21 Days in Italy in May

Am I biting off way too much, ...... I am feeling a bit overwhelmed with the planning

Yes, ...that is why you are feeling overwhelmed.

You need to cut down the number of destinations and give more time, especially to Rome and Venice, than you mention.

One way to cut down is not doing 2 seaside destinations. Eliminate AC and go to Ostia Antica as an easy day trip from Rome for your ancient Roman city experience. Save Pompeii for another trip.

Going no farther south than Rome will simplify your planning and make for a better vacation.

One way car rentals in Italy usually have no ( or little) one way drop fees.

I personally prefer Ostia to Pompeii as you can mingle among the ruins. www.ostia-antica.org. It's a favorite of mine.

IMO Venice is a better place to get over jet lag than Milan. I suggest you go directly from airport to Milan central Station to Venice.

Unless you land extremely late, or there are things you need to do/see in Milan, or there are other reasons.

Yep, Emily, you are overwhelmed because you're trying to do much too much.

Understand that the tighter the itinerary/more locations you have, the more time is spent in relocation processes, the less time spent sightseeing, and greater the chance of something going awry that could throw a wrench in the plan. 2 nights anywhere = only one FULL day of sightseeing. It can be unfortunate when it pours rain on that one full day you planned to spend exploring outdoors or it's the day most of the art museums are closed.

I looked at the Rick Steves suggested itineraries and sort of formed
my own based on that.

Personally? I think those itineraries are unrealistic. For instance, we could not have done Rome and Florence any sort of justice at all in just 4 days; one of them being a partial arrival day and the other a partial transfer day. IMHO, 4 nights/3.5 days is the minimum for Rome. Love art? Then I'll say the same for Florence, although you maybe can get that one down to 3 nights/2.5 days and skip some stuff but it's a gold mine of Renaissance art. Anyway, we've spent more time in both without running out of things to see OR having to run to the point of exhaustion to do it!

Save the Amalfi Coast for another trip; not worth it for just 2 nights/1 day. It's time-consuming to get to, time-consuming to get around in, and there's too much ground to begin to try and cover in 2 nights/ 1.5 days. As mentioned above, should that 1 full day be a wet one.... The coast deserves a minimum of 4 nights/3.5 days, IMHO.

I'd also add at least one night to Venice.

Cinque Terre: if your trip is this year, you're going to want to get reservations as soon as possible. Accommodations there book up fast and far in advance of high season. Hopefully you've read about the mobs which have descended on that region so know what to expect?

While other posters are saying to spend more time in the Big 3, we actually prefer smaller towns and have been perfectly happy with 24 hours in Venice and day trip to Florence on one trip to Italy. Second trip was 2 nights 2 1/2 days in Rome and we were fine with that. Next trip was 3 days in Florence, but I was sick, so no fond memories. We are going back to Florence next week for two nights. Destinations outside of big cities can be less expensive for both hotels and eating, so that helps stretch the budget. Think about how you like to travel.

Assume you will be back to Italy, and easy enough to visit one or all of Big three again when you fly in or out. So my suggestion is that when spending time in Tuscany, do it justice. Or Almalfi Coast. For your trip, pick one or two of the non city destinations and plan to see lots within short proximity.

Since you fly into Milan, staying or heading to Venuce right away depends on your arrival tim at MXP. From the time you get off the plane and get to Milan Centrale is about 1 1/2 hours, more if you checked bags. Then if you take the next train (no cheap advance tickets) 2 1/2 to 3+ hours to Venice. Arriving after 2 or 3 in the afternoon would not put you in Venice until 7 or later. Unless you’ve navigated trains in Europe before, you will find it takes longer to figure out the logistics of train travel. If you decide to spend night in Milan, take a train to Venice the following afternoon and buy cheap tickets in advance. Milan us a beautiful city to wander in the evenings and mornings. If you stay near the Doumo, easy to take 5 minute metro to Train station.

Well, I hit Venice travel weary and needing places like a laundromat and internet cafe. I purposely am putting it in the middle of my upcoming trip so as to not hit it jetlagged. I would keep with the current plan for Milan.
Every accommodation move costs half a day so current schedule loses 3.5 -4 days just in travel. Rick's itinerary doesn't tell you that. They are always too fast for new travellers.
Shorten to 5-6 must do locations. Some may be well situated for day trips. It may work to expand a bit from there but start with fewer moves to feel more comfortable with the plan. Lucca and Pompeii can be day trips.

