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Anniversary trip to Italy

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I have been busy trying to plan a 40th anniversary trip to Italy for my husband. We are retired so length of stay is not a big issue. We were planning to go near the end of May 2014.
We like history, wine and people. We enjoy walking but obviously due to age we can not handle having to walk extreme distances. We obviously want to see Rome, but if possible would like to see Venice and some of the Tuscany district...

Looking at all these forums etc is getting confusing. Where do I start to plan this? Can you suggest a hotel recommendation for the three areas? And a potential itinerary? We were planning to be away about two weeks. Is this sufficient to see what we want?

I apologies for the length of this message. But I hope you can assist us.

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    As others on this forum are sure to tell you, it's best to get a few guide books out and start reading. Only you can decide what cities and sights appeal to you the most. You can't possibly see it all in one trip (or 10!), so relax and decide what you really want to see and do. When you've narrowed it down a bit--at least to the main regions or cities you are interested in--come back to this forum with specific questions. It's a great resource for facts. Europe is wonderful, and Italy is especially so.

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    And a potential itinerary? We were planning to be away about two weeks. Is this sufficient to see what we want?>

    OK start by flying into Venice - city of romance spend 3 days there

    Move on by train to Florence - 3 days there and do a day trip or two to some of Tuscany's iconic hill towns - Siena would be my recommendation. You may want to day trip also to Pisa to see the Leaning Tower.

    So that's about 8 days all told

    Move onto Rome - do a day trip from there to say Orvieto, another classic hill town.

    fly back from Rome - so-called open jaw - fly into Venice and home from Rome.

    Trains are best bet for doing cities like those where cars are a liability in many ways - Venice and Florence are eminently walkable and so is Rome in in its compact city center but buses and tubes go everywhere too.

    For lots of great info on Italian trains check out www.trenitalia.com (official site of Italian State Railways) for fares and schedules; www.seat61.com;http://www.budgeteuropetravel.com/id12.html; and www.ricksteves.com.

    You can IME always get on trains even on short notice and buy tickets once there but if you can get the rather fickle www.trenitalia.com site to work there are some nice discounts if you book weeks or months in advance - those tickets are non-changeable non-refundable however I believe so be sure of your dates and times. Otherwise just buy tickets as you go along. All long-distance fast trains require seat reservations which you will get automatically when buying a ticket.

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    Actually the OP has a good start on an itinerary already: Rome, the Tuscan countryside, Venice. That would fill up 2 weeks nicely.

    The most efficient route is to do an open-jaws flight, into Venice, out of Rome, or vice versa. This should cost about the same as round-trip and save you the time and money spent backtracking. (For open jaws tickets, click on multi-city at airline web sites.)

    Assuming you're arriving on a long overnight flight, it's best to fly into Venice. You'll be jet-lagged and sleepy. Wandering around Venice in a jet-lagged daze, getting lost, is appropriate sightseeing there. Whereas Rome is more intense with lots of noise and traffic. Better to save it for when you're wide-awake and more used to Italian ways. Also most long-distance flights from Venice are not direct and require a leg with an early morning start, cutting more into your time there.

    What do you want to do in Tuscany? If you want to stay in the Tuscan countryside and poke around hilltowns, a car is best. Are you willing to drive in Italy?

    For hotel suggestions once your itinerary is defined, give us a budget in euros per night.

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    Are you trying to build one itinerary by looking at one city at a time? This method probably leads nowhere if you are not familiar with what the regions offer, and you have not already formed priorities in your mind to make decisions.

    It would be useful if you start with what exactly you are looking for. Italy is full of wine, people, and history everywhere. This type of general list will not help you guide decisions.

    If you need "some" starting point, you can look at "top attraction" sections of SEVERAL guide books. Fodors, Rick Steves, etc have such sections. I am not saying these are your must do. Many people don't agree with others recommendations. However, if you are starting from nothing and don't know how to build such list, these are possible starting points. Undifferentiated guidebook like Cadogan can make your head spin as they provide massive facts and you have to decide which one matches your interest.

    An itinerary would be a result of many trade-offs. It might help to build several, perhaps six or more, different itineraries quickly. This gets you over "one perfect" itinerary mental block to get things going. Look at each itinerary. What do you like about them and what do you not like about them. After several attempts, you start to get an idea of which routing do not make sense, which destinations you want to include, etc.

    Looking at hotels before you have reduced the number of destination options would just slow you down your planning unnecessarily.

    The length of the trip is driven by what you plan to do.

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    You probably won't get hotel recs here until you provide your budget.

    Personally, I like ending the trip in Venice. It's just a more leisurely, relaxing place than Rome, and a nice way to finish. But that's just me.

    As a rough itinerary (you could do it in reverse):

    Fly into Rome. 4-5 days. You probably can settle on what to see and do, depending on your interests. There are tons of recommendations and trip reports here for Rome.

    Train to Florence. 4-5 days. I suggest instead of rambling around the Tuscan countryside on your own, you take day trips from Florence to, for instance, Siena, and maybe hire a guide for a day to take you into Tuscany. A lot of people here, including me, have used Luca from hillsandroads.com. He's good. If you're interested in museums and seeing David, make reservation ahead for the Accademia and Ufizzi by using the phone service, not the website. Take a bus or taxi to Piazzale Michelangelo. Have a glass of wine there and watch the sun set over the city.

    Train to Venice: 4-5 days. Wander around, see the sights, maybe take the boat to Murano or Burano. Have a glass of win in San Marco while listening to the orchestras. It's going to be crowded in May, as will most other places, but you'll do fine. For a splurge, take a water taxi from your hotel, about 100 euros, to the airport when you depart. It's a nice way to leave and, hey, it's your 40th, so why not?

    You can make the trip a little longer or a little shorter, but what I've outlined takes a little over two weeks, including travel time between cities.

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