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Italy in 20 days

I’m going to Italy for the art and architecture. I have a special fondness for Byzantine art so I want to do Palermo and Ravenna. I’m thinking of 3 nights each in Palermo Naples Milan Venice Florence Rome. Is lake Como worth a day trip in January? Is Sienna and/or Assisi worth more than a day trip? For Palermo I’ll actually stay in a nearby seaside village. I have 2 more nights I could spend somewhere or spend somewhere longer. If I don’t do Lake Como day trips I’ll probably spend only two nights in Milan. I could add days to Rome and do day trips to Assisi and Sienna.

Posted by
2685 posts

Sounds like a wonderful trip! Are you thinking of Ravenna as a day trip from Venice, or...? Since you are keen on Byzantine art, I'd suggest spending at least one night in Ravenna -- preferably two -- so you can have a full day or 1 - 1/2 days to soak up all there is to see there.

I think you're wise to go in the winter since this indoor art is your focus. When I went to Ravenna it was October and still very noisy with beach vacationers. Same for Siena, as its historic district is small and gets very congested with visitors during the warm months.

Posted by
4532 posts

I'd add those two more nights to Rome. I wouldn't add any more cities (or a mountain lake in January) to this already-busy itinerary. You're already spending five of your 20 days moving between cities.

Posted by
2773 posts

Have you traveled in Europe before? You've listed 10 different places that you want to see in 20 days ( I hope that is 20 nights in Italy and doesn't include your travel days there and back. That is a very aggressive plan. With so few days in each place you may have problems with regular closed days in some cities. Have you considered the amount of travel time required between places ( and I mean total time from hotel to hotel), and subtracted that from your available sightseeing time? You aren't giving yourself much time actually in each city. I'd recommend making a list of the things you want to see and do in each place, and figure out how much time you would realistically need to accomplish that. Then either reduce the number of places or add additional days. Lake Como would be one of the last places I would consider going in January.

Posted by
700 posts

Hi Sam, you have a nice itinerary. You might be able to fly non-stop from the US to Venice, but you’ll need to connect within Europe if flying out of Palermo or vice vs. I would fly into one place and out another called an open jaw.
First, buy Rick Steves’ IT and Sicily guidebooks. Not the Best of IT though because it’s older.
You can take a train from Venice to Ravenna, but it’ll require two connections taking 4h 30m.
From Ravenna you can take a train to Milan (two connections) that’ll take 4h 45m.
You can take a direct train from Milan to Varenna (Lake Como) that makes a good day trip (1h 15m). If the ferry is running, hop on and check out Bellagio too (15m) which you can see from Varenna.
Florence is a 2h direct train ride from Milan. You’ll want to buy your Uffizi Gallery tickets when you book your airfare and make your hotel reservations. This place sells out two months in advance.
Instead of sleeping in Siena, take a bus to Siena for the day (1h 15m).
In Florence you can take a 1h 45m direct train to Rome. I would sleep in the Trastevere neighborhood while in Rome, it’s very bohemian like, it is cool.
You can take a direct 2h 15m train from Rome to Assisi and sleep there two nights.
From Assisi you can take a direct train back to Rome. From Rome take the non-stop train to Naples (1h 15m) and try to stay in the Spanish Quarter so you’ll have a very authentic experience and eat fantastic food. You can then take an overnight train to Palermo (9h 45m). You’ll need to rent a cabin to sleep in, but you won’t waste time getting there.

Posted by
4439 posts

I second what CJean has written. I have been in Venice in January and some things were closed several days a week plus the recommended walking tours only ran one day a week. It was cold. Many restaurants etc close for January to get energised for Carnival in February.

Lake Como isn’t where I would head in January. Most of the places you have named can easily fill 4 nights, especially Venice, Florence and Rome, even without allowing travel time between destinations.

Posted by
700 posts

The recommended walking tours only ran one day a week. It was cold.

Why take a walking tour when it's more fun to get lost. You're on an island and it's not that big. You will find your way back, just make sure you carry the name of the place where you are lodging and address, or better yet, a business card.
Wear layered clothing, a warm coat, hat, gloves along with hand and feet warmers. Cold weather can be dealt with as long as you're prepared.
Another thing I highly recommend in Venice is taking a water bus from one end to the other i.e. the train station to San Marco Square at twilight. This way you'll miss seeing the decay on the palaces that line the Grand Canal and be able to get a glimpse of the palace interiors. It will take you back in time.

