Italy Planning Questions/Advice/Tips

WOW! What a wonderful way to spend your silver anniversary! You've started the right way - doing your own research. AND asking for advice from this forum - you'll get plenty of excellent ideas! I've flown Air Canada a few times. Their flight to Rome gets in early in the morning, which I think give you a chance to start your vacation almost right away. If you want to start in Tuscany, maybe take the train directly to Florence (it's a short trip on the Freccia line). You could check in at a hotel (have you thought about apartment?), unpack, take a nap, and get out for a mind-blowing walk before drinks and dinner. A few days in Florence would give you time for day trips to Siena and even the Cinque Terre. I don't see Venice on your agenda. There is no place like Venice! You don't go to Venice to see museums. Go you to Venice to "be" in a museum.

By this time I would head to Rome and, sorry, finish your FIRST BUT NOT LAST trip. The lake region of Northern Italy is beautiful but maybe save it for another trip when you can fly into Milan (easier to get to the lakes from there). Also, the Amalfi Coast and Puglia are spectacular but take lots of travel time in both directions. I love Sorrento and spend a week there at least so that I can day trip to the Coast, Pompeii, Capri, Naples. You could get a few nights there on your schedule but, for me, that would be painful. But from Rome you can do some amazing day trips to Ostia Antica (ancient Roman ruins), Tivoli Gardens and even the town of Orvieto. Rome itself is far more than museums. There are neighborhoods to discover and several centuries and cultures to wander around. If you get tired of one, just turn the corner! It's also very easy to get back to the airport from Rome's city center.

Do your homework and include train schedules as you do the planning. On the plane coming home, start planning your next trip. Every region has great discoveries and great differences for you to enjoy. Remember: you deserve this!

Since Rome didn't make the final cut, why not fly into Milan and start your trip in Northern Italy?

I think what Rick says is generally true: the farther south you travel in Italy, the more challenging and gritty it gets. For that reason, and since this is your first trip to Europe, I’d also advise that you concentrate on places north of Rome.

(I wonder if that’s why you want to avoid Rome this time around? If so, definitely plan a return visit! Once you have a bit of travel experience, I think you’ll love Rome. But if Rome seems intimidating, I think Puglia or any areas south of Rome would be equally stressful for you.)

The Milan airport (Malpensa) is a great idea. It has lots of international flights, and is closer to the things you want to see.

If you want to fit in “must see” places, consider Venice.
I would definitely choose only one of the lakes, but not both, on your first trip.

Enjoy your planning and dreaming!

Both North and South has it's charms, but my thoughts are that. for a first timer, the North offers quick easy transportation connections, easy to develop a varied list of places to go and things to do, yeah, a bit more popular with tourists. but for a reason.

Happy Anniversary a tad early and what a great way to celebrate!

What time of year will this trip be?

When you say 16 days I am assuming you will have 15 nights on the ground in Italy. Is that correct?
Given that you have listed 4 major locations- I think you’ll need to drop at least one and to me the one that makes the most sense would be Puglia- it is a trek to get there and as a first time visitor to Italy maybe a bit too daunting? You’d probably need a car in that region as well, so something to consider. (3 trips to Italy for us and we’ve still not made it to Puglia).

When you say “Tuscany” what do you envision? Stay in Florence and day trip or base in a hill town and rent a car? (needed for the area) You’ll need to decide if driving in Italy is OK with you and educate yourself about all the ins and outs.

That said I would advise you to try hard to avoid lots of 1 or 2 night stays. In fact- avoid any 1 night stays!
2 is not much better but sometimes necessary.

Going with Lake region, Tuscany and Amalfi something like this might work

Fly into Milan-
To Lake Como OR Garda- I’d pick one- Garda you can base in Verona if you like. 3 nights here. You’ll need 1 to get over jet lag

Train to Florence- 5 nights with day trips as Robert mentioned.
Or spend 2 nights in Florence- pick up car for hill towns 3 nights.

Train to Salerno (direct from Florence)- then to your Amalfi town of choice- by ferry—we prefer Amalfi for the better transportation and less expensive lodging. Spend 3-4 nights on the coast then work your way to Sorrento for 2 nights- any interest in visiting Pompeii?

You can fly home from Naples. If your flight is later in day it’s ok to stay in Sorrento the night before, if not you’ll need to spend night in Naples.

