Thoughts on a possible trip

I think it is too aggressive. You'll be packing up and moving every other night. Two nights in Florence and Rome will not do either city justice. I would pick two bases for the 8-nights. Lake Como and Florence or Rome - not both.

David, " Also I've heard the mudslides from last year mean some parts of the Cinque Terre area may not be available to us." The mudslides took place in October 2011, and the damage has almost completely been repaired. I was there last September, and found that there was little that was "not available". The Sentiero Azzurro trails are still closed, but it's expected that at least some of them will be re-opening shortly when tourist season starts. My first impression of your Itinerary is that it's far too busy! Keep in mind that each time you change locations, you'll lose at least half a day. That will only allow a day a bit for touring in each place - not enough IMO. Keep in mind also that August is PEAK touring season in Italy, and that's when many Italians take their holidays also, so everywhere will likely be HOT and CROWDED. If I'm reading correctly, your trip is only EIGHT days? Does that include your two flight days from the U.S.? To begin with, I'd suggest skipping Naples on this trip. IMO, you'll only have time for either Lago di Como OR the Cinque Terre. If you add a day in Florence, a day trip to the Cinque Terre would be possible, although it will be a LONG day. You could also take a day trip to Siena (by Bus), so that's another possibility. Whichever locations you choose, I would highly recommend getting hotel bookings SOON (especially in the Cinque Terre if you want to stay there). Happy travels!

Clarification, please: "put together a custom package" How locked in to this trip are you? Have you already booked/paid or are you still in the planning phase? This is a lot in 8 days...valid concerns already raised by other posters. Is this your first time to any of the places you've mentioned? Also, will you be using public transportation or renting a car?

To clarify, nothing is booked yet. We have never been to Italy so all of this would be new to us.

Some explanation of your custom package might be helpful. For most of us on this site, two night stands are really one day because of the time lost checking in and out, finding the train, waiting, find new hotel, checking, orientation to new location, finding something to eat, water closets, etc., will consume a lot of your time. A tour group can do that because much of the routine activity is handle by someone else. Your Florence comments are a good example. By the time you get to Florence and checked into your hotel, it will midday to afternoon with limited time to see Florence and next day you want to do a day trip from Florence. Stay in Florence and see Florence. If you are really looking at an 8 night trip. Assume you are landing in Milan. Stay in Milan two nights, then three in Florence, and three in Rome. It it was my trip I would fly into Florence for three nights and Rome for five with a day trip to Pompeii. And home from Rome.

I'm so relieved...thought you had already paid. Assuming the 8 days is actual time in Italy (not including air time from US to Italy) your original plan will leave you exhausted and frustrated in my opinion. What are your true interests: art? - must go to Florence; culinary? perhaps Bologna; hiking/outdoor - Cinque Terre or Como; romance - Venice (or any number of places); archaeology - Pompeii; wine - Chianti. Deciding this will help shape the trip. With 8 days, I think I would only go two places, perhaps 3. But they need to be either north (Milan, Cinque Terre, Florence) or South (Rome, Florence, Amalfi). I know those are very loose definitions of North and South, but my point is that a Como - Rome - Amalfi trip is a lot of pure travel time and will minimize your time actually experiencing those places. As Rick says, assume you'll return. for example: fly in one place (Boston to Milan) and then out the last place (Rome to Boston). Then plan your trip working your way down from Milan to Rome.
The posters on this board will help tremendously - be as specific as you can in asking your questions and follow your heart. Good luck!

an afterthought - always - I know from experience that planning a trip to Italy can be a tad overwhelming. So many incredible options! BUT once you narrow down your locales, a lot of the planning is fairly straight forward because so many have done it before. If you decide Florence is a base any number of people can tell you the best way to day trip to... or buy tickets to see... or find a cooking school specializing in...

If you've never been to Italy and have only 8 nights, I would include Venice instead of Como in your itinerary. For a first timer Venice, Florence and Rome are kind of a must. I would fly from BOS to Venice (via any European major hub). Stay in Venice 2 nights (1 day). Then go south to Florence (2 hrs by train). Stay in Florence 3 nights. Then go to Rome and stay the last 3 nights. From Rome you would fly back to Boston (Alitalia has a non stop flight, and Alitalia is a partner of Delta/AirFrence-KLM). If you want to take a day trip from Florence to the Tuscan countryside (or even the Cinque Terre) you can too. Likewise from Rome you could take a day trip to the Naples area (Pompeii). Naples is only 70 min away from Rome with high speed rail. However with only 8 nights you'll be busy visiting just Venice, Florence and Rome.

David, these other people - are they carrying you from place to place or do you have to find your own way around stations and cities by yourself? Have you and your wife found ways to beat jetlag? Most people are semi-zombies the first 24 to 48 hours after landing. If you will stick with Lake Como most people on here would suggest other towns than Como. 2 nights equals one day. At this rate you will be able to check a box saying you have "been" to these places. You won't see much, but you will have been to them. If you leave Como after breakfast you will be in Florence at lunch time. Are you flying home from Naples or do you have to get back to Rome, or worse, Milan?

