8N Italy itinerary

I would switch your itineraries for 5/21 and 5/22 - just in case you still have some jet lag.

I think you're giving Florence and Venice a short shrift. If you're choosing Venice over Florence, drop a day from Siena, skip Florence altogether, and add that day to Venice.

But at the end of the day, it's your trip - go with your gut.

Agree with Frank- you are shorting Venice as well. It looks like you would not even get there til the evening- then you have just 1 full day before departure in am.
If at all possible try to fly IN to Venice, OUT of Rome. Several reasons- Venice is a lovely place to get over jet lag and not as intense/busy sightseeing as Rome. Most flights to US leave very early in the am so it’s a pain to get to VCE- not impossible- just more planning/possibly more expense.

It’s OK to skip Florence, really it is. You will be back. You can always day trip from Siena if you change your mind or weather is lousy for driving around Tuscany. And I do love Florence, I feel like a quick few hours would just frustrate me!

Fly to Venice 2 nights
Train to Florence- change to Siena. 3 nights
Spend this day/evening In Siena
Pick up your car in Siena on your 2nd day there. Make sure your lodging has easy access parking. Visit Montepulciano on 1 day, visit SG/Volterra on the other.
Train to Rome- 3 nights
Fly from Rome.

Venice 2
Siena 3
Rome 3

5/19 – flight DEN to VCE

5/20 - N1 – Venice
5/21 - N2- Venice
5/22 - N3- Train to Florence- change to Siena
5/23 - N4 –Siena— pick up car this morning in Siena and day trip SG/Volterra
5/24 - N5 – Siena- day trip Montepulciano/Val d’Orcia
5/25- N6- Drop car —train to Rome (change in Florence, probably) arrive Rome 12ish? And not jet lagged- you can see a lot this day- Pantheon, Heart of Rome, P, Navonna etc
5/26 - N7 –Rome- Vatican/St Peter’s
5/27 - N8 – Rome- Colosseum, etc

5/28 - fly back to DEN from Rome

TBH- since you said not so many museums, I would skip the Vatican and go to Borghese instead. Borghese is a timed visit- 2 hours- just wonderful and not the mob mess/time suck that the Vatican is.
Walk thru Villa Borghese park and down to P Popolo for a spritz after your visit.
You'll return to Rome.

I didn’t check days of week so don’t know if that itinerary order works as far as openings/car pick up, etc.
Make sure you do your homework about driving in Italy- lots and lots of threads here on forum.

Another thought, 5/25 can you do the day trip to San Gimignano then on to Florence? Return the car and take a late afternoon early evening train to Venice. This would give you 5/26 and 5/27 for Venice. Two days is short for Venice but better than one

Thank you all for the comments. I wonder why it never occurred to me to go to Venice first and then fly out of Rome. I am going to look into that! Appreciate the feedback that Venice needs more time, at least 2 full days. -M

To give Venice 2 full days you would actually need 3 nights
Your arrival day only counts as a half day

3 night stay = 2.5 days, 2 night stay = 1.5 days …

Each change in location will take a half day minimum
Pack up, check out , get to train or pick up car, travel to next location, find your lodgings, check in, unpack, get oriented.

I urge you to reconsider driving on this trip. I had a very frustrating experience driving in Tuscany and Umbria this past spring. I have driven in mountainous regions of Portugal and Spain, in rural France and in Sicily from end to end. I even spent a few days on the Amalfi Coast with a car and never ever had the difficulties I had in central Italy. Here's the link to my April report. Learn the ins and outs of driving in Italy before you commit. I went to Montepulciano in mid-March and had no trouble finding a parking place. Italy was just reopening to tourists and the town was nearly empty. In mid-May next year, I would not be confidant of finding parking right away. San Gimignano, I was told, was worse (one of the reasons I deleted it from my itinerary). Consider taking the train (preferably from Venice, but Rome if that ends up being the plan). Use the bus to visit Volterra or San Gimignano. I really don't think you'll see more with a car than by bus and train.

