Best home base

@eulloa24.. I like option 3. It fits better with your itinerary. Florence is not far from Bologna. I would go with option 3.

You can also try this Itienrary:

Arrives in Rome Thursday Nov. 27

Nov. 27 - Explore Rome
Nov. 28 - Rome
Nov 29 - Rome
Nov 30 - Bologna
Dec. 1 - Bologna (Day trip to Florence)
Dec. 2 - Venice (Meet friend in Venice and explore Venice)
Dec. 3 - Venice
Dec. 4 - Venice Day trip to Verona (The town of Romeo and Juliet) 1 hour by train from Venice
Dec. 5 - Venice
Dec. 6 - Venice (Friend fly out - You can continue to explore Venice or possibly do another day trip to the town of Padua) 40 minutes by train from Venice
Dec. 7 - Venice - Fly Home

I like Option 2
You can day trip to Bologna from Venice (with your friend)

Most museums are closed on Monday in Florence so plan accordingly

Rome 3 nights
Florence 2 nights
Venice 5 nights with 1 or 2 day trips

Nov 30 - Bologna Dec. 1 - Bologna (Day trip to Florence)

JMO- What would be the point of staying in Bologna for 2 nights (1.5 days) to spend your only full day traveling to/from Florence?
You would see more of Bologna on a day trip from Venice than you would with just the half day on arrival from Rome.

Dec 1 is a Monday so not a good day to tour Florence if any museums are of interest.

If you have to spend 5 nights in Venice (not a bad thing!) that is where you should plan day trips from- and there are several good ones as RJean has listed (Verona, Padua, Vicenza) but do give Venice itself at least 2 full days.

Keep in mind days are short in Nov/Dec.

Perhaps your friend who is arriving in Venice could take the train to Florence and meet you there. This would allow all three of you to spend a few days in Florence before heading to Venice and flying home. I love Florence and there are so many great day trips from there including wine tours in the Tuscan countryside.

Consider flying into Venice, then taking a train to Florence, then ending up in Rome and flying home from Rome. I can't tell how that works with your friends, but it makes a lot of sense transportation-wise. And, as you may have read here already, Venice is so much easier than Rome as a first stop than as a final stop. It's great for getting over jetlag and its flights out tend to be super early in the morning and harder to manage with public transportation than Rome's many flight times and airport train or a taxi

I vote that your friend meets you in Florence, then you can all enjoy Florence and the area and then proceed on to Venice for departure (for however long you want to be there)

Thanks all!

Sorry I’m not sure how to reply to individual posts.

The reason for potentially staying in Bologna is we feel bad about the friend who is flying in to Venice having to travel via train longer to meet us. Not a super experienced traveler and feels a little flustered about traveling on their own. Trying to figure out the best way to meet with them but also get time to explore as we travel up from Rome.

I have faith in your friend! It looks like there are trains from Venice to Florence that take only about 2 hours and 13 minutes. They can take the bus (or I bet a taxi for ease?) to the main station, and then buy the next train that works. There are COUNTLESS youtube videos on journeys such as this, they can watch enough of them to be able to do the transfer with their eyes closed! (I had an Olympics trip last year that we were planning since 2022 and I street viewed SO MANY TIMES that I literally could have walked all around while blindfolded) I don't want you to limit yourselves to an inconvenient trip just because someone is flying into an airport that is far away.

Another sad, yet possible, option is for you to drop your luggage at the hotel in Florence and then get on a train to go get her from the airport to transport all of you back to Florence (or whatever city you end up in). I had to go to the Naples airport (yeah, I know its not the same) from Salerno which was a hike to go pick up people, and with y'all already there, and already did the "airport run", you know how to do it the opposite way.

I agree with Katherine and would also like to add that Bologna is nice, Florence is spectacular. In my humble opinion lol.

What time do you arrive in Rome? What time do you depart from Venice?
What time does friend arrive in Venice and from where? what time does she depart?

A 3 night stay equals 2.5 days, a 2 night stay equals 1.5 days, etc

Having friend meet you in Florence is a great idea- if she wants to experience both Florence and Venice. It’s not much further on train than Bologna and easy enough to do. She takes airport bus to Venezia Mestre station and then purchases tix on next fast train to Florence (or can use the app once en route from airport). Look up train possibilities ahead of time, they are frequent and direct (no changes)

You and friend #1 would then spend 3 or 4 days in Rome before heading to Florence for 3 or 4 days.
Make a list of what you want to see/do in both Rome and Florence then decide which location gets 4 nights. (2 with other friend)

If you want to do a day trip from Florence (Siena, Lucca/Pisa?) then then you should give Florence 4 nights and day trip should probably be on Monday or other friend would not really have much time in Florence (depends what time she arrives but I have to assume it would be mid to late afternoon)

Then you all take train to Venice on Thurs 12/4

You and friend #1 get Rome 3, Florence 4, Venice 3 (or 4-3-3)
Friend #2 gets Florence 2, Venice 2

That’s a pretty standard first 10 day trip to Italy- covers the Big 3.

Would look like this:
Thurs 11/27 Arrive Rome- jet lag day
Fri 11/28 Rome
Sat 11/29 Rome
Sun 11/30 Florence or Rome
Mon 12/1 Florence (museums closed- good day for day trip)
Tuesday 12/2 Florence- friend arrives Venice- takes train to Florence
Wed Florence 12/3
Thurs Venice 12/4
Fri Venice 12/5
Sat Venice 12/6- friend departs
(while there are great day trips from Venice I wouldn't since now you only have 2.5 days in Venice)

If you don’t have a good guide book- get one. RS Best of Italy works. You can get it quickly on Amazon.

Meanwhile you can start here:
https://www.ricksteves.com/europe/italy
Check the At a Glance for each location you are interested in.

Trenitalia- the official train company- fast trains and regional trains
https://www.trenitalia.com/en.html

Use Italia Station names
Roma Termini
Firenze SM Novella
Venezia S Lucia
(Venezia Mestre)

ItaloTreno- private fast trains only
https://www.italotreno.com/en

Both have easy to use apps.

You can book your tickets to Florence and Venice once you have itinerary set and save some money but you don’t have to book in advance- there are multiple trains all day long.

There are hundreds of threads here about all things Rome, Florence and Venice-use the Search function (filter by Type and Date) for anything- lodging, sights/tickets/tours, how to get around, eats, etc

Post any questions here- you will get tons of help.
If Friend #2 decides to met you in Florence we can give specific directions for how to do that.

Be sure you all figure out how you will get to the airport for departure- it’s a bit involved from Venice. Lots of threads on that topic here as well.

If you book any venues in advance (most big ones will need) make sure you are using the official sites- ask here for those links as you need them.
There are some spammy websites out there now that must be avoided!