Italy Itinerary for 8 days
 

I'm planning a last minute trip (in 1.5 weeks) for two to Italy. It'll be my first time going to Italy. I've done some research and decided to go to Venice, Dolomites, somewhere in the Tuscany countryside/vineyards, and Italian Riviera. Round trip flight tickets have been purchased to/from Milan (MXP).

Day 1: Arrive in Milan on Saturday at 9:00 AM, travel to Venice by train. Spend evening in Venice
Day 2: Day trip to Dolomites (night in Venice or Dolomites)
Day 3: Spend day in Venice, night in Venice
Day 4: Tuscany Hillside
Day 5: Tuscany Hillside
Day 6: Cinque Terre (night at base or CT?)
Day 7: Italian Riviera
Day 8: Italian Riviera, travel to Milan
Day 9: Leave from Milan at 11:00 AM

Suggestions welcome on where to base, best way to travel between destinations, and days to spend in each location (if different from above). I'm flexible to make changes to the itinerary if that will make the trip smoother. Thank you in advance.

>>>Tuscany Hillside<<<

Tuscany is a big area. You need to narrow that down a lot.

I think you are spending too much of your short time traveling between towns/areas instead of spending time in the them.

As I count, you have 7 full days (8 nights) and you've listed 8 places you want to visit. Wildly unrealistic. Choose two places in the time you have, otherwise you will be spending all of your time in transit.

Thank you. Would it be possible to stay somewhere in the Italian Riviera for day 4- day 8 and make a day trip/tour to a vineyard and another day trip to Cinque Terre? I thought these areas were close and that is why I included all in the itinerary.

Don't rush off on a day trip your first whole day there. Stay in Venice that day.

Can you pay a little extra and change your ticket to a multi-city or multi-destination (not two one-way), and fly into Venice? It would save a lot of time the first day, plus cost of train from Milan to Venice.

Allow at minimum a half day or more to get anywhere in Tuscany from Venice. Would you be renting a car or going by train? Where do you plan to base in Tuscany? You will have only a day and a bit there.

Any interest in Florence?

This is good advice. Train schedules here using italian city names:

http://www.trenitalia.com/tcom-en

You mention Tuscany. Venice to Florence 2:05, a day trip to Siena or San Gimignano; Florence to Milan 1:40.

Venice to Monterosso 5 to 6: Monterosso to Milan 3 to 4.

Roundtrip was much cheaper (even considering train prices from Milan to Venice). I'm thinking about removing Dolomites from our itinerary. All travel will be done via train or bus. No interest in Florence for this trip. We could base in Florence if Florence is the easiest way of travel from Venice to Tuscany... The main reason to go to Tuscany is to see the countryside/winery. Any recommendations? From there, we'd like to go to Genoa/Portofino area as base. Then return to Milan.

Of course Dolmites are out, you don't have the time. Florence is in Tuscany. That's the point. You could hire a guide for a day, or you could rent a car. Or do a train or bus day trip.

http://wikitravel.org/en/Tuscany

Florence is a valley bottom based city as are Pisa and Lucca. If you want to see hillsides you need Siena or Cortona for example

If you want to see Tuscan hilltowns, considering that you're traveling by public transportation, I'd suggest staying in Florence or Siena, and taking a guided day trip.

Siena is on a hill, but it's a pretty big town. If you want to see little rural hill towns, you'd have to get away from the train lines. I think the best way to do this would be to spend three nights in Siena so that you could take a guided tour on one of the days. However, Florence is easier to get to by train from Venice, and it's also easier to get to the Italian Riviera from there.

You could spend two nights in Venice, which would give you one full day there. Then three nights in Florence, which would give you two full days there, and allow you to take a day tour. Then two nights in a town on the Italian Riviera, which would give you one full day. Then a final night in Milan, or at Malpensa airport. If you have no interest at all in Florence for this trip, you could cut Florence to just two nights, and add a night somewhere else.

So, basically, you have eight days in Italy, including your arrival day, four of which will be travel days. This is without the Dolomites, which I think you are wise to drop.

Another possibility would be to spend all your time near Venice, maybe split between Venice, Verona, and someplace on Lake Garda. It would cut down a lot on the travel time.

If you're leaving in one and a half weeks, you'd better get busy.

<<Roundtrip was much cheaper>>

Probably because you were looking at two one-way tickets instead of open-jaw, which is almost always the same or cheaper than a RT.

IMO, you're rushing all over the place with no focus, but maybe that's how you like to travel. With a mere 8 days I'd be happy with Venice and a few nearby places like Padua, Verona, Lake Garda....

Actually, at the moment fares into and out of Milan are a real bargain, so I can believe that it was cheaper to do a roundtrip than a multi-city fare in this case.

I also think the airlines have gotten wise to open jaw (multi-city) booking. I have found recently that open jaw fares are often higher than round-trip, single city fares.

If something is good for travelers, you can be sure the airlines will eventually exploit it for money.

I just tried comparing a round trip NYC to Venice, and round trip NYC to Rome with a multi-city flying into Venice and home from Rome, an option that's often recommended to people doing the classic Italian Rome-Florence-Venice trip. The cost of the multi-city option was almost exactly the average of the costs of the two round-trip fares, so it doesn't look as though they're loading the cost for multi-city flights.