Need advice on Italy trip (in two weeks)!!!

Welcome!
Looks great
If you are iffy on both Siena and CT might consider a 1 night stopover in Orvieto instead
That will give you a small hill town experience that is on your way to Rome

Cinque Terre is beautiful. When the weather is nice. When it isn't, there isn't much to do. One of the days we were there all the paths between the villages were closed because of a threat of bad weather which never materialized. I really liked Siena. Two days covers Siena pretty well. We used the bus to get to Siena. I think it might have been faster, however the big advantage was the bus stop was on top of the hill that Siena is on while the train is at the bottom. I know other options for Florence would be wine trips into Tuscany, or trips to Lucca or Orvieto.

In Siena, we enjoyed a seat on the balcony looking over the Campo at Bar San Paolo. It seemed right to order an Aperol Spritz.

Welcome BBB90! Were you born in 90? My son was and he uses Reddit’s travel forums for his research and planning (he travels a lot), you might find helpful info there from others closer to your age, most of us here are 60+. I’d say don’t miss 2 nights on the Mediterranean, whether it’s the Cinque Terre or somewhere else. Swimming in the Med, relaxing in a town/village on the Med, will be a highlight. Enjoy, have fun, cheers!

Hey Susan -- you're as young as you feel! Maybe BBB is 90 years old! ;-)

BBB -- I'd take Siena over CT for history and art, and also proximity to your main cities. CT would mean additional travel time in a trip that's already short.

Thank you Jules, Susan, and Christine!!

I appreciate the welcome and responses thus far. I am in fact born in 1990. A friend and I have bonded over Rick's show for years and often play his bingo card with a few Aperol Spritz'. I figured the message boards here would be a wealth of info as I plan this trip in two weeks!

In terms of a coastal towns, do you have any recommendations that have great swimming / atmosphere? And if I were to dedicate a 2 nights to a side trip which of Rome or Florence would be better to trim a day off of?

It looks to me as if you'll have 4.5 days in Rome, not 3.5. That strikes me as a good thing. This month might be a very, very good time to see the Cinque Terre, though I wouldn't much care for trying to do it in one day. I think surely the number of visitors will be down a lot. There aren't many cruises and bus tours running yet, I don't think.

Orvieto is also a very good suggestion. It's a lovely hill town with a nice historic district and a stunning cathedral. For a fairly small place it has a lot of sights; it's not the sort of place you can see in 90 minutes.

Although Siena's totally worthwhile, I don't think I'd switch hotels for just one night there. From looking at a map, you might assume the trip from Siena to Rome would be faster than from Florence, but that is not the case at all. Traveling from Siena, you'd be on a regional train that takes about 3-1/2 hours, whereas the Frecce cover the distance from Florence to Rome in about 1-1/2 hours. (The Frecce from Florence cost quite a lot more, though.) So decamping to Siena for a night won't actually reduce your travel time at all, plus there will be the hassle of checking into a new hotel and dealing with your luggage on the day you shift to Siena. So in your case I'd recommend a day-trip to Siena instead (by bus) if that's to be your third destination.

The same travel-time warning applies to Orvieto as well. Yes, it's physically between Florence and Rome, but it's not on the Frecce rail line, so you have to use regional trains. Florence-Orvieto plus Orvieto-Rome would take over 3 hours vs. the straight-shot from Florence to Rome at 1-1/2 hours.

Dick, BBB could have been a 90 yr old on his way to grad school but I thought the odds were better that BBB was born in 90... lol.

I think BBB is already getting a lot of art and history with Rome and Florence and experiencing the Med is super fun and a nice addition. Plus, my son and I aren’t fans of Siena so I’m biased.

BBB, that’s so great you like Rick’s shows, my son does too. But for clubs, bars, cool experiences, he prefers younger opinions.

I’d take one night from Florence or Rome and spend 2 nights in the CT. But that’s just me.

As you are arriving Milan 'early', had you considered going directly to CT, then Florence and end in Rome? ( should eliminate some back tracking)

If you find you have "extra" time in Florence you could do a day trip to Siena ( save the bother of packing/unpacking etc)

I will let you decided how to allocate your time. Overall looks good.

joe of course is right, the best route would be Milan > CT > Florence > Rome.

“The Cinque Terre is beautiful. When the weather is nice.”
CT weather in June will be amazing.

This is the year to go to Cinque Terre I would think.