Posted by
18147 posts

The most miserable travel experience I've had in my life was the night train to Sicily. Don't do it. The carriage jerked from side to side constantly; I didn't get one wink of sleep. Naturally, I slept for a good part of the day I arrived in Sicily, and my sleep schedule was messed up for a couple of days.

I agree with the others who have suggested that you are not allowing much time in some cities with a lot of great sightseeing options. Three nights somewhere is just two full days and some random hours. You've got a lot of city-to-city transfers that will chew up valuable time.

Palermo is a major geographical outlier. Given that you (trust me) don't want to use overnight trains to get there and back, you'll need to fly. By making Palermo your first stop or your last you can at least avoid one mid-trip flight.

Posted by
864 posts

In Venice, you might want to check out the architecture of Carlo Scarpa.

Posted by
3040 posts

As is usual, you are getting a lot of contradictory advice. I’ll add to the stew.

Lake Como in January, NO.

Overnight train to Sicily. NO. I took an overnight train once. Never again! You can get inexpensive flights from Rome.

If you add a night or two to Venice, You could do day trips to Vicenza (Palladian architecture) and Padova (Scrovegni Chapel).

Definitely add some time to Rome. After spending time and money to get to Sicily, you should stay longer. Some people like Milan. Me, not so much. I’d eliminate it and add those days to Rome and Sicily.

Naples is also a bit of a geographical outlier, one I must say I hated. Eliminating it would give you more time for Rome and Sicily.

Posted by
47 posts

Milano is so under rated. If you are in the neighborhood, go to Stresa on Lago Maggiore and If you are looking for a special treat - - Isola Bella is a gift from god. It's the home of the Borromeo's. Beautiful gardens, white peacocks and architecture that -- - well, it will be one of the best days of your life.

Posted by
4 posts

Now here’s what I’m thinking:
1 Arrive in Palermo, stay in Cefalu
2 Palermo, stay In Cefalu
3 Sicily, stay in Cefalu
4 Fly to Naples, stay in Naples
5 Pompeii, stay in Naples
6 Naples area (Amalfi?), stay in Naples
7 Early train to Milan, day in Milan, evening train to Venice, stay in Venice
8 Venice, stay in Venice
9 Padua, stay in Venice
10 Train to Ravenna, stay in Ravenna
11 Stay in Ravenna
12 Train to Florence, stay in Florence
13 Stay in Florence
14 Stay in Florence
15 Stay in Florence, day trip tour to Sienna & Pisa?
16 Train to Rome, stay in Rome
17 Stay in Rome
18 Stay in Rome
19 Stay in Rome, day trip tour to Assisi & Orvieto?
20 Stay in Rome
21 Depart for home

Posted by
18147 posts

I would definitely not try to hit Orvieto and Assisi the same day by train. I wouldn't take a bus tour, either. Both those towns have a lot to see, and I wouldn't want to be constrained by what someone else thought I wanted to see in those places. I'd explore the possibility of hitting one of the two in transit on the day I moved from Florence to Rome. (I think Orvieto would involve considerably less time on a train, but it's also easy to hit as a day-trip from Rome.) Unless you plan to travel very light and with a backpack, a mid-day stop-off for sightseeing would require determining ahead of time that there's a place to leave your luggage. That is not a trivial task in Italy, where many/most of the train station luggage facilities have been closed. Googling may bear fruit. Incidentally, I think stopping off like that would mean buying two separate train tickets unless you planned a very short stopover (not prudent).

I'm not sure Cefalu is your most convenient option in Sicily. That depends on what you plan to do on your third day in the area. Unless you're planning a side-trip somewhere east of Cefalu, you're going to be making three round-trips between Palermo and Cefalu over the course of about 72 hours, only one of which would be needed if you stayed in Palermo instead.

I have a feeling the Amalfi Coast isn't a great idea in January, but I have no experience with winter travel in Europe.

Siena and Pisa are not places I'd want to try to see on the same day. I suppose there may be bus tours that combine them, but they are in quite different directions from Florence. I'd focus on Siena. If you consider Pisa a must, a combination of Pisa and Lucca would be easier logistically. Many of us like Lucca considerably better than Pisa.

I liked Padua a lot (I spent several nights there), but given a choice of 2 days in Venice or 1 in Venice and 1 in Padua, I'd opt for the former. But you can make a decision about that side-trip after you've spent your first day sightseeing Venice. However, if the Scrovegni Chapel is your main target in Padua, it can't be a spur-of-the-moment decision. You must get your ticket to the Scrovegni Chapel no later than the day before you plan to visit, even in the dead of winter. I assume that can be done online.

