Milan to Dolomites, to Florence, to Rome -- Honeymoon!

Welcome to the forum! It sounds like this is your first trip to Europe so I'd lean towards staying in Milan and heading to the Dolomites the next day. Otherwise you'll need to get from the airport to the train station, take the train to Bolzano, and then the bus up to town. It's doable but can be a lot after a flight from the US, and it would already be late afternoon. Given that flights can be late you'd want to do a lot of research to understand the train times to Bolzano from Milan and the hours the bus runs before planning on going all the way after landing.

I recommend staying in Ortisei. It has 2 cable cars and a funicular in town, more than enough for a few hikes. Kastelruth is the recommendation in the RS book but it doesn't have any mountain access in town. Given your short stay it seems easier to stay in the town with the easy access.

We were there last Sept and If I was going on our trip again I'd stay at a place with half-pension so breakfast and dinner are provided. There weren't that many restaurant choices in Ortisei, a bit to our surprise. Some low-end places and a couple that were very pricy. Then again on your honeymoon maybe the splurge places will be right for you. Generally breakfast is going to be provided where you are staying.

As your trip gets closer look up the activities offered including guided hikes on the https://www.valgardena-active.com/en website (summer activities probably aren't posted yet). We did several from Ortisei last year and they are free if your hotel is a Val Gardena partner which most are. Keep in mind the weather in the mountains can be anything from the 80's down to snow so you might want to pack to accomodate a reasonable range of possibilities.

Spend the night in Milan. It’s a long trip to the Dolomites, at least 4.5 hours with two transfers by train. You might also consider flying into Munich instead.

Ortesei is a great location for access to the lifts. Make sure they’re still running on your dates. Don’t miss Seceda and Seiser Alm. From Santa Cristina, we also went up to Col Raiser. We stayed in Santa Cristina at La Tambra. It’s a fabulous family run restaurant/hotel. Ortesei is a lot busier. Maybe not so much in September, but in June it was very busy.

Yes, spend the night in Milan. It will likely be at least 6pm before you get to Milan after clearing the airport and taking the train into the city. Then it's a series of trains and bus to reach Ortisei- another 4+ hours, if they even run that late. Too bad you already have your flights booked. Travel time from Venice would be about half of that from Milan.

Up to you, but many recommend Orisei.

Trains (at least 2 connections) to Ponte Gardena or Bolzano, then bus to Ortisei. From there, bus to Ponte Gardena or Bolzano and then trains (with connections) to Florence SMN station. From Florence it's a direct train to Roma Termini. Book tickets on the Trenitalia website and use the Italian Place names (Milano, Firenze, Roma)

Budget in €?

You have very limited time in each of the places you want to visit. Why waste any of that time taking necessarily longer train routes?

I’m here looking for tips on the Dolomites as I’m in the middle of planning our trip there for this July 1. But one idea for your first night would be to hop on a train to beautiful Verona for the night (or maybe two?), then rent a car in Verona to drive up into the Dolomites (then return it in Verona and train to Firenze). Of course, a 4pm arrival may mean you’re at the airport until 6pm and will just want dinner and bed. But definitely get a car for the mountains so you can get to whatever trailheads you want. Europcar is great. Cable cars can get expensive (at least in France they were). Download the Trenitalia app to plan your train trips. Verona to Florence is only 1.5 hrs on the high-speed train! Upgrade your tickets to make sure they are changeable, just in case you get on the wrong train (ask me how I know, haha), and higher class tickets mean you get Prosecco and a snack delivered to your seat. I love that. Florence will take your breath away. I thought I’d seen some exquisitely beautiful places, but the duomo brought me to tears. Highly recommend doing the Taste of Florence tour with Toni on your first day (so you get her food recommendations for the rest of your time!). Rick interviewed her on his radio show. [email protected] @tasteflorence on instagram

Another thought: Everyone is going to tell you how easy it is to take buses from Ortisei, and that may be true. But because you are not city people, and even if you were— planning your day around bus routes and bus schedules adds a layer of things you have to worry about while you’re on vacation, and you may not want that on your honeymoon. I lived in a big city for decades and got around by bus and metro, my husband grew up in a huge city taking buses everywhere, and we still found it to be quite a burden trying to plan our days around public transport schedules last year on vacation. We took “everyone’s” advice and didn’t rent a car (for the French Riviera), and then we literally lost huge parts of precious vacation days waiting for buses and trains, not being able to get on a bus/train that was packed full and having to wait for the next, etc. We are just not that disciplined while on vacation.

