Itinerary guidance

For the Dolomites check out:
https://www.suedtirol.info/en/en/experiences-and-events

Your Hotel in the Dolomite region will give you a free bus pass good for your stay. However the costs for lifts have gone up a lot.

And if you are into hiking Gillian Price has wonderful hiking guides to the Dolomites.

You're covering a lot of ground. I would re-examine any locations less than two nights.

Florence 3 nights Lucca 1 night (possibly 2 - short 1/2 day trip to Pisa)

We recently spent 3 nights in Florence, which included a day trip to Pisa in the morning (leaning tower climb, of course), then to Lucca for the long afternoon. It would be possible to add a 4th night in Florence and do a similar day trip just to save time checking in and out for only one night. It would be a long day.

Vernazza (Cinque Terre) 2 nights

Navigating in and out Cinque Terre via train can be cumbersome. Perhaps leave out CT and add more time to other locations?

Bolzano 1 night (possibly 2? - Just a pitstop after a long travel day) Castelrotto (Dolomites) 3 nights (use buses to explore)

Combine into one stay or consider replacing both with Ortisei.

Looks like a great start! However, I'm exhausted just reading your literary. 3 weeks will go by fast---I would think about fewer hotel changes. Giving you time to stop and "smell the roses". But you know your travel style so really think about how much time you actually have in each town. Good luck! You will get lots of great advice on this forum.

Agree, it’s hard because it’s such a personal thing, but even though you have the cruise to look forward relaxing on, I’d want at least one more significantly longer (4-5 day) stay in there somewhere, preferably two.
Of course you must decide what to leave out based on what is appealing to you, but you could do some consolidating to be sure. I’d rework the order so as to avoid the long train ride from Florence to Cinque Terre. Just a thought to ponder: could you insert some mountain exploration/hiking while you have the car, or did you have your heart set on Dolomites?

The RS guidebook recommends Castelrotto but many people (including me) have found Ortisei a better base. There are lifts from Ortisei up the mountain to hiking, no bus needed. Or you could take the bus to another area. I suggest looking online at walking videos people have posted of Castelrotto and Ortisei so you can get a sense of the two towns. If I was doing your trip I would push on via bus up to Ortisei (just one hour further) to avoid the pack/unpack nite in Bolzano. The Dolomites are a bit pricy, so you may want to check lodging prices before you commit to going there.

Instead of Vernazza you might want to consider Levanto which is where the Rick Steves tours stay these days. You can probably find more affordable options than in the CT itself, yet the CT is only minutes away by train.

Yup, IMO too much moving around and too many short stays.

One other suggestion would be to do the Italy trip at the end of your cruise so you take advantage of lighter crowds and lower prices.

Welcome Ange!

I have to agree with above- too much time spent traveling to and from and too many location changes.
Keep in mind a 2 night stay gives you just 1 full day in that location. Each location change eats up at least a half day- be brutally honest about how long it takes to pack up, check out, get to train station, travel to next location then find your lodging, check in, unpack, get oriented.
I count 30 nights and 13 location changes- that means you are doing all that almost every other day. The RS itineraries are too fast paced for my liking and his tours are nothing at all like traveling on your own. They are on a bus with guides that get them basically door to door to each location without all the in between time consuming stuff.

Check in time is usually 3-4 pm- hotels will hold your bags before and after check in/out but apartments usually won't. Don't know about monastery stays

I would try to combine a few locations and probably drop a few as well.

Rome 4- this is fine. More days would be nice if you are planning to see a lot. Make your list then decide how any days you need here
Colosseum/Forum etc on one day, Vatican on another day, Other stuff on third day but you also will have a jet lag day at the start where I wouldn't plan much- so consider adding a night to Rome.

Orvieto- 1- this is probably fine as well. We really loved Orvieto, I would give it 2 nights. Your only car rental option here is Hertz. The agency will be closed on Sunday, closes at noon on Saturday and closes mid day from 12-4 ish on weekdays.

