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10th Anniversary Trip (A Year Late) To Italy - Need Guidance Please!

Hi all!

One year ago, I posted a topic on here asking for help planning travel to Italy in September 2015 to celebrate my wife and I's 10th wedding anniversary.

The help I received here was valuable, and I ended up booking my trip shortly after. Then, a month after THAT, my wife and I found out we were expecting our first child. A joy and blessing, to be sure, but we didn't want to do a wine country themed trip while she was 6 months pregnant.

We cancelled, had our baby in December, and have decided to do our trip this September. So our 10th anniversary celebration on our 11th anniversary if you will.

Last year, I booked flight into milan, one night there. then train in cinque terre - 3 nights at la cabana.
then rental car, and drive to siena to stay at Aia Mattonata Relaishen for three nights, then on to florence for three nights at Golden Tower Hotel and Spa. Then, i was going to have to train back to milan to catch my flight the last day.

Well, now that I am booking again, I am hoping for the following:

  1. Any hotel recommendations or changes recommended? I am also looking at Hotel Pasquale in Cinque Terre...we want to stay in Monterosso. Also, anyone stay at Golden Tower in Florence? Or should I look somewhere else?

  2. Here's the BIGGIE: how do i end my trip? Should i book my return flight out of Venice or Rome instead (already been to both those places two years ago, by the way) since both cities are closer to my endpoint of Florence than Milan? (or is trekking back to Milan at the end a better idea for some reason?) Alternatively, should i pick a different airport to fly into to start my trip? Bear in mind, it takes an extra day to get to Florence or Pisa Airport from my starting point in U.S. vs other major cities in Italy. It also takes an extra of travel to return home from Pisa or Florence airports versus the others mentioned. I have to fly American Airlines because of my miles, so I am limited to them.

  3. Was planning on spending my night in Milan at Park Hyatt, but with baby, budget for that hotel won't allow. anyone have a good recommendations for within the city of Milan, in a good area, in the 200-300 dollar (American) a night range?

  4. Is Milan nice enough I should allot an extra night there, and take away a night from somewhere else? if so, where would you recommend subtracting a night?

Sorry for the long post - any help would be most appreciated! Thank you so much all!

Posted by
11983 posts

1. No specific hotels to recommend, since I don't have a lot of experience staying in hotels in either place (I usually stay with relatives).
2. If you end your trip in Florence, why not fly out of Florence (airport code: FLR)? FLR doesn't have direct flights to the US, but it's connected to several other major European hubs (e.g. FRA and MUC with Lufthansa, CDG with AirFrance, ZRH with Swiss, AMS with KLM, MAD with Iberia and Vueling, or even FCO with Alitalia). Lufthansa is a United partner, AirFrance-KLM is a Delta Partner, Iberia and their affiliate Vueling are American Airlines' partner). If you want to fly via London Heathrow (LHR), nearby Bologna has 3 daily flights with British Air.
3 and 4. If you fly out of Milan, you need to spend at least the last night in the area, since your flight is likely in the morning (unless you fly Emirates to JFK). If you have a car you could also consider a couple of nights in Stresa on Lake Maggiore, which is only 45 min drive from the Milan Malpensa airport. If you fly out of FLR, then you don't need to spend any nights in Milan area obviously.

Posted by
38 posts

Roberto, I appreciate the reply - but it is a problem. I forgot to add in my original post that it takes a full extra day to get to (or fly back from) florence or pisa via air than it does from/to venice or rome (or milan). which sucks. completely kills both our vacation schedules that extra day - and we would have to subtract another day out of our trip just to cover than extra day of travel.

Posted by
11983 posts

Why should it take a full day extra to reach your destination?

A flight from Florence to Paris or Amsterdam takes less than 2 hours. Even less to Frankfurt or Zurich. From those European hubs to you can travel around the world in the same time it would take to fly from Rome. I go to Florence once or twice a year and nearly always fly directly to/from Florence (from San Francisco) because it's faster than flying to Rome or Milan and taking the train.

Of course you are not specifying which airport, or country, or even planet you are writing from, therefore I cannot be sure until I know. Maybe if you tell me where you live or which airport is your home airport, I can help you better.

Posted by
5399 posts

Important question -- is this a trip for 2 or for 3?
If for 2, have you left the baby before? This can be a BIG adjustment.

When my daughter was 6 months old, we took her on a cruise ship which provided child care so we could do day trips. Another couple on the ship had a same-age child and the mother told us everyone had said to leave baby with Grandma so she could have a good time -- but she didn't seem to be having that great a time.
(And the first time we left for a weekend alone, we spent most of the time talking about her.)
If it's a trip for 3, other considerations which parents of small children can provide.

Posted by
11613 posts

There are a number of good hotels near Milano Centrale station, Hotel Garda and Hotel Berna are frequently recommended here. Garda is lower cost, but both are reasonable. The train to the airport is convenient, takes just under an hour. Make sure your hotels know you have an infant so they can provide a crib.

