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3 Week Italy Itinerary - 1st Timers

Below is the outline of our itinerary for 3 weeks in Italy 9/8-9/30. My wife and I are flying Alitalia RT JFK to Milan $655pp. We plan to travel between destinations primarily by train. Have not decided on side trips from Florance as yet but we may rent a car for a day or two. Being first timers, we will try to see as many top attractions as possible while leaving time to simply "be there" and also include some more personalized experiences, such as kayaking in Venice and seeing Ennio Morricone at the Roman Arena in Verona. I welcome your comments, suggestions and recommendations - a favorite site, tour, restaurant, side trip, stop between destinations or off-the-beaten-path discovery? If you have a criticism or caution, I invite that as well. We can still make adjustments.
Grazie! Steve

1 night in Milan at Gran Duca di York, 2 nights at Lake Como (Varenna) at Eremo Gaudio, 1 night in Verona at Hotel Torcolo, 4 nights in Venice at Pensione Guerrato, 5 nights in Florence & Tuscany at Morandi alla Crocetta, 4 nights in Rome at Relais Teatro Argentina, 3 nights in Cinque Terre (Vernazza) at La Toracca (apartment) and the last night back in Milan at the Gran Duca di York.

Posted by
6 posts

Have fun! I will be spending 4 weeks in Italy first time, too. Instead of moving from place to place, I put 1 week in Venice, Florence, and Rome (another week is in the Alps) to see the big 3 and take day trips to surrounding attractions (Viator trips).

The only thing that freaks me out is all the talk about pickpockets in Italy. Be very careful with your valuables. There are many blog entries on line on how to safeguard and be on the lookout when you are in Italy.

Posted by
1001 posts

If your first night in Milan is the day of your arrival, I would suggest going directly to Varenna and skipping Milan. You will not have much time (or energy assuming jetlag, customs, etc.) to see Milan. That would give you an extra day at Lake Como. The Hotel Eremo Gaudio is a hike from the train station so I would suggest taking a taxi to and from the hotel. Also perhaps buy your train tickets from Varenna to Verona in advance at the train station in Milan. There is no ticket agent at the station in Varenna. There is a travel agency nearby in Varenna where you can buy the tickets but they are only open certain days and hours I believe. You may want to research this. The Hotel Eremo Gaudio has lovely views of Lake Como but is again a bit of a walk to the ferry and the lakeshore. We also had a very bad experience there so it's not on the top of my list of hotels. But this late in the game you will probably not be able to secure lodgings elsewhere. One night in Verona is also not enough. I would steal one night from Venice for this trip. The rest of the trip looks fine. The Gran Duca di York is a lovely little boutique hotel in Milan. We enjoyed our stay there.

Posted by
14014 posts

There are sights that should (or must) be booked in advance. Have you done that? Other than that, I'm not sure what you are asking. This late in the game, you don't have much chance - or would want the hassle - to change several of your hotel reservations, so your itinerary is pretty much fixed. What are your interests? What are your tentative plans? What sights are already on your must-see list? Have you taken advantage of discounts and bought any train tickets?

Posted by
24 posts

Hi 33chanteuse, Sounds like you have a great approach... closer to what my wife prefers, so we ended up with a compromise. I too have read, and heard, many stories about the theft problems. It seems like a very real problem, but I also keep in mind that for every incident, there are 10 people out there telling the story. My plan is to employ all the recommended precautions, stay alert and then just enjoy myself. Thanks for the reply, Steve

Posted by
24 posts

Hi Mary, Thank you for your thoughtful and helpful reply. I will book the train from Varenna to Verona in advance. I was hoping to take the slow boat from Como to Varenna and thought if the weather was bad, or we were just too jet lagged to care, I could save it for the backside departure to Verona but it might make more sense to just have the train tickets in advance. We wrestled with the location of Eremo Gaudio (and hotel availability was tight even back in early April) but thought the trade-off for the views, value and uniqueness was worthwhile. We have a high room with balcony. I wonder about the nature of your bad experience? Feel free to PM me if preferable. I think I will love Verona and want more time but it was an add-on for the concert experience so we carved out the one night. We'll plan to arrive earlier and stay later to make the most of it. We are scheduled to arrive in Milan at 10:40am. Our hope is to get settled and over to Santa Maria delle Grazie in time for a 3:30 english speaking tour of The Last Supper, followed by walking and at least seeing the Duomo (if not Galleria VE II & La Scalla), our first supper and bed. We'll have another night at the end of the trip to fill in a few things. Any restaurants you might recommend in the area of Gran Duca di York? Best, Steve

