3-4 nights, which gave us enough time to settle into a place and explore. I would suggest that you choose no more than 2 bases in Tuscany (you've identified 3 for approximately 7 days), even consider staying in one of the lovely agriturismos in the region, as all of the places you mention are pleasant drives. I would recommend staying at least 1 night in Orvieto after dropping the car. It's a beautiful town and worth a visit.

We, too are retirees, and we recently made a 5-week trip to Italy (mid-September to mid/late October), with 2 weeks in the region of Naples and the Amalfi Coast. Our itinerary was, as follows: Naples (4); Capri (2); Sorrento (4); Atrani - a small town a short walk from Amalfi (2); and Paestum (2). So, in our experience, we found Naples and Sorrento to be the best for day trips to the Roman archeological sites; we visited Herculaneum & the Villa Oplontis from Naples, and we visited Pompeii from Sorrento. It's easy to tour from these towns as these sites are stops on the the commuter train, the Circumvesuviana. In fact, the connections from Naples seemed the easiest.

We really, really liked Naples a lot, and stayed in the lovely Hotel Piazza Bellini. I loved the hotel and recommend the terrace room - the room itself was small, though comfortable, but the terrace was wonderful! Now we are NYers, and enjoy cities, and given all the negatives about the city, we had no idea how we would feel. It's got a grittiness, true - but it also has a vibrancy and it reminded me of NYC! Don't miss the archeological museum there - one of the best museums of this type we've ever seen.

Now, the archeological sites...while Pompeii is usually on everyone's "must-see" list (and it was on mine), we actually preferred the smaller, better preserved town of Herculaneum, a wealthier town that was also destroyed by Mt Vesuvius, only slightly later than Pompeii. It is far less crowded, and the experience allowed us to have a more intimate connection to the town. Pompeii is large, and there are large crowds. I'm glad I saw it, but it was more work to explore and harder to "feel" it. Villa Oplontis is another small site worth visiting - a private villa in surprisingly good shape, with beautifully frescoed rooms. We went from Herculaneum toward the end of the day, and there were virtually no people there. It was a pleasure! And, to add, we were surprised, but at least along the Amalfi Coast, mid-October is still high season!

We opted to stay in Sorrento as it was a convenient location for touring and is, despite tourist crowds, a pleasant and lovely town to stay, with enough to do in town. I had intended to make a day trip to Positano, but had sprained my ankle so took the time here to rest a few days.

But we LOVED Atrani, a small town just a few minutes walk from Amalfi, and a world apart from the tourist crowds. This is a gem of a place to stay, and I can't tell you how happy we were that we didn't stay in one of the more popular towns along the coast. Beautiful, charming, and though there were tourists, it's a place that retains a strong local presence. It was the one place I left that tugged a bit at my heart. We did visit Amalfi (liked it a lot but was glad to get away!).

From our guest house terrace in Atrani

We did visit Capri, but while it was pleasant, we didn't love it. We were there over a weekend, and it was a bit grey and at least one of the days had some rain. Certainly, we saw beautiful vistas and had some pleasant experiences, but the day-trippers were overwhelming, and at times, we had to fight our way through crowds. I wasn't thrilled with that. I had also sprained my ankle while we were there, which also added to that feeling that we had to "fight" our way through crowds. If I had to cut any place out, it would've been Capri. FYI - it was easy to travel by ferry from Naples, and then we took the ferry to Amalfi, a very short distance from Atrani.

From Positano, it looks like the best way to get to Rome is to return to Naples, whether by train, shuttle or private car, and take the fast train from there. It doesn't look hard. As we had made a trip to Paestum, which is just off of the Amalfi Coast, we returned from Salerno, where we had picked up a car.
progol is offline  
Dec 8th, 2019, 09:27 AM
Join Date: Jul 2006
Posts: 17,417
The CT will depend on the weather but by your dates any mud etc should have dried out. The train from La Spezia is a great way to get into the towns and of course, you can follow the paths (those that are open) as you will. After CT from La Spezia, the whole of Tuscany opens out before you and there are so many spots to see it is hard to imagine anyone can pick any.

I found Pienza fully of tourists and tour coaches. Certainly worth visiting in the evening when it gets calmer but during the day can be overrun. I prefer Buonconvento down on the valley floor, but I also like Montepulciano (though I prefer the high town rather than the touristy bits down by the gate). Certainly you should be able to find either an agriturismo or a B&B in the area to suit your eating needs and a chance to meet with real Italians. Staying in apartments is also fine but you don't get to meet the locals the same way. There is also Chiusi for its museum (but not to stay) and San Quirico which is small but perfectly formed to stay.
bilboburgler is online now  
Dec 12th, 2019, 08:41 AM
Join Date: Mar 2007
Posts: 3,039
Milan (3N, 2 days) We have reservations for the first 3 Nights in Milan but no where else yet.
Venice (3N, 2 days)
Florence (2-3 days) Would you recommend an extra day here?
  • It depends on what you want to see/do--I'd fist add another day to Venice, which just seems like you need time to absorb and get past the crowds.
Cinque Terre (3 days) Base either in Monterosso or Vernazza. Train or private driver to La Spezia to rent car (its the luggage thing!).
  • The luggage comment caught my eye--I get that it's a full month, but I would not pack any more than I do for a 11 day trip and just do laundry a couple times. Having less to lug around can really make the trains easier and of course you need some down time--I find hanging laundry relaxing and rent places with washing machines, or pay for a laundry service if needed.
Tuscany area (approximately 1 week + - still working out details (San Gimignano & Voltara (1-1/2 days), Siena (1N) then drive to stay somewhere near Piezna or Montepuliciano area to stay the rest of the week.
  • You have SO many options here, just keep reading until the place calling you crystalizes. I'd dispense with the one-night stays and pick one or two bases.
Naples/Amalfi coast area (approximately 1 week stay
  • You might go from Rome to Salerno, then ferry to Positano, then finish in Naples, from which you can see Pompeii, etc.

Lucky you, enjoy!
yorkshire is offline  

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