You're going to be traveling at a time of year when the days are quite short. You won't have nearly as much daylight for sightseeing as summer travelers do. Normally you could figure on doing a good bit of outdoor sightseeing in your base city after returning from a day-trip. I'm not sure how practical that will be in January. I've noticed a big difference between mid-September and mid-October.

Posted by
7113 posts

6 Naples area (Amalfi?), stay in Naples
7 Early train to Milan, day in Milan, evening train to Venice, stay in Venice

The earliest train from Naples ( 530AM departure) gets you to Milan at 11AM

The last train from Milan departs at 830 and arrives in Venice just before midnight.

Hopefully you are the type that can sleep on trains. Be sure your lodging in Venice has late check in.

Posted by
345 posts

I cannot imagine a more hectic or draining trip. I wish you the best.

Posted by
700 posts

Hi Sam, I agree with arriving or departing from Palermo, but I would fly home from the furthest point of the places that you’re visiting and that’s Venice. I know that plane fare might cost more, so look at Milan to see if that’s more affordable. It’s usually cheaper than Rome.
Train travel in IT is long and boring because there’s much poverty and trains don’t run through the best areas. However, the train in Sicily does run along the coast but that to gets old after a while.
I understand wanting to sleep in Cefalu where the elderly men still dress for their evening passeggiata and the cannolis are the best you’ll ever eat, but trains don’t always run-on time and delays can be long, especially during the winter months. Instead, consider making a day trip to Cefalu from Palermo. You can even store your luggage there while you sight see and hop on the direct overnight train to Naples (9h 45m). I know people will talk you out of this option, but that’s what I did and recommend it. If needed, you can store your bags in the Naples train station before your check in time. However, if you stay at a hotel, you’ll be able to drop off your suitcase(s) when you arrive, even if your room isn’t ready.
If you do fly home from Rome, don’t fly from Palermo to Naples, instead, fly to Venice. Ryanair has a non-stop flight for $57, however, if you check luggage, it’ll cost you so pack light and do laundry often. Nobody regrets packing light.
From Naples, you can take a train to Sorrento (don’t carry valuables and a small amount of money that’s in a secure spot) and hop on the bus just outside of Sorrento’s train station. Make sure you sit on the right side (facing the driver) with a window seat and take it to Amalfi. I also recommend wearing motion sickness bracelets because most likely you’ll need them to prevent nausea. If you can take a boat back from Amalfi to Sorrento, do it. You want to do it in this order to because the bus from Amalfi to Sorrento drives on the back roads, not along the coast.
Florence is closer to Ravenna than Milan, so that works but still requires two connections. You can take day trips from Florence to Sienna one day by bus and Pisa by train (1h 15m) another day. If you have to choose between the two, pick Siena.
I do not recommend a day trip to Assisi from Rome because that requires a 2h 15m train ride, however, it’s direct. On the other hand, Orvieto is 1h 30m so go there instead.

Posted by
3523 posts

Sam, you're crisscrossing the country too many times. Try this to cut down on transfer times.

Multi city ticket. Into Venice out of Naples.
While it might sound more expensive than say a RT Rome ticket, a more or less straight line itinerary will save you time and $$.

Arrive Venice, much softer intro to Italy.

Day trip to Padova.


Ravenna> Florence.

Day trip to Siena.

Florence> Rome.

Day trip to Orvieto.

Rome FCO> Palermo PMO
1hr 10m Ryan Air. $36.

Palermo> Naples NAP.
1hr 05m Ryan air and Volotea Air.


day trip to Amalfi Coast? Temps 50s.
Lots to see in Naples itself.

Flight home from Naples.

This can be done in reverse.

Edit: Venice is harder to fly out of due to its extreamly early flights and transportation to the airport.

I eliminated Milan since you planned such a short time there, I'd add that 1 day elsewhere, but it's easily done from Ravenna then onward to Florence

Posted by
864 posts

Just about every suggestion that has been made is just a list of places, towns, cities. That ignores WHY a visit would be made to that place.
A couple of examples:
Milan for a day en route to Venice. Figure out what is to be seen in that flying visit.
Venice for a day or two, and those days maybe include a side trip to Padova. That means maybe seeing the Ducal palace, the Piazza, maybe the Academia, maybe the Ca Rezzonico or the Correr and little else.
The Original Poster has indicated an interest in Art and Architecture. Most suggestions so far do not acknowledge those interests.