You can do: Milan 1n (pre book Last Supper ticket for 9/12 AM / train by noon from Milan to Bolzano / bus #350 to Ortisei 3n / bus and train to Florence 3n / train to Rome 3n.
Lodging in Ortisei will provide free bus pass, and you most likely only deal with one bus line #350. Some cable cars are within walking distance in town.

You do not want a car in Florence, all the big attractions are in town, within walking distance.

You do not want a car in Rome, learn to use subway, frequent and easy. Beware of pickpocket (anywhere crowded)
Pre book attractions in Rome and Florence.
Pre book train early with huge discount, non refundable non changeable though. Pay a little more to changable to allow some flexibility (no change for departure and destination though). Regional trains (R) has no assigned seat, I will not take a chance for long ride. Look for IC, Freccia etc which assign seats, or pick particular seat if you pay.
Hope it helps.

Congratulations! Milano Malpensa Airport to Verona Porto Nuovo Train station 2:30-3:00. Verona Porto Nuovo to Bolzano by high-speed Italotreno or Trenitalia train: 1:35-2:40 Bolzano to Ortisei by Bus #350 departing about every 20 minutes directly across the street from Bolzano’s train station: 50 minutes. After Ortisei stay, return to Bolzano: 50 minutes. High-speed train from Bolzano to Firenze Santa Maria Novella train station: 3:15-5:40 hours by high-speed train. Firenze Santa Maria Novella train station to Roma Termini train station via high-speed train: 95 minutes.
For train schedules and fares www.TheTrainline.com
www.Trenitalia.com
www.Italotreno.com
Some train tix for September may not be available to buy online until June 15.

Have a great Honeymoon!

4pm is too late to leave from Milan to Dolomites area; by the way, if you are landing at 4pm, you will be in Milan downtown at 6 or 7pm, there is little you can do but having a dinner and a good sleep.
Basically, every time you switch destinations, half a day is lost in transit, so you have 2 days and half in two places and 3 days and half in one place. Do not plan to do a lot of things as you won't have really much time. One cooking class should be enough.
There is not really a choice between scenic and non-scenic itineraries. Even when there are two itineraries one is a slow and one is a fast line over the very same scenery.

Thank you everyone for your help! We will stay the night in Milan, and go up to Ortisei in the morning. I think we will currently plan on risking the bus/train system to get to and from Ortisei, I've done a fair bit of traveling in Asia and North America, and think I can figure it out. We may change our minds though, we will see. We will skip a scenic train route.

Now just figuring out hotels! Grone is unfortunately booked up in ortisei, it was my first choice. Any other ideas? We have our Florence hotel picked out, just need Ortisei and Rome!

I stayed in Kastelruth last May and loved it. I was there for three nights at Hotel Zum Wolf. You can hike directly out of the town but, as someone already said, not directly onto the mountains. I enjoyed walking through the rolling hills. Day one I hiked to Siusi and from there went up into the woods to see the Rovine Della Rocca and another ruin, then took a bus back to Kastelruth. The next day I took a bus to Ortisei and took a gondola up to the Alpe di Siusi. The most gorgeous hike of my life- ended up being 23 miles because I missed the last bus down from Compatsch- I loved every second though. Even in the pouring rain! The last day I hiked again to Siusi as there was a festival and then up into the mountains. I found the buses very easy to use other than missing the one in Compatsch. My stay at Hotel Zum Wolf came with a pass and a really good breakfast. Enjoy your time there!