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re: 25th anniversary trip to Italy, review my revised plan
Posted on 4/11/25 at 5:24 am to hawgndodge
Posted on 4/11/25 at 5:24 am to hawgndodge
Try and talk her out of Pisa. The tower leans. That’s pretty much it.
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Posted on 4/11/25 at 5:59 am to hawgndodge
I will echo the "way too much in one trip" mantra you're seeing here. I get it. It's the "we need to see it all while we're there" feeling when you go to such an amazing place like Italy. So much to see and do. I want it all! 
I'm going to throw a curve ball here and tell you if you're going to Florence, and taking the train to Rome, you HAVE to stop over along the way to Orvieto!
Orvieto is a stunning hilltop town in Umbria, Italy, perched on a volcanic tuff cliff. It's known for its rich history, breathtaking views, and architectural marvels like the Orvieto Cathedral, which boasts a colorful Gothic facade and frescoed interiors. The town also offers unique attractions like St. Patrick's Well, medieval streets, and underground caves that date back to the Etruscan era. It's a perfect destination for history buffs and those seeking a picturesque Italian experience. Have you been there, or are you planning a visit?
A few pics from Orvieto.
I've been to Italy 4 times and love it. We stopped off in Orvieto and spent the night. Best part of our trip. Amazing history. Views. Food. A quick cab ride from the station up the hill.
So, what would I can? You have some good suggestions and it's ultimately up to you. I will say I was never a Milan or Venice fan personally. Same with Pisa. At least compared to your other locations. Not sure if that'd work out airfare wise? Maybe fly into Florence, Italy - Peretola [FLR] and start there instead?
Either way, don't stress it. Whatever you do will be amazing and you will go back one day. Mark it down!
I'm going to throw a curve ball here and tell you if you're going to Florence, and taking the train to Rome, you HAVE to stop over along the way to Orvieto!
Orvieto is a stunning hilltop town in Umbria, Italy, perched on a volcanic tuff cliff. It's known for its rich history, breathtaking views, and architectural marvels like the Orvieto Cathedral, which boasts a colorful Gothic facade and frescoed interiors. The town also offers unique attractions like St. Patrick's Well, medieval streets, and underground caves that date back to the Etruscan era. It's a perfect destination for history buffs and those seeking a picturesque Italian experience. Have you been there, or are you planning a visit?
A few pics from Orvieto.
I've been to Italy 4 times and love it. We stopped off in Orvieto and spent the night. Best part of our trip. Amazing history. Views. Food. A quick cab ride from the station up the hill.
So, what would I can? You have some good suggestions and it's ultimately up to you. I will say I was never a Milan or Venice fan personally. Same with Pisa. At least compared to your other locations. Not sure if that'd work out airfare wise? Maybe fly into Florence, Italy - Peretola [FLR] and start there instead?
Either way, don't stress it. Whatever you do will be amazing and you will go back one day. Mark it down!
Posted on 4/11/25 at 6:39 am to hawgndodge
If you aren’t sure if your wife will enjoy it or not, then definitely do less on this trip. Not a drinker? Ok no problem there. Do y’all like food? Like to cook? History buffs? Fans of art? Outdoors enthusiasts?
If your wife really wants to see pisa, great do it. But are there things that you know she likes? If so maybe sprinkle a few more of those days in. If she gets sick, forced marches across Italy every other day is going to put some strain on that train.
This board is a fantastic resource. If you want to plan a more likely to succeed trip, heed its warnings.
ETA Milan for the duomo, last supper, and La Scala is worth a night. It is not a bad launching point.
If your wife really wants to see pisa, great do it. But are there things that you know she likes? If so maybe sprinkle a few more of those days in. If she gets sick, forced marches across Italy every other day is going to put some strain on that train.
This board is a fantastic resource. If you want to plan a more likely to succeed trip, heed its warnings.
ETA Milan for the duomo, last supper, and La Scala is worth a night. It is not a bad launching point.
This post was edited on 4/11/25 at 6:41 am
Posted on 4/11/25 at 6:55 am to VABuckeye
You’re also counting on the trains working, especially outside of the major cities. We spent a month in Italy last year, and ran into multiple instances of trains not running or not stopping at stations, even though we had prepaid business class tickets.
Agree with others that the Amalfi itinerary is too aggressive. Probably too late, but would have recommended visiting the lake region in the north early in the trip, and cutting out Amalfi.
Agree with others that the Amalfi itinerary is too aggressive. Probably too late, but would have recommended visiting the lake region in the north early in the trip, and cutting out Amalfi.
This post was edited on 4/11/25 at 7:00 am
Posted on 4/11/25 at 7:01 am to hawgndodge
Way touch packed into one trip
Posted on 4/11/25 at 10:31 am to Nole Man
Agreed 100%. Orvieto, Siena, Todi, Cortona, and Volterra are towns that will be a much more enjoyable spot than the major cities that will be swamped with tourists during the OP's travel dates. Orviet, Siena, and Todi aren't that far off the A1 between Florence and Rome, while Volterra and Cortona would be a detour.
Posted on 4/11/25 at 10:37 am to GeneralLee
Dude's got a packed beyond belief itinerary and yall are giving him more places 
Posted on 4/11/25 at 11:17 am to Fun Bunch
I've gone back to the drawing board. I'll update with another revised plan once I have it. I'm truly interested in getting feedback
Posted on 4/11/25 at 11:23 am to Fun Bunch
We're saying drop the whole itinerary and do smaller towns instead.
Unless his wife loves big cities and hates the countryside, a much more slower paced trip to Tuscany/Umbria is the way to go.