Posted by
24 posts

Hi mulder_80, Great tip on kayaking from Bellagio! I'm looking into that. We booked a half day tour in Venice with Venice Kayak. Both seem to stress the importance of booking in advance. Have a great trip! Steve

Posted by
24 posts

Hello Chani, It is late, but with an onslaught of personal and professional circumstances our planning got derailed for months and I'm just now able to return my attention to the trip. Thankful that I at least got the air and hotels back in March/April. We're looking for a broad overview on this first trip... history, art, architecture, culture, food, scenery, daily life. We did book The Last Supper, Venice Kayak, concert at the Verona Arena, a couple of tours in Rome (Friday Night Vatican, Colosseum/Forum/Palatine) and we'll get the Firenze Card to cover most of Florence. We plan to book the Borghese Gallery in advance and we're considering some additional tours. What other sites would you suggest booking in advance? I have been considering booking some trains in advance, for the considerable savings, but that seems like a value trade-off for flexibility on the fly. Probably will book a few this weekend and others as we go. You seem like an experienced Italian traveler, so if you would hit me with even one of your favorite gems of an experience, anything from a Florence side-trip to a restaurant in Rome, my ask is fulfilled. I appreciate your input! Steve

Posted by
1001 posts

Hi Steve,

Sorry to sound so negative about the Eremo Gaudio. You will have spectacular views from your room. And I am hoping your experience is a good one there. Our first morning at the hotel we had no water to our room. I called the front desk and was told to leave the water tap on for 5 minutes and water would eventually flow. It did not work. Then we were told they had a water delivery problem from the neighboring town. Several waterless hours later we finally got water from the tap. Brown water. Eentually we had clean water but this was a huge inconvenience. Luckily we had bottled water to brush our teeth but were unable to shower. Our last night at the hotel we had a massive ant invasion in our room and, no, we did not have food in our room to attract them. I have seen other reviews on Tripadvisor reporting this issue so we are not alone on this.Our final morning, we looked out our window at the lake and saw a massive storm cloud across the lake. My gut said "Take the luggage down with you to breakfast." We didn't. Lightning struck somewhere near the hotel and knocked out the power. To get to our room on the top floor of the hotel, we had to walk up a steep, slippery, overgrown with vegetation stairway in the rain because the 2 funiculars and the elevator were inoperable due to the lack of electricity. This was not the hotels fault but only added to the bad experience. The desk manager was a very grumpy old man but I hear he is no longer there. Hopefully. The breakfast was terrible. This in a country known for its cuisine. So we can laugh about this now but in all my years of travel in Europe this was the worst place, thankfully, that I have ever stayed. And it was not cheap by any means.

Posted by
3341 posts

Steve,
Personally, unless there is a compelling reason to spend the night in Milan I would head straight to Varenna to get over the flight and get acclimated. Add that night to Verona or Venice (or maybe Rome). Actually, Verona can be done as a day trip from Venice if you get an early start and plan on an evening return. Of course it is between Milan and Venice so an overnight is not unreasonable. The rest looks aok.

Posted by
20718 posts

The only thing that freaks me out is all the talk about pickpockets in
Italy.

You have the right attitude about pickpockets and theft in general. It is well discussed by the few people who have had problems and by many people who heard about problems but no direct experience. We have spent nearly a year in so some of the great pickpocket capitols of the world over the past 20 years, and have never had a problem or even close to a problem. But doesn't mean something could happen on the next trip but, in general, few travelers have problems especially if they take some simple precautions.

If the discounts are not available for the on-line purchase, then I would purchase when you arrive. The base fare is the same on line or at the station. That way you have max flexibility. And remember, do not for any reason purchase Regionale tickets on line. Those should be purchase at the station and then validated (time stamped) just prior to boarding.