And not judging at all but give Rome a chance at some point in your future travels. Our first trip I was not too excited about Rome, worried it would be too crazy, etc. We fell in love with this living history museum, just an amazing place. We have since returned 3 times and are going again next spring. Can't get enough of Rome! (Same for Venice)

I’d also recommend flying into Milan. You could take the train to Varenna and start with a couple nights on Lake Como. Or splurge for a private transfer.

You don’t mention how you plan to get around: rental car or train. This might impact which towns you get to, and how much time you spend traveling from place to place. A rental car gives you much more freedom, but has its draw backs.

If you’re not heading to Rome or the Amalfi coast on this trip, you could fly out of Milan or even Venice. I’m currently planning our 4th Italy trip, including our 4th trip to Venice. So I guess you could say I love Venice! Our trip will also include Lake Maggiore, Lake Orta and a stay in Orvieto in the Dolomites. Just a few more ideas for how you could easily spend the whole time in Northern Italy. A trip on the Bernina Express would be fabulous, too.

You don’t mention when you’re going, but do consider that summer is hot and crowded. If you can go in shoulder season, it would be well worth it.

Think about what month you want to go. I would not visit Tuscany in mid-summer, and the Amalfi Coast will be super busy at that time. So whether you choose north or south, think about a spring or fall trip. Not too early in the spring for the “north trip”; we found early April bit early for Lago di Garda. It would however be great for Tuscany, so you could start a North trip there and end at Garda 2 weeks later.

For the North trip, Milan is the best airport in terms of flights and prices. Other airports to consider would be Pisa and Florence for your flight to Italy, with a return from Milan.

For the South, you could fly into Rome or Naples, or even Bari ( British Airways has flights there). Open jaw (into Rome or Bari, then out from Naples after the Amalfi Coast would be good.

Whatever you choose, travel by train (or a mix of car plus train for Puglia) is least stressful, in our experience.

if you want to focus only on northern Italy, you might consider flying into Florence instead. it is more central to Tuscany and Lake Como. You might consider spending a few days in Florence, and then also over to Cinque Terra. that would give you an alternative to Amalfi coast if you don't make it to southern italy.

If you are skipping Rome, you could fly into Naples and focus on the southern area.

If you don’t want to visit Rome, is it because you don’t like cities? If so, then Naples and Milan would be out too. Please explain so we can give you more of what you desire.
We didn’t head south of Rome until our 8th trip to Italy. Northern Italy would be much easier for a first trip to Italy.
Venice, Tuscany, Umbria, Lakes Como or Garda, Bologna. Liguria with Santa Margherita Ligure or Camogli. The Cinque Terre and it’s five villages. The Piemonte with it’s charming wine villages. The breathtaking Dolomites. Study these places with a good guide book.There is a great variety of places to visit in this part of Italy.

Just wanted to mention that RS does offer a Southern Italy tour, might be worth considering since this is your first trip to Europe and to Italy

You could add time before or after the tour to see Tuscany, after might be better since you’ll learn how things work in Italy while on the guided tour

https://www.ricksteves.com/tours/italy/south-italy

If you can fly in or out of Milan and Naples that would be ideal, if so, here’s what I would do if starting from the north, but make sure you check air travel in both directions i.e., CA to Milan / Naples and Milan / Naples to CA then choose the cheapest fares on where to begin.
Day 1 - fly into Milan and take a train from the airport to the Milano Centrale station and transfer to get to the Varenna-Esino station (2h 15m); sleep in Varenna (Lake Como).
Day 2 – boat ride to Bellagio (15-minutes) and explore there; sleep in Varenna.
Day 3 – train to Firenze S. M. Novella station (3h 30m and requires a change in Milan); sleep in Florence (Tuscany).
Day 4 – visit the Uffizi Gallery (buy your tickets two-months in advance) and then walk over to Accademia to see Michelangelo’s David. These are two spectacular museums that you will not regret visiting. It takes two-hours to browse through the gallery and 30-minutes to see David; sleep in Florence.
Day 5 - take a bus to Siena (1h 15m); sleep in Florence. s
Day 6 – take a direct train to the Pisa S. Rossore station (1h 30m) and visit the leaning tower and Field of Miracles. Afterwards take a train from the same station and go to Lucca (30-minutes) and stroll the wall and have dinner. Take a direct train back to Firenze S. M. Novella (1h 30m); sleep in Florence.
Day 7 – take a direct train from Firenze S. M. Novella to Salerno (4h). You can then take a ferry to Amalfi or Positano and make that your base to explore the coast. The most scenic part of the coast is just west of Positano where the road meets the coast and almost the halfway point between Amalfi and Salerno. I would explore by ferry and bus. When taking the bus, you want to travel west to east because the opposite direction travels along an inside road so you won’t see the coast. Also make sure you sit on the right facing the driver.
If you follow this itinerary, you can knock Tuscany (days 3 – 6), Amalfi Coast (day 7…) and Lake Como (days 1 & 2) off your bucket list. The total amount of time you would spend moving from one destination to the other is approximately 15-hours. Train routes lack scenery and IT is larger than AZ but smaller than New MX in square miles, meaning it can take awhile to get to where you want to go. You do not want to lose a day trying to get somewhere. Furthermore, long train rides with connections are boring. Wouldn’t you rather be sitting outdoors with a glass of vino people watching and savoring the moment?

