20th Wedding Anniversary Sept'27 Venice/Dolomites

I would do 4 and 4. We stayed 4 nights in Venice on our first visit and I thought that was a good amount. And we stayed 5 nights in Ortisei and enjoyed it all.

One reason to stay longer in the Dolomites is that you increase your chances of good weather. We only had one rain shower and it was late afternoon but you never know.

We have been to Padua and while we also enjoyed our time there, I would give the day to the Dolomites. It really is a lot of trouble to get there so it makes sense to stay awhile.

You might look into flying out of Munich as I think it is the closest major airport.

We just spent a week in Ortisei and flew home from Munich. We had a driver take us to Bressanone/Brixen and took the train from there. Very easy.

We just did a very similar trip. My recommendation is that you spend at least 4 nights in Ortisei, as it was our favorite stop in Italy.

I highly recommend a stay at Casa al Sole in Ortisei. Manuel and Alexandra are the consummate hosts; beautiful home with food and wine that is fabulous. It is a truly memorable property. I had a private driver pick us up at the train station, and then drive us to Ortisei in order to avoid taking the bus.

Four nights in Venice was just the right amount of time for us. If you enjoy staying in local B&B's then consider Corte Campana which was the host Riccardo's childhood home. He and his American wife, Grace were so helpful in providing us with insider's tips on visiting Venice. It is a beautiful, small property that books up early, and the price point is so much more reasonable than other options that I found in Venice.

If you have not been to Milan, then I would suggest you fly home from there, and if time allows, try to obtain tickets to view DaVinci's "Last Supper". If that is of interest to you, then only purchase tickets from the official site, and do the research to determine the date they will go on sale, because those tickets are snatched up as soon as they go on sale. I set my alarm for the middle of the night to obtain ours. Enjoy your anniversary trip!

The South Tirol (Dolomites) website.
https://www.suedtirol.info/en/en

Check out Gillian Price's hiking guides for the Dolomites.

I personally would split the trip 4 nights = 3 full days in Venice (not that there isn't LOTS more to see there) and 4 nights = 3 full days in the Dolomites (not that there isn't LOTS more hiking there too). Padua's Scronvegni Chapel is spectacular but would eat a lot of a day from Venice where you have few enough.
https://www.cappelladegliscrovegni.it/index.php/it/

You can come back through Milan, or return to Venice through Bolzano-Verona-etc. Or you can take a local bus across the Grodner Joch from Ortisei to Corvara and then the Cortina Express buses from Corvara to Cortina d'Ampezzo and then back to Venice Marco Polo airport. See the "Getting There" section of the Suedtirol website.

https://www.cortinaexpress.it/en/

I don’t think anyone has ever gone to Ortisei and wished they had not stayed longer, so 4+4 is my recommendation, or even 3+5 although I love Venice, too.

There are many easy hikes — really mountain walks — right from Ortisei or the neighboring villages which are reached by convenient buses. Your lodging will give you a pass for the buses which is good for your entire stay. To use the cable ways and funicular, you might want a Val Gardena Pass. There are good walking options at Rasciesa, Col Raiser, Ciampinoi and Mont Sëuc.

We could easily spend 4 or 5 nights in Ortisei taking nice easy hikes without even going to Selva or S. Cristina but one of our favorite things to do is take the bus to Selva and walk the easy path to S. Cristina, have lunch there at La Tambra, then walk the rest of the way to Ortisei. Simply a lovely mezza montagna walk with terrific views..

BethFL-Thank you! I think the 4 and 4 split makes sense. You are correct we had no time accounted for weather. We will take the possible Padua day trip out. I will include Munich when we are looking for our plane tickets. Thank you so much for your help!

Thank you, fraubarr. I will look at Munich and see if that's a good option for us.

TravelBug79-Thank you all of your ideas! I hadn't heard of Casa al Sole. It looks amazing and all wonderful reviews. Most of the stays I have seen have 1/2 board, it looks like Casa al Sole has wine/appetizers to order in the afternoon/evening. What did you do for meals besides breakfast? Yes, I have seen recommendations for Corte Campana. Thank you! That will be my top choice for our Venice stay. I will look at Milan too! I think that could be a good ending for our trip.

NickB- thank you! I think the 4 and 4 split makes more sense too. Thank you for the links! I will look up the hiking guide too!

Thank you, Laurel! It looks like an amazing place! We are so excited for our trip. I will keep researching and come back with more questions I'm sure.