Posted by
5 posts

If you end up with two nights in Milan, have you thought about taking in a performance at La Scala (assuming there are still tickets available)?

I was looking at Venice Kayak, particularly the night tour, but I would have had to do a day tour, too. As much as I love kayaking, it was going to take too much time away from my other sightseeing and the price was a little high. So, I booked a 1 hour tour with Venice By Water. Not the ideal tour, but you have to make compromises sometimes. :) I hope you enjoy yours!

Posted by
24 posts

That sounds dreadful, Mary! Thanks for providing the details. It will help me better manage my expectations and plan to pack in a backup breakfast and plenty of water. With decent reviews overall, the lack of alternate availability and those amazing VIEWS, we'll just roll the dice and keep our fingers crossed. I'll report back on our experience.

Posted by
24 posts

HI Frank, Thanks for your input on the theft problem. I'm glad to hear you say that. "We went to Italy and got robbed" is a story. "We went to Italy and didn't get robbed" is not a story, so it rarely gets told. Then there are stories, like the one that my dental hygienist told me at the mere mention of visiting the Spanish Steps, about a friend of a friend who witnessed someone having wet cement thrown on them as a diversion so they could get pick-pocketed by accomplices pretending to help. Probably somewhere between gross exaggeration and urban legend... at most, extremely rare. But look, here I am repeating it again myself. How many thousands of people a day visit the Spanish Steps without incident?

Good tip on the Regionale trains. Thanks.

Posted by
24 posts

mulder_80, I would love to see an opera at La Scalla, even though it's not my thing. Unfortunately, there is not a performance on the nights we're there.

Simply getting on the canals in a kayak should be very worthwhile and memorable. Many difficult choices and compromises must be made on a limited cursory overview. One would need to live in a place to truly immerse themselves.

Posted by
24 posts

Skip Milan, seems to be common advice, well beyond just Mary and TC here on this thread. I guess this is a lesson I will need to learn first hand. Is it not worthwhile for an overnighter to see The Last Supper, The Duomo, the Galleria VE II, the Quadrilateral and possibly another site or two (La Scala, Basilica Sant’Ambrogio, Castello Sforzesco), have a nice meal and just get a feel for the city? By the time we land at Malpensa, get our bags and clear customs we will have been traveling for 12-14 hours. Jumping on the 35 minute express to the Cadorna Station, very near our hotel, seems more appealing than possibly waiting longer to take the 2hr 10min train (with a connection) to Varenna. Is it not advisable to try and stay awake, walk outdoors and get to bed early for jet lag anyway? If I had not taken advantage of the favorable fare to Milan, admittedly, I would not have made it a priority on my tour of Italy, but if I'm there, why not have a look?

Posted by
1001 posts

It's very ambitious to attempt to see all that on your first day in Milan but sure go for it. We enjoyed Milan but had 3 nights there. And the Gran Duca di York is a lovely hotel as I said. It is very well located. Don't worry so much about the pickpockets. Wear your money belt and keep your hands on your belongings and you'll be fine.
When we were in Milan a couple of years ago, there were guys with small hand braided bracelets in front of the duomo. They were trying to put these on the tourists' wrists and then demanding payment. They may or may not still be there.
I always find that I am a bit disoriented and not as wary as I should be on the day of arrival in Europe due to jetlag. Knowing that, I tend to go a little slower on that first day and try to have my scam artist radar up. Have a great time in Italy. It's a lovely time of year to be in Europe.

Posted by
11613 posts

I love Milano and slways spend a few nights there if I fly into/out of Mslpensa, an overnight is a good idea. Plan to see Leonarfo's Ladt Supper the next morning, so you don't have to worry about a late plane arrival invalidating your entry ticket.

Everything else you mention seeing can be done that first day/evening, or if you have a late entry for the Last Dupper, you can see everything you listed that first day and take an evening train to the Lake.