Tuscany- I would give this bit at least 4 nights, or better yet- 5 nights. Drop the stay in Siena- you can day trip there from your agriturismo. Split those 2 nights between Florence and Tuscany agriturismo.

Florence- drop car here. 4 nights gives you 3 full days, one can be a day trip to Pisa/Lucca. Most museums are closed on Monday.

I would drop CT- a hassle to get to and extremely overcrowded, not really worth the trouble for just 1 full day.

Head to Lake Como next for 4 nights- drop Milan unless there is something you must see/do there.

To Dolomites- it will take better part of the day to get there- stay 4 nights.

Venice- at least 3 nights, I would give it 4 as it is a long haul from Dolomites

Ravenna 2

HI everyone!

Wow - a big thank you to all of you that have replied so far! Your advice is extremely encouraging and interesting. I am digesting & considering everything you have written. It certainly helps to hear from people who have actually travelled to these places vs heartless research online. (NickB) The link to the Tyrol site is awesome thanks!. I was aware of the free public transport pass, but this site is just what I needed. I like the idea of basing ourselves in Levanto for the Cinque Terre (thanks John), so am checking that spot out as an alternative. (Valadelphia) I hear you re: train route - my reasoning for that was there is 5 direct trains daily from Monterosso to Milan that take under 4 hours and I like the sound of the scenic coastal route vs inland one from Florence (which apparently includes alot of tunnels and basic farmland) but will relook at our plan. (Everyone/ChristineH) I can definitely see the wisdom in reducing our overnight locations and reduce wasted time, so I am working on that. In Tuscany, Orvieto appears to be the only place to rent a car (for a one way hire) if you don't want to drive out of Rome, and it's at the southern end of Tuscany so that is the logic behind my idea. Let me know if there are other options. However I think we will delete our Siena stay and increase our Agriturismo stay as a base rather than chop things up. (Nixit71) Yes I think we will increase our Florence stay and just do Pisa/Lucca as day trip rather than stay there too. Additionally we will drop Bolzano and increase our Dolomites stay. In the Dolomites - Oritsei would be ideal as a base but the accommodation prices there are through the roof. Plus I love the look of Castelrotto - I know this will just a be a taste of this area, as clearly you could easily spend several weeks exploring this area alone doing walking tracks etc. (Chris) we have to do the 10 night cruise last (after Italy) due to the time of year for our jobs (the lead up to Christmas in NZ is nuts), so Italy beforehand is a must. It will be a nice rest though! After the cruise we will have 3-4 nights in Athens before flying home.

I did have questions regarding the rental car in Tuscany: Is it easy to find petrol stations? I hear some people have had trouble with credit card payment using machines at unmanned ones? Is Florence hard to drive into if we opt to return car there instead of Siena (giving us a chance to drive through Chianti)?

Also: If you have any affordable accommodation suggestions for these places let me know. We aim to stay in Monastery's in Rome, Florence & Venice (if we cannot find anything that fits the budget). Aiming for an average of up to NZD$250/EUR125 per night but obviously some places may be more/less). We might be a bit old for hostels?!

Anyway with all this excellent advice in mind, so far my revised itinerary is down to 10 locations - with more perfecting to come:

Rome 4 nights
Orvieto 1 night (to pick up car - drop off either Siena or Florence if not too hard or scary?)
Tuscany/Val d’ Orcia (Agriturismo) 5 nights - New base
Florence 4 nights
Vernazza/Levanto? 3 nights
Milan 1 night (Hotel by station. We only want to see Duomo, Last Supper, Galleria Vittorio Emanuele)
Varenna 3 nights
Castelrotto/Oritsei 4 nights
Venice 3 nights
Ravenna 2 nights (need time here to see mosaic churches and do final laundry etc as no laundry facilities on cruise ship now).

Thanks again everyone for your help! I really appreciate your time and words! Keep it coming!