Yes, Orvieto is a good place to rent a car as well as to return it. There is a gas station directly across from the rental where you can re-fill it and the rental is a short walk to the train station.
I agree with the suggestions to plan travel South of Rome for a future trip...I have done the same...
Last year I did a 23 day trip starting in Venice, ending in Rome...with stops in CT, Firenze, 4 nights in an Agriturismo near Civita de Bagnoregio.. 5 days in Rome...we shortened up on Firenze. Three nights there are plenty....one day was spent in Sienna.
My wife loved Venice for the lack of cars. I loved exploring around Orvieto and the surrounding areas North to Montepulciano, West to Tarquinia. You can't see it all in one trip...start planning your next trip with the list of places you don't go now.... Milano is not one of my favorite places in Italy.... one and done in my book...that's why we flew into Venice.
Enjoy

Thank you all for your speedy replies! Yes, we fly into Milan late (7 pm), so I figured by the time we got into town and settled we would not feel much like negotiating trains the next day. I will try to add a day to our Venice schedule. Yes- I have read about the mobs at Cinque Terre but have also spoken with people who said you can avoid them if you hike early, and go to the more out of the way towns. I haven't booked that yet. So far I have an airbnb in Milan and 2 nights at a hotel in Venice. I did book 2 nights in Amalfi but can still cancel that. I so appreciate everyone's opinions about going South of Rome. I'm thinking maybe basing for longer in Rome at the end of the trip and a day trip to a closer archeological site. If anyone has suggestions for a good neighborhood to stay in in Rome that is not super touristy I would appreciate that. We are trying to keep it around $100/night or less but that may be unrealistic in Rome. Also a suggestion for a base town to explore Tuscany? San G? or a smaller nearby town? Thank you!

Emily, take a look at the Prati neighborhood? That's a quieter, more residential area than some of the others in the city. It's a longer walk to some of the attractions from there but we never had a walk - long or short - in Rome that didn't offer much to see along the way! Also, some accommodations will be just short strolls from Metro stations. Monti is another fave neighborhood with a fair amount of the folks here who've stayed there.

Yes, $100 U.S. per night is a bit of a stretch in high season, depending on what sort of accommodation you're looking for, so you might want to be prepared to increase that budget.

Thanks Kathy, I will check it out.

hello Emily i live in Sorrento, near the Amalfi coast. I write with the Google translator. southern Italy is very beautiful and the Amalfi coast is a jewel. you can stay here 3 days, one day for the tour of Positano, Praiano, Amalfi, Ravello, Maiori and Minori (in Minori there is one of the most famous Italian patisseries, Sal De Riso).
another day you can see Pompeii and Herculaneum, Vesuvius and Naples.
and then you can rent a boat and go around Capri. you can drive the boat, the Mediterranean is not an ocean, it is a sea and it is very calm. Capri is in front of Sorrento and with the boat it will take you 40 minutes to get there, go all the way around the island and don't forget the blue grotto. if you rent the boat on the Amalfi coast you will pay about 30/50 euros per hour, if you rent it there in Sorrento you will pay 150/200 euros from 9:00 am to 6:00 pm, if you rent it in Piano di Sorrento or Meta or Vico Equense you will pay 100 / 150 euros from 9 to 18. if you are afraid of driving, you can also hire a sailor. much of the Italian culture comes from the Mediterranean and it is really interesting for an American to see the south and the millenary culture of the sea. you can sleep anywhere on the coast, Sorrento, Positano, Amalfi, Salerno, Naples, Capri, wherever you prefer. there are ferries that connect all the main cities. if you look on the internet you will find sites with all destinations. you can move anywhere by ferry, except on Vesuvius!

So much great advice from Kathy, Joe, and Maria. I will join the chorus of recommending you stay to points Rome and north. The Amalfi Coast and Sorrento are lovely, but save them for another trip or you will find your memories a blur.

Think in terms of number nights you will sleep somewhere. Your usable time are the full days between those nights, i.e., 4 nights equals 3 full days. Your arrival and departure days are fractions. We think 3 nights is the minimum anywhere we go and longer is usually better, especially if you want to day trip.

Our first trip to Italy was in 2010 for 21 nights. Here’s how we broke it down and I will tell you in advance it was too rushed in places.

• Landed in Milan and took the train straight away to Venice (we had arrived before noon. 4 nights Venice was perfect, and it has become a place we return to often.
• Train the the Cinque Terra for 3 nights. Long long train day. This was a first-timer error (the travel time required) but 3 nights was perfect for a first visit. Many of us can help you with hiking recommendations away from the more crowded trail.
• Train to Siena where we stayed 3 nights. Another first-timer error as this took 4 trains. Yikes! If we had realized how tiring this would be we would have rented the car in La Spezia. Siena was our base for day-tripping. After a one day tour with Tour by Roberto, we rented a car to go to Volterra and Monteriggioni on a day trip. Then we drove said car to
• Montalcino where we spent 3 nights, Day-tripping around that part of Tuscany.
• Next stop Orvieto for two nights, where we dumped the car. This was probably a weak point in the plan.
• Last stop was by train to Rome for 5 nights, a perfect amount of time as Rome is a bit chaotic and hard to “do” in a rushed manner.

We did have to spend one final night in Milan as (first timer error)we had RT in-and-out of there. It did give us a chance to see The Last Supper, though.

