1st trip to Italy

Return to Rome by rail and fly home.

Hopefully the flight is the day after the train ride.

Simpler to put Rome at the end of the trip, i.e., go from Siena to Amalfi area and then to Rome for the 3 nights before flying home.

Suggest an additional night in Cinque Terre and skip Amalfi coast as with you limited time it is a lot of travel for just one full day there. Add and additional night in Rome and go to Ostia Antica to satisfy the Pompeii like ancient Roman town experience.

Save Pompeii and Amalfi for another trip when you can spend several days in the area.

You need to remember that it takes time to travel between places. I would cut out a few places or you’re basically doing a Great Race. Put it all out on a calendar, add in travel time and see what kind of time you have for each place.

I would never advise you to 'wait for another trip' for anything. I think your plan is realistic.

If you think it might be overkill to go to those 6 villages, then it probably is! All of those towns are close enough to each other, but transportation in that area is not as easy as other parts of Italy. You can't hop on a train to go between them, so I guess you would need a car, and I think 4 days in Cortona is too long, unless that is actually where you want to spend the most time.

Since you haven't been to Milan, I recommend you spend at least a night there upon arrival.

Cinque Terre is amazing, and if you plan to do the hike to all 5 villages, I would keep it. If not, I would train to Como from Milan.
2 nights is enough in Florence and Pisa.
Rome is a must see.

I think that the Amalfi Coast is a must see. I find the easiest way to tour this area is with a car and driver. An 8 hour day (round trip from Naples) to see ceramics, limoncello, lunch in Ravello, then Pompeii was a highlight of my trip last year. Pompeii can be done in an hour and half. I doubt anyone else will recommend that, but that's all the time we had and it worked for us.

Have a great trip.

Welcome!

We're thinking of going in April or

> late September early October for 2 weeks but can add a day if needed.

April 5 is Easter, April 25 is Italian holiday as is May 1.
Sept/Oct is nice but both time frames will be busy-there is hardly a shoulder season anymore.
I would add all days that I could.

If you count your tip in NIGHTS you will have a more accurate picture of how your itinerary flows.
For a 13 night trip- 4 locations would be my max. A 2 night stay really means just 1 full day in that location. Every location change eats up at least a half a day. Some of your transitions will take longer.

I would drop either CT or Amalfi. They both take time and effort to get to. Both are crowded areas with difficult transportation to/from.

Train from MXP to CT will take at least 4 hours- are you sure you want to do that on arrival?
Where are you flying from?

CT- going to take most of day to get there from Milan, same for from Rome- so I wouldn’t start in CT. Start somewhere closer to your arrival point.

Florence- 2 nights is fine for your interests- give it 3 nights and day trip to Pisa from there.

Cortona would not be my choice for a Tuscan base. It’s too far east and doesn’t have the best connections. Stay closer to your towns to visit list ;)

Montalcino, Pienza, Montepulciano all need a car.
Have you considered renting car and driving for just this portion? Make Siena your base if you want to be in a hill town. Better connections and tour/driver offerings.
We stay in Pienza now- love it and it is flat.

There are ways to enjoy this area without a car. Private drivers, etc.

Getting to and from AC is not quick or easy. There are dozens of threads that address transportation in the area.
It will take most of the day. Staying just 2 nights allows for 1 full day.
If you choose to go all the way to AC- give it the time it deserves. Getting to Pompeii is not as easy from Amalfi as it is from Sorrento or Naples. (Sorrento is not on the AC but best transportation hub for the area.)
Hundreds of threads on this topic here on forum- use the Search

Rome- you won’t regret giving Rome more than 3 nights.

You must be in your departure city night before departure flight so move all Rome nights to end (if that is departure).


Use Trenitialia to research your train routes. Use Italian names:
Milano Centrale
Firenze SM Novella
Roma Termini
Napoli Centrale

https://www.trenitalia.com/en.html
Get the app.
(Next year schedule not out- just search same day of week to see your probable options).

Google Maps will be very handy as you plan.

Rome2rio.com/app is a fun tool. Use it just to get an idea of transportation options and travel time but use it only as a simple (not always complete or totally accurate) starting point. Always look at and book on official sites.

If you let us know where you are flying from we can make flight suggestions. Flying in to Florence, Pisa or Bologna might work for you.

RT Rome- makes the most sense to me- Milan is far from any of your destinations. MXP is also 1 hour outside Milan in the wrong direction.

Suggestions- you have a lot of time to plan. Do lots of searches here on the forum.

Arrive Rome- train to Florence 2.5hr
Florence 3 nights w/day trip to Pisa, Lucca?
Train to CT- 3hr
CT 3 nights
Pick up car or hire driver to Tuscany- Siena-no car, Pienza-with car
Tuscany 4 nights-car or hire driver for day trips www.toursbyroberto.com
Drop car- Chiusi, Orvieto
Train to Rome 2 hr
Rome 4 nights
Fly home Rome

Or
RT Rome
Florence 2 or 3 nights - skip Pisa?
Pick up car
Tuscany 3 or 4 nights
Drop car- Chiusi, Orvieto
Train to Naples > Amalfi - driver w/stop at Pompeii
Amalfi 3 or 4 nights
Ferry to Salerno, train to Rome
Rome 3 or 4 nights
Fly home Rome

First, a couple of questions. Do you think you will be coming back to Italy again in the future? And is it possible to extend your trip by another 4-7 days? Those two answers will help a lot to give you an answer.

I love Italy, its my favorite foreign country, been there many times.

