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Italy is very easy to get around using the trains, but for your convenience, I'd pick 2-3 cities and stick to those (depending on how long you're planning on staying). Rome tends to be the easiest/cheapest to fly into. From there, its very easy to go north to Florence/Tuscany or south to Venice.
Personally, I preferred Tuscany and the older cities (Sienna, San Gigiano, Florence) to Venice. I also found that food in Italy is fairly affordable compared to what you might pay for on a cruise - wine is very inexpensive, and its very easy to grab sandwiches/snacks and things for a few euros.
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Have any bees out there created their own tour of Italy, and by that I mean (for example) landed in Venice, obtained some form of transportation, and toured how you wanted to tour. If yes, was it easy to travel around Italy? Where did you go? How much $ do you think you spent between transportation, food, places to stay and activities? Positives and Negatives?
Have any bees in the same essence done a cruise around Italy and the Mediterranean? What cruise line did you go through? Where were your port of calls/ what stops did you make? Was it worth it? Did you get to see everything you wanted to see? Positives and Negatives?
Hoping I can get some bees to help me out here! FI and I are struggling because we really want to see italy, and were originally thinking Cruise, but with our wedding date being July 9, there are very few cruises that are leaving any where near that date, and the ones that do, only stop at 2 places in Italy, lots of places in Greece, and then theres either a random Turkish stop, or Barcelona Spain, which i don't mind per-say, but we both were wanting to spend a bit more time in Italy. So I'm wondering if it would be better to just tour Italy by land our selves, but have no idea of what we should expect if we do that, and the cruise is still appealing because it's mostly all-inclusive and we'd be able to see Greece also...ugh decisions, decisions.