Tips for itinerary planning

Where are you going? That's a good place to start! I know it's hard to not get overloaded, first make a list of the places you want to see. Then look at a map and look at where they're located so you can save time travelling back and forth.

Milan, Florence, Perugia, Rome, Venice. I have gotten that far :)

How long is the trip ? excluding the two days of travel

Also where do you fly in and out of matters

We fly in and out of Milan. we have 1.5 days in Milan. 4 days in Florence, 2 days in Perugua, 4 days in Rome , and 3 days in Venice and then back to Milan for the night before we fly out.

Dee: We returned from our first Italy trip in October. Although I planned the route, like you, well in advance, and made all the lodging reservations many months prior, I tweaked and tweaked until the bitter end! As Rick Steves says, "If you want to have a A+ trip, you have to be an A+ planner." What I finally did was cut back on what I planned for each day, and made a list of things to do/places to see "if we had extra time." On the ground in Italy, I felt less stressed about missing something, and we took more time to go with the flow. If we discovered something we didn't know about, we were able to take advantage. Do make reservations in advance where you can: tour of the Vatican, for example, or the Borghese. Have some idea of the trains you want to take. I made up a spreadsheet that listed my preferred trains by date and time, then used it to ensure clarity with the ticket agents. Buy your train tickets as far in advance as you can when you arrive. There may be discounts available to you if you do. Make sure you know the hours and days of operation for the sites you want to see. (My nephew missed the Vatican Museums because he assumed they'd be open every Sunday.) Get to your first site as soon as it opens each day and avoid the crowds. See the Trevi Fountain at 7:30AM -- no one else is there! USe guides if you can manage that in your budget. They are real time savers in the Vatican, Colosseum, Forum.

Dee, Based on the information you've provided, you appear to have about 16 days for travel. Does this include your travel days? You'll lose one day on the flight over and the last day will be spent for the flight home. My first suggestion would be not to add any more cities to your list. Milan, Florence, Perugia, Rome and Venice is quite enough for that time frame. Try to minimize your time in Milan, so that you'll have as much time as possible in the other locations. Be sure to factor travel times between locations into your planning. Even though the duration of the actual rail trips is only a couple of hours in most cases, by the time you add checking in & out of Hotels, getting to the station and waiting times, it's more realistic to allocate about half a day for each move. I assume you'll be travelling by train? Although you're more "go with the flow type of people", some pre-planning will be necessary, depending on which sights you plan to visit. It shouldn't be difficult to get into the Uffizi or Accademia at this time of year, however you might want to verify the hours of operation. One location where reservations are compulsory is the Borghese Galllery in Rome (if you were planning to visit that?). As you prefer "less structured" touring, one method you might try is to make a list of the sights you want to see in each city, ranking them in order of "essential" to "if I get time". Review the list at breakfast and decide which places you feel like visiting that day. That way, nothing is "set in stone" and anything you don't see can be put on a list for the next visit. I'd highly recommend packing along a copy of the Italy Guidebook as it's a valuable source of reference during trips. Buon Viaggio!

Planning is something I struggle with too; its hard to know what you'll like and how much time you'll want to spend at a given sight (or city) until you've been there, which kind of defeats the purpose of planning! But a few tips I can give are (1) figure out what you're interested in, and what you'd skip. If you're not an art museum type person, for example, plan minimal or no visits. Don't be because people tell you not to "miss" something, its your vacation. (2) rather than a tight daily or hourly schedule, my approach has evolved over the years to one of information summary. I read thru the guide books to figure out what I might like to see and mark in the book so I can quickly find them. If there is something I really want to see (for example the Uffizi) then I note what days it is open, read thru the tips about avoiding crowds or making reservations, days they are closed, etc. (3) when possible keep planning flexible so you can shift based on weather and how you're feeling. I still like to come up with a rough guide for a day, but I've also found that putting too much down is counterproductive. I might start with a museum in the morning and play it by ear after that; however I'm not wasting time since in (2) I did the research in advance to find out what is in the area that I'd want to see. And keep in mind that sitting and taking it in is not "wasting" time; allow yourself to relax at a table and people-watch while you drink an overpriced coffee. (4) I'm a big fan of guided walking tours. A guide in 2 hours will tell you much more than the few paragraphs in a guide book, and you can ask questions. The RS lists good guide companies. The sunset walk in Rome, for example, was one of my favorite memories. Look up in advance what days and times they are offered.

