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Seeking Advice on Itinerary for Summer 2015 Northern Italy Trip

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I am traveling with 5 friends next summer (June 2015) to Italy. We are flying into Milan on Weds, June 17, and departing on a 7-day cruise from Venice on Saturday June 20. We will return to Venice on Saturday, June 27 and are flying out of Milan on Weds, July 1st. We would love some advice on how to spend our few days pre- and post-cruise in Northern Italy! We are a mix of novice and experienced travelers ranging from 24-32, with limited Italian.

We are interested in the following, in order of importance:
-Food tours, cooking classes, wine tastings/tours
-Markets, coffee shops, local culture
-Taking in local scenery and architecture
-Museums, art, famous sightseeing spots

Here is our tentative itinerary:

Weds: Fly into Milan
Thurs: Day trip to Parma (or Reggio Emilia, or both in one day), return to hotel in Milan
Friday: Explore Milan, late afternoon/evening train to Venice
Saturday: Morning in Venice, depart for Cruise
Saturday: Return from cruise, day in Venice
Sunday: Day trip to Verona
Monday: another day trip?? Or spend in Venice
Tuesday: Morning in Venice, afternoon train to Milan
Weds: flight home

I am thinking day trips are the best bet from our "home bases" in Milan and Venice, rather than, say, doing a night in Milan, a night in Parma, a night in Verona, etc. I'm worried we would spent half the day checking out of a hotel, dragging our luggage around, waiting to check into another hotel, then finally getting to explore. Though Verona is on the way to Milan, so maybe it would be worth spending a night there?

If we're really interested in doing some food/wine stuff, is Parma our best bet? Is there another nearby town to either Venice or Milan that would better meet our needs? One member of our group has been to Bologna and would rather visit a new place.

What do you think? We would love any advice!! Thanks! :)

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    At that time of year, much of what attracts you to Emilia-Romagna may be is deep summer sleep mode, and you may not find the food and wine all that congenial in the summer heat. Plus, Parma and Emilia-Romagna is not really great wine country. Period.

    If you think you have the energy for a busy trip, consider flying into Milan and going directly to Torino. It might be fairly hot there too, and some of the food and wine is not all that summer friendly either, but it has great coffee and gelato, and the museums are fun. Loads of chocolate and some very tasty eats. It is really a great town for your age group.

    If you really want to do some sightseeing in Milan you could make a pit stop on your way to Venice (stow your luggage in the train station), but since you have to fly out of Milan, why don't you save your sightseeing there for the end?

    After your cruise, your plans look fine, but personally I might do it this way:

    Return from cruise, 2 nights Venice

    3rd day, head to Verona for lunch and afternoon, and spend the night so you can enjoy the cocktail and wine scene. Next morning, do a bit more sightseeing, head to Milan, do some sightseeing, and have a great dinner.

    I realize that gives you a bunch of hotel switches at the end, but you might find sightseeing in more congenial in the evenings. Splurge on taxis to help you with luggage, including a water taxi in Venice if need be.

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    Specifically on this:

    "'I'm worried we would spent half the day checking out of a hotel, dragging our luggage around, waiting to check into another hotel"

    When you leave the cruise, pack up all your major luggage except for a tote with enough to get you through your final days. Just live out of the tote.

    If you are switching hotels, check out of the hotel after breakfast, but leave your bags there and do a little more sightseeing or shopping. Get a simple, early lunch, collect your bags and then get on a train around 2pm for the next town. Check into your next hotel and freshen up, but head out for sightseeing after 4pm. Most Italian towns are DEAD in summer in the middle of the afternoon. People don't come out and stores don't reopen until 4pm anyway. Even museums stay open until 7.30pm. So you have hours of sightseeing, and the sun doesn't set until 9pm, so you can stroll around and see things and enjoy the piazze at night.

    Next morning, you can get up enjoy a bit more sightseeing before moving on.

    Forget the 9-5 mentality and create a mini-pack that you can live out of for a couple of nights. Day trips in Italy in the summer can be a drag, being tied to train schedules, waiting on hot platforms, only arriving in towns in the middle of the day when shops are shut and Italians are indoors resting. And the cities are most alive at night and are lit up gorgeously.

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    You are already getting good advice, and I second putting time in Milan at the end. Also, don't split the time in Venice. Put it all together at the beginning.

    Day trips are good to avoid checking into and out of hotels too many times, but your itinerary still has you staying twice in Milan and twice in Venice, so it doesn't make things easier.

    Since you want a couple of days in Venice anyway, on Wed, upon arriving in Milan, You could head straight to Venice and see Venice before the cruise.

    When the cruise ends, catch the train to Verona to spend the afternoon and evening, which as Sandralist says, is lovely there. Your choice for the two in between days - day trip from Verona or stop on the way to Milan or one place for two nights. This just seems more cohesive.

    Wed, fly into Milan, train to Venice
    Thur, Venice
    Fri, Venice (could do a day trip, but could decide that on the spur of the moment)
    Sat morning, Venice? Depends on departure time of cruise
    Sat, cruise
    Sat, end of cruise, train to Verona
    Sun, ?
    Mon, ?
    Tues, Milan
    Wed, fly home

    If your cruise is departing late afternoon on Sat, as many do, you could possibly have another 1/2 day in Venice on Sat, so if that is the case, this could logically be another option:

    Wed, arrive Milan, train to Verona, spend the night. Verona isn't that far and is very easy to navigate.
    Thur, train to Venice, arrive mid morning, most of day in Venice
    Fri, Venice
    Sat morning, Venice
    Sat-Sat cruise
    Sat, train to Bologna or Parma or other choice.
    Sun, ?
    Mon, ?
    Tue, Milan
    Wed, home

    In Verona, my rec is get a hotel right in the city center so you can just walk right out for sightseeing and restaurants. The train station is not far, and there is bus service, but I would get a taxi to the hotel, just a lot easier than dragging luggage or waiting for a bus after your flight and train.

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    Here was our itinerary:

    Monday, June 15 - arrived in Milan around midnight, spent the night at the Holiday Inn by the airport

    Tuesday, June 16 - Took a bus to the train station in Milan. We checked our bags and walked around the city for a few hours, checking out Duomo, the Castello Sforzesco and the neighborhoods of Brera. Took a late afternoon train to Siena, where we spent the next 3 nights.

    Wednesday, June 17 - wine tour with Donatella through Montalcino. Dinner and late-night people-watching at the Campo in Siena.

    Thursday, June 18 - explored Siena. Toured the Duomo, climbed the tower, shopped and wandered through the many winding streets surrounding the Campo. Had a picnic lunch with items from a cool local market.

    Friday, June 19 - Morning bus from Siena to Florence. Spent the morning walking around the Uffizi, and the afternoon walking around the Ponte Vecchio neighborhoods. Took a pizza and gelato making class at 6pm, boarded a 9pm train to Venice, where we spent the night.

    Saturday, June 20 - Spent the morning walking and taking the waterbus around Venice, drank espresso and ate produce from the Rialto farmer's market, then boarded cruise ship at 4pm

    CRUISING Saturday-Saturday

    Saturday, June 27 - morning train from Venice to Sirmione. Took a bus to Gardaland and spent the afternoon/evening at the theme park. Spent the night in Sirmione.

    Sunday, June 28 - Rented a car and drove to Verona for the morning, then drove around Lake Garda in the afternoon and evening, stopping at the cute towns of Garda and Bardolino.

    Monday, June 29 - Spent the morning walking around the Sirmione peninsula, took a late afternoon train to Milan, flight back to USA

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