Trying not to freak out about our first trip to Italy

With as much traveling as you have planned I don't know how you can be an authentic traveler. You'll be going from site to site without much time to get to know any of the destinations you plan to visit. 4 days is not a lot of time in Rome, Florence or exploring Tuscany (which Florence is a part of). If you really want to explore you might want to cut out a location and add days. I would say cut the CT and add those days to exploring the small towns of Tuscany. Rent a house or apartment for a week and really take the time to explore.

Donna

Travelers are just tourists who think they are superior to everyone else.

What the heck is an authentic traveler? What is WRONG travel? The right trip is one where you have a good time. Figure out what you will enjoy the most and just do it. I like to plan ahead but that's just my personality. It may not be yours. I'm flexible and don't follow my plan slavishly. It's okay to have an idea of what you want to see. And it's even okay to wear a fanny-pack. It's not fashionable but who cares? You will have a better time and less pre-trip anxiety if you focus on what you want to do and stop worrying about labels. I think your schedule sounds good. Have fun!

Ben, I hope I can help to allay your anxieties. First, keep in mind that this is your (plus your travel partner's) trip, so I suggest asking yourself, what do we want to see and do the most? We had the same itinerary in 2013 and had an amazing trip - in 14 days. If your desire is to see the Cinque Terre, Florence, Tuscany and Rome, do it. We did. We just didn't cram every single activity and fill in every single moment with structured activity. This allowed us to get a feel for each locale without making us harried. Hitting all four of those destinations enriched our Italy experience, because we got a taste of the city, the country, small town life, and the seaside. If you appreciate all of those things, what could be better?

What my husband and I found helpful in planning our trip was to make a "must-do" and a "maybe" list of things we wanted to do and see. Fortunately, we were able to do most of what we wanted and we came home enormously satisfied.

I hope you have a wonderful trip and discover at least MOST of the wonderful things there are to discover about Italian life. It won't be that difficult, trust me!

Ben,
You have what every first time traveler has. Too many expectations. Take a break from planning!
Where are you flying into and out of? Do you know how long it takes to get from point A to point B?
Donna has the right approach, spend a week and Tuscany. If you position yourself right in an agriturismo, you will be able to take a day trip to the Cinque Terra, visit a lot of quaint villages and visit Florence.
All without packing and moving around.

I don't think your plan is too fast paced at all. 4 areas in 17 days is quite reasonable and even leisurely compared to some people's itineraries. I also think your plan of having an outline of places you want to see but being flexible enough to change it and even let some desired things go if necessary is the way to go. I'm also a planner, usually have all destinations and reservations for accommodations there determined ahead of time, as well as transportation between destinations. Within that plan my days of sightseeing are quite flexible (except for places that require advance tickets or reservations). I also leave enough time in each day for some relaxing and enjoying a picnic in a park or just sitting at a cafe and nursing a beverage and people watching. This plan has worked well for me for many many trips to Europe.

If this is your first trip abroad (not just the first to Italy) the anxiety is certainly understandable. Until you do a trip or two and find your travel style it will be there, and maybe always will be. Most people I know, including many on this forum, who are well traveled still have pre-trip anxiety before each trip. It goes away as soon as you land at your first destination.

There are lots of ways to travel. I spend a lot of time at the beginning of planning, mapping out destinations, airlines, trains, reserving places to stay. Also I make a timeline of when things need to be done, ie train tickets by date to get the economy rates. And then I forget about it for a few months. Otherwise, I would be burned out by the time I leave. I know what I want to see but sometimes while on a trip, I need a day or two for wandering or resting or sitting in a park or church. For me a trip shouldn't be so scheduled that there is no room for some down time as needed. As the trip grows near, I get into travel mode and think about it more.

For some people, freedom is arriving at a town and looking for a place to stay. For me, freedom is having a place that is in the neighborhood that I want, at the price I want and don't want to spend my travel time looking for a place. There are all kinds of ways to enjoy a trip.

Happy planning

Ben,
Recognizing your desire to achieve a balance between planning and free spirit is a great step towards obtaining your goal. Here are some tips for enacting your goal:
Create the list of all the things you think you might want to do, but keep in mind it is only a list and not a mandate.
Ask, and allow, your travel partner to help define the destination and pace. Keep in mind 17 days can be a long time traveling together so allow for each person to have some time alone to do what they want to do.
I suspect you will come off the plane highly charged to "get going" and nothing will sate this need until you "get going". However..... When you arrive at your hotel make your first destination a walk around the block/immediate area of the hotel. Stretch the legs, smile and find a place to sit down outside and drink a beverage and savor a snack while watching humanity flow past. Relax. Now you are absorbing experiences and increasing the probability of creating wonderful memories.
In order to "explore" consider trying to get lost. Jump on public transport without a set destination and get off at a place capturing your fancy. Walk about an see what you can find. We often do this in order to get out of the main tourist zone in order to find places to eat. We like the adventure, and often less expense, of eating in non tourist places. Can language be a barrier? Less so today w all the available translation devices, but even so "who cares?" as this is part of the adventure.
You are going to "miss something" dispite all your planning. You are going to "find something" as a result of not following all your planning. Most important, strive to allow the time to create wonderful memories.
Ciao!