I love the planning stage. Thats why my wife leaves it all up to me. :) We have it down to a science. First we determine how much money we want to spend. Then that goes in to a special account we call our Italy Fund. And we don't even start planning till that fund is filled up. Then we lock down on our time frame, from and back to the point of origin. We decide what we want to visit as to cities and how long we want to stay in each: One City or several. Then decide if we want open jaw or RT from the same airport. I scan the airlines for the best deal at least 3 months before. Lock down airline flight. Now I look for hotels. We have a certain kind of hotel in mind. Usually in the center of town, but always close to the metros, buses or train stations. I lock that or those down. Now we have an open day by day sheet that we negotiate what we want to see in each town or day trips: Things we do together and things we do apart. We make a 1st draft which will have way too many things to do in it. Then I recheck for when places are open and what places are grouped close to each other. 2nd draft, we pair this down to what we really want to see and do and adjust the logistics so that we are not backtracking.
We let the 2nd draft just sit for about two weeks while we try and think of anything else we might want to see that fits in with the general flow of the trip and I add up what the total costs are going to be and if its in budget. Things get added and a few things get subtracted and then we make a 3rd draft.This becomes our pre-trip itinerary. That we both "sign off" on. This is the trip we intend to make. It never works out that way in a perfect fashion, and some days will need to be switched around. But we still get to see what we wanted to see. And we leave in at least 3 days where nothing or very little is planned for a 2 week stay.

Wow! Thank you for all your responses. I definitely won't be adding any more cities to the list. I already made a spreadsheet with the train times but I read on another post that the schedules were changing on December 12th, so I guess I'll have to take another look again. I like the idea of just having a list of the places, including hours of operation and costs and then seeing what we can, and what we cant - well then I guess my husband will have to take me back to see!! Thanks so much for all the tips. 16 days =)

The only thing I would add to your list is to use one of the mapping sites and mark your chosen sights. It's much easier to manage when you can see what's close to what. Also ask your hotels for help after you get there. Often they will be able to help you with reservations if they are needed, recommend anything special going on, help you figure out a day's itinerary, etc. Plus restaurants, shopping, etc in the area. Lastly, do not stress about what you miss on your trip. Just enjoy everything as it comes. You WILL be back, and you can never see everything anyway.

Chani, thank you for replying. Do you have any recommendations for a good mapping site? I've played around with several but haven't found any that I stick with. That was definitely part of my frustration with planning!

"Do you have any recommendations for a good mapping site?" viamichelin.com Google Earth (a separate download that is free) - takes a couple of minutes to download it initially, but worth it. You can turn on various overlays, such as "show all restaurants" in a given area.

Awesome, thanks Kent. I was using Google maps but as a street view to get a little sneak peak.

Oh my God, how did I not find ViaMichelin.com in all of my research?!?! This thing is amazing!! Thank you Kent!!

Yep, glad you like it. Michelin is all over the Europe map thing. They've been doing maps in Europe for 'bout a hunert years now (pretty much since cars have been around). And then there's the Michelin hotel and restaurant reviews, and guide books, etc. French chefs have been known to kill themselves over Michelin restaurant ratings. And Google Earth is pretty cool, too. Not Google Map, but the free Google Earth download, takes a few minutes but it's worth the trouble.

I, too, am a over planner, right up to the moment we leave for the airport. I've discovered recently that no matter how much planning I do, we won't see everything on my must-see list. And this was driving me crazy, made me think we were "slackers" once we hit the ground, and were getting too old to accomplish all of my goals. Now I am trying real hard to relax more, enjoy more, and just plan on coming back if its something we really want to see. My prime example of this is the fact that we've already spent a total of 13 nights in Rome, in two trips, and still haven't seen everything on my list for the first trip. And that's why I'm planning trip three! Go, enjoy, and if wanted, go back.

In general, I like to know all my options. Here's what I do in the months before my trips (sometimes years as I'm always compiling at least a few future trips). Each time I read about something that might be interesting, I categorize it as "must see", "like to see", or "good if I have time". I condense it down to the necessary details: name, rating, location/how to get there, hours/days, admission price, contact number, plus a catchall category for notes to myself (e.g. reservation needed). I have a list for each city reduced to about 1/4 of an 8 1/2 x 11" sheet of paper and keep it available. I start each day with two major (must see) sights in mind. As the day progresses, one might not work out due to weather/unscheduled closing or we may not spend as much time as I thought we might. In either case, I consult my list to see what our options are. Sometimes, the best option is a relaxed picnic rather than trying to squeeze in another sight - other times we're motivated to keep going. While it sounds a little anal, I see it as doing a lot of homework before I arrive so I can use my time effectively on vacation. On the ground in Europe, I play it by ear more often than not - but always with the most complete knowledge of my options possible.