Posted by
24 posts

Thanks Zoe! Our flight is scheduled to arrive at 10:40 and we have Last Supper reservations for 15:30 (with an english speaking guide). Barring the worst case scenario, I figure we can make it there by 15:00... even if it means leaving our bags at Cadorna station for awhile. A lot of these other sites can be quick visits for us or just a walk-by. I'd like to be on the roof of the Duomo for that final, golden hour, before closing. We'll only do what we can, given the jet-lag and time constraints. I'm banking on excitement and world-class caffeine to keep me going. Other than the Last Supper we have no commitments. We'll also have the following morning and another bite-at-the-apple on our overnighter at the back-end of the trip. I'm looking forward to it all... including Milano!

Posted by
72 posts

Hi SteveM... You got a great price on your airfare at $655 pp on Alitalia. We are paying $1400 pp on Delta. Do you have any secrets on getting such a good price? We want to return to Italy in the spring. Thanks... Pam

Posted by
24 posts

Hi Pam, When we originally began planning, back in March, we thought we'd do an open-jaw Venice-Rome or something like that. Then I noticed this very low JFK-Milan RT fare on Emirates. I watched while we discussed alternate plans and then it seemed Alitalia began to match the fares. Were these fares brought on by additional service for Expo '15 or Emirates entering the market with large unfilled Airbus A380's? I can only speculate. We ultimately decided on Alitalia having a better departure time and a seating layout that allowed us to have a two seat row to ourselves with both an aisle and window. It also seemed like the more Italian thing to do... "when in Rome" and all that. While the open-jaw seems the general recommendation, the good people on this forum helped convince me that the roughly $500 savings pp was well worth rerouting the trip and helped me with some of those ideas. Link to original topic below. Good luck!
https://community.ricksteves.com/travel-forum/italy/milan-rome-open-jaw-vs-milan-rt-1-000-savings

Posted by
5 posts

I began looking around the same time and also saw the JFK-Milan flight on Emirates in the low $600s, but I couldn't commit at the time. Once the price started going up, it gave me the idea to do an open jaw flight instead so I could do a few days in Berlin before returning to JFK.

My plans for Milan are La Boheme at La Scala (assuming no extensive flight delays), the following day my day (maybe half day) trip to Como, Duomo, and maybe the Milan Expo (mixed reviews on this one), and the last day the Last Supper and some walking around Milano Centrale which is supposed to be a gorgeous train station (I can walk around Grand Central for awhile, so I'm reserving a couple of hours to explore Milano Centrale before departing for Venice). I see no reason to not stay in Milan for awhile. It may not be a city to stay in for a week or two, but there's definitely some interesting things to see there. If I wasn't catching a show at La Scala (I like classical music, but opera might be a stretch for me), I'd visit the venue anyway.

Thanks for mentioning the tip of going to the top of the Duomo near Sunset, I hope I can make it then.

Posted by
24 posts

mulder_80, An opera at La Scala is life-list stuff. Familiarize yourself with the story (libretto) and the music before you go and I'm sure it will be a powerful, beautiful and memorable experience. The theater, crowd and scene is probably worth the price of admission.

Rick Steve's guide lists the closing time of the Duomo as 7pm (19:00) but the official website lists the hours below, which would take you through sunset.

If I find myself with extra time on my hands at the end of the trip, personally, I'd walk around the Monumental Cemetery and/or the Brera district or go in search of the perfect risotto all before bothering with Expo.

Visitors
Every day: 8.00 – 21.00. Last ticket at 20.00. Last admission 20.10

TERRACES
Valid from 26th June to 31st July 2015
Everyday: 8.00 – 22.00. Last ticket 21.00. Last admission 21.10
Valid from the 1st August to 30th September 2015
Everyday: 9.00 – 21.00. Last ticket 20.00. Last admission 20.10
Valid from the 1st October to 31st October 2015
Everyday: 9.00 – 20.00. Last ticket 19.00. Last admission 19.10

Posted by
14014 posts

We're looking for a broad overview on this first trip... history, art, architecture, culture, food, scenery, daily life. We did book The Last Supper, Venice Kayak, concert at the Verona Arena, a couple of tours in Rome (Friday Night Vatican, Colosseum/Forum/Palatine) and we'll get the Firenze Card to cover most of Florence. We plan to book the Borghese Gallery in advance and we're considering some additional tours. I have been considering booking some trains in advance, for the considerable savings, but that seems like a value trade-off for flexibility on the fly. . . . anything from a Florence side-trip to a restaurant in Rome,

Ah, now I understand.

