Bologna-bound for wedding, then where??

Why not fly directly into Bologna? After that, decide on a region and explore. You could stay in Bologna and do the amazing food tour with Alessandro.. http://www.italiandays.it/

After that, perhaps go to Venice for 2-3 nights to really enjoy the town, getting out to the islands of Murano and Burano.

From there, perhaps Verona for 2-3 nights, with a day trip via train to another town further north. OR, get yourself to Lake Garda and relax!

Another option would be to head west and go to Florence, base there, and take some day trips to Siena and into Tuscany.

Fly out of Florence.

Just food for thought to start.

I'd suggest taking the train over to Venice for 3 days. Then rent a car and head north into the Dolomites.
Or you could find accommodations on Lake Garda and do day trips out of there.

Since you have 2 votes for Venice, let me give a no vote. You want to visit a place with canals to wander, sights to see in town, interesting local atmosphere -- you are describing Amsterdam. Venice is largely a hollow shell, facades along the canals maintained but the buildings empty because its just too expensive to live in a town where everything has to be brought in by boat.

If I were in your shoes I'd stay in the half of Italy above Rome since you'll lose much of a day if you try to go much farther South. The Rick Steves videos are all available to stream for free from this website; watch all the Italy ones, see what captures your interest. And from that list you can play with times/dates and build an intinerary.

I would suggest Florence (35 min train from Bologna) and Venice (2 hours from Florence) you'd have about 4 days in each city for an easy going trip. Both cities are really nice, have a a lot to see and do, while giving you the option for day trips to smaller towns.

As for airport, flying into Bologna is pretty easy but you can look into Milan, which is sometimes $100+ cheaper than other airports. It's only about an hour from Bologna by train (it's about 20 euros) I ran out of stuff to do (tourist attractions) in one day or so in Milan but it's good for strolling around, shopping and eating. you could do Milan to Bologna as soon as you get there then after the wedding split 7 days between Florence and venice and train back and spend 1 day in Milan before flying home. Verona and como also sound and look lovely but I took them off of my list when I did my trip so I've never been (I didn't have enough time)

if you're willing to sacrifice some hours & fly, the possibilities are endless!! You can easily fly anywhere in France, Spain, Germany, etc in just a few hours for pretty cheap but since you're trying to maximize your sightseeing time & want a leisurely trip, I'd recommend the train trip, if you haven't been to those cities before.

I would spend 3 days in Venice, 2 days in Varenna, and the rest of the time in Florence. I disagree with the comment about Ansterdam over Venice. I have been to both and I would much rather spend my time in Venice.

Bologna airport (BLQ) is the 4th busiest international airport in Italy north of Rome (after the Milan area airports and Venice). The airport is well connected to all major European hubs.

It's hard to give advice on what to do after the wedding. The choices are limitless, so I'd recommend picking up a guidebook (or do online research) and decide for yourself. Based on the fact that your time is very limited, I wouldn't travel to far away from Bologna. That basically means stay north of Rome and don't cross the Alps. The regions of Tuscany, Veneto, Emilia, Trentino-Alto Adige are all good choices. Bologna is also the most important rail hub in Italy, therefore a good base unto itself.

There is nothing in the world to substitute for Venezia. Especially in the evenings/early morning between bouts of cruisers and daytrippers.

You could visit several places from Bologna with easy rail connections (Ravenna, Ferrara, Modena, Parma), or as suggested, go to Venezia for a few days.

Thank you all for your suggestions! I'll consider your much appreciated recommendations as I continue to research.

Venice, Venice, Venice!!! There is nothing like it! Smaller towns--Verona, Ravenna, Parma. Totally relaxing go to Lake Garda.