Remember to breathe. Travel is adventure, not work, so you can't do it "wrong".

To balance your desire to experience the places you visit and not miss your must-sees (emphasis on your) I would suggest making travel days between destinations your "free" days, rather than have plans that can be undermined by a late train or bus, traffic detours, etc. I like to travel in the mornings, leave my stuff at the hotel if it's too early to check in, and wander around for the rest of the day. If I can put in something from my "must see" list, it's a bonus and frees up more time the next day. But I need some "flex time" and this works for me.

I am a micro-planner on paper, but I often scrap the day's plan (or part of it) if something else presents itself. I don't schedule more than two major sights, or one major sight and two minor ones for the same day (for example, Vatican Museums and Saint Peter's Basilica, the rest of the day free), but I don't have the energy I did 30 years ago, you may be able to add more and still be happy rather than stressed. This leaves time to sit in a piazza and have a drink, just enjoy the place, and reflect on what you've seen and done.

I also have a lot of pre-trip anxiety about whether I have planned the best possible trip. One day more or less here or there - I really stress out about these things. You have enough time for each stop to not walk away feeling shortchanged. Assuming you mean seventeen days on the ground in Italy, I might allocate five nights Rome, four in Florence, two in Cinque Terre and four in Tuscany outside of Florence. Just remember, it does not have to be perfect. Your job is to fill seventeen days, not to see everything. You will make mistakes, but still will remember this as a great trip, I am sure. Your itinerary is very do-able in seventeen days. Don't worry about traveling in the wrong way, there is no wrong way as long as it makes you happy. There is a strong temptation to focus excessively on goal-oriented tourism in Rome and Florence - by which I mean just checking things off a list of things you "must" see. There is really that much that is great to see in both places. As RIck says, assume you will return. Set aside time to slow down and just be there. Cinque Terre and Tuscany outside of Florence are good for that as well. Don't feel as if you have to see all of Tuscany, because it's too much. Sienna and Lucca are nice stops. San Gimignano is a nice stop from what I recall, although I think some may say that it panders to the tourists. Orvieto is in Umbria, not Tuscany, but I always thought it looked nice in Rick's videos. Book your Uffizi tickets in advance, and consult Rick's book for advice on the Vatican Museums (our last visit we stood in line for three hours). The Borghese Gallery in Rome is a gem that we only made it to on our third visit. I would advise booking your hotel for each night and working in spontaneity elsewhere. Italy is expensive and otherwise as in much of Europe you will end up compromising on location, value, comfort. The only part where you might consider driving is the Tuscany outside of Florence portion. I have driven in seven or eight countries in Europe, but personally I would avoid driving in Italy. Transportation is very good in Italy, although for some stops you might find yourself taking the bus instead of the train.

Ben,

You have received very sound advise thus far.

My 2 cents:

It's good to plan for you trip but just keep in mind that this is your vacation & it should be a fun experience, not one where every second of the day is perfectly planned.

I don't know if you've traveled abroad before, but one big mistake that many tourists make (including myself)
on their first trip is to over-pack.
If you travel with a medium to large suitcase, it will be more difficult to travel, especially if using public transportation.

So... travel light and enjoy your trip!

Ben, I think you are on the right track. You will be both a traveler and a tourist, and hopefully will not be obnoxious at either. It is important to visit the places and sites that are the most important to you, and it is also important to take the time to smell the roses, taste the foods and enjoy getting to know some Italian people. So, don't even try to program every part of every day.
You don't indicate what season you will be traveling. High season, roughly May through September will be crowded with visitors in the most popular areas, and will often be very hot, especially in the late mornings and afternoons in the summer. During those months, it is probably more important to map out your trip and book rooms in advance. Also, plan some down time during the afternoons, ideally in your room, but at least in a shady park. In the off season months, you will have more flexibility if you choose to not lock in lodging in advance, you likely will not have such heat, but you will have shorter daylight hours and.likely some rain.
You also don't indicate the particular interests of you and your traveling partner, whether those include history, art, being outside in nature, cuisine and wine, photography, shopping, etc. etc. if you give us a better idea, many here on the forum could share their own top "must see or do" sites.
Italy is wonderful, you really can't go wrong, as long as you avoid some of the pitfalls. Do not travel with many or large bags that turn every travel day into drudgery. Follow basic safety guidance, so no one takes your passport, credit/debit cards, stash of cash, or valuable electronics. And, don't program your time so much that you return exhausted with bunches of photos but no real memories or experiences or passion to return again and again!