I would go upon arrival as suggested above. Being outdoors is a great way to get over jet lag. I would spend two nights here.

Some years ago we spent three nights in Florence. We took the bus on our second day to Siena. I would do that rather than moving. We saw a lot in one day and enjoyed the contrast with Florence. If you don’t move to a new accommodation, then can even decide when you get there.

Hi BBB, it’ll take 4h 30m from Malpensa (Milan) Aeroporto to Monterosso (CT) that requires one connection in Milano’s (Milan) Centrale station. It’ll take 3h 30m from Malpensa Aeroporto to Firenze SMN (Florence) with a connection in Milano Centrale.
I too recommend going to Monterosso first because there’s another connection involved if going to either Florence (2h 30m) or Rome (4h 30m). However, there is a direct train between Florence and Rome (1h 45m).

You are 7 years younger than me or part of a year older or part of a year younger. My trip to Italy was in 2018, one night on the plane and 13 nights on the ground, I did a round trip from Detroit to Rome to Detroit - who knows whether I would have been better off flying to Milan and leaving from Rome or arriving in Rome and leaving from Milan. I don't remember looking for flights to Milan. I spent 6 nights in Florence. I think that was too many nights. From Florence I took a day trip to Pisa. I didn't give myself time for sienna or Cinque Terre. I was in Rome for 4 nights. I was in Naples for 3 nights. I wanted to see the archaeology museum in Naples and the ruins of ancient Pompeii.

I guess I could have landed in Rome, taken train trips to Naples, back to Rome, to Florence, and to Milan - thats 4 long distance train trips. If I could have left or arrived in Naples I could have cut the number of train trips to 3; If I could have landed in Florence and left from Naples or the other way around, I could have taken just 2 long distance ground trips. I thought if I couldn't find a good way to take flights to Florence and fly home from Naples, or the other way around, I had to leave and arrive from Rome.

Wow so much great information thank you all so much!

I did mistype my original post, I am headed back on Monday the 28th. I am beginning to look into that straight shot to Cinque Terre from Milan. I wish I was able to stay in Italy a bit longer, but my program starts up mid July and I have to move across the country when I return. I may shave a Florence night to get another in CT so that I get a full day over there. I land in Milan at 9am so if everything goes quickly I still won't be in CT until 2-3pm after my COVID test and the train. Would be a waste to go right to Florence the next morning ha.

Mary- Thank you for the train suggestions, I will say that is the most intimidating part for me. Don't want to take a wrong connection.

If anyone has any must try restaurants, bars, or coffee shops in the three areas I will be in I'm all ears :).

" I may shave a Florence night to get another in CT"

That would be a really good idea! One night won't provide much time to look around the five towns. You will of course have to decide which of the five towns you want to stay in, and my favourite is Monterosso. Depending on what time you arrive at MXP, you may be able to connect with the express train to the C.T. Other trains have one of more changes, which will increase the travel time (not desirable after a long international flight). Use the Bahn.de or Trenitalia websites to plan your rail trips.

You'll first have to get from MXP to Milano Centrale, using the Malpensa Express (DON'T forget to validate your ticket prior to boarding the train). If you're not familiar with using the trains in Italy, there are a few other potentially expensive caveats to be aware of. Most of us here recommend NOT buying a ticket for the express trains if you're connecting from an international flight, as the ticket will be specific to train, date and departure time. You can easily buy your ticket from Milano to Monterosso using one of the Kiosks in the station.

Another vote for CT! My daughter, a touch younger than you, is headed to Florence for fall semester and CT is a must-do for her! Old villages, the Mediterranean, a hiking trail, great cafes with amazing views!

I also love Orvieto and would choose that over Siena.

Hi,

Here's another vote for starting in the CT. I did that about 5 or 6 years ago. I took a direct train from Malpensa Airport to Centrale Stazione in downtown Milan (there used to be two per hour and about a 50 minute trip). You can then take a train from there to CT (I think it was about a 3 hour trip through Genoa). The five villages are gorgeous and I suspect they won't be as crowded this year due to Covid.

Good luck,

Yet another vote for CT -->Florence-->Rome, though I really like Siena. You probably have a rare opportunity to see CT before it was "discovered". Before Covid, it had become a nightmare. Be aware there's not really a lot to do except walk/hike. There's no sights, but you'll more than make up for that when you get to Florence and Rome.

Have a great trip and best of luck on your graduate studies!