Europe Itinerary - 1st Trip Overseas
 

My husband and I are planning our 1st trip to Europe. We are planning on 3 weeks total in August or September traveling from the USA.
Our initial plan was to visit Rome, Florence & the countryside, Switzerland, Munich/Bavarian region of Germany, Neuschwanstein Castle and Austria (Salzburg & Vienna).
We are interested in history, castles, cathedrals, museums, mountains, lakes, hiking and photography and good local food.
We want a good mix of time visiting the cities and the countryside. We have not yet identified the countryside/small town areas that we would like to visit, but thinking somewhere in the Alps maybe.
We would like to spend at least some of our trip experiencing the local culture.
We tend to be more in depth travelers who often spend an entire week in one national park in the states, so our original plan is too ambitious for 3 weeks. We will have to go back for a second trip.
We are willing to rent a car when needed and travel via train where we can.

We are having trouble narrowing down which countries & places to visit on our 1st trip. We could also use suggestions on countryside/small town areas to visit where we would get a more cultural experience.

Any recommendations for our itinerary, must visit places?

Thank you!

We did a 3 week trip visiting central Italy picking up a car at the Rome airport and stopping in Tarquinia for our first night. We spent our time between Rome and Florence, by-passed Florence, and eventually returned our car in Rome. Here are the photo albums for the trip:

https://flic.kr/s/aHsjoYPRAt

https://flic.kr/s/aHsjoYPf3H

https://flic.kr/s/aHsjoYNAUB

https://flic.kr/s/aHsjoYQoCx

We did the trip in early October.

Sounds like a great holiday but agree that you'll struggle to fit all that into three weeks. You could easily spend 3 weeks in any one of these countries.

There are a million possible variants but one which may fit much of what you want may be:
Rome - Florence - somewhere in the Dolomites (e.g. Ortisei) - Innsbruck or Salzburg - Munich. That's still a lot but would give you heaps of variety in things to see and do.

Another alternative which includes a taste of Switzerland might be:
Rome - Florence - lake Como - Innsbruck (via Tirano and the Bernina Express) - Munich. (You'd probably want to break the journey between lake Como and Innsbruck.)

Try to focus on what you'll be able to see, not what you'll have to leave to next time - which is never easy! Enjoy your holiday.

My thoughts are

1) Just check how comfortable you are outside the US. If you want to have a few days to deal with any culture shock you might prefer to have say 3 days in London, Dublin or Amsterdam. If nothing else you get a lot of English with a European flavour before moving deeper into Europe. The main tourist spots you mention will have plenty of English speakers, but if you stray away from the core life gets a little bit harder, but nothing that should worry you.
2) If I was doing this I'd plump for starting in Munich and head south or Rome and head north. All of the sites you propose together are too many for 3 weeks. I'd also look at open jaw flights so as to save on back peddling to the original airport
3) Italy can offer you much of what you want, certainly smaller towns are often better than cities but Rome is not a big city, but it is full of a lot of great things to visit. I'd get over jet lag in Rome using public transport for 4 or 5 days, train to Florence for 2 days in the city with a local driver/tour of Tuscany to get a flavour of its beauty (the Tuscany part of this trip can be as long as you want, roads are relatively peaceful and "white roads" are walkable with almost no danger of meeting a car for days. You could do a cycling tour out of Florence or walking and the normal top spots are Pienza, Siena, St Gim etc but there are lots of smaller places with incredible stories. But you could take a train to Pisa along the valley bottom and make a point of visiting some of the towns along that railway line, often overlooked by tourists many have medievel town centres including Lucca.
4) The onto the lakes like Como for a few days of walking before a train trip to Venice, Padova, Verona, Ferrara and other old cities, the list of lovely cities, often walled or with castles is pretty long and a good book like the Rough Guide to Italy will cover them but of all of them Venice is special and well worth 4 days.
5) You may have spotted that the Po river is central to much of the land described above and this offers fantastic bird watching opportunities especially at the mouth of the river but also along its length. Italy has a farm-stay concept called agriturismo.it (click on the UK flag for English) and I'd urge you to take advantage of this sort of stay. You will almost certainly need a car and English of the host may not be perfect but will be understandable if you book where they say they can speak it. This is an opportunity to see the incredible Italian family in action and eat food from the farm, visit the farm, horse riding, bike riding, wine tasting, cheese making etc etc
6) Once you have a car then it is worth heading into the mountainous north of Italy and the Dolomites.

August the 15th is a sort of high water mark for locals enjoying holidays and many Italians start to go back to work from that date, though some take almost all of the month off. July and August can be very hot and humid, but getting into September it becomes more reasonable so your dates are sensible.

Munich, some love it and some find it a bit meh, I'll leave it to others to talk about

Unless you're comfortable in high temps and humidity, I'd push this trip to September.

I'm in the less-is-more category. With your list of interests and wants, I'd recommend you spend the entire time in Italy. I would fly into Milan, Venice or Munich and out of Rome.

There are infinite itinerary options and countless sights to see between northern Italy and Rome. Spend some time researching the different regions and towns and find what appeals to you. I know everything sounds equally wonderful, but there are differences between the regions... in scenery, in food and wine, history, architecture, etc. Calculate how much time you want/need to spend in the major cities (so much to see!), because that will determine how much you have left for the rest of your itinerary. If you can narrow your plans a bit to at least a couple of priorities, you can get some great suggestions here for the days/places in between. Without some focusing on your part, you'll get ideas that are all over the place.

Stay in one country due to differing COVID restrictions. We prefer one country at a time anyway. Each one has it’s own culture and ways of doing things.
Take a good look at your itinerary and narrow it down to one country. You will have a much better experience. Go to Italy and add the gorgeous Dolomites for your Alpine experience.