You've received a lot of excellent information from the other responders so you'll have a lot to digest while you plan your own itinerary.
We celebrated our 50th a couple of years ago with a trip to Northern Italy ... not unlike what you have in mind except that we (1) had about 5 weeks for the trip and (2) we had already been to Italy in general and Florence in particular,several times before so we didn't feel pressured to "see everything", instead opting to take our time enjoying one of our favorite travel destinations - it's why we chose Florence in the first place after all.
Our trip was divided up between visiting some of the cities we loved from previous trips (mainly Florence and Siena) along with others we'd never visited before, like Assisi, Montepulciano, Pienza and Lucca with a car. In retrospect I must tell you that it was the couple of weeks just meandering around Tuscany and Umbria with the car that stands out as a pleasant memory of the trip. Though we both love Florence the crowds were particularly off-putting for us during a 3 week stay in May/June, to the point that we started looking around for day trip excursions just to get away from the crush of people and away from the city.
So I guess my first suggestion is to rent a car and explore the countryside for at least a portion of your own trip. I'm betting that the Val D'Orcia is what you think of when you think of Italy anyway so why not see it at your leisure?
I'd also echo the previous advice that with so little discretionary time at your disposal you should concentrate on a single area, ie Tuscany rather than running yourselves ragged trying to see and do too much. If there's a country that's meant to be savored at a relaxed pace it's Italy.
If schedules permit do try to visit during shoulder season, ie before school gets out in late May or after it's back in session in September.
Florence would be a good base even if you're not particularly into winged cherubs. As a regional transportation hub it's central for short day trips by train to Pisa, Lucca (go there), and Montecatini (for a real treat). Getting to Venice would be another possibility but I'd suggest at least an overnight there to enjoy the place in the evening and early morning before the (other) tourists start to arrive.

If you like churches, you must go to Orvieto. The facade is a wow! I may be the only person on this forum that says this, bit I'm not a fan of Venice and I think it's more expensive than some of the other areas. Rome is a really spread-out big city. I love the Roman ruins and Vatican Museums, but Florence is an enjoyable city to walk around and not spread-out.

Fourteen to sixteen days gives you a lot time to see a lot of places. For what it's worth, I've been to Italy on parts of 3 different trips. My suggestions for must sees in the order I visited them are: the Vatican Museums and St. Peter's followed by wandering through the Roman Forum, Palatine Hill and over to the Coliseum (both in Rome), the Duomo and the nearby Uffizi and Accademia Galleries (all in Florence), the Venice experience including riding down the Grand Canal, St. Mark's Square, Basilica. Doge's Palace and just wandering around, relaxing in Varenna on Lake Como, the Duomo and The Last Supper in Milan, and the Pompeii archeological site. Even though you don't seem to have an interest in Rome it would be worth staying there a couple of nights - plus your friends are going to want to know what Rome is like. In my travels there have been times when the places I least expected to be the best turned out to actually be the best.

Hi cjacksun!

This:

Please also know that I do have specific towns and cities to see in
both northern and southern Italy

It might help to know which ones those are, and what time of year you plan to travel? Season can make a difference as I wouldn't advise Lake Como/Varenna (mentioned in one of your previous posts) in November or other winter months. On the reverse side, the heat in the South will be brutal in summer.

