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Italy for 5 nights!

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Hello, my husband and i are planning a trip to Italy and Germany for the end of September 2015 to celebrate our one year wedding anniversary. We are being a little ambitious because the plan is to fly into Rome and do two nights in Rome, two nights in Florence, and one night in Venice. The plan is to rent a car and take a day trip to Siena when we are staying in Florence as well.
Does anyone have suggestions on the best places to stay in any of the three areas, best way to go about renting a car in Florence, any less touristy restaurant suggestions?
Also, with such limited time what are your absolute must sees? We already plan skipping the Colosseum. I hear vatican city would take up a good portion of a day on it's own? We want to see some historical monuments, art, museums etc...but we are also really interested in less touristy experiences and of course shopping! Any and all advice is welcome! Thank you so much!

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    Two nights somewhere is just one day. One night somewhere is just that - one night - little to no time for sight seeing. You seem to have forgotten that it takes time to get from place to place. Once you consider the time from checking out of your lodging in one place until you get checked in at the next destination, you will have lost most of a day.

    So, you have one day to sightsee in Rome,
    You have one day in Florence, but you are driving to Sienna for the day, so 0 days in Florence,
    One night and basically no days in Venice...

    My advice is to choose one city in Italy for your five days and take a day trip while you are there. With your current itinerary you will rush from place to place and have no time to see/do/experience anything.

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    If that is what you want to do, millions of people take day trips to Rome, Florence, Siena and Venice and enjoy them. Many people go to one city for 5 days and hate it. It's an individual choice.

    You should take a bus from Florence to Siena, not rent a car. It will be quicker to just get on the bus than to hassle with a car rental.

    The most efficient way to see the highlights of the places you are going is probably to take a half-day walking tour, especially if you want to leave time for shopping. Otherwise, any guidebook will tell you what the famous sights are and whether you need tickets. Some require reserving in advance to avoid waiting on long lines. There is really no way to see the famous highlights of these cities and yet avoid lots of crowds and being around a lot of touristy things.

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    You say you are also going to Germany. How much time do you have there, could you take at least one night from there and add it to Italy.

    However, you can get a quick taste of the three cities you are visiting. Definitely do not do anything that requires several hours, tickets, or standing in line - unless you are going for that one or two specific things. If you want an 'overview' you don't have time for long lines. Fortunately, in those cities there is absolutely wonderful art, architecture and 'culture' outside on the streets without even going into a museum.

    I've been to Rome multiple times for multiple days each visit, but last summer my brother and sister-in-law were traveling with us to the Amalfi Coast but since we were all landing in Rome they wanted to see just a little - so we had two nights there. I put together a couple of 'walks' that cover the highlights. Trevi Fountain - Piazza Colonna - Piazza d. Rotunda (Pantheon, go inside - no need for tickets) - Piazza Navona - Campo de Fiori. Stop for pizza, glass of wine, gelato. We did all that on their arrival day and they didn't get in till afternoon. On the next day, the 'full day' take a walk that includes the Colosseum (don't go 'in' but it's a wonderful sight from the outside. Walk around to the Campidogio and look down onto the Forum. That's three more major sights that can be enjoyed from the outside. Then either walk around Trastevere or walk (or take bus) to St. Peter's Square. Depending on the length of the line going into the basilica doesn't take that long (it's the Vatican Museums that take a long time) and it's worth seeing from the outside.

    All of that can easily be done in the day and a half you have if you're decent walkers. Probably even more. Get a good guide book that has 'walks' in it such as Frommers.

    Then take an early morning fast train to Florence, see Florence by a walk similar to the one I described for Rome. The next day take a one day trip via bus to Siena. Then the next day take an early morning fast train to Venice. But that's where it would be really helpful if you could find one more day.

    If you look at maps, plan out intelligent walks you really can see a lot. It's when people pick several things geographically distant from each other, require admission lines, etc that they end up just hopping from one thing to another without really seeing or enjoying anything. The historic centers of these cities are all quite small - but planning is the key. Don't just show up with a list of a things you want to see without any knowledge of where they are in relation to each other or where you are staying.

    To pick hotels in a good location - once you have roughed out your 'walks', go to booking.com and bring up the map for each city and then look at hotels via the map (rather than the long list) to choose one in a central location. Especially since you aren't staying very long in each city I'd look in the area between the train station and the Trevi for Rome, between the train station and the Duomo in Florence.

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    With only one full day in each city (and not even a full day in Venice), you won't have time for day trips. You will barely have time to get oriented to each city and get a quick look around. You don't have time for the main things let alone trying to get off the tourist path and find less touristy areas.

    Depending on what time your flight arrives at FCO, you might have a partial day that day. It depends on how jetlag affects you whether you are up to doing much that day.

    Day 1 - Arrive FCO - transport to Rome - check in hotel (what time does your hotel allow check in? do they have luggage storage if rooms aren't ready?). Orient yourself to getting around a city you've never been to before.

    Day 2 - Rome

    Day 3 - Check out, transport to train station, train to Florence, transport to hotel (again what time does hotel allow check in). Orient yourself to a new city.

    Day 4 - Florence

    Day 5 - Check out, etc. Transport to Venice

    Day 6 - Check out.

    Although you don't have time to go to Siena with only one day in Florence, if you decided to skip sightseeing in Florence for Siena, the bus is the best option (about 8€). You aren't allowed to drive in central Florence (read up on ZTL in Italy). I think Siena is restricted driving too (I've only picked up cars departing there and not attempted to drive into Siena).

    You need to make a list of things you want to do in each place and see if it's even possible in the short time you have.

    Did you just randomly pick these cities? If not, why did you pick them?

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