Rushing through Italy, wasting 1/3rd to 1/2 your time in transit, is a very American thing to do. Italy demands that you slow down.
Unless his wife loves big cities and hates the countryside, a much more slower paced trip to Tuscany/Umbria is the way to go.
Rushing through Italy, wasting 1/3rd to 1/2 your time in transit, is a very American thing to do. Italy demands that you slow down.
This post was edited on 4/11/25 at 11:24 am
Posted on 4/11/25 at 11:24 am to hawgndodge
If this is your 1st trip to italy then definitely do the "big 3", Venice, Florence, Rome.
Choose your side trips carefully. FOR ME, the more done, the less good of a vacation it is. But not everyone is like that. Do the trip YOU WANT.
I have done trips like this.
The first time my wife and I went to Italy, we did 3 nights Rome, 3 Nights Florence (with a short day trip to Bologna), 2 nights in Cinque Terre, and 2 nights in Venice.
That was a LOT, but it was still a great trip.
Find out what you really REALLY want to see and do those things. Try to minimize the travel if you can.
Does your need to see something outweigh the amount of time traveling on trains? If so, do it. If not, not.
And remember...you can just go back in a year or two and do other things. If you're a smart traveler, its not that expensive.
Choose your side trips carefully. FOR ME, the more done, the less good of a vacation it is. But not everyone is like that. Do the trip YOU WANT.
I have done trips like this.
The first time my wife and I went to Italy, we did 3 nights Rome, 3 Nights Florence (with a short day trip to Bologna), 2 nights in Cinque Terre, and 2 nights in Venice.
That was a LOT, but it was still a great trip.
Find out what you really REALLY want to see and do those things. Try to minimize the travel if you can.
Does your need to see something outweigh the amount of time traveling on trains? If so, do it. If not, not.
And remember...you can just go back in a year or two and do other things. If you're a smart traveler, its not that expensive.
This post was edited on 4/11/25 at 11:25 am
Posted on 4/11/25 at 11:28 am to GeneralLee
quote:
Italy demands that you slow down.
THIS RIGHT HERE. My favorite days were the ones where I "did" very little but sit at a cafe and watch the world go by. Talking to locals, eating some amazing food and having a glass of wine.
I am going back in a couple of months and am sticking to Amalfi coast (one of the smaller cities) and Sicily (I haven't been yet). I have zero tours or plans beyond taking it easy and seeing what I see.
Posted on 4/11/25 at 11:32 am to hawgndodge
This would be how i would wind my way from Milan to Rome...
Day 1: land in Milan, just see the Duomo and last supper. Nothing else to see there.
Day 2-3: Florence (get a rental car on your way out from Florence, you'll need it for these smaller towns in Tuscany/Umbria)
Day 4: Volterra area
Day 5-6: Siena area (go see Brolio castle and Meleto Castle in Chianti region)
Day 7-8: Montepulciano area (make sure you see Pienza, Monticchiello, and Castiglioncello del Trinoro)
Day 9: Orvieto
Day 10-12: Todi area (Todi is the GOAT, I'm moving there someday. Go visit Montefalco, Assisi, Spello, Bevagna and Deruta as well)
Day 13: Pitigliano area (visit Civita de Bagnoregio too)
Day 14-16: Return rental car, then visit Rome by train/cab
Day 1: land in Milan, just see the Duomo and last supper. Nothing else to see there.
Day 2-3: Florence (get a rental car on your way out from Florence, you'll need it for these smaller towns in Tuscany/Umbria)
Day 4: Volterra area
Day 5-6: Siena area (go see Brolio castle and Meleto Castle in Chianti region)
Day 7-8: Montepulciano area (make sure you see Pienza, Monticchiello, and Castiglioncello del Trinoro)
Day 9: Orvieto
Day 10-12: Todi area (Todi is the GOAT, I'm moving there someday. Go visit Montefalco, Assisi, Spello, Bevagna and Deruta as well)
Day 13: Pitigliano area (visit Civita de Bagnoregio too)
Day 14-16: Return rental car, then visit Rome by train/cab
This post was edited on 4/11/25 at 11:54 am
Posted on 4/11/25 at 2:46 pm to GeneralLee
Y’all don’t drink?
If you get taken to the right places in Tuscany, you will become drinkers.
If you get taken to the right places in Tuscany, you will become drinkers.
Posted on 4/11/25 at 2:49 pm to geauxpurple
Yep. I wasn't a wine drinker until I went to Italy. Now I love old world wines.
Just ask for vino tabile (table wine) at any small restaurant.
Just ask for vino tabile (table wine) at any small restaurant.
This post was edited on 4/11/25 at 2:50 pm
Posted on 4/11/25 at 2:56 pm to hawgndodge
Going Economy on the overnight there and Premium Economy on the daytime flight back.
Posted on 4/11/25 at 3:19 pm to VABuckeye
Or better than that, the top of the line stuff in Montalcino, Montepulciano or Chianti.
Posted on 4/11/25 at 6:03 pm to BlackenedOut
quote:
’d build in a day or two to breathe and have no plans.
Freestyling can provide some awesome memories. Listening to a tour guide....
Posted on 4/11/25 at 8:48 pm to H2O Tiger
We're in premium economy on both flights, over and back
Posted on 4/12/25 at 8:26 am to hawgndodge
If there is any way you can upgrade to business class on the flight going there I'd do it. Jetlag after an overnight flight can be tough.
Posted on 4/12/25 at 12:45 pm to VABuckeye
I wish. That's a 7k upgrade each way right now.
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