Need help with Italy itinerary!

For me, this is very fast.
Skipping Milan, you're spending part of a jetlagged day in Florence, a full day and then part of a day. Florence has been my favorite place in Italy thus far, so I would like to something more like:7/3: Depart Early for CT. It's a minimum 2:25 to get from Florence to Monterosso, with at least 1 change. Then it's 7/3 explore CT.
7/4 I would train straight to Rome, and do Rome through the end of the trip. Alternatively, I would spend more time based out of Siena for Tuscany, and only don an overnight in Rome ahead of a flight home.

That's me. I'm more of a city guy, and I'm amazed when people want to spend 8 hours or one night in Florence.

Perhaps use either Florence or Siena as a base for day trips, rather than stay at both places.

With four cities in one week you may very well end up "wearing down"

Although the implication of your post is that you are in your 30s so, for one week the pace may be OK.

Too much checking in and out. Save C Terre for another trip. Much to rush without adding in the stand by situation. Not going to see a lot. ..more relaxed setting. ... Not going to happen. I would also check into a flight from Milan to Florence given that you are at the airport.

And agriturismos work best with a car and multi-night stays. Not really designed for a one night stand. Probably cannot book an agriturismos for one night.

If you're flying into Milan, I suggest you go ahead and take the train into Cinque Terre. When you're leaving the C/T, catch the slow train into La Spezia and switch trains that take you into Florence.
The best way to get to Siena from Florence is to take a bus that takes you into the city center. The buses park across from the Florence train station--to the right of McDonalds' restaurant.
If you're going to stay at an agriturismo, you'll need a rental car to see the countryside and other Tuscan towns. (My favorites are San Gimignano and Volterra.)
It's about a 90 minute drive down to Orvieto from Siena on 4 lane highways and toll roads. Orvieto's a very popular hilltown and many people return Hertz rental cars across the street from the train station. It's a 70 minute regional train ride into Rome Termini.
This itinerary will be smooth and easy for you.

I fly stand by as well and I excited that you can get seats in the summer. So kudos but as know, everything can change and I always book directly with the hotel and can cancel. Easier in the cold low season when I normally go.

Assume you will be back and I try to find 2 home bases and stay there and do Day trips in the train.

I fly into Milan and on one trip , I used Venice as one home base and the other Rome depending on where I am trying to fly out of. I leave my luggage at the hotel and bring a backpack to train to Florence.

So many things to see so my advice is less is more. But if you don't plan to return, then really immerse yourself as the joy of Italy for me is finding the back streets and strolling in the evening with Gelato.

So many others have such great feedback. I have been back 4 times and now planning Sienna or towns that have good train access of course.

Also I want to do Bologna but have to pick my region.

And the RS book in Italy is a Must.

Enjoy,
Kathy

You have 8 nights in 4 destinations, 2 nights per destination. You'll spend a fair amount of time traveling between destinations. You will have to move fast (which you say fits your travel style, so that's fine), and you won't get the full taste (which you say you're also okay with).

I would eliminate one destination, but I don't have a strong opinion of which. Probably Rome because it's a long way from the other destinations (though fast trains mitigate that).

But it's your trip, and if you're okay with the pace, go for it!

Thank you all so much for your replies. This is very helpful! I like the idea of having a base or two and then doing day trips if we are up for it depending on how much we get done, how we feel, etc. Looking back over everything, would it make more sense to skip Rome? The reason I originally added it is because of the airport. We are going to either have to backtrack to Milan or go to Rome since Florence doesn't have flight options for us. I thought Rome would actually be easier to get to from Siena/Tuscany area than getting from Cinque Terre to Milan but it may be pretty similar.

So I guess the options are:
1. Fly in/out of Milan and stay in Florence the entire time with day trips whenever necessary, even possibly spend 1-2 nights in Tuscany if we want a change of pace
2. Stay in Florence 3 nights, Tuscany 2 nights, Cinque Terre 2 nights, and then last night back to Milan
3. Stay Florence 3 nights, Tuscany 2 nights, Rome 3 nights and fly home from there

Yes, we are both 30 years old and move quickly but we also want to build in enough time to relax and really immerse ourselves in the Italian culture and get out of the busy sightseeing crowds. Finding that balance can be tough with a short period of time, but we would like to get a nice feel of both. Thank you again for all of your suggestions!