In retrospect, we had one too many stops. We should have eliminated Orvieto and added time in Siena so we could see more of that part of Tuscany. I think I let Rick Steves woo me into Orvieto as he makes it sound so delightful. It is delightful, but that is where I learned the lesson of moving too fast. We could have added a day to Siena and one to Rome then day-tripped to Orvieto from Rome, for example.

So drop something and do some consolidating so you make most of your stays 3 and 4 nights. Or will appreciate Italy more.

Try this itinerary, I've eleminate the Cinque Terre.
Travel times are approximate.

Day 1. Travel.

Day 2. Arrive MXP, Malapensa Express to Milan
52 minutes.

Day 3. Milan, sleep in, late breakfast, late morning train to Venice. 2hr45m.

Day 4. Venice

Day 5. Venice.

Day 6. Venice-Florence 2hr05m.

Day 7. Florence.

Day 8. Florence.

Day 9. Early train, 7:46 Florence-Cinque Terre. 1hr49m. From Firenze Campo di Marte station

Day 10. Cinque Terre

Day 11. Rent Car La Spezia. Visit Lucca on way to Volterra. Spend the night. Seeing this town at night is well worth the stop.

Day 12. Drive to San Gimignano on the way to Tuscan hill towns. Stay?

Day 13. Tuscany

Day 14. Tuscany to Orvieto-Naples/Sorrento. Option, Drive is 3hr50m or drop car here , train 4hr18m.

Day 15. Naples/Sorrento/Amalfi Coast.

Day 16. Naples/Sorrento/Amalfi Coast.

Day 17. Naples-Rome late afternoon/evening train. 1hr10 min.

Day 18. Rome.

Day 19. Rome.

Day 20. Rome.

Day 21. Travel.

Reguarding the Garden of Ninfa, do you realize you will have 2hrs travel time each way for a 50 minute guided tour? You can't just wander this garden.

Hope this is of some help.

Oh My, can I hire all of you to be my personal travel agents?!!! You are helping so much! I have been tearing my hair out researching train times/distances etc., but then since I have no idea how much time I will want to spend in any area It has been so difficult to know how to allocate the time. I love the redone schedule that allows time on the Amalfi Coast. We will have to decide if we can fit it in or save it for next time. I can envision a Rome- Sicili-Puglia trip in my future! Much of my travel in the past has been in off or shoulder season where one can go somewhere without reservations and go where the winds blow you and stay or go when you feel like it. I am pretty clear that May in central Italy is not the time to do that, thus all the planning. Yes, I would love recommendations for the less crowded Cinque Terre hikes. We are pretty sturdy. If we do go to Amalfi we are hoping to walk part of the Path of the Gods trail as well, if anyone has intel on the most scenic parts of that. I have read a few blogs about it already but any suggestions appreciated. Also if we do go to the Amalfi Coast, we are considering staying in Atrani to avoid the hustle bustle. Other suggestions welcome. Thanks a million.

Emily,
I've slightly adjusted your itinerary above. Have eliminated your second nite in Milan and added 2 nites in Cinque Terra. See what you think.

Edit. Here's a beautiful garden in a spectacular setting.
https://www.marthasitaly.com/articles/127/la-foce-garden

Also if we do go to the Amalfi Coast, we are considering staying in
Atrani to avoid the hustle bustle.

If you were to do this, I'd skip the CT entirely and add that time to the Coast. Personally, 7 moves in 21 days would be 1 too many for us but that aside, the Coast is, as I noted before, a time-consuming place to get to and get around in, especially during high season and especially if you don't stay in a transport hub such as Sorrento (which Gerri has specified on her itinerary) or Salerno.

Thank you Gerri and Kathy. I am definitely leaning towards fewer moves and more day trips thanks to all of you. And perhaps saving Amalfi Coast for another trip, off season. And we will try to be tough and get to Venice after our first night in Milan. I am wondering- once we know our schedule, should we try to book train travel in advance from the US, or the day before from Italy or just show up a little early at the station?

Book your tickets as soon as possible. Use

https://www.trenitalia.com/en.html

There are substantial savings by doing so.
Just did a quick look, and the trains you'll need, are all showing super economy fares are still available.

The only regional train would be Orvieto to Rome. This you can purchase at the station the day of travel.

Use Italian names. Milan/Milano Centrale. Venice/Venezia S. Lucia. Florence/Firenze SM Novella, traveling to the Cinque Terre, the station you'll use is La Spezia Centrale. From there you'll use the regional train to the village of choice.
Edited to add.

If you decide to travel on to Venice on your arrival day, ask here on the forum about what might be a good amount of time to allow (though there are no guarantees your flight will be on time). Sometimes the advance-purchase (non-refundable) fares are so cheap that it's worth the risk that you might miss the train and have to buy new tickets. But you want to allow a rational amount of time to reduce the possibility that will happen.

I prefer Loco2 for checking train schedules and booking. Easy and excellent service.
I would spend no less than 4 nights per stop. 5 is perfect and you’ll appreciate your trip so much more.

Have fun
Greg