You can pick up a car in Chiusi-right on the train line and closer to your Val d’Orcia destination
Avis/Budget right near train station
Same open hours as I listed above
Probably better selection of cars in Chiusi
(Hertz in Orvieto doesn’t have a very good reputation)
That would eliminate Orvieto stay

We always book our cars thru AutoEurope.com -broker with excellent customer service
Always with Full insurance/No deductible
See what they offer
You can sign up as a member-they do have sales
Too early to book now but keep an eye on rates
Once you have booked you can still monitor rates and rebook if you see a better one

We have never had an issue getting gas
If you get a hybrid car you may not even need to fill up if you do the “bring back empty” option
(last 3 rentals we did that, really nice and eliminates some stress)

There are many threads here addressing pick up in Chiusi drop off in Florence with good directions
Search the forum -filter by Type and Date, look for posts by Roberto

Milan- you will need to grab Last Supper tickets as soon as they go on sale
Since you want that along with Duomo etc you might consider 2 nights
You won’t get to Milan til mid day so you’d only have a short window to fit all those things in
I believe both Duomo and LS close at 5

125 euro/ night seems a bit low-is that per person or for both of you?
Sept/Oct still very much high season and all of your locations are top tourist spots

We had a hybrid this year and it was great only having to gas up once! Just Google for the instructions on the gas station payment machine—I usually figure it out eventually but I have found them tricky on occasion. They do have English on them, it’s more that my bank is very security minded and has declined my card. Plus some of them charge you a larger amount and refund what you don’t use at the pump and that can alarm some people but it always credited me accurately.

I wonder if a lot of those stories about payment issues are from years ago when Chip and PIN was the thing in a lot of Western Europe. For Americans without that system being common, they would sometimes run into issues in not have a PIN. But now in 2026 with contactless payment being the standard, your phone or card eliminates all of that.

TLDR: I have never had a problem since moving to contactless payment.

Be sure to mix in a day somewhere around day 10 where you are not doing anything. The plan is to have no plan that day. You sleep in, grab a late coffee, read, relax, catch up with correspondence or journaling.

You are spending $10k on this trip. Splurge and have your innkeeper do your laundry for €40 while you enjoy the sights.

We stayed in Garni Cittadella in Ortisei last year. I found it on the Val Gardenia web site. It is a two star accommodation. We had a one bedroom apartment but they also have a small number of rooms.

It is hard to find places to stay in this area because little is listed on the big name sites like booking.com.

We were very happy there and thought it was well priced. There were many return visitors.

We loved being located in Ortisei which had has three different lifts and buses everywhere. We did not have a car.

Thanks people for those last replies as well. All so wise. Am looking up all details suggested. Love the Ortisei accomm suggestion thankyou - best I have seen so far. Yes you are right - resting is important so will try and factor that in. The hybrid car idea is an excellent economical suggestion also. As we currently drive a 30 year old Toyota Prado, it will be a treat to drive anything new! Driving on the opposite side of the road will be fun! Isn't it incredible how much research is required for Italy. Loving the process but my budget keeps increasing! Appreciate your experience and advice - it been massively helpful.

Question to Beth: Did the Garni include the free transport card for the area? (Guest Pass). They don't mention it on their site.

Yes, we got the free transport card. And it wasn’t mentioned on the site at that time (2025) either.

The owner does not speak much English. She speaks German (first language) and Italian. My husband speaks a bit of German and enjoyed using that. I used goggle translate to communicate in emails.

If you stay there, there is a very good pizza type place right behind and a gyro place not too far. Otherwise, we found the food in town to be pretty pricey. The Refugios have wonderful food at far better prices.

We are planning 5 nights in Rome, 2 nights in Tivoli (very close to Rome), 5 nights in Florence, and two final nights back in Rome. While I would love to see all the sights on your itinerary, all the location changes would make me insane. My brother in law spent three weeks DRIVING around Europe so his family could see EVERYTHING, and came home utterly exhausted. You'll enjoy yourself more if you "see" less.