14 Day Trip to Italy (Thoughts?)

Just off the top of my head:

Two days (1.5 days, actually) in or near the Cinque Terre probably isn't worth the effort to get there. I would skip it for this trip and add more time to Rome and/or Florence, especially because Lake Como has a similar vibe to the CT.

If you fly out of Rome, you will need to spend the previous night somewhere closer than Venice.

Keep planning!! It'll be an awesome trip.

I agree with Stacy. I think you're trying to visit too many places in the time available, and short changing a couple of places. I would also be concerned about travelling all the way from Venice to Rome for your return flight on the same day as your flight. Can you do a multicity ticket, flying into Rome and home from Venice? (Or vice versa).

If you must fly on a return Rome ticket, then consider travelling to Venice on your arrival day, flipping the itinerary, and ending with all of your days in Rome.

What time is your flight home from Rome?
I would be IN Rome the night before that departure no matter what time the flight is
Too risky otherwise

Bologna isn’t exactly “on the way” to Florence

A half-day in Bologna is barely enough time to enjoy a proper meal, never mind all the other attractions of that picturesque city.

Hi -
So what time of year are you looking at making this trip?
Who is traveling? You and.....??? Ages?
What are you most interested in doing/seeing on this trip?

I'm in the same camp as the others: you need to be IN Rome the night before a flight home. I'll also agree that Bologna is not on the way to Florence from Rome - it's north of Florence - and that you've too many destinations for the time that you have.

As Portovenere isn't accessible by rail, you practically have to travel to the CT (La Spezia) to get bus or ferry (in season) service there so you may as well just spend 2 nights in the CT versus 1 partial day + hotel change in both. Still, without knowing much about your interests, your travel group (if not traveling alone) or what time of year you're planning this for, I'd scratch both the CT + Portovenere, add one night to Rome and the other to Florence. If you haven't yet booked flights, a Venice> Lake Como> Florence> Rome order works better (fly into Venice and out of Rome) OR Lake Como>Venice> Florence> Rome order; fly into Milan Malpensa and out of Rome.

But some more info would help us to best help you. :O)

Is there any way you could prioritize these and narrow it down to 2 or 3 cities? It's easy to spend a week in any of these cities/regions, but especially Rome, Florence and Venice. Trying to squeeze in Bologna (not of the way, BTW), Portovenere, Pisa, Cinqueterre and Lake Como and the Rome, Florence and Venice isn't a great plan, especially when you add in transportation time, in and out of hotels, meals, laundry, etc. I haven't taken the time to check travel times or transportation methods, but based on my experiences, I doubt that it would even be possible logistically. It's pretty much impossible to do any of them justice if you're trying to do it all in less than 2 weeks.

I find trip planning works when you start planning out your days, what you want to see and do to know how many days you will need in one place, then start chopping things out. Without knowing this information it is hard to advise you.
Also one of the golden rules of travel I adhere to is no less than two nights in any one place.
For Rome is that Arrive in Rome day 1?If so you only have two full days in Rome not sure what you have planned, but that would allow you to go to two large places like the Vatican and The Colosseum. Things just take a lot longer than you think.
Florence, you are only spending 1/2 a day? I would omit Portovenere and Cinque Terre and add those days to Florence, while in Tuscany there is so much to experience. Lake Como and Venice looks like only two full days in each place.
How do you plan to travel between all these places?

At the risk of 'piling on', I will add/re-iterate these thoughts

1- Unless your flight from Rome is in the evening to a Euro destination, you need to be in Rome the night before the flight
( You do not indicate where home is so we just have to guess)

2- Bologna is between Florence and Venice, not Rome and Florence

3- Spending one night in Portovenere and one in CT creates a waste of time moving from one to the other and you have no time to waste
3a- Questionable to try to cram this area into the agenda, given the limited time available

4-If flight planning is still flexible, fly into Milan, go to Lake Como then Venice, onto to Florence ( make your stop in Bologna en-route) and then end in Rome

That''s my $0.02

I appreciate all the great feedback. Home is Anchorage, AK.
2 Couples/ No Children

Trip is through ItalyLux not sure if anyone has used them or heard of them. We've only done preliminary planning, travel to each location is either through private driver or rail. I've heard a lot of people can plan these trip on their own, I just wanted a one stop shop place to take care of all logistics. Let me know if this is not smart or I'm putting way to much trust in a 3rd party.

1st is the obvious, if the itinerary stays the same sounds like we need to get to Rome the night before. No issue.

Trip is May 4th through 18th of 2023, so there is plenty of time to make changes which is why I came to this site. You guys have some great ideas.

I guess I need get with the group and see if stay in Florence and scratch off Portovenere/Cinqueterre?

Food/Wine/History are our priorities.

I hope you haven’t paid a lot for this plan you were given.
If they think Bologna is on the way to Florence they need a better map

Your trip will be VERY easy to plan by yourself with some help from this forum and a good guidebook

I had not heard of ItalyLux, and after looking at their website, have no idea what it is they do.

If it was their idea to stop over in Bologna 'on your way' from Rome to Florence, I would dump them like a plague infested hot rock.

Never heard of the package tour company you are using. As Christine has said, I wouldn't trust a company who said Bologna was on the way to Florence from Rome.

Yes, i think you're placing too much trust in a 3rd party. There is wishing for someone else to do all the work, or ending up with the trip YOU wish to have for a fair price. They can be different animals.