Thanks to everyone so far for the input. It's been really helpful. We thought last night on changing up our plan. We're avoiding the package and started looking at flights and hotels ourselves. Here's what we came up with: Fly Boston to Milan 2 nights in Varenna on Lake Como 2 nights in Monterosso al Mare in Cinque Terre 2 nights in Florence 3 nights in Rome
Fly Rome to Boston This is still aggressive but feels like it flows a little better. We found the train map here to be very helpful. We can take the train from Varenna to Vernazzo and instead of a day trip to Cinque Terre we have a little over a day and less rush. The time in Florence is still short of course, but not as bad coming from CT instead of Milan. Cutting out Naples and adding a day to Rome makes this feel a bit less rushed as well. Keep in mind my wife and I have always enjoyed the slower paced areas over the city on our trips. On our Germany/Austria trip we enjoyed Rothenburg ODT more than Salzburg or Vienna. On our Ireland/Scotland trip we enjoyed Dingle over Edinburgh. Don't get me wrong, the cities are great, but we don't want to spend all our time there. That's why we're leaving something like Venice out to save room for the other areas. This will most likely be our last trip for quite a while which is why we're being so aggressive. It's so hard to cut stuff out when we're going to be so close to everything! Also, my wife is a teacher, thus the August time frame. Nothing booked yet of course but if anyone has any thoughts on this I'd love to get more feedback, this has already been really helpful!

Your new plan is aggressive, but not as bad as your first plan. You've allowed one day (2 nights) everywhere except Rome. If that works for you then go for it. I think you're smart to save Rome for last. Especially with your preference for smaller places, Rome can be overwhelming. It's kind of like NYC on steroids in my opinion. It's going to be hot and crowded. If that's not your thing, you might think about substituting Venice for Rome on this short trip and stay north.

Will Florence be as crowded as Rome? Or is Rome where we're really going to feel the biggest crunch out of all the stops we're planning?

I can't say for sure if Florence is more or less crowded than Rome, but my guess is Florence is less crowded. The biggest difference I felt was that Rome is chaotic and noisy with all the traffic. Florence was not that way at all, as traffic is more limited in the city center and there are more pedestrian zones.

There will be a fair few folk in Florence. Even with many fewer than Rome, Florence is very much smaller so the people are all squashed together in a very much smaller area. It is true that all the buildings, roads and other hard surfaces in Rome collect the summer very hot heat; however Florence is in a natural bowl so the heat gets in but can't get out - Florence is always a very very hot place in summer because of the oven effect.

Do your plans go into August 15? If so, that's a national holiday in Italy and many places are closed and the mountain villages and coastal villages fill up with vacationing Italians, often for the whole week. You may have a hard time finding lodging on Lake Como and in the CT as people try to escape the heat.

Yes, our plans would include the 15th. We are planning on booking everything very soon. Will the holiday lead to some sites being closed?

Better, but still a lot for such a short trip. We did two nights each in Florence, Siena and Rome before embarking on a 12 day cruise. If we had it to do over, we would add a day to Florence and two days to Rome, although you could spend a full week in either and not see it all. Is there any way of extending your trip? For the cost of getting there, making it a two (or 3!) week trip would make it much easier to see all you want to see and more cost effective. Cinque Terre is beautiful, but cramming in so many major cities will leave you exhausted and frustrated at what you will have to miss. Siena has the most wonderful Cathedral and was an incredible medieval village. Florence had way more than we could see. Don't miss the Ufuzzi and Accademia museums, and the Duomo. We did make take another cruise two years later, and were able to return to Rome for just a day, and hope to go back for a little longer next year. You didn't mention Venice, but that is my favorite city in the world! I'd go there before Lake Como. Just my two cents worth. You'll have a wonderful time whatever you do and wherever you go! Jan B PS Everywhere we stayed was recommended by Rick, all were reasonably priced, and we were happy with all.

Sadly our travel time is limited due to a wedding early in August, my lack of vacation time, and school workshops my wife needs to be back in the country for. On train times - we're seeing 2.5 hours from CT to Florence and 1.5 hours from Florence to Rome. If we were to go CT straight to Rome though we were seeing train times of 4.5 to 5 hours. Does this sound right?

The problem with including Lake Como in this trip is that it's not on a direct train route. You'll fly into Milan, take a bus or train to Milano Centrale (which will require at least a short wait), catch a train to Varenna (more waiting timie), walk to your hotel. Depending on what time your plane arrives, you'll get to your hotel early afternoon (best case), and you'll be tired from all that travel. You'll have 2 nights, then will have to repeat the trip to Milano Centrale and possibly waste some valuable time waiting for a connection. I agree with Roberto that Venice is a better choice for a first trip. Can you fly into Venice? Then it's a straight shot to Florence, a short trip to CT, and a fairly direct trip into Rome.

Is it better? Better is a relative term. Most of us here have tried to discourage the two night stands but you seam determined to do it. It is a drive by trip but so was our first trip in 74. Although we were very young at that time, it was so exhausting that we have almost no memory of that trip. Fortunately we do have pictures. My young wife keep saying we will have to see that next time and she was correct. Give it your best shots and take notes. I am sure the next trip will be different.

I do lots of whirlwind trips and also prefer the countryside and villages many times to the big cities...however, when I do these kind of trips I usually have a car and tend to spend my time exploring with my car. Having been to all the places you are thinking of a number of times, if it were me I would spend the majority of time in more quiet places and less in the city, given your preferences on other trips. I do like Lake Como and it was a highlight, and I love the sea and CT (although it will be busy) but I would give up Florence for Venice. I think you will be spending far more time getting packed up and waiting for trains than you realize.