You're moving around way too much. You'll need a vacation from your vacation. Do you plan on a rental car for your agriturismo stay? Most are located a ways out of town, so a car is necessary. If not, try something like this.

Arrive Milan.

Train to Florence which is the transportation hub for Tuscany.
4 nights Florence.

Day trip to Siena by bus is faster and drops you off in the city center. Or one of these tours.

https://www.getyourguide.com/-l32/-tc172/?cmp=ga&campaignid=111694542&adgroupid=10549991742&targetid=aud-196325823449:kwd-1736448572&loc_physical_ms=9021706&matchtype=e&network=g&device=m&creative=192246960142&keyword=day%20trips%20from%20florence&adposition=1t3&loc_physical_ms=9021706&keyword=day%20trips%20from%20florence&adposition=1t3&partner_id=4E76E&gclid=CP6dseDTp9QCFQEpaQodBw4BaA

Train to Monterosso. 2nights.

Train to Rome. 2 nights.

While you can see the same places, you're just not changing hotels as often.

You might be jet lagged the first day and if you only have
2 nights (= 1 day ) you could miss Florence entirely.

Yep, what's too much for one person may be just fine for another but based on this....

The biggest challenge is that we will be flying standby so nothing is
set in stone...

....I think you're biting off too much. This is a tight enough schedule (!!!) that if things don't go like clockwork, the whole enchilada may be thrown all to heck. Also...

...as well as the true Italian culture in a smaller, more relaxed
setting. My favorite place in Italy is Cinque Terre...

I think you're going to find that things have changed in the CT over the last 10 years. Middle of high season? Busy, busy, busy. Hotels started booking up months ago so personally, I wouldn't land into Monterosso (or the other 4) without a prior reservation lest you're faced with a time-consuming search for a bed.

...stay in Agriturismo
As already noted above, stays in these often require renting a car.

That said, if the CT is a must for you and Firenze is a gotta-do for the S.O. I think you need to give both more time. Go directly to Florence but stay there for the duration and day-trip to Siena. This will add flex and eliminate 1 hotel move.

6/29: fly to Milan
6/30: Land in Milan, train immediately to Florence (stand-by timing is the wild card here)
7/1: Florence
7/2: Florence
7/3: day trip to Siena
7/4: AM train to the CT
7/5: CT
7/6: Early train to Rome
7/7: Rome
7/8: Fly home from Rome

Random comments:
Someone mentioned above that bus was the most efficient transport to Siena but a very recent poster reported that her bus got hung-up in dead-stop traffic ("we literally were stuck on the road behind hundreds of cars") and she'd wished in hindsight that she'd taken the train. Just something to consider. :O)

Based on that stand-by challenge, I wouldn't pre-purchase train tickets from Milan to Florence: buy them when you arrive.

If you could make flights work, skipping Rome and flying out of Florence would give you more time in Tuscany for another day trip or a night or two in Siena.

6/29: fly to Milan
6/30: Land in Milan, train immediately to the CT
7/1: CT
7/2: CT
7/3: AM train to Siena
7/4: Siena
7/5: AM train to Florence
7/6: Florence
7/7: Florence
7/8: Fly home from Florence

From reading these responses, I definitely think we are trying to pack in too much, especially if flights don't go our way. After talking to my husband, we decided we would rather focus on Florence and Tuscany, then add in a little bit of Rome at the end to fly home.

The one thing we would like to do between the two cities is spend time in the Tuscan countryside. We thought it would be fun to do wine tastings, maybe a cooking class, and just sit and enjoy the scenery. We have this vision of staying at a local farmhouse and eating authentic Italian meals with the family. For that to happen, is staying at an agriturismo and renting a car the way to go? Or is there another option that allows us to have these same experiences without a car? I know we can take day trips from Florence or Siena, but is it worth it to stay in the countryside or will the day tour be just as nice?

Florence doesn't have flight options for us

Apologies, km2013: I didn't see your latest post until after I'd posted my own, thus the suggestion for air out of Firenze. I'm a slooow typist!

The one thing that you probably learned as an exchange student is slow down and enjoy life!

To go to Italy in July and not experience a beach scene is sad! Go to the seaside and enjoy! Even a half day from Rome to Ostia is a real pleasure and much needed break from the heat
:)