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Help with Italy Itinerary

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Hi everyone! I've lurked on this board a long time, reading everything I can get my hands on, and now I think I'm ready to ask about an itinerary. Sorry in advance for what will probably be a rather long post.

I'm currently studying abroad in Rome, and after my program ends on May 14, I have about a month to travel (solo). As my student visa expires on June 3, I've decided to head to Ireland for my remaining time until I fly home to the US (from Dublin) on June 13. I know it might be possible for me to exit Schengen on or before the 3rd and then re-enter as a tourist after the 3rd, but I would rather avoid any problems and just get out of Schengen when my visa expires. I'm going to do a separate post with the Ireland portion of the trip to keep things organized. Anyway, here's my tentative Italy itinerary:

May 14: Train Rome to Bologna
May 14-17: 3 nights in Bologna, including a day trip to Ravenna
May 17: Train Bologna to Verona
May 17-18: 1 night in Verona
May 18: Train Verona to Venice
May 18-24: 6 nights in Venice (Venice is the one place I've always wanted to visit, and I want to have plenty of time to see the sights, wander the streets, and get out to Murano, Burano, and Torcello)
May 24: Fly Venice to Catania and Train Catania to Taormina
May 24-27: 3 nights in Taormina (possible day trip to Siracusa)
May 27: Train Taormina to Milazzo and Ferry Milazzo to Vulcano
May 28-31: Kayaking Tour of Vulcano, Lipari, and Salina with Sicily in Kayak
June 1: Ferry Vulcano to Milazzo
June 1-2: 1 night in Milazzo (tour to Stromboli)
June 2: Train Milazzo to Catania and Fly Catania to Rome
June 3: Fly Rome to Dublin

The only thing set in stone is the kayaking tour. I'm very interested in history, architecture, and natural beauty. I like art, but prefer it in small doses and/or as part of a historical building (e.g. I LOVED the frescoes in the Duomo and the mosaics in the Baptistery in Florence). I'm very active, hence the kayaking trip in Sicily. I want to try different foods (I'm especially fond of sweets!) and I enjoy a glass of wine with dinner, but I'm definitely not into partying/nightlife. I also enjoy just wandering around cities, exploring and going into interesting shops.

I've already visited Florence this semester, and will visit the Naples area and Palermo before the end of the semester. I'm trying to take it relatively slowly and not try to see too much, so I'm a little concerned by the number of one-nighters. I'm considering dropping the night in Verona and adding it to Bologna or Venice. If I add it to Venice, I would have the possibility of a day trip to Verona, but am I shortchanging Bologna? Especially with the day trip to Ravenna? I can't see a way around the one-nighters in Sicily. I need to be on Vulcano the night before the kayaking tour starts, and since the tour doesn't end until "around 5pm" according to the website, I'm nervous to plan on making a ferry on the night of the 31st. I'm also nervous about planning to catch a flight in Catania the same day I ferry from Vulcano (and I would like to do a trip to Stromboli, which seems to be easiest from Milazzo), which is why I have the night in Milazzo. Then, I have to return to Rome before I go on to Dublin because I'll be leaving the large suitcase I brought for the semester in Rome while I travel around Italy.

I'm also unsure about the time in Taormina. I was back and forth between staying there or Siracusa for those three nights, but it seems like Taormina would give me better access to Milazzo. Also, I know Taormina is very touristy, but one of my Italian program directors highly recommended it. Would Siracusa make a better base without making it too difficult to get to Milazzo for a ferry on the 27th?

Thanks for reading all that, and thanks in advance for any responses!

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