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Munich to Bologna with 9 nights, 2 nights undecided

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Hello! This is my first post, but I have been lurking for awhile. I have received quite a bit of help from the slowtravel people, but I feel this trip is probably a bit too fast-paced for them.

Brief Introduction
We are a couple in our early thirties, have traveled to Germany and France previously, are celebrating our 10th anniversary on this trip. Our primary focus for this trip is to enjoy spending time together and experiencing new places. We want to eat some delicious food, drink some wonderful wine (and beer), admire architecture, and enjoy a bit of art. We are especially interested in sampling regional specialties in the places we visit.

Our tickets have been purchased. We are flying from Seattle to Munich and arrive on Saturday, Sept 19 at 1pm. We fly out of Bologna on Monday, September 29 at 11 am.

Possible Itinerary

Saturday: Marienplatz, sleep in Munich
Sunday: Oktoberfest, sleep Munich
Monday?: Train 6.5 hours to Venice, B&B in dorsoduro
Tuesday?: St Marks/Secret itineraries tour in morning, explore and sleep in Venice
Wednesday: Peggy Guggenheim, lunch, then train to Bologna
Thursday: Italian days food tour, sleep bologna
Friday: day trip to Florence, see David, markets, Oltrarno, Piazzale Michelangelo, sleep Bologna
Saturday: Bologna
Sunday: Bologna
Monday: fly out

Monday and Tuesday are the nights in question. We do not want to stay longer in Munich. Our apartment in Bologna is not available before Sept 24. I know the general advice is more nights in Venice or Florence, but if we do not want to spend a lot of time in museums and enjoy generally strolling and eating and chatting with people, how does this look? My husband is very adverse to swarms of tourists. I know we are tourists too, but it just sounds like Venice and Florence have been overrun. I provide more information below, but my question is, does this look like too much?


Right now we have our first two nights booked at the Marriott Courtyard City Center. We have visited Munich previously, but my husband wanted to experience Oktoberfest. My plan is to take it easy on Saturday, catch the parade on Sunday and then visit the tents for lunch and find our way to Marienplatz Sunday evening. On Monday we will head to Italy.

We have the last 5 nights of our trip booked at a nice little apartment in Bologna, between the train station and Piazza Maggiore. We chose to spend the bulk of our time in Bologna as it has excellent rail connections, interesting food markets and experiences, and is not as overrun with tourists as other cities in Italy. My husband is especially concerned about seeing the "real" Italy and not just places that may be compromised by the overwhelming amount of visitors.

So, there is a large convention in Bologna at this time, things are already booked and prices high, but we found an apartment we loved and were able to get it for Sept 24 - 29. We have two nights between Munich and Bologna that are undecided.

We have looked at Bolzano, Trento, and Verona as possible two night stops,but I kind of want to see Venice. My husband fears it is a huge tourist trap with poor food.

Given these details, what would you change about this itinerary? We like to hit one or two "must sees" a day, then take it easy.

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