21 day trip

You might want to stay in Milan area for a day--to decompress from the flight.
I'd suggest working your way down to Rome from there--depending on what stops you are making.
Hitting the ground and then getting on a train is just a little too much. Point to point tickets are preferred, and many will purchase their tickets on Trentalia.com up to 120 days ahead of time to save $.
It's a shame you're not flying open jaw--into Milan and out of Rome. That's the preferred way of travel.

By 21 day trip, do you mean that you plan to do Rick Steves entire itinerary as written? Just so you known, if you are not doing this as part of a tour most people would find it overwhelming and/or completely crazy unless you are young and super energetic. Take out a few of those cities and go at a more relaxed space. You'll be so glad you did!

Rick's Italy plan has you sleeping in 11 different beds over 21 nights. I think this is too much to manage comfortably on your own without extensive prior experience. I would suggest a maximum of 7/8 stops, allowing a 3 night average stay.

Como - 2nts
Venice - 3nts
Florence - 3nts
Orvieto - 2nts
Sorrento - 4nts
Rome - 4nts
Cinque Terre - 2nts
Milan - 1nt

This is the Rick Steves travel forum. I don't agree with recommending a pace that's slower than his ideal three-week trip.

I basically did a very similar trip to his ideal itinerary 12 years ago, minus the Dolomites and Assisi. We still feel it's the best trip we've ever taken.

It all comes down to your personal traveling style. But if this is your first trip, you probably don't know what you're really going to like best. If his recommendations don't sound too intimating, by all means soak it all and look forward to spending more time in your favorite destinations in a hopefully soon future trip.

I just read the suggested 21 day itinerary. It is certainly one way to visit Italy. I don't think even Rick Steves describes it as "ideal." If a person travels light (quick to pack/unpack, quick to move around with luggage) and just wants to get a taste of each place, it's possible. It does involve a lot of moving around and you certainly have to know in advance what the bus and train schedules are and be prepared for delays. Also, you have to be able to get your bearings in a new place very quickly, or you'll waste all your time just trying to find your way around.

Does the book give you more directions - like whether to take the train or the bus, if you should stay near the station (you have to drop your bag before sightseeing on arrival, pick it up after sightseeing on departure)?

This 21 day plan is almost identical to the 17-day RS guided tour, without Sorrento/Naples. With a guided tour, you have door-to-door (or near enough) transportation, no backtracking to/from hotels to pick up or drop off luggage, no hassles figuring out how to get from the bus/train station to the hotel, little or no waiting to get into sights, and a guide who knows the way. Frankly, I don't see how someone on his own can duplicate a tour schedule and still manage to see the sights, take the self-guided walking tours and enjoy the trip.

Those of us who think the plan is too fast-paced are just trying to alert Nicolas to think carefully about the plan.

Ditto to Chani's post. Rick's suggested itinerary might be right for some travelers but it has too many moves for us in too short a time. As she explained, the types of itineraries presented for his organized tours eliminate some time independent tourists would have to spend to accomplish the same. While the 21-day plan is presented as an independent itinerary, it's pretty close to the 17-day tour + Sorrento/Naples, as Chani pointed out.

Getting to/from train stations, finding the hotels and unloading the luggage and then acclimating yourself to new city by yourself are all pieces that can eat up more time than having a driver that takes you more directly to where you need to go, no need to unload bags until the end of the day, and a guide to lead you around. We don't mind doing the job ourselves but allow more accommodation nights to get that done at a more (for us) leisurely pace. Our interests also require more days in certain cities which provide oodles to keep us engaged.

You know best what your travel style is, and it's YOUR trip so if you're confident and comfortable that you can keep the pace then by all means have at it! It's worth the conversation, though? Personally, djp_syd's itinerary looks to be more manageable.

I see none of us have really answered your ticket question, and I'd guess that's because most of us just purchase point-to-point with the more expensive segments on fastest trains booked early to snag super-economy/economy fares when available.

IMHO you are better off just renting Rick's videos than doing this kind of rush rush trip where logistics eat up half your time. We used to do 3 week European trips every year; now that we are retired we do longer trips. For 3 weeks, we usually anchored in an apartment somewhere in week one and three and road tripped or moved to several locations during the middle week. One week of hit and run even when we stopped for 2 or 3 nights was enough. If you base in a large city like Paris or Rome you also can vary the experience with dozens of day trip options in the region without having to uproot and move hotels every day or two.

To put it as simply as possible, you will be waiting for buses and trains, they will not be waiting for you (as on an organized tour).