I looked up ItalyLux, and it seems to be run from Italy.
However....Bologna is not at all on the way to Florence; and you would need a helicopter to get to Rome for a flight, from Venice, on the same day.
Balsamic tours sometimes take quite a few hours out of the day, as they take place outside the city generally.
Driving from Venice to Rome takes at least 6 hours; and that is with no traffic, no accidents, no holdups, no tolls.
Trains take nearly 4 hours, then you still have to get out to the airport from Rome, to check in.
Security and checking in at airports takes longer these days...3+ hours pre flight, depending.
Not trying to put you off, but this is a trip you could easily plan yourself....and you have over a year to do just that!
If you do go with a tour company, you definitely need to be in Rome the night before your flight home.
Or...could you fly home from Venice?
That would solve that aspect.
A good thing to do is to first get a big paper map of Italy, so you can spread it out to see where everything is in relation to the other places...easier than looking at it online.

Google shows them located in Aurora Ohio

No, no money paid (still well over a year out, May 2023). I think I need to dedicate some time to plan this ourselves. Sounds like this forum knows what they are talking about. Glad my friend who visited Italy put me on to this site.
I will get with my group and put a plan in place. Appreciate all the insight. I just reviewed the itinerary and saw where everything is, yeah doesn't seem to make sense.

Private Tours vs. Group Tours? Is there a place you can set this up or is this more of a once you get to Italy you set all this up?

There are lots of options for tours both private and group that will be recommended here and listed in Rick Steves Italy guidebook
You have plenty of time to figure out where you will want or need a “tour”
So much can easily be done on your own

Would it be possible to fly into Venice and out of Rome? Unless you can get a late morning flight out of Venice then I would consider flying home from there. Most people fly into Venice to avoid the early morning departure that will cost over $100 to get to the airport. Taking the bus to the airport is much cheaper but does not operate all night.

If you do want that one stop shop I would look at Costco they have some great trips and are reputable. My Sister in Law did an Italy trip through Costco and they really liked it, and they are experienced travelers, just did not want to put the work in on that one. All the Hotels were top notch and they provided all the train tickets, plus some meals were included (The hotel probably provided). I think it may have included private transfers from the airport too.

If you do plan it yourself (totally doable, these are all major cities), know that once you get to say Rome there are plenty of reputable tour companies that offer walking tours of the Vatican (Walks of Italy) or a Food walking tour (eating Europe). Same in Florence. Adding a tour to the day gives you structure and gives you insight on what you are seeing.

A good place to start is with a guide book and reading trip reports and watching you tube videos of people traveling to the places on your wish list.

If you have not already done so you may want to look at the "itinerary" of each of the Italy Tours.
https://www.ricksteves.com/tours/italy

Not trying to sell you a tour but it can give you ideas on a logical order to do things and highlight what the major attractions are in each locale.

Do not try to cover a tour's itinerary on your own. You will not have the dedicated bus to deliver you door to door, nor have a guide to take you the most efficient way from sight to sight. On your own it will take longer, but can be done.

The RS travel books do contain recommendations for local guides so you can set up specific tours on your own if you choose a DIY itinerary.

Happy planning

Joe32f has given you the best path for you’re locations. This is what it would look like excluding the Cinque Terre area.

1. Travel from Anchorage > Milan Malpensa (MXP)
   about a 20 -24 hour trip.

2. Arrive MXP. Train to Milano Centrale then Milano C. > Varenna Esino 2hrs 11m. (2H11m).

3. Varenna.

4. Varenna.

5. Train. Varenna Esino > Venice, Venezia S.Lucia. 4H07m.

6. Venezia.

7. Venezia.

8. Venezia > Firenze SMN, Florence. 2H13m.
   (Option to visit Bologna on the way.)

9. Firenze.

10. Train, Day trip to Bologna 38 min. Return 37m

11. Train. Firenze SMN > Roma Termini 1H36m.

12. Roma.

13. Roma.

14. Travel home.

If possible adding 3 days, one each to Venice, Florence and Rome will give you a much better experience. To enhance each city I’d do an intro walking tour.

Gerri’s plan is perfect as usual

If you really don’t want to do your own planning or just don’t have the time you might consider booking one of RS tours

This is the longest Italy tour he offers
https://www.ricksteves.com/tours/italy/best-italy

Or take a look at the My Way tour
https://www.ricksteves.com/tours/italy/my-way-italy

I will say that a lot of us here feel his tours are a tad too fast paced so use them as a starting point as needed if you do your own planning

You should definitely work on planning this yourself. Time & money are both precious, for most people. We are going to Italy July 2022 - me my husband & 2 college -aged daughters. I’ve gotten alot of valuable info from this website - the general info & replies to my questions in this forum. You go w/ a pre-packaged plan you may end up stuck w/ things you don’t want to do.. and researching /planning is half the fun!

Yep, that "My Way" tour Christine linked might just be a good option for your group. It's one way to have someone else manage the hotel bookings and transport logistics from place-to-place + have a certain amount of ongoing support during the trip, yet for your group to be able to explore the destinations on the itinerary at your own pace. You would need to order tickets yourselves for attractions you wish to see but you'll find lots of help about that here.

I will say that the itinerary is too rushed for me personally but you could (and should, IMHO) plan to arrive in Venice one or two days in advance of the tour start, and add at least two more nights to Rome after the tour wraps up. Rome, especially, needs MUCH more time than the 2 nights/1.5 days the tour allows. Many of us consider 4 nights/3.5 days to be minimum for that one.