Italy Itinerary Help

Welcome to the forum!
Wow 24 nights is a lovely amount of time. I get that you are trying to “see everything” but honestly your itinerary is a bit too much and some just doesn’t make sense.

Are flights booked? Are accommodations all booked? Are they changeable?

A 2 night stay gives you just 1.5 days in that location. Each location change will eat up a half day or more.

Be sure you do your homework about driving in Italy. All drivers must have an IDP.

OK so this is what I am seeing:

Rome 2 nights
Pienza? 4 nights
Florence 2 nights
CT 3 nights
Milan 2 nights
Venice 3 nights
Bologna 2 nights
Alberobello 2 nights
Amalfi 3 nights
Rome 1 night

May 1 Rome, Landing around 8:30am, overnight flight, coming from Miami, FL. hoping the night flight helps with jet lag and I can sleep in the plane. So hopefully we can do plenty this day in Rome.

Everybody handles jet lag differently but I would not count on getting a lot done this day. I definitely would not plan anything major like Colosseum or Vatican so that leaves you just 1 full day in Rome which is woefully short.
If Colosseum and Vatican are both on your list- doing those 2 on same day will be exhausting.


May 2 Rome,

May 3 Train from Rome to Orvieto, pick up a car and check in to Agriturismo in Pienza, Siena,

It’s a shame you are not spending anytime IN Orvieto. Hertz is your only option for a car rental here.
Where are you staying Pienza OR Siena?- they are an hour apart. We love the Pienza region- perfect for exploring the Val D’Orcia region. Assisi would be too far for us as a day trip.


May 4 Tuscany (would like to see different towns while in this Tuscany region- Montepulciano, San Gimiggiano, Assisi etc),

May 5 Tuscany,

May 6 Tuscany,

May 7 Travel by car From Siena to Florence (drop off car),

May 8 Florence,

I’d give Florence more time- you have 1.5 days now


May 9 Train from Florence to Cinque Terre stopping at Pisa,

May 10 Cinque Terre (during my time in this area would like to stop by other towns in area),

May 11 Cinque Terre,

May 12 Travel by train from Cinque Terre to Milan,

May 13 Milan (possibly the lakes or train to see the swiss alps),

This will be your one full day in Milan


May 14 Travel by train from Milan to Venice,

May 15 Venice (during my days in Venice would like to see the dolomites, murano/burano),

May 16 Venice,

2.5 days is just enough time to enjoy Venice. Dolomites as a day trip is too far.


May 17 Travel by train from Venice to Bologna,

May 18 Bologna,

May 19 travel (not sure by car or train yet) to Alberobello (actually staying at Locorotondo near by),

This makes no sense to me- it is a 9 hour train trip to Bari then bus or rental car to Alberobello. It is at least a 7 hour drive.


May 20 Alberobello (would like to visit Lecce if possible),

You really only have 1 day here so a day trip to Lecce probably doesn't fit


May 21 travel by car from Alberobello to Amalfi (staying in atrani- smaller village next door),

May 22 Amalfi,

May 23 Amalfi/Capri,

Having a car in the Amalfi region will be a nightmare. I would drop it in Salerno. Please read thru all the posts on this forum about Amalfi Coast.


May 24 Travel by car to Naples/Pompei on the way to Rome (Quick day visit to this area before spending last night in rome),

I don’t see how you fit both Pompeii and Naples in one travel day and I definitely would not be driving in to Naples or anywhere near.


May 25 Flight home from Rome at 10.30 am

I would drop a couple locations- (Milan, Bologna and Alberobello) and add those nights to Rome, Amalfi and Florence, possibly Venice.
From Venice take train all the way to Salerno then ferry to Amalfi/Atrani. Since it takes so much time and effort to get to the AC - stay 4 nights at least to make it worth the trouble,

If it is possible to change flights, etc I would start in Venice

Venice 3 or 4
CT 3
Florence 3
Get car
Pienza 4
Drop car- train to Salerno
Amalfi 4
Rome 4 or 5

That leaves 1 or 2 nights- add Bologna or Orvieto.

Welcome to the forum. How exciting for you to take your dream trip. Yes what you’re planning is just a bit crazy; too rushed. I’d drop anything south of Rome for more days in Rome, Florence and Venice. There is lots to see in those cities. You can add day trips if you want to see more.

The way you’re scheduled now, you are moving too much and will see only roads and rail tracks. You just don’t have time to see it all. It takes longer than you think to move from one area to another. Google maps and Rome2Rio don’t take into account meals, sights and potty breaks. You haven’t given enough thought to jet lag the first day. You can get out and walk in the sunshine and see a few sights but I wouldn’t want to schedule anything major.