3N Venice (2 full days)
2N Siena (morning train, 1.5 days)
3N Rome (morning train, 2.5 days)

I suppose you could return to Tuscany and only go to other towns. But you only "need" to visit Siena once. While it is especially suitable for an overnight, it's very different from the smaller hilltop villages. It's also a different kind of art destination than the places where the Renaissance arrived earlier. Because your trip is so short, it may be better to eliminate Siena and the car rental. I'll accept Florence as a substitute, and as on-the-way to Venice. But Florence is not "hill towns of Tuscany" either.

Because it's such a transportation hub, the chance of returning to Rome is very high. Because of continuing over-tourism, I would make the most of an immediate visit to Venice.

Chani,
Thank you for the caution about renting a car. I see another word of caution to research driving in Italy before committing, so we will definitely research options before doing so. Loved your trip report too! You did have some adventures with navigation. I live on Google maps and I do whatever it tells me to do here in the States, but see from others it will probably lead me astray in Italy. LOL

My only other experience driving in Europe was in Spain. Rented a car (automatic) from Granada and drove to Nerja and then to Ronda and Arcos, and then to Seville. It was pretty painless, and they drive on the right side of the road there. I can drive a manual transmission but it has been a few years since I have done so. Also wonder at the size of car we would need. While I managed to only need carryon size luggage for Spain, I wonder if I would be able to do the same for Italy with probably colder weather in the evenings in May. We might have larger luggage is what I'm saying and wonder if it would fit okay in a car.

Also - putting a manual transmission in reverse - I had a similar situation but right here in Denver where I live! I had to drive my BF's car, manual, one day and when I went to go in reverse, it just kept going into 5th gear. Turns out I had to pull up on the shifter to go into reverse. Took me like 5 minutes of just going into 5th gear over and over again!

Anyway, thanks again for all the advice!

If you are going to have a car in Siena, you will need to have lodging that has parking.

Late May will probably be quite warm, so you don’t need to worry about luggage size. I am not a pack light fanatic, and I do fine with a 21” case and a carry-on. The car rental sites are a bit misleading when they show how many bags in each category. Maybe they mean big (26”) bags?
Between San G. or Volterra, I recommend Volterra. It has lots more to see, and there is easy parking in an underground garage just at the edge of town. San G. has become overrun with tourists.
Btw, many years ago, we had the same experience with trying to get into reverse with our rental car. We were actually about to go back to the rental office to get instruction, when a kind, helpful, English-speaking man came to our rescue and showed us how to do it. I believe that set up is peculiar to one brand of cars. Now that you know about it, you’re good to go. Getting an automatic is iffy,even when you reserve one.

Thank you, Rosalyn, for that input. Was not sure if we'd try to visit both or pick one. And I see Tim's suggestion of skipping the Siena part altogether.

I'm seeing the Siena portion of the trip as the "relaxing" part where we visit these hilltop towns, not so much to see sites, but to just "be" in Italy. I envision us just strolling around these towns, maybe through narrow roads and finding cafes on the piazzas to sit in and drink wine and eat gelato. i'm asking you more experienced others if I'm being too idealistic here. Am i just seeing myself in a movie about traveling to Italy? LOL (I'd be played by Charlize Theron BTW).

Thank you again!

We’ve rented a car and driven in Italy twice without any issues, but I have to say if I only had 2 days I’d find an alternative rather than a short rental like that. Having a car in Tuscany is almost necessary if you really want to see the countryside and enjoy the small hill towns.
I wouldn’t consider Siena a small hill town at all- it is a rather large city and can be overrun with tourists. It is also a pain to drive in and out of. (For the record- all mainland European countries drive on the right)

We did stay in Siena after picking up our car in Florence but STAYED in Siena after parking at our hotel for those 2 nights rather than attempting day trips - we had a week to explore the rest of Tuscany with our car.