You also mentioned in that previous post that you're not interested in Venice. Like the others, I'm a bit curious why you're opposed to that one and Rome? Lots to see in both of them, and that doesn't mean museums, necessarily. Anyway, knowing more about how you intend to pass your time would be helpful as well. For sure, DO visit the churches as many of them are museums in-and-of themselves but without needing to spend a ton of time in any single one.

All that said, I'd be inclined to go with the North for the first-timer's trip. Knowing HOW you prefer to get around is another conversation tho as, yes, some locations in Tuscany almost demand a rental car to efficiently get around to. There's some homework involved with driving in Italy, including limited driving zones (ZTLs), speed cameras, and understanding that you won't be able to drive right IN to all of the towns. You can get some tips about that here in the forum. Alternately, you could base, say, in Florence and easily day-trip to any number of locations - Lucca, Fiesole, Pisa, Siena, etc. - by public transport. I really like longer stays in fewer bases as the process of changing locations + accommodations eats precious time and increases the possibility for something to go awry. Those longer stays also provide flexibility for day-tripping should the weather not cooperate. Pouring rain? Stay in town (preferably a larger one) and do indoor activities. Sunny and nice? Take the day trip.

So could you help us out with a bit more info?

Welcome to the forum! Congrats on your upcoming 25, that's an accomplishment in this day and age.

My wife and I have made several European trips as well as traveling through many parts of the US. Over time, our traveling philosophy has changed from "cram it all in" to staying in one spot and soaking up the atmosphere of the area. I think the first thing you need to do is determine what kind of traveler you are and what kind of experience you want.

On our last trip to Italy, we stayed in an agriturismo just outside of Greve in Chianti. That was our hub and from their we explored Tuscany, mainly the small hill towns of the region. We rented a car and had a lovely time exploring. We did spend a day in Florence, leaving the car behind and taking a commuter bus into the city. If you did something similar, you could get a taste of the two sides of Italy, the historic cities and the rural countryside.

We visited Florence, Siena, Radda, San Gimignano, Volterra and other very small villages. Staying in one spot allowed us to besome friends with the staff at the agriturismo. We went two weeks before Christmas and had the place pretty much to ourselves.

Traveling off season allows you to have an unhurried, uncrowded experience and if possible I recommend it. We've been in Italy in July/August and the heat was brutal, highs above 90c.

Be sure to build in some down time instead of scheduling every minute. For the length of your trip, I suggest two days completely unscheduled. On every trip we make we discover something we didn't know about but wanted to do. Having a flexible schedule allows us the ability to work in these surprises.

Have a wonderful trip. Italy holds a special place in our hearts. We met as high school students on a People to People trip to Europe in 1966. Our first kiss was in Florence and we've been going steady ever since.

• What month? It could really make a huge difference. Do you have any issues with heat?
• Are you open to driving? Some areas are better without a car (the Amalfi coast for example), but rural Tuscany and Puglia are both better with a car, though of course parts of both can be seen without one.

A) Have you checked other airport options? While it is easy to hop on a train to Florence at Rome airport, do be sure to check all of your options. If you are flying out of Milan, Tuscany and the lakes sounds good for two weeks, but of course it helps if you flesh out the Tuscany part as there is just so much to see there.

B) I would find Puglia and Amalfi coast in two weeks too tight time-wise, but if you specify which places, we can advise if it's doable. Into Naples and out of Bari or Brindisi (or vice versa) would be ideal, but Rome works if you have a bit extra time at either end. When trip planning, I typically google "Italian airports" and I check them all--I have gotten good fares to smaller airports (which I prefer) on many occasions.

How I always plan, even after over a dozen trips: write out each day with specifics. That does not mean every second of the trip must be planned, but it does help you visualize if you have allotted enough time for everything.

Thank you for all the wonderful advice and suggestions! Here is a little more insight into our thoughts on the trip (ideas swirling through my mind).

1. First let me say that I will be taking Bari out of the equation for this trip.

2. many were curious as to why we are a no to Rome and Venice. It is not that we don't ever want to visit to see either place but for my top choices personally I ideal of Italy is Tuscany and Amalfi Coast. It wasn't until I started researching and watching videos including Rick Steves' that I learned about Northern Italy and what it had to offer and started falling in love. It's the scenery, the views, the wine and cheese......that is what appeals to me.