Tell yourself you will return to Italy. Head North this trip and south next trip. Christine has good ideas for you. I’d prefer to save anything south of Rome for another trip. My first trip to Italy, we rented a car to drive from Naples to Calabria for an overnight. It took 4+ hours driving each way. Your idea of going from Bologna to Alberobello is going to take a full, exhausting day. I loved seeing Alberobello tulli houses while on the RS South of Italy tour but not enough that I would drive all day to get there.

https://www.ricksteves.com/europe/italy/itinerary

Above is a link to RS's recommended 3 week itinerary. Give it a look. The trip you sketched out looks like loads of fun. You will get many folks here who will tell you it's too fast paced but pace is personal choice and you'll see Rick Steves tours and advice also are pretty packed so the choice is yours! Sometimes less is more. But also other times less is just less. Whatever works for you! One thing Rick does suggest is scheduling vacations within your vacations-- a slow day every week or so. Looks to me you've got some of that-- so well done.

You'll love it either way!

Happy travels.

What a nice amount of time to enjoy your drream vacation!

Jet lag affects people differently. I do the best if I can be outside walking outside to try to acclimate. So, I wouldn’t schedule any indoor museums that first day.

I see water locations at Cinque Terre, the lakes north of Milan & Amalfi Coast besides going to Venice. Since you live near water, you might want to consider reducing this by one so you could give more time to Rome and Florence.

I was tracking along with you on your choices until you mentioned Alberobello. That is a long, long train ride for one full day in the Puglia region! If you’re serious about Alberobello and Lecce, then I would give up the Amalfi Coast and spend time in the Puglia region and fly home from Bari.

If you haven’t already, look up train transportation times on www.trenitalia.com and write them in for each day of transportation. Then you will know what time you will arrive at the next city and what you can plan for the afternoon or evening when you arrive, Venice is Venezia, Florence is Firenze, Rome is Roma, Naples is Napoli.

Since you are asking for feedback - for transportation time, I add up all of my hours of transportation on a trip - (any hours going to/from day trips, hours going to the next city). I divide that total by the number of days I am in Europe. I want that average to not be greater than 1.0 hrs/day. That is because I want as many hours as possible walking, sightseeing, enjoying the locations vs. looking out the window of a train or vehicle.

I agree with the others who've said this itinerary is way too hectic. (Yes, Rick's suggested itineraries are nuts.) Aside from all the things you will not see at each destination because you'll be heading back to your hotel to pack, or to the train station, there's the issue of sheer exhaustion. While you might be able to keep up this pace for 7 or 10 days, I think expecting to do so for 3-1/3 weeks is unreasonably optimistic.

You'll have a much nicer time it you allow yourself the opportunity to breathe rather than practically running from sight to sight.

A warm welcome to the forums from me as well, mfive! So exciting for you to finally be able to take that long-awaited dream trip!

There's lots of very good advice above aside from using Rick's itineraries as a guide, IMHO. We all travel differently, sure, but many of us feel that his plans are much too rushed (I'm one of that many). Very tight itineraries, such as yours, also leave no wiggle room for things to go wobbly...and they can go wobbly. For instance, you're planning on using arrival day in Rome to actually get some serious sightseeing done? A flight delay could throw a wrench in that plan as well as a bad case of jet lag. Rome is a great city with much to see; you want to be awake for it! :O)

As well, May 1 is a big national holiday (International Workers Day). Rome will be especially busy, and not everything will be open. The attractions which are may have more limited ticket availability due to a larger number of people trying to get them. In short, due to the combo of potential jet lag factor and closures, this day may be best for simply walking around and trying to stay awake than serious indoor sightseeing.

Speaking of sightseeing, you'll need to get advance tickets/tours for the most-visited attractions, and those can be a scramble to get for high season. Working around the crowds in the bigger cities and the CT can also wear you down in a fat hurry. Short story long, I HIGHLY recommend giving Rome, Florence and Venice more time. I don't see a quality visit to both Naples and Pompeii happening en route to Rome either.

The Dolomites are not an option - much too far - and I'd drop anything south of Rome & lose the car for anything but Tuscan countryside. Fly into Venice and out of Rome.If you have a car for Tuscany, do read up on the ins and outs of driving in Italy, especially a thing called a ZTL, and never leave anything you can't afford to lose in the car when it's unattended. I'd consider dropping Milan too.

Why Orvieto just for picking up the car?

None of us are wanting to throw wet blankets at your plan; we want you to enjoy this much awaited trip and not spend it in an exhausted fog - not the sort of 'dream' you're looking for - so less can be much more! Worth mention also is that it's late in the game for booking accommodations for May so the clock is ticking for nailing down the itinerary and getting all over those. Having to research and book fewer rather than more at this point would be a plus.