Milan has attractions and you won't regret your time there. Most of us usually say "skip it" because there's so much more to see elsewhere, but you have the Last Supper reservation which makes it a must. Walking around the roof of the Duomo is special. If you're short on time, skip the interior or do it briefly. Be sure to walk through the Galleria Vittorio Emanuele II. On the other side, there's a charming square and just passed that you'll see La Scala. If you have time, it has an interesting museum as well as getting a look at the elegant theater. Not far from there, and a pleasant walk, is the Sforza castle and its museums.

Verona has lots of interesting sights besides the Arena. It's one of my favorite places. Look at Verona Card for more info.

In Venice, I liked Rick's self-guided audio tours (as elsewhere in Italy). They are mostly about 45 minutes long and have interesting information. Be sure to print out the accompanying maps. Others rave about Alessandro's cicchetti tour. He didn't have enough people for a tour when I was there (off-season). The Doge's Palace Secret Itineraries tour is great, needs to be booked in advance. Get the earliest tour you can, it gets hot. Visit San Marco between 11.30-12.30 when the mosaics are flood-lit and visit the museum - you get great views of the nave and the mosaics and access to the balcony.

Book train tickets in advance. Besides saving money, you'll save time - lines can be long at the train station, both at the ticket counters and at the machines. Flexibility isn't what you think it will be - you are going to want to stay longer everywhere and be sorry you didn't get to your next destination earlier! I find that knowing my train time in advance helps me focus on my "goals" and not get too distracted by everything else I see along the way. I'm not a foodie, so as much as possible I travel in the late afternoon or evening, and relax after the day's sightseeing. Sometimes I take a picnic dinner to eat on the train, sometimes I arrive early enough to go out for dinner after checking in to my hotel.

Posted by
1747 posts

There are a lot of stories about pockets being picked, and I had a friend who was a seasoned traveler get paint dropped on her and had her belonging stolen. But, if you are aware, wear your money belt and just keep everything "buttoned up tight" you'll have no problems. We keep all valuables : credit cars, passports, money etc. in our money belts, I keep my camera in a fanny pack and lace it through my belt loops on my pants. I use a safety pin or produce twist tie on my zippers of my fanny pack and on my day bag that just has sweaters, water, etc. I think I must look paranoid, but never have we had anyone even try to pick pocket us. Too many other easier targets. However, we do this in the big cities where there are problems and take off the twist ties and safety pins outside the city where it is safer. I'd rather be safe than sorry!

And, I am a dental hygienist passing on those stories :-)

You'll have a great trip!

Posted by
7124 posts

I would endorse heading straight to Varenna after you arrive at Malpensa, and spend 3 nights on Lake Como.
If you can, tack on a 2nd night in Milan at the end of your fantastic journey.
Ennio Morricone at the Roman Arena in Verona sounds wonderful. Enjoy.

Posted by
24 posts

Flexibility isn't what you think it will be - you are going to want to stay longer everywhere and be sorry you didn't get to your next destination earlier!

Chani, So true! Some very good tips and wise perspective. I haven't set foot in Italy yet and I'm already thinking about my next trip. :-)
Thanks!

Posted by
24 posts

Susan and Monte, That's so funny that you're another dental hygienist telling Italy crime stories! Then again, you guys do tend to do most of the talking. :-) I'll be taking all the precautions - I tend to be a suspenders and (money) belt kind of guy. I grew up in LA, lived in Manhattan for 25 years and worked there for 40. I'm well acclimated to big cities and scams. I'm a gentle soul, but I look like I'm straight out of central casting for Sons of Anarchy... generally not a first choice target. Grazie!

Posted by
189 posts

Booking a concert in Verona was a great choice. I loved Verona, and I stayed at the same hotel you have booked. I was there in winter so it wasn't too crowded, but I hear that Juliet's balcony gets quite crowded. It's not worth it.
Have a great trip. And make sure you have plenty of gelato.