I think one thing that really helps one feel less jumpy about travel is to start learning about local customs and manners - here are a few things I learned about Italy, some in advance and some as I went along: in a shop, say hello to the people working there before examining the merchandise. At a produce stand, ask for what you want rather than picking up the fruits and veggies yourself. In a restaurant, the check will not be brought until you ask for it - leisurely dining is a virtue (and a pleasure). When checking in at a hotel, you will need to give your passport - it is copied and a copy given to the local police. You'll get it back perhaps as much as a couple of hours later. At checkout, you pay a separate city tax in cash. If you visit churches, modest dress is a must - no bare legs or shoulders. I'm sure there's a lot more, but that's for starters.

Ben, we did four cities in 10 days back in November. While it was most definitely not enough time (and knew this going in), we went for it anyway, and had the best time of our lives.

The key for us was having a short list of non-negotiables for each location, planning out a logical, sequential sightseeing path that eliminated redundancy, and remaining fluid on everything else. It made all the difference. Anxiety subdued. And because we were so relaxed, we ended up seeing even more than I expected.

I'd suggest reading Rick's Europe Through the Backdoor Guide from cover to cover and then do the same with his regional travel guides. A solid plan "should" go a long way to reducing any anxieties. It did for us.

I see it like this: planner + explorer = "authentic traveler"

Happy Travels!

And realize that there may very well be glitches - which sometimes make for the best stories. I say that as a planner myself of 15 trips to Europe with a variety of different groups of friends. I have always been the "leader" and in charge of organizing. I know what anxiety is. Sometimes I make a mistake or there is a strike or a lost drivers license, etc. but it is amazing how it all works out. And we are always "making memories" and lots of things to laugh about. Just tell yourself that you can do it and it will be wonderful - and it will be. It is possible to be organized and still relax.

We spent a week in Florence, the best thing we invested in was the Firenze card, allowing us to bypass all the queues to major attractions. Don't miss Boboli Gardens, for a wonderful relaxing day.

Also, very "touristy", (which isn't a problem for me), is the city tour open top bus. You see all the city, jump on/off at your leisure & learn some fascinating history & information, at a great price.

We found the CT far too busy, beautiful, but crazy. When you catch the trains, walk well into the tunnels to avoid the crush. It really is that bad.

Italy is beautiful, relax & enjoy it. Take your time, sit outside a cafe, with a coffee or ice cream, & simply watch the world go by.....

Well, it is a constant struggle to try to "be a local" and try to see as much as you can, because there are so many great sites. I think the best way we have found is to make a possible plan of things to do, make sure you prioritize them, then take it as it goes. Make sure you get in your "must sees", then from there just see how you feel and what seems good at the time. That way you will have time to just wander, but still see the things you want. When I plan this way then the pre-trip anxiety lessens.

I think what you mean by being an authentic traveler is to be off the path of tourists. So, take time to wander back streets, talk to locals, eat where there are few tourists. But, unfortunately, you will still look like an American tourist, but you don't have to be obnoxious. And, I do wear a fanny pack, am not obnoxious, and spend time off the beaten path.

17 days to explore 4 areas allows you time to see many highlights. Try to visit your top priorities first thing each day, when you're feeling fresh, so you don't miss those. In Florence and Rome, make reservations for the major museums. Once you've covered the must-sees, you have time to improvise, mixing some of your might-sees with serendipitous discoveries. "Follow the wind" for an afternoon. It's one day at a time and one step at a time when you're there. If you had twice as long, you still wouldn't see everything. Expect that you will return.

Everybody's first trip to Europe is a true learning experience. You have received a lot of great advice so far. The piece of advice I like best (from Laura) is to expect to come back and for me? Well, I try to remember to always leave something to come back for.

And, of course, you are going to Italy. No matter what you do or how you do it, you are guaranteed to have an amazing time! Feel excited!

The 'planner' part of me wants to have a great itinerary for every city and make sure I don't 'miss' anything.
But the 'explorer' part of me wants to taste this country like a local. Follow the wind. Explore the town on my own terms.

BTW when you say 17 days does that exclude the arrival and departure day? Otherwise we're down to 15 days, and each time you change towns count on losing 1/2 a day as you pack up, travel, then find the new hotel & get settled in.

You'll have time to see main sights but the "casual explorer" part may be harder. That takes time & serendipity. For example we were staying in Perugia and they have a small privately operated railroad line (FCU) there; actually it felt more like a streetcar like you might see running down Market in SF than a train. We took it to Todi and had a delightful day there. But we could do that because we had the time to say "lets take this and see what Todi is like" and not 3 places to cross off the list that day.

I don't think there is "right" or "wrong", but you'll have a different set of experiences depending on how long you can stay in each locale. Also a car is advantageous when visiting Tuscany/Umbria. We have visited the area both ways, and a car gives you the flexibility to go to hilltowns & villages not easy visited by train, as well as spur-of-the-moment sights you see driving down the road. If you rent a car just be careful of the ZTL areas.