If you are going to end up with only 2 nights for this portion of your trip I would suggest skip the car and actually skip Tuscany as well. Take the train from Venice and stay in Orvieto. A gorgeous hill town in Umbria, very close to Tuscany and right on the train line to Rome.
It has a magnificent Duomo, some great ceramic shops, good restaurants, delicious gelato, fantastic views and plenty of interesting things to do.

Train from Venice will drop you at bottom of hill, take funicular then bus to the center, walk to your lodgings. It’s not a big town at all. It’s a day trip destination for many but we thoroughly enjoyed our 2 nights there, I wished we had stayed longer. After the day trippers leave it is quiet and lovely. (My sister and her husband just did a week long stay in Orvieto without a car and I was so jealous!)
Sitting on the duomo piazza with a spritz watching the sun go down, changing light on the Duomo was a highlight of our trip this past May.
From Orvieto to Rome is just over an hour by train- which in essence will give you more time in Rome- you can never have enough time in Rome!
Since your time is short in country you’ll have more time to enjoy where you are and less time getting to/from picking up/dropping off car. Although a car is needed in Tuscany it does add a certain layer of stress. We are always very relieved when we DROP off the car!

This past year the rental rates were super high, don’t know what next year will be like but cost is something to consider.
If you do get a car make sure your luggage is hidden if you plan to stop anywhere en route.
Also be very careful about planning wine tasting while you are out driving. The alcohol limits are very very low. Designated driver would be needed.

Another option that gets very high marks is a day trip with Tours by Roberto.
https://www.toursbyroberto.com
His tours generally leave from Siena, he really knows the area and you’ll cover a lot more ground that way.

Venice 3-- (agree with Tim to make the most of Venice time this trip, the extra day allows time to visit the outer islands of Burano, Torcello)
Orvieto 2- this is your "sit in a piazza sipping wine" time, a bit of a break between 2 major cities
Rome 3

Since you mentioned staying in an airbnb in Rome I wanted to share some thoughts on apartments vs hotels. For a first trip to Italy I highly recommend you stay in a hotel, especially on arrival day. Most apartment rental check ins are rather late in the day so you have nowhere to drop your luggage on arrival, whereas a hotel will hold your bags when you arrive even if your room is not ready (or get lucky like we usually are and get into your room). It’s really nice to have a front desk to answer any questions and just be there for you- to call a cab, recommend restaurants, etc.
Another issue is breakfast- stay in a hotel and enjoy a nice breakfast. Stay in an apartment and you are on your own- unless you are OK with a quick espresso and sweet pastry at the corner bar as that is breakfast in Italy. We need a heartier bkft w/protein!
For any stays less than 4 nights we always chose a hotel, we will consider an apartment for longer stays but for 2-3 nights- just not worth the hassle IMO.

Our go to hotel in Venice is the Hotel Ala- also a favorite of many others here. It is perfectly located in a quiet campo about a 5 min walk to San Marco, right on the SM Giglio vaporetto stop- no bridges or steps- no chance of getting lost when you are a bit foggy after all night flight!
Has a fantastic bkft, roof top terrace and super nice staff. We have no need to ever stay anywhere else in Venice.
https://www.hotelala.it/en/

In Orvieto- should you decide to go there consider the Hotel Duomo- really lovely, right next to Duomo.
https://www.orvietohotelduomo.com

For Rome- anywhere in the Pantheon/P Navonna/ Campo d’ Fiori area is perfect and you can walk most everywhere from there.
(Rome is very walkable, we have never used public transportation there after 4 visits)
A favorite here on the forum is Hotel Smeraldo
https://www.smeraldoroma.com/en/

If you keep Siena I recommend
Hotel Palazzo Ravizza
https://palazzoravizza.it
The view from their terrace is amazing, they have easy access on site parking- just behind/below hotel, it's a short walk to center and Campo.