Posted by
14227 posts

Cefalu is basically a resort town. In January I wonder how many cute shops and restaurants or even (few minor) sights will be open, other than the cathedral. I spent 2 weeks in Sicily in April, Cefalu was the most expensive room and the hotel was mediocre and was walking distance from but not in the old town. The beach was beautiful but that was in warm, sunny April. Palermo has more and better hotels and restaurants, lots of sights, and is closer to the airport. For Byzantine, you'll want to visit Monreal which is some distance from the center of Palermo. Sicily has much more to offer, including the Villa Romana del Casale with its many stunning 5th-6th c. mosaic floors, which is way too far to visit from Palermo. There are also an extraordinary number of extremely well-preserved Greek temples. I recommend putting Palermo on hold until you can spend more time in Sicily, in better weather.

I would put Naples toward the end of your trip. I enjoyed a few days there, but I'd been to Italy several times already and was prepared. Naples is "in your face" Italy and also the scariest for pedestrians - at least the foreign ones. BTW Palermo is only slightly less so. It's actually safer to cross the street in the middle of the block than at corners, where a vehicle can come at you from nowhere. And you have to be really careful at traffic lights (drivers take them as suggestions). The Amalfi coast is likely to be pretty dismal in January, with the towns mostly shut down. The joy of the AC is the scenic beauty, so you want a sunny day. It is doable as a day trip from Naples - If you manage to catch a good weather day, take a train to Salerno (35-45 minutes and €5) and then a SITA bus to Amalfi. From there you can take another SITA bus to Sorrento and take the Circumvesuviana train/metro back to Naples. The scenic area of the AC is mostly from Salerno to Positano. From there the road is mostly inland to Sorrento. That would give you a full day on the AC (easy to stop at several towns on the bus route) and leave for Sorrento when it gets dark. It's about an hour by bus from Positano to Sorrento, then another 1- 1.5 hours on the Circumvesuviana back to Naples. The Circumvesuviana at that time of day may only run once an hour. at best it's every half hour.

If you follow my advice above, then fly into Milan and spend your first night there. Try to take an early afternoon train to Venice, so that you have at least one hour of daylight on arrival Trying to find your way around Venice is hard enough in daylight when you have exact directions, it's nearly impossible without getting lost after dark, and the later it is in the evening, the fewer people will be out and about who can help you with directions. One day in Venice is definitely not enough. Drop Padua. It'll still be there next time you visit. If you drop Sicily you'll have time to stay another night in Venice and even one in Padua on the way to Ravenna. Or you could take an early train to Padua, check your bags, and then an evening train to Ravenna.

After Florence, you could go to Naples, then back to Rome or to Rome and fly home from Naples, depending on flight schedules and prices.

Posted by
864 posts

One can travel like eating fast food, experiencing a bunch of dishes with little depth. The McD’s or KFC approach.
Or maybe take a little longer, visit fewer places, experience if you will a bit of fine dining.

Posted by
1 posts

Two years ago my adult son and I traveled by rented Volvo from Rome to Sicily. I learned several things about auto travel having never done it before, using trains and public transportation in earlier trips.
In Italy on the AutoStrade, always observe the traffic laws. Every few miles they auto cameras photograph your car and measure if you got from the last point to the latest point at the proper speed or if you were speeding. A few times, we did exceed the speed limit. Since the car was registered to Hertz, Italian authorities send the speeding ticket to Hertz and then it made a demand upon us with a hefty service charge for the ticket and they had our credit card number. It was quite expensive.
Next according to the guide book we used 2 years ago, it was not recommended to stay in Naples, unless you could park your car in a secured, fenced area or your car may be stripped to stolen. This was alarming enough that we simply skipped Naples but enjoyed a little more time at Pompei. Give yourself at least a whole day at Pompei if it interests you at all. Later on Rick Steve's show, I realized how much we missed by bypassing Naples.
Also, we have visited Trieste which is currently part of Italy. I always wonder why Rick never seems to visit that interesting city which has influences from both the Austro-Hungarian empire in architecture and also classical Italian. Emperor Maximillion II, who was assassinated in Mexico, had built a castle (the Miramar) overlooking the bay at Trieste which is well worth the visit.

Posted by
1526 posts

As part of a longer trip we hit the big 3 in Italy and as a surprise for my wife I added two nights in Assisi ( she’s a big St. Francis fan ). I loved it and we will certainly visit again should we get go Italy. We stayed in a room at the convent across the street from the Basilica of St. Francis. It had a spectacular view.