Posted by
38 posts

hey all - thanks for your comments.

so with my AA miles, i booked from jfk to milan - i arrive at 820 am Friday September 16th.

From there, I need to get to Milan Centrale train station - i am going to book a high speed train from there to florence. florence we're spending 3 nights there...

anyway, my question is this: i can't look at the schedule for the train yet since it's too far out, but it would appear the typical first train i would be able to catch after my flight will depart from the station around 10:20 am. If i take that train, i will be in florence before noon, which would be ideal.

if i'm arriving at Milan Malpensa airport at 820 am, is it reasonable to get baggage, through the airport, get a taxi, and get to Centrale train station by 10:05 am or so?

or is that allowing me too little time?

also, what is the taxi ride cost usually from that airport to that train station?

thanks in advance for your help!

Posted by
11733 posts

Nathan, it's a long way from Malpensa to Centrale. The Malpensa Express train is a cheaper (12,00€ pp) and probably faster option depending on traffic.

Or the Malpensa Airport Express bus (10.00€ pp) although traffic delays could still be a bit of a risk:

The airport lists taxi prices at 90€ :

It's not usually recommended to pre-purchase train tickets for arrival days as flight delays and long immigration lines are all too common these days. I personally think trying to make a train leaving just two hours after landing at an airport nearly an hour away is too risky unless you buy base-priced tickets which can be changed at no cost if you miss it.

Posted by
38 posts

how bad is traffic from airport to train station around 930 am on a weekday/friday? never been there, so i don't know.

I'll do the train if that is the best way - but i am willing to pay more for convenience/speediness of trip from airport to train station. i've read the cab ride averages around 30 minutes, while the train ride is around 50 minutes. but of course, if traffic is bad...

anyone who has hands on experience with that - please chime in. would be much appreciated!

Posted by
11733 posts

I haven't done it at that time of day but I have a hard time believing a cab can do it in much less than 50 minutes. We did the express bus at 5:30 AM or so, and it took about that amount of time leaving Milan to Malpensa in less than rush-hour traffic.

Posted by
359 posts

Hi Nathan,
I agree with the others above that it would be risky to book your train to Florence that early. Timewise, Malpensa is a long way from Milano Centrale. Re: Albergo Pasquale in Monterosso, when we were there all of the rooms in our Sept. dates were filled by RS tour members as was most of their sister hotel Villa Steno, both great properties BTW. SO I would get on your bookings for CT soonest.
Buon viaggio,

Posted by
11733 posts

We stayed in La Spiaggia in Monterosso (a May trip) and booked 6-7 months in advance: barely got a sea-view room. That was our choice as we wanted to be close to the train station, restaurants and the water.

Posted by
1160 posts

Malpensa airport is so distant from Milan that is actually closer to the Swiss border than to Milan. Train is the fastest and most reliable way to reach downtown Milan; road travel is slower and traffic is very intense but on festive days. A taxi would be easier if you have a lot of luggage, but it would not be faster and probably much slower.

Posted by
171 posts

Hi Nathan

I would strongly recommend Albergo Marina in Monterosso-nicest people ever, good value and wonderful extras


Posted by
7124 posts

Perhaps fly into Venice Marco Polo and head straight to Padua for 2 nights. Then to Florence, Siena, Cinque Terre and Milan (where 1 night is fine).
Or consider Siena as a day from Florence, allowing you to include Bologna.

Posted by
38 posts

thanks everyone for your replies -

yes, i had already booked up my hotel for cinque terre - we are staying in the junior suite at La Cabana - really looking forward to it! we're booked there from september 23rd through the 26th!

Again, the previous 3 nights we're staying at Aia Mattonata Relais in Siena. The first 3 nights of the trip - September 17, 18, 19 - are in florence, but we're still trying to figure out our hotel there (leaning toward booking the junior suite at Golden Palace Hotel and Spa, but not sure).

The advice about train vs taxi from Milan Malpensa has been very helpful. I see now that i would prefer the train to take the guesswork out of taxi drive length, but convincing my wife has been another matter. she is concerned about having to deal with all our luggage when we got off our flight from JFK in Milan and get it to/on the train to get to Milan Centrale.

So as of now, looks like i'll be doing the taxi. the cost doesnt bother me, but the threat of it taking longer than an hour with traffic at 930 am on a friday does. i'm just going to have to keep working on her to try and convince her train is the way to go.

Posted by
11733 posts

OK, so we've already said that 2 hours from landing through immigration, through baggage and to Centrale in two hours total via road is a good-luck-with-that (might happen; might not) so it's in your hands.

But if her concern is " having to deal with all our luggage", you're going to have wrestle those bags through stations and in-and-out of trains for the rest of your trip. If it's going to be an immediate problem from the time you land, it's going to be a problem for the duration. It sounds as if you've booked upper-class accommodations but I don't know if all of them have lifts? Not all train stations have them either, or they're not always in working order. It's something to think about? Maybe reducing the amount of luggage to what is more manageable is a wise idea so that they don't reduce your options.

