First time to Italy

You can do a side trip to Pompeii from Rome, but it will be a very long day. It is much better to spend more time and visit Sorrento, Capri and the Amalfi Coast.
The Amalfi Coast is a bit similar to Cinque Terre, being on the Med. Frankly, I like the Amalfi Coast more than CT.

Also, why are not visiting Florence. It is an amazing city and very historical with two fantastic art museums.

With 8 persons, I assume you will be taking the train. There is a high speed train from Rome to Florence and Florence to Venice.

Also, have you researched what you plan to visit in Rome and Venice? Three days in Venice is fine, but three days in Rome is not enough to do the key sites.

Thank you for the tips. In Rome, we would like to do theColosseum and Vatican City. SistineChapel. The Colosseum is the main historical site that the whole family wants to see. Our family is mostly hikers and that is why we want to go cinqua Tera and not spend days in art museums more than what we’ll see in Rome. I just fell in love with CT and would love to go there. Before I visit Amalfi. And Venice would like to just spend one day again not into a lot of art museums, but we would like to do a gondola ride.

When is this trip?
Reverse your order, as flying into Venice is easier than flying out.
I'm confused- how many nights are you sleeping in Venice? Pls give Venice more than one night. You can have a wonderful time walking off jet lag and just wandering the peaceful back canals. We visit Venice every few years, and never go to museums anymore. Venice offers charming outdoor walks and ambience. And - try Row Venice instead of a gondola ride- small group rowing lessons on the back canals, about 100 euros total for 4-5 people, 90 minutes.
Have a great trip!

June 2026

Hello catone5, and welcome to the forum,

Pienza has no train service and would require a car or an arranged tour from someplace nearby. You might want to double-check a train map and plot out your route some because the quickest route to Cinque Terre (note spelling) is to take the coastal train from Rome to La Spezia at about 3:30 hours. The coastal route takes you far away from rural Tuscany where places like Pienza are. I know the obvious train route is to head to Florence but the fast train to Florence doesn't stop anywhere so you'll pass rural Tuscany at many miles an hour. If you wanted to visit the Pienza area you would need to do something like the slow train to Chuisi and then rent or arrange for transportation to Pienza. If you wanted to spend a few days in the area this could make sense but there is no flying visit here.
From La Spezia it is a quick local train to any of CT towns or you can head to docks and take the ferry.

Unfortunately CT to Venice is crossing Italy at nearly it's widest point and will take 7-8 hours door to door. Since CT is the outlier to your plan I might suggest looking at something like swapping out CT for Lake Garda or the Dolomites. Someplace like Malcesine on Lake Garda would give you access to Mount Baldo for hiking and the Dolomite area near Venice is much more dramatic for hiking or mountains than coastal hiking. From there Venice would be easy to reach. But you don't say when you're going at weather and snow make a big difference for outdoor activities - especially in the alps.

If you do get to CT for hiking be sure to check out the High Path - this something I've wanted to do for a long time.
https://www.incinqueterre.com/en/trail-number1-high
This is more serious trail and is not the tourist hiking trail most people are looking to take.

Hope that helps, have a great trip,
=Tod

CT to Pienza is almost impossible by public transportation - I mean, there should be a way with a combination of trains and buses but overly, overly long - and still quite long by car. You are trying to cram too many things in difficult places in short times. Also consider that moving 8 persons will take time and through planning - you are too many for a car (with baggages, you are too many even for two cars) and you should better reserve trains where possible.

So Roman/Vatican = 2
Pompeii = 1
Cinque Terre/Hill town = 3
Venice =3

• I've seen much more phrenetic/bloated itineraries so I appreciate limiting your packing and unpacking.
• I think Pompeii is maybe waste given your short itinerary. Independently, you're looking at a 5 hours of travel sandwiched around an exhausting, hot day of exploring the site during the hottest part of the day. I guess maybe investigate guided day trips or Just save it for next time.
• Alternatively, Check Alltrails for hikes near Sorrento. That may cause you to rethink a bulky detour to the Cinque Terre and you could get to Pompeii bright and early. If you're locked in to Cinque Terre, no worries. It just eats up a LOT of time in a short vacation.
  