With all due respect, Rick Steves Itineraries used in his books, used on this website and also used on his tours are not nuts. Tens of thousand of folks take his tours every year and are given surveys and those surveys say from people who actually took his itineraries is that they are great. I know! I took his tours and raved about them like everybody else who was on them-- they were fantastic!

With that said, they are not for everybody. His tours are selected by the more adventurous and those who can adhere to a couple of his policies— carry your own luggage and don’t be grumps. Likewise his itineraries are not for everybody. I use them and love them.

You are can have an outstanding three plus week trip to Italy and only stay at several cities— Rome Florence, Venice— ah, delightful. You can have a great trip and spend only a couple nights in places as you tour the whole country. There is no wrong answer!! It’s Italy after all and its grand!

The pattern of looking down on Rick Steves advice on this forum is odd to say the least. Nothing wrong with telling people slow down but looking down on Rick Steves style travel is perhaps not a good practice. I know as I age slowing down a bit is natural. But in the meanwhile carpe diem! What I like about the OP's plan is that it's a dream to see it all! If they decide to skip parts, rearrange the order based on great advice on the forum and RS's books, all the better!

Oh, well! Happy travels everyone!

David, you are right on that thousands have taken his tours and enjoyed them very much! No one is disputing that fact! The difference comes in with trying to match the multi-location tour itineraries when traveling independently, when there isn't a bus to drop you off or just waiting to pick you up near accommodations and attractions, ferry your luggage around, and guides to manage tickets and shepherd you from place-to-place. Different deal. Make sense? It's firsthand opinion from some of us who've traveled Italy on our own.

Heck, it's firsthand from some of us who've experienced not everything working like clockwork too! 😬

Like Kathy said, there is one thing that differs between Rick's tours and someone doing it on their own.....the benefit of Rick's tours are the fact that logistics are taken care of, you can easily see something on the way to another thing, much of the "in between times" are minimized or eliminated because you don't have to worry about getting from place to place, getting to and from train stations, finding restaurants without guidance in a new place (even during free time on a Rick tour they probably have some good guidance for you to find food), having to wait for a tour guide to have to corral strangers into a group tour, heck, you don't even have to manage finding your way to the meeting point of a tour to meet said tour guide. If one of his tours was driving 7 hours across country for just a two night stay, you would be stopping multiple places of interest on the way there and back and wouldn't have to worry about what to do with your luggage in the meantime. David, I'm not sure that Rick would even travel at the speed of his tours if he were doing it independently.

Our first trip to Italy was with a RS guidebook and nobody was arranging transportation. Indeed we ran into a rail strike and just rented a car! I personally find RS tours slow you down-- we do less on his tours than we did with just his guidebook,

You have to wait on a group of people to assemble, you have group bathroom breaks every couple hours, you take the bus when there are faster trains, planes and rental cars. There is always someone who likes to linger a bit longer than us. But the company is great! The tour guides are great!

It is wonderful for the OP to hear the great advice of seasoned travels such as yourself who urge them to rearrange the order, make sure they know the logistics of decisions-- like going to the dolomites or whatever. That's great advice! That's helpful. I am impressed by the regular posters on this forum every day!

Taking swipes at RS itineraries, well, that's a bit disappointing. There are tradeoffs. Educating people on the tradeoffs is helpful indeed.

Congratulations on your dream trip!
I think you have taken a great first step in stating your wish list, now it is time to edit.
You should remember that even if you had twice the time, you couldn't fit in all your dream spots, so just savor the ones you go to without regretting that you can't get to them all.

It sounds like your flights are already purchased, is this correct?
I also get the impression that this is your first trip to Europe?
I think, with your wonderful length of time you need to build in more down time and have more savor the moment experiences.

Are you museum people? Art lovers? Hikers? Beach lovers? Foodies?
Do you crave scenic vistas? City energy? Historical sites?
This will greatly influence your decisions.

The only place I see getting a car would be Tuscany. You should start playing with train schedules and maybe one flight within Italy to get a feel for travel times. I definitely see getting rid of everything south of Naples, unless there is a family connection there.
We loved Lake Como and Cinque Terre but I think you should choose just one.

I normally would suggest starting at the southernmost point and hottest point(Naples, A/C?) and working your way up to the cooler locations, but transportation would be a key factor. Maybe land in Rome and immediately get the train to Naples? Give Rome 3 nights at the end? I love your time allotment in Tuscany, what a beautiful time to go.

Rick Steves tours are wonderful and very popular, it is a great resource to look at their itineraries and other tour groups, for instance Tauck, to get some planning ideas. Kathy was spot on, though, when she said you would not be getting the door to door help and a guide with you the entire time. And if this is your first experience, there will be a learning curve that will slow you down. We would never go on a tour because we love having more flexibility and downtime, but I am so grateful for this site and all of the advice. Enjoy!