3. We figure we will be going in mid to late September.

4. we would be basing our travel off of train. Would love to rent a car for a couple of days in Tuscany but I'm a little afraid of it. Neither myself or my husband drive manuel cars....all automatic and I've heard it is really hard to find automatic cars to rent there. Also afraid of all the potential of fines or tickets for doing the wrong thing.

5. My husband and I are not afraid to be busy on our vacations (we have done Disneyworld 3 times with 3 young kids with non-stop 10 day schedules). Although now both in our early 50's we would like some downtime to relax and soak in some fantastic views. A mix is good for us.

Here are some places I have saved on my to see places:

1. In Tuscany: Florence, Montepulcanio, Cortona, Volterra, San Gimignano, Orvieto, Bolgheri, Montalcino, Pienza, Pisa, Castelina

2. Amalfi Coast: Positano, Ravello, Sorrento, Capri, Pompeii

3. Northern Italy: Lake Como (Varenna, Bellagio, Lenno), Lake Garda (Limone) and whatever flows from there), Verona (?)

Like Rome and Venice, I do not feel like spending any time in Milan is for us. If I were to pick a spot out of the three to work in a day or 2 it would be between Venice and Rome but might take too much travel time out of the way of everything else especially if we to say focus this trip on Tuscany and Northern parts of Italy.

Another question for you all - I read somewhere that there is a train trip (day trip) from Verenna that takes you into the Alps? Anyone heard of this? Has anyone done it? Any comments if you have?

Hope this helps you all a bit more! Thank you again and can't wait to hear more of your thoughts!

We stayed at Villa Trasimeno in Umbria in 2018, and had 2 stays booked there (and cancelled) last year. The owner is a professional chef and the included meals were great! He also drove us to visit all of the cities in Tuscany that you mentioned. I thought his prices were very reasonable for accommodations, touring, breakfast and dinner, and a one way transfer from Rome.

http://www.villatrasimeno.com/

September will be great.

we would be basing our travel off of train. Would love to rent a car
for a couple of days in Tuscany but I'm a little afraid of it. Neither
myself or my husband drive manuel cars....all automatic and I've heard
it is really hard to find automatic cars to rent there. Also afraid of
all the potential of fines or tickets for doing the wrong thing.

I was worried because of my husband's profound hatred of driving in the US (we're both bike commuters and live where we can use public transport), but we have now had five amazing driving trips in rural Italy and Greece--going places with ease that we never could have without the car. I assure you, driving is not a big deal IF you do the necessary research so you know how to avoid ZTL and how to park (and don't speed of course). It is not a problem to get an automatic. If Tuscany is your biggest dream, you need to focus on this dilemma. You will read stories of people getting tickets, etc., but people with complaints always find an outlet. And the way I figure it, if you can afford to go overseas, you can afford a measly 50 bucks for a driving violation you may not even get. It is totally worth it for exploring villages in rural areas, but there is also nothing wrong with taking a tour or using private drivers--it just depends on what you want out of the trip.
If you don't choose Tuscany first, the Amalfi coast and the northern lakes are quite easily explored without a car--a car would actually be a hindrance on the AC. You can take a train or fly between, and do about a week in each (but that will be a little tight). Then once you fall in love with Italy, you may feel more confident about driving on the second trip.
Your guide book may give you a general sense of how you would get to all of those villages without a car.
Good luck!

we would be basing our travel off of train. Would love to rent a car
for a couple of days in Tuscany but I'm a little afraid of it. Neither
myself or my husband drive manuel cars....all automatic and I've heard
it is really hard to find automatic cars to rent there. Also afraid of
all the potential of fines or tickets for doing the wrong thing.

Just addressing the driving and renting a car question-

Driving in the Tuscan countryside is easy and fun. It really is. Many many folks do it without incident- without getting tickets or into trouble. I suspect those who DO get ZTL, parking and speeding tickets simply neglected to do their homework.

You will want car to visit a lot of the Tuscan towns you have listed.

We thoroughly enjoyed our time with a car in Tuscany and had zero problems.
We always rent thru AutoEurope.com- a US based consolidator with stellar customer service and usually the best rates.
Pick up your car as you LEAVE Florence (outside the ZTL is possible but not necessary if you follow advice you’ll find here) and drop it off elsewhere- a smaller town with train station nearby works well.