• Are there hill towns with better train connections than Pienza?
• Venice will be very crowded in June. Book ASAP and just be prepared for occasional short tempers from locals. I do like the fact you're actually staying a few days. Escape the crowds by hopping the taxi to Gudecca or a visit to Cimitero if you love beautiful cemeteries/macabre history.
• I do like the idea of landing in Venice. It's just a great "first impression" city and, like someone said...it's more chill than arriving jet lagged and exhausted in Rome.
• If there's any way possible, try to add days. The transatlantic hop a lot of cost and time. My advice is always to try to amortize that over additional days

Have you considered doing a reverse itinerary? Fly into Venice and out of Rome. Or even fly into Venice and out of Naples if Pompeii is a must do. It looks as if you have 10 days actually in Italy, correct? You are losing a lot of time to long train journeys. On your current itinerary they are: Rome to Cinque Terre - 4 to 7 hours depending on changes; CT to Venice - 6 to 7 hours depending on changes; Venice to Rome 4 hours no changes. These times are approximate from the Rome2Rio app which is useful for looking at routes. For the most accurate timings and cost use the Trenitalia website, they run the trains. The Venice Rome route is quick as it is a fast train with no changes, the other journeys are a mix of fast and regional (frequent stops) trains. Pienza, with no train station, is indeed difficult from any of your stays; Rome might be possible with either a car rental or a driver/van. Oh and when using the Trenitalia site, use the Italian names - Roma, Napoli etc.

Without knowing what your groups interests are it is difficult to comment on the amount of time in any of your stays. Certainly Rome deserves more especially if you are going to Pompeii. Oh, and how do you intend to do that? Naples is just over an hour on the fast train and the local train to Pompeii is about 50 mins. While the site is vast, there is only one small cafe with limited choices so it is suggested bringing water and food. Lots of bus tours go from Rome to Pompeii which might be easier for a group.

Good luck with your planning.

The 18 year old is an adult

I am planning to fly into Rome spend three total days in Rome with a
side trip to Pompeii then take the train to cinqua terra for three
days with a side trip to Pienza if possible. Then the last three days
for a trip to Venice and fly out of Venice.

How many NIGHTS do you actually have on the ground in Italy?
Counting your trip in nights gives you a better picture.

To get 3 days IN Rome you need to spend 4 nights.

Pienza from any town in CT (Cinque Terre) makes no sense for all the reasons stated above. It is too far, not accessible by train. With 8 people you would need to rent a van and that comes with all sorts of requirements. It’s also about a 4 hour drive each way.
Pick a different hill town closer to CT if you must- but honestly you hardly have enough time in CT anyway.

Rather than Pompeii and the long day away from Rome- visit Ostia Antica. You hardly have enough time Rome either.

Start in Venice- end in Rome- much easier to fly IN to Venice than out of.

Where are you flying from? With that many people, some of them are likely to be too jet-lagged to enjoy sightseeing the first day in Rome. I agree that it would be better to fly into Venice and depart from Rome. I've done Pompeii as a day trip from Rome twice, but would not do it when you really only have 2 1/2 days in Rome.

Another vote for flying in to Venice and out of Rome. You have to take some kind of water transportation between the main area of Venice to the airport. For myself, there is less anxiety if I am coming FROM the airport into town instead of trying to make a flight. Plus, unless your home airport has direct service to Venice then you may have a fairly early morning flight to a European hub to get a flight back to the US (assuming US is your home). Getting to the airport in Rome is no problem...you can have your hotel book a taxi a day or 2 before for your group and it's straightforward to get to (no water involved, hahaha).

I also agree with needing to know how many nights you are dealing with. To me 2 nights = 1 full day so I would think you might have 4 nights in Rome for 3 full days....is that how you are counting?

AND welcome to the forum!

Thank you all for the tips and I will review my itinerary with the family…

Obviously, your time in Rome isn't enough to see everything, but I think Rome is better off digested in small bites. Spend your 3 nights on this trip and plan on coming back. Rome can get exhausting and it'll be crowded so I like the idea of balancing that with more "rural" days