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Help planning our Italian Vacation!

San Jose, California
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Help planning our Italian Vacation!


My husband and I are planning our first trip to Italy in celebration of our 25th wedding anniversary! We will be landing in Rome on April 16th, and departing from Milan very early in the morning on April 29th, where we will be flying to Funchal, Madeira for 3 days, and then off to London for another quick 3 1/2 days before returning home to the US on May 6th. We were granted 2 tickets for the Papal Mass on Easter Sunday, so the first part of our trip has been planned, and this is what we have so far:

April 16th, Arrive in Rome - Small Group Tour of the Vatican in the afternoon (Booked)

April 17th, Tour Rome (haven't decided if we will do this on our own or take a tour)

April 18th, Train to Naples - Final Destination Positano (Hotel Pupetto) - trying to determine the best way to get to Positano... Private transfer from Naples can be pretty pricey, Also considering second train into Sorrento then Hyrdrofoil to Positano? We will be leaving the bulk of our luggage in Rome, as we will be returning to the same hotel, and will only have an overnight bag.

April 19th, Enjoy a lazy morning, and the day in Positano, head back to Rome late afternoon/early evening.

April 20th, Easter Sunday Mass in the morning, Borghese Gallery late afternoon (booked)

April 21st ?


April 27th ?

April 28th - Milan - Stay at the Sheraton Milapanesa

April 29th - 5:55am flight

So far so good... more or less, even though I still have some things to work out. However, once we leave Rome the morning of April 21st, we have a list of places we want to see and go, and I am not sure of:

1) the best order/route to take to make the most of our time,

2) If it's even possible to see/do everything we want in the days we have left,

3) Is there some place amazing that I am forgetting, and maybe should add to my list, or swap out a less desirable destination?

4) all this while trying to remember the fact that we are on vacation! I don't want to feel like we have a rigorous schedule to keep.

5) April 22nd is our actual anniversary. Would love to be in a lovely Tuscan Village, and find a small chapel where we can ask the local priest to allow us to renew our vows and have him bless our marriage. This is a dream of mine more so that my husband's =).

Here is the list of places we would like to see/visit:






Cinque Terre

San Gimignano


We are not opposed to renting a car, but once we leave Rome. Is there a good "Home Base" area that we could use for 2 or 3 days here and there? or are we looking at a different city/hotel every night? We are not Hotel snobs... meaning we don't have to stay in "5 Star" hotels, since we are going to see the country and not stay at the hotel. As long as it is clean, has an in-room bath, and a comfortable bed. And while we might splurge a night here or there on accommodations (which I expect will be the case in Venice) we are trying to be modest with the amount of money we spend on lodging. Would rather spend our money on food and wine! =D

Sorry for the long history/question. If you read the whole post, then you are truly a good person who want to help, so please know that your advice is greatly appreciated!


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1. Re: Help planning our Italian Vacation!

Most people would tell you that trying to squeeze all those cites into 7 days is asking for overload. You could base in Florence and see Lucca, Pisa, Siena from there as day trips avoiding hotel transfers. I think most day trips give a very restricted view of places but that is how some people like to travel. You said you don't want a rigorous schedule but that is exactly what you have planned. You've only allowed 2 full days in Rome. Have you worked out travel times between your cities? You will lose at least half a day checking out, traveling, checking in.

Cinque Terre is too far out of your other requests although some people do it as a day trip from Florence. I'd split your 7 days between Florence (4) and Venice (3), allowing for day trips to Lucca/Pisa (1 day), small village chapel (1 day) and Siena (1 day) from Florence and at least 2 full days in Venice. You could route yourself through Cortona between Florence and Venice for a look.


Edited: 13 March 2014, 22:13
San Jose, California
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2. Re: Help planning our Italian Vacation!


Haven't worked out much after Sunday the 20th. The only thing I have worked out is that we are staying 2 nights in Rome, then one night in Positano, and then another 2 nights in Rome at the same hotel. Have figured that if we leave Rome at 8am, that we could be in Positano having lunch by noon... is that unrealistic?

I know my post is filled with contradictions, "don't want a rigorous schedule, but I want to see EVERYTHING" ha ha ha... I am trying to figure out the best to proceed... i.e., would it be better to take a fast train from Rome to Venice, then back to Florence, where we could make our way up to Cinque Terre, and then hop over to Milan from there? Or does it make more sense do to something else entirely. Also... I didn't think that we would need 2 full days in Venice? It seems so small, do you really advise 2 full days?

Thanks for taking the time. =)

New York City, New...
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3. Re: Help planning our Italian Vacation!

I'd hate to see what you think is a "rigorous" schedule - this, so far, is grueling.

For one day, I'd honestly skip Positano - it will take you at least 4 hours to get there - If you go, I'd suggest a minimum of 2 days there; add another day to Rome and, no 2 days in Venice is not enough (neither is 3 but it is better than just 2) - these places are all thousands of years old and have the most extraordinary sites/history/architecture/art - it's not like doing a run up highway one from LA to San Francisco stopping off at Carmel, Santa Cruz -

With what you have so far outlined, you will see so little of each of these treasures - be sure to carefully prioritize sites from your guidebook so you don't miss out on what you most want to see in these places.

I don't think you have used a guidebook as yet or you really couldn't imagine these kinds of timings - and, a map.

If doing Positano, I'd skip Cinque Terre - they are both beautiful but you really do not need (for this length of trip) to go to two somewhat similar seaside areas - cut out at least 1.5 days of travel.

Well, good luck - just be realistic about what's there to see, travel times, etc

San Jose, California
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4. Re: Help planning our Italian Vacation!

Hi Momcat...

I think that I just got so caught up in the "That is only an hour away by train", that we started thinking that we could do more than what is really realistic... and now that we have thought of the places we would like to see, I can't imagine not dropping anywhere from the list! It's causing me so much anxiety.

It's just that I don't know when we will have another opportunity like this. We haven't done a lot of traveling... everything we've done has been focused around our kids - Disney Vacation in Orlando, Washington DC, cross-country adventures for Cycling National Championships. Other than a 4 night trip to Victoria, BC for our 10th Anniversary, 15 years ago, we haven't done a lot of traveling that didn't wasn't kid-centric or tacked on to a work event (i.e. Washington DC - with the kids)

Which is why I am trying to make the most of this trip. But I am realizing that we can't do it all...

New York City, New...
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5. Re: Help planning our Italian Vacation!

I get that - but, in a country as steeped in history, etc Italy, it's just not really possible to see anywhere quickly - maybe some of the smaller Tuscan towns but not cities like Rome, Venice, Florence - and many others.

It's a choice, I think of deciding if you just want to "see" them vs experience them in a more meaningful way. I've been to Rome more than 20 times and still have a list of things to see - Going to the seaside areas is somewhere to kind of slow down, enjoy the amazing scenery, some hiking - and each of those areas too have extraordinary history.

In 14 nights, I'd suggest considering 4 places to stay - a few of which you might do a day trip from - i.e., a day trip from Florence to Lucca (or whatever you choose)

It all comes down to the type of trip you want to have - And, knowing you can't see anywhere near everywhere you want to see - it's just not possible.

Add about one hour (average) to each side of train travel (to include checking in and out of hotels, getting to and from train stations, being at stations about 15 minutes pre-departure time - then getting to new hotel where you are going where you can't usually check in until about 2pm or 3 pm (though you can leave your luggage with the hotel while you wait).

6. Re: Help planning our Italian Vacation!

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