You will also be looking for places to eat, you will not be taken to them. You will have to figure out the correct bus stop or walking route to get where you want to go. A stop at the TI office can take time, even if there is no line. Don't have appointment times for the big venues? Wait some more.

I'm guessing Rick Steves would say a 21 day trip to Italy is not ideal, but for a trip that length, his itinerary is his best. That's why it's listed as "Italy's Best Three-Week Trip" in his guidebook. If it wasn't, I am sure he would recommend otherwise. I have his book right here and I don't recall anywhere that he recommends slowing down or that his itinerary is too much for independent travelers (and it isn't - I've basically done it). Instead, he constantly suggests getting the best bang for your buck and making the most of limited time.

And let's be honest. It's really not that hard. Even for big cities like Rome, you can get off a train, get to a hotel in a suggested Rick Steves home base and off sightseeing in under an hour most of the time. Worried about finding a place to eat? Make a reservation beforehand at a recommended Rick Steves restaurant. Or be adventurous and try the little hole in the wall on a random side street. Making early reservations at big sites? Rick recommends doing just that before arrival for smart touring. It's all about preparation (and a little flexibility when things don't go exactly as planned).

Sure, this is worth the conversation, but I'll bet most people suggesting to slow down have more time as retirees or have had the good fortune of being able to visit Italy multiple times. That's a nice luxury to have. But I'm guessing that's not the OP, who is trying to make the most of his 21 days and doesn't know when or if he'll be back.

Frankly, suggesting the OP is better off watching videos instead of attempting Rick's best 21 day trip is both laughable and wrong. There can be a big difference between rushing and making the most of your time. Yes, we all have different travel styles, but Rick lists his "best" itinerary for a reason.

As for the OP's itinerary, while not necessarily answering his train question, if flying in and out of Milan, you might consider taking the night train from Venice to either Rome or Naples/Sorrento and then working your way back up the Western peninsula. That could eliminate some back-tracking and save a day for better touring.

I know that the recommended itinerary is feasible and have followed similar plans since my first trip to Europe. It's correct that you need to be organized and also you need to get an early start each day. If you read the Italy book all the way through during the planning stages, you'll have all the info you need, such as where to take a bus instead of train - uphill from Bolzano, to/from Siena (1x/day to Assisi, see p. 657), and along the Amalfi Coast.

The easiest single change to reduce different hotel stays would be to skip the night in Milan and go straight to Varenna by train on the arrival day (Malpensa-Milano Centrale-Varenna takes about 2 hours, no need to book tickets ahead). In that case, I'd give the extra night to Venice, since it's my favorite.

The price of the 8-day Italy pass depends on your age and number of travelers. For two adults traveling together, 2nd class costs $286 per person or 1st class costs $356. Only a couple of those travel routes would have hop-on convenience, since you have to stop to activate it in Milan and to get some seat reservations (another $60).

For 2nd class, this exactly breaks even with the full-fare ticket rates shown on the map, which I add up at $345. If there's any longer leg that you want to book ahead, some advance discounts could bring the total a little lower, so I think point-to-point tickets come out ahead.

Sweeny, it's interesting that the majority of respondents think it's too much. I respect Mr. Steves but it's too much for our style (and we're not retired, BTW) and just because it's in the book doesn't mean it's right for everyone. You're certainly entitled to your opinion but sorry, NO guide is the do-all, end-all, and NO itinerary will work well for everyone. And I mean that very respectfully. Honestly? I think Rick would applaud intrepid tourists who bring different perspectives to the table and alternatives to following his suggestions to the letter. They are suggestions; not hard-and-fast rules.

I think a lot of us here aren't even recommending slowing down to a significant extent but enough not to be packing up and moving as much. There's more to Italy than Top 10 lists, and this sort of schedule doesn't allow for those things. The majority of places my Husband and I have stayed or eaten at aren't in the book (we never make reservations, BTW) and we've had a marvelous time on ALL of our trips. Many independent travelers bring their favorite experiences and first-hand knowledge back to the forums to share, and we're encouraged to do so as The Man himself recognizes that one size does not fit all.

What Kathy said.

Kathy, yes, I do agree it's very interesting that so many on this thread are at odds with Rick's best itinerary. Again, I'm guessing the main reason is difference of perspective. Maybe referencing retirees wasn't my best choice, but I'm sure the advice is still coming from folks who have more available vacation time than the average American (and you didn't deny you had been to Italy multiple times). The game changes when it's potentially a once in a lifetime trip when you go in not knowing you will ever make it back. It's exactly from this perspective that he recommends his itinerary. Sure, it's only one man's opinion. He says as much in the book. But he also says he's developed a sixth sense for what travelers enjoy. Considering the empire he's built, I think he's probably right.