It is not difficult to get an automatic- we’ve never not been able to, that may have been true years ago but not anymore.

Just do your homework, have a good GPS, a paper map, carry your IDP with you, etc.
Realize that you will not be driving IN to any hilltown- you will be parking outside the walls/outside ZTLs.

I very carefully researched each hotel we stayed at - Siena, Montepulciano and Assisi- to confirm that access/parking was easy and legal.

Here is a good starting point- a bit old, but still relevant.
http://driventoit.blogspot.com/2015/01/driving-in-italy-including-dreaded-ztls.html

Once you settle on an itinerary- we can help you sort out where/when to get/drop the car.

ETA
be careful if you plan to visit wineries or do any wine tasting
Very very strict alcohol limits, better to do that with private driver or just in towns you are staying/not driving

Toursbyroberto.com might interest you

In Tuscany: Florence, Montepulcanio, Cortona, Volterra, San Gimignano,
Orvieto, Bolgheri, Montalcino, Pienza, Pisa, Castelina

Given this list I’d recommend choosing 2 bases in Tuscany-
Somewhere between Florence and Siena- Castelinna in Chianti? Certaldo?- visit SG, Volterra, Cortona, Siena- while there. And Pisa if you must.
Never heard of Bolgheri.

Another in Val D’Orcia- we loved Monetpulciano- visit Pienza, Montalcino, San Quirico, Bagno Vignoni from there.
You could visit Orvieto ( in Umbria not Tuscany) from there as well but it makes a nice place for a 1-2 night stay. Drop your car in Chiusi take train to Orvieto. (Orvieto does have a Hertz location but AutoEurope no longer uses due to very bad service over the years)

Re: train from Varenna into the Alps——yes, you can board a north-bound train from Varenna to Tirano on the Swiss border, changing there to a Swiss train over Bernina Pass to any of several alpine villages. The so-called Bernina Express panoramic train plies this route, or you can take a regular Swiss regional train on the same tracks. The Bernina Express website shows the route:

https://www.rhb.ch/en/panoramic-trains/bernina-express

It is a long-ish daytrip, however; 3.5 hours each way from Varenna to Pontresina, which would be a good turnaround point. Get off the train, walk around, have lunch in Switzerland, maybe ride a lift up to a restaurant above the valley and take a short hike there.

https://www.pontresina.ch/en/experiences/mountains-and-railways/mountains-railways-summer/

But it is 7 hours on the train, which we would find too long for a day’s excursion. Maybe consider spending the night in Switzerland to break up the journey?

More on Bernina Express
https://www.seat61.com/trains-and-routes/bernina-express.htm#Route_map

another option:
Lake Maggiore Express
https://www.illagomaggiore.com/en_US/26400,Poi.html

If you’ve narrowed it down to Tuscany and Northern IT, here’s what I would do:
Fly in or out of Milan / Rome. Let’s say you fly into Milan since the days will be getting shorter…
Day 1 - fly into Malpensa and take a train to Milano Centrale and transfer to the Varenna-Esino station.; sleep in Varenna.
Day 2 – ferry to Bellagio for the day; sleep in Varenna.
Day 3 – ferry to Lenno (45-minutes); sleep in Varenna.
Day 4 – train from Varenna-Esino to the Firenze S.M.N. station; sleep in Florence.
Day 8 – Florence
Day 9 – direct train to Pisa; sleep in Florence.
Day 10 – direct train to Bolgheri (2h); sleep in Florence.
Day 11 – rent car and drive to Castellina in Chianti (1h 15m). Continue on to Montalcino (1h 45m); sleep in Montalcino.
Day 12 – day trip to Pienza (30-minutes); sleep in Pienza.
Day 13 – drive to Montepulciano (1h); sleep in Montepulciano.
Day 14 – Montepulciano
Day 15 – drop off car in Orvieto and explore town; sleep in Rome near the airport.

Day 4 – train from Varenna-Esino to the Firenze S.M.N. station; sleep
in Florence.

No direct trains from Varenna to Florence. You will need to change at Milano Centrale

Day 10 – direct train to Bolgheri (2h); sleep in Florence.