Your plan is feasible, but you are not much in going into depth when you visit.
It is good that you want to visit smaller towns in Tuscany, we have done that and it was wonderful. We did a tour that used Siena as our base. We did Cortona on a day trip from Siena. Not sure I would use Cortona as a base, but I suppose it will work. Do you plan to rent a car? If you plan rail have you checked the Italian rail site to determine rail connections to those cities. Regional trains in Tuscany travel very slow and stop and many places. Also, the rail stations tend to be away from town centers.

Why did you skip San Gimignano, it is amazing.
https://culturedvoyages.com/best-towns-in-tuscany-italy/

Sorry, but two days in Florence and three in Rome is way not enough. Have you checked TripAdvisor.com for what the key sites are in those cities?
Why not one of the most special cities in Italy, Venice!!??
2 days for Pompeii and the Amalfi Coast, I guess you don't plan to visit Capri or Sorrento?

I agree with Maggie, this sounds exhausting to me. I think it's do-able but In my opinion you will be spend a lot of time packing and unpacking, checking in and checking out, getting to train platforms on time etc. You will need a vacation when you get back and will remember the rushing and finding your way to stations more than actually being in Italy. But that's just "me". Personally I like to take my time in a spot and get to know it.

Thanks everyone for your terrific feedback and tips and have made some adjustments accordingly. If you had to choose between CT and AF, which would it be? I'm now leaning towards CT and holding AF and Pompeii for another trip as it seems more in line with the other stops on my itinerary. Also, based on feedback, thinking dropping Milan and arriving in Venice as a starting point (2 or 3 nights?). After Venice , should I go to CT or Florence next? Then onto the Siena and the numerous Tuscan villages previously mentioned adding Sam Gimignano and dropping Cortona. Lastly Rome, The Vatican and Ostia Antica. In Summary- Venice 2 or 3 nights, Florence & Pisa -3 nights, CT & Lucca -3 nights, Siena 4 or 5 nights with day visits to Saint Antimo, Moltepulciano, Pienza, Montalcino, San Gimignano. If you had to cut 1 or more of these towns which would it be?, Lastly Rome, Vatican City & Ostia Antica for 4 nights. Fly Home. I believe this works out to 18 nights max.

If you are flying into Venice, I would give it 3 nights. The first night you will be tired and maybe jetlagged. Train to Cinque Terre from Venice is 6-7 hours. Cinque Terre to Florence is approx. 3hrs. Pisa and Lucca are about 1 1/2 hrs from Florence. You could do both in one day from Florence. Siena you don't need a car either, there is a bus from Florence. The other hill towns you definitely need a car. Keep in mind all of your traveling time between places, save time to actually the places.

CT and AF,

Assuming you mean Amalfi Coast or AC?

day visits to Saint Antimo

Assuming you mean the Abbey of Sant’ Antimo?

Moltepulciano

is Montepulciano
Correct spelling will be important as you plan

It’s great that you are able to add 5 nights to your itinerary. You will enjoy your trip more if you can slow down a bit.

Venice should get 3 nights and it’s good you plan to fly IN to Venice as flying OUT if Venice its decide more complicated/expensive.

Venice to CT is a long haul 6 hours or more. Are you planning to hike- if so- 3 nights, if not 2 is fine

See Pisa and Lucca on a day trip from Florence- or stop in Pisa on your way from CT to Florence- you will have to store bags at station.

If you had to cut 1 or more of these towns which would it be?

Honestly I would probably drop San Gimignano. It is extremely crowded, full of of tour bus groups and very touristy. You can’t really see the towers while in town but you can get a nice view of the skyline from outside of town.
We weren’t real impressed with Lucca either- there are no sights there, a few churches. The wall is the big draw- walk or bike it.. We just didn’t see the “charm” that others report.

All the other towns do not take a lot of time to visit- they are tiny.
Note- you will not be driving IN to any of these towns. You will be parking in lots outside the walls and walking in.
Ex- Montepulciano, Pienza and add in San Quirico can all be seen in one day. One of our favorite stops is nearby Bagno Vignoni
Montalcino, Sant’ Antimo (check times from Gregorian chants), and maybe Buonconvento can all be seen in one day.

Siena is a city- not a small town at all. It’s a bit dicey driving in and out and parking is an issue. (There are a few hotels that offer parking but without a car you have lots more lodging options)
I would not want to drive in/out every day for day trips. Consider splitting your Tuscany time. Maybe 2 nights in Siena- pick up car in Siena and head to a Val d’Orca location for the remainder. Hate to add another hotel change but that is probably what I would do. Siena itself is worth a few nights.

Lastly Rome, Vatican City & Ostia Antica for 4 nights

Rome could use 4 nights or more just for the sights-- 1 day for Vatican, 1 day for Colosseum/Forum, 1 day for other sights- Borghese, Trastevere, etc. Don’t plan on a day trip to Ostia til you know you have sufficient time just in Rome. (4 nights is 3 full days)

Be sure you do your homework on driving in Italy- ZTLs, parking, speed cameras.
All drivers must have an IDP- get it at your local AAA

Venice 3
CT 3- for 2 if you are not hikers
Florence 3- w/day trip to Pisa/Lucca
Siena 2
Pick up car
Tuscany hill town 3 or 4 nights
Drop car
Rome 4 or 5 nights

Pro tip: on your way to Ostia, you will change trains at "Pyramid". Plan to stop for a bit and see the actual pyramid across the street which was built after the Romans saw the Egyptian pyramids as a tomb for a Gaius Cestius18BC. There is a hill nearby made of millions of smashed olive oil amphora...really cool!