I do also think that Rick appreciates the differences of opinions, even when it's different than his own. Where I'm really taking issue are the over-the-top comments that suggest his best 21-day trip is "completely crazy" or that "you are better off just renting Rick's videos" than attempting it. Sure, everyone has a right to their opinion, but I'm guessing even Rick would find those comments silly. And just plain wrong.

to each his own. We have been traveling for decades -- so we once were young travelers -- and have never understood the idea that 'covering' lots of destinations in a short time necessitating spending most of one's time on logistics made sense. My mother had one 'trip of a lifetime'; She was 80; I escorted her for two weeks in Italy. We spent a week in Florence, a night in Siena (on a drive to Rome to make it easier on her than public transport) and then a week in Rome. I was just looking at the photo album I made for her after that trip and had pride of place on her coffee table the rest of her life. What makes a trip a trip of a lifetime is the quality of the experience not how many boxes you can tick off as you drive by.

Being there beats getting there. But if you do want a hit and run 'best of' type trip then an organized tour has its charms because then the logistics are taken care of.

I personally would never want to be part of an organized tour. I want to go at my own pace and I've never felt logistics are that big an issue if you are organized and prepare beforehand. But I would never disparage those who prefer to travel that way. My in-laws preferred tours when traveling overseas. Yes, to each his own.

It's great you were able to have a trip of a lifetime with your mom that was at a pace ideal for you. Twelve years we had our own trip of a lifetime with our then nine-year-old that was similar to Rick Steves' 21 day itinerary. We still consider that the best trip of our lives and I guarantee we were not "better off just renting Rick's videos." At no point do we feel our quality of experience suffered because we were on the go. In fact, we are using our own pictures and videos from that trip in our plans for this summer's return visit with our now 11 and 9-year-olds. Other than closing with five nights in Venice, it will otherwise be at a similar pace as our first vacation. It sounds like you wouldn't be able to handle that, which should be fine. But I'm sure our memories from our trips will be every bit as cherished as yours.

(and you didn't deny you had been to Italy multiple times).

That question was not asked so I didn't deny anything. Rome has been the only repeat Italian destination so far.

But that's not the point, which is while all of us agree that there's no 'wrong' where personal style is involved, the itinerary proposed would involve too much moving around for most of us. We're speaking with the benefit of firsthand experience with our own independent travels and are simply sharing the rationale for trimming a bit with the poster. You've been free to disagree from your own perspective as would anyone else who would be/has been fine with the more aggressive itinerary.

I'm not taking issue with that as much as the idea that just because Rick has a suggested itinerary in the book means that "his itinerary is best" for all: period. It's not, and I'll bet you a shiny new 2016 guidebook that he would agree. :O)

"But that's not the point, which is while all of us agree that there's no 'wrong' where personal style is involved."

I 100% agree, but reread some of the posts here. When someone calls Rick's Best Three-Week Trip "completely crazy" and "you are better off just renting Rick's videos", that suggests that doing so is the wrong way to travel.

It looks like you are taking issue with something that has never been suggested. I never said his Three-Week Trip is best for all. Rick lists his best itinerary for a reason, but also it isn't for everyone. In my very first post in this thread, I state it comes down to personal traveling style. But for those who are attempting to follow Rick's Best Three-Week Trip, I can confirm it is not only feasible, but enjoyable.

Ideal certainly seems to imply "best".

I think some can do it, but the OP might not understand how much is taken care of for the traveler on a guided tour versus duplicating it on your own.

"Ideal certainly seems to imply 'best'."

Look folks, it's really not that hard. When Rick Steves puts together his 21-day itinerary for his guidebook, he is listing his best/ideal three-week trip. It is only his opinion and that doesn't equate to meaning it's the single best/ideal itinerary for everyone. No one in this thread, including myself, has said otherwise. But just because it's at a pace that's not desirable for some posters, that doesn't make it the wrong way to travel. And saying so on Rick Steves' own travel forum is just silly.

I have been to Europe on five vacations before taking Rick Steves 17 Day Best of Italy Tour. On those 5 vacations I have planned the vacation and have traveled without being on a tour. I consider myself a pretty savvy traveler, but there is no way I could duplicate the 17 Day Best of Italy Tour in 17 days. Trains don't always run on the schedule that you want them to run on. You could waste a good portion of the morning just waiting for a train. Rick Steves might be able to do it, but I wouldn't recommend it if you haven't traveled a lot in Europe.

@the Sweeney, is it okay to have a different opinion from yours? Just checking.