As far as I can tell there is only 1 direct train from Florence to Bolgheri a day- leaves at 11:28- takes just under 2 hours. That is a bit far to go so late in day for a day trip.
All others connect thru Pisa or Livorno- taking up to 3+ hours.
Return from Bolgheri to Florence- only 2 direct at 3 and 4:30- all others change in Pisa or Livorno and take 3+ hours.
Makes for a very short visit in Bolgheri or a very long day trip.

Day 11 – rent car and drive to Castellina in Chianti (1h 15m).
Continue on to Montalcino (1h 45m); sleep in Montalcino.

Day 12 – day trip to Pienza (30-minutes); sleep in Pienza.

Day 13 – drive to Montepulciano (1h); sleep in Montepulciano.

Day 14 – Montepulciano

Montalcino to Pienza is a 25 min drive
Pienza to Montepulciano is a 15 min drive.
No need to make 3 hotel changes in the val D’Orcia area. You don't want to be driving around making any stops with luggage in your car. Pick a base and day trip to all those towns easily.
We found Montalcino to be a bit dull, spent just a few hours there.
Pienza is lovely, quiet and flat. There are several nice hotels with parking just outside the walls and it is easy to come and go.
Montepulciano is also a good option- although very steep! and you’ll need to confirm parking and access if you stay there.
There are lots of agriturismos in the area if that interests you. We prefer to be in or walking distance to a town for the evening hours/dinner.

Day 15 – drop off car in Orvieto and explore town; sleep in Rome near the airport.

As mentioned above the only car rental agency in Orvieto is Hertz, limiting your car rental options.
Chiusi is closer to Pienza/Montepulciano and has several options- Avis and Europcar- both walking distance of train station. Train to Orvieto is a just few euros, runs about every 30 min and takes just 35 min.

A handy tool for checking transportation options and transit times is
www.rome2rio.com
Confirm what you see there with the actual train site- www.trenitalia.com or www.italotreno.it and with Google Maps.

No direct trains from Varenna to Florence. You will need to change at Milano Centrale

Who said it was direct? If you read my first response, I made it clear on day three that a transfer was required in Milan.

Hi Cjacksun,

So many choices, so little time!
You’ve received great advise by everyone here!

I’ll share a couple of my own itineraries to give you more ideas.

My mom and I visited Northern Italy and this was our itinerary:
Flew to Milan (Malpensa Airport) > Malpensa Express train to Milano Centrale ( Milan’s Central Train Station) > Train to Verona (3N) > day trip to Lake Garda (easy 15 minute train ride) took ferry and visited some lakeside villages > train to Padua (Padova) (4N) > day trip to Venice (mom had already visited previously) >> train to Ravenna (known for its amazing mosaics) stayed one night but 2 nights would have been better >> train back to Padua (1N)
I’d wanted to stop in Ferrara for a few hours before returning to Padua but mom was too tired [BTW, Ferrara is still on my list] >> train to Varenna ( train transfer at Milano Centrale) (3N) > Bellagio via ferry, and Como via bus >>
Train back to Milan (1N) >> Malpensa Airport > Home.

In 2017, I wanted to visit Lake Maggiore before heading to Tuscany & Umbria.
My itinerary: flew to Milan (Malpensa) > bus to Lago Maggiore (stayed in Baveno just north of Stresa) took ferry to Borromean Islands, took day trip to Lago Orta (via train and taxi) >> train to Lucca (skipped Florence due to previous visit) >> train to Siena >> day trip to San Gimignano vía public bus >> train to Orvieto >> train to Assisi >> day trip to Spello via train (bus option available) >> train & bus to Montefalco >> taxi and bus to Trevi >> day trip to Spoleto >> Rome >> home.

You could do something like this:
Fly to Milan >> Lake Maggiore, or Lake Como >> Florence >> day trip to Lucca and Pisa>> bus to Siena >> day trip to San Gimignano (vía bus) >> Orvieto >> fly home from Rome (spend night before departure in Rome)

Happy planning!

if you hope to spend some time in the lake region (Maggiore and Como), I would choose Piedmont rather than Tuscany as part of your trip. The Langhe part of Piedmont provides you with miles and miles of beautiful wine country, with many hilltop towns, many with castles, the best food in Italy, far fewer torists than Tuscany, less expensive and ideal biking conditions. Maggiore is actually part of Piedmont and you have easy access to the Alps including MT Blanc.