Posted by
14 posts

We are hoping to do something similar in June for our 10 year anniversary....not pregnant...he is 9!!! We are starting in Prague for 3 nights...Easy Jet to Milan at 3pm. Train to Central station, then to Genova same day. Stay in Genova one night. Hopefully this is a good idea, keeps most of our travel in one day...Then off to Cinque Terre (Monterosso) by train for three nights. Staying at Villa Steno, very excited! After that we go to Florence just to jump on a bus to Sienna (same day), Siena for three nights. Our last stop, back on the bus to Florence, there for four nights. We fly out of Florence 6:30 am, back to the west coast. Yay!!

Posted by
38 posts

Michelle, good luck on your trip! we aren't pregnant/expecting now (or else we wouldn't be doing this trip).

your itinerary sounds awesome - hope you have fun! let me know if you have any suggestions after going there!

And Kathy, I get what you're saying - I will use your post/rationale in my plea to my wife. thank you.

Posted by
11733 posts

You're a sport, Nathan; thank you. I didn't mean to sound cranky AT ALL but the reality of Italy is that things just do not work like they do in the U.S. It's part of the charm, really, but takes some advance awareness. :O)

I'm 61, a hiker, and a 5'1" female who has to handle my own bags when we travel so I'm familiar with what's involved!

Posted by
48 posts

Just a few comments on the train travel.

Assume that you might miss a connection and check the schedules to make sure a back-up train leaves in the not too distant future. Trains can arrive late and mess up a tight connection or you might have trouble locating the correct track, etc. Anything less than a 10 minute gap between trains is dangerous.

Keep the amount of luggage down because often the storage space on the train is filled quickly by the lucky early arrivals or persons already on the train from an earlier station. Then you end having to leave the bag in the aisle and move it every time a person needs to pass, or worse yet leave it at the end of the car near the doorway.

I'm headed into Malpensa myself this July and doing the high speed Trenitalia down to Rome (a return visit for 5 nights), Assisi (3 nights) , a night in Florence to hit a few places that I missed in the past, 6 nights in Corniglia, Cinque Terre. Then the final two nights for a nostalgia stop in Lago di Lugano where I was in '91 during my student years. Lugano is closer to Malpensa than Milano so it made sense and I can get a bus direct to the airport from there.

FYI, I got a ridiculously cheap flight to Milano for July - $544 round trip (direct) from JFK. I had to book it and figure out the details later. This was a month ago. Must be a fare war to that airport. I do well searching all the fare possibilities on

Posted by
14 posts

Hey Nathan,

My husband and I are both carrying backpacks only. Mine is a sweet, fancy Osprey and my husband's is a utilitarian Rick Steves Job. Not sure if it would be possible to get away with minimal luggage and a baby at the same time. If I was hauling a baby I would expect to pay a bit more, budget more time and try to figure out how to make it easier ahead of time(like you are doing). My biggest issue is trying to squeeze TWO extra pairs of shoes into my pack and making sure the places we stay have blow dryers :) One thing I am planning, that may be something you could do also, is arranging transportation to and from airport. Our hotel offers to arrange this for us, one less thing to worry about! Any time you can get those little but critical trips covered...perfect. Then just figure out the train schedule...expect to be late. If you miss the first and second train, when is the next one going to arrive ?

Posted by
11733 posts

One thing I am planning, that may be something you could do also, is
arranging transportation to and from airport. Our hotel offers to
arrange this for us, one less thing to worry about!

But Nathan+ wife aren't staying in Milan: they are going directly on to Florence so a hotel-arranged transfer isn't probably an option. Even if it is ( I suppose anything is possible for a price) that doesn't solve the problem of having to get to Centrale in a limited amount of time: whether by taxi or hired transfer service, it takes the same amount of time with the same risk of traffic delays.

It's also unclear if they're bringing their infant: no mention of having to haul a carseat/stroller along with bags.

Posted by
38 posts

no, we aren't bringing our infant. just the wife and i for this trip.

and yes - going to be talking/convincing the wife this week why we need to do the train. transfer or taxi carry same delay risks.

thanks everyone for your help!

and yes, i decided to go with golden tower hotel and spa in florence. i got a free upgrade to the junior suite (best room) from the regular suite as compensation for having to cancel our room last year there when we had to cancel our trip (they would not provide refund, they offered this instead). Hopefully its nice; i have read its in a convenient location to everything.

Posted by
1589 posts

" no, we aren't bringing our infant. just the wife and i for this trip."

Took a long time to add this & this is , by far, your biggest issue.

Posted by
38 posts


input always appreciated, as it was from everyone else on here, but two things:

  1. Glad to know you think there is a time limit for posting.

  2. pretty sure my wife and i don't need your approval on the baby or not.

negativity isn't what i was looking for when i posted to this board. or judgments.

thanks anyway.

Posted by
11733 posts

I got a free upgrade to the junior suite (best room) from the regular
suite as compensation for having to cancel our room last year

Ooooh! Nice!