Welcome to the Forum!
How exciting to be planning your dream trip to Italy! I am currently planning our first Italy trip for 2025.

I agree that your itinerary looks overly ambitious, but I also understand that what works for one doesn't necessarily apply to another.
We made our first trip to the UK last fall, and everytime I asked for advice on our itinerary I got several comments saying we were doing too much and would only see the inside of a car. Well, we had a nearly perfect trip and never felt rushed. Sometimes you just really want to see someplace, even if you can't stay a while and really get to know it. Most people advised against our planned single night in the Lake District, which was between our time in Wales and our connection in Edinburgh. I'm so very happy we ignored the advice, because I now have lovely memories of our day and night in the Lake District. Yes, I would have loved to have more time there, but I'd take my memories of that day over regrets of not seeing it at all.
So, read the advice from others, look carefully at the travel times involved, and then make the decision that is right for you.

maryellenhowen makes many excellent points and it is your trip. You just have to know yourself, your energy level and your style and make your decisions from there. We have had many 1 night visits in the course of our travels and loved the small taste of somewhere special in each instance. I just know that in our longer trips, we were getting weary by the end.

Thank you everybody for your advice. This will be very helpful. I am not too concerned with packing as we decided to only each take a carry-on backpack and do laundry there. Our flights are booked already and because we are using credit card points its much cheaper (point wise) to come in and out of Rome (vs Venice or Milan which was my original idea) so I was trying to make one big circle and see as much as I can. I had originally wanted to add Sicily to the trip as well and knew that would be too much. I do notice in many guided tours that it is possible to do the southeast regions and Sicily in one trip so I'm going to drop Alberobello and take the train from Bologna to Salerno. My hotels/b&b were already booked but all were with free cancellation and my B&B in the amalfi coast was flexible with dates. I decided to do one more night in Almalfi and then one extra night in Rome, giving me some time to see more or even just relax before the flight the next day. I like the idea of the train from Rome to Orvieto, picking up a car at the Hertz car rental across from the train station, then visiting the town for a few hours before driving to our agriturismo in Pienza an hour away. Hopefully with 4 nights I get a chance to visit Assisi as a day trip too. So it might look something like this:
Rome 2 nights
Pienza 4 nights (will have a car here so will try to see as many tuscan towns as possible)
Florence 2 nights
Cinque Terre 3 nights
Milan 2 nights
Venice 3 nights
Bologna 2 nights
Almafi Coast 4 nights (hopefully here I can take one day to do Capri, maybe another for Naples)
Rome 2 nights

Thanks again everybody. This is our first trip anywhere outside of the United States. I'm hoping my husband will fall in love with Italy and we can go back many times. Grazie!

Just a few quick notes about the rental car in Orvieto. I thought it may be fun to rent a car for 1 day during my April visit to Orvieto (3 nights, 2.5 days). I was hoping to drive around to explore the nearby countryside, pick up and drop off same day.

1. I could never successfully confirm an automatic transmission. I called Hertz 3 times and never got an answer. I was told by Hertz that there is ‘sometimes’ an automatic transmission available. If you can drive a manual transmission, keep in mind: I think this area of Italy has a lot of hills.

2. My original estimate was something like $300 for a single day rental.

Decided to skip the car. Instead, we’ll be taking the bus or even using a taxi or private driver (probably costs less than $300!!).

Hi Mfive, from a fellow South Floridian (born in Hollywood) now living in Utah (just retired here). I like your changes and I agree with David. We've led many trips as tour guides, and enjoyed many trips ourselves and with our now 20 year-old son. The itinerary will be a whirlwind but you will enjoy it. Rick Steves guidebooks are awesome, especially for first timers. It's going to be ok. Just pack half the clothing and twice the money you think you need. Enjoy and be positive!

I think you have mapped out a delightful dream trip! Congratulations!

Pienza is fantastic. While in Tuscany treat yourself to lunch at Podere Il Casale. It is reasonable and delicious. You could also tour the farm, go to a cheese making demonstration or do a cooking class. The views are what you dream of. Enjoy!

https://podereilcasale.com/en/restaurant/

I like the pared down trip but I’d make one switch. I’d go to Ischia instead of Capri. Also, welcome to the forum and most of all, ENJOY!

Wow what an amazing trip you have planned.

I just got back a week ago and I would consider Salerno vs Atrani (although Atrani is beautiful as well). It's really lovely and you can reach all those towns vis bus or ferry. There's a great B&B in Salerno with a fabulous host if you'd like to research, Salerno Antica B&B.

Driving along the amalfi coast would completely stress me out because of the traffic but that's me.