Thank you, Christine, for all of this. Sounds like Siena is not the best "home base" option I was thinking. I will check out Orvieto. for sure, as we are looking for that more laid-back smallish town experience between Venice and Rome.

As far as hotels versus Airbnbs, I guess I was thinking Airbnbs cost a little less and may have more space. But I hear you on the breakfast part - I like eggs and meat too to start the day! We'll check out your options.

I think where we are at now is definitely starting in Venice and leaving from Rome. Probably not Siena, maybe Orvieto instead. Still struggling with no car versus car for the middle part of the trip. Looking at rome2rio, looks like getting from Venice to either Orvieto or Siena involves a combination of train and bus and travel time is a bit more. I will keep thinking on it, though.

Thank you again! All of this is very helpful and much appreciated.

I hear you on having more room- I always look for the largest room at best price within our budget. You won’t be spending that much time in your room, at least we don’t! We are out after bkft thru lunch til maybe 3-4ish then we take a break, get off our feet- (OK we nap, we are old), freshen up for the evening and out again til home after dinner for bed. Again short stays are different than longer stays.
I like to use Booking.com. Most of their listings will tell you how large the room is, look at all the pictures to get an idea. I am often surprised at how large some rooms are once we arrive. booking.com also good for reviews as only those who have actually stayed at the property can leave reviews there.

I love rome2rio for initial research to get an idea of what my transportation options are but always go to the actual train site because rome2rio is not always complete or accurate info.

From Venice to Siena you will definitely have to change in Florence- to a regional train or to bus. Bus drops you close to center, train is outside of town, but changing to train will be easier than heading outside to find bus, etc.
From Siena to Rome will always be a train back to Florence then change to fast train to Rome (I believe)

Venice to Orvieto- (you want ORVIETO not Orvieto Centro) there is an IC train that leaves from Venezia Mestre (1 stop from the main station in Venice -Venezia Santa Lucia) direct (no changes) to Orvieto. 4hr 37 min
IC trains are pretty nice, similar to fast trains but with a few more stops and you will have an assigned seat.
Or there is a fast train to Bologna from Venezia SL then change to another fast train to Orvieto.

From Orvieto to Rome is a direct regional or there are a few IC trains. The station you want is Roma Termini.

https://www.trenitalia.com/content/tcom/en.html
They also have an easy to use app.

The schedules for next May are not up yet- updated Dec 12? But you can look now- just use same day of week - as the schedules don’t change much if at all.

Also wanted to say that Siena is a good home base, it's just that in your case you don't really have the time needed to see much of Tuscany. Perhaps save Florence, Siena, Tuscany hill towns for your NEXT trip to Italy, maybe paired with the lakes or head to the Amalfi Coast. Fly into Milan- to a lake then Tuscany and head south to AC then back to Rome for more time there.
We've done combinations of different areas and honestly you can't go wrong with anywhere in Italy.

You may already know this but when you search for flights be sure you are searching for open jaw or "multi-city" flights/routes. Not 2 one way tickets. Set up some alerts on Google flights, monitor for a while and purchase when you see a price you like. Don't look back.

If you're looking for more laid back experiences, first drop the idea of a car - it will just add stress. Second, stay in Bologna and day trip by train to other towns. Absolutely stress-free, lots of great food and a small-town atmosphere. It's about a 20 minute walk from the historic center to the train station. If you stay between them, you'll have the best of both worlds. Bologna is a rail hub, so there are lots of places to visit for a day. I've been to Padua, Ferrara, and even Ravenna (a bit far but so worth it). There are others like Modena and Parma. No, they aren't hill towns with scenic vistas, but they have lots of history and atmosphere.

Thank you, Chani! Definitely leaning against renting a car at this time. Still considering Siena, though, partly because the Tours by Roberto looks really fun and it appears they leave out of Siena (or would need to take a bus from Florence to Siena to catch the tour).