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First Time 16 days to Italy with Family: NEED HELP & ADVICE with ITINERARY

Hey folks!
We are a family of four( 2 kids: 6 and 12). Our primary objective of this trip to explore a few places for a longer period of time, relax and enjoy the charm of each particular region. We want advice to modify our itinerary to a fewer and must see places. We would rather stay in one place for 4 nights! I have been reading RS Italy 2019 for the last one week and trying not to get too immersed imagining the descriptive artistic towns in my head and plan our 16 day trip :) phew!!
The only confirmed booking so far is our round trip flight to Milan.I have not booked our accommodations in any of these places. I am really hoping to get some head start with some good budget friendly( $80-150/night) reasonable places to stay. I would like advice, suggestions to modify our itinerary.
I have a few roadblocks my way:
1.biggest dilemma is how long to stay in Florence or somewhere near like Siena? Our plan is to stay near or in Florence and do day trips to Pisa, Tuscany and some wineries tours/trips? I would appreciate some suggestions for places to stay based on y'all experiences ( rustic houses, cabins, airbnb, b&b etc.)
2.How many days to stay in Rome?4-5 days?
3.suggestions on winery tours near Florence, Tuscany regions

Here's our itinerary:
Sun,May 26: reach Milan ( 8am): malpensa express to Milan Central: stay? ( preferrably in milan cenrtal)
Mon,May 27: Milan ( Monday being holiday except Duomo) walk around Milan central explore?
Tue, May 28: train to La Spezia (Cinque Terre) Sleep in Levanto? (to enjoy crowd free beaches)
Wed, May 29: Explore 5 towns: slowly: monterosso, Manarola may be two towns
Thu, May 30: bike ride Levanto to Bonassola, chill out in the beach, explore one town
Fri, May 31: train to Venice ( if possible stop at Lake Garda on the way ) Sleep in Venice?
Sat, June 1: roam around Venice
Sun, June 2: Lagoon tour and enjoy Venice night life going to concerts
Mon, June 3: train to Siena? or Florence? need suggestions on which place to stay to explore this region
Tue, June 4: Day trip to Pisa. Is it possible to see more places on this day trip? Lucca?
Wed,June 5: trip to Tuscany? any suggestions on tours?
Thu, June 6: walking tour of Florence only a few tourist spots, winery tour
Fri, June 7: Train to Rome ( Sleep in Rome or any small quiet village near Rome?)
Sat, June 8:Explore Rome
Sun June 9: any suggestions on tours in and around Rome
Mon:June 10: Train to Milan ( sleep near malpensa airport)?
Tue: June 11: Flight from Milan @11.15am
Thank y'all!!

Posted by
4761 posts

Just a few notes on your proposed trip. First, I hope this is for a trip next year, and not 2 weeks from now! I think you are underestimating the accommodation costs, especially if you really are travelling this month. Hotel rooms for 4 are not that common, and will book up quickly. You maybe better off booking apartments, but again, these books up months in advance. We dont use Airbnb, so others maybe able to offer advice. Also look at booking.com.

  1. The Cinque Terre are towns, not islands, and are connected by train.

  2. Look at Trenitalia for train tickets. The train from CT to Venice is 4-6 hours, with changes. Doubt you will have time to see lake Garda.3. Yes, sleep IN Venice, not on the mainland.

  3. Pisa as a day trip from Florence is easy. Some people also combine this with a visit to Lucca on the same day. I would stay in Florence and day trip from there, since it is a good transportation hub. You can buy a day tour to the Tuscan villages or wineries.

  4. If you are going to see Rome, then definitely sleep IN Rome, not outside it.

Posted by
5 posts

That's one heck of a trip!

I would stay in Florence. You'll have more options in trains for side trips.

I would rather stay in Florence for an extra night over Rome, especially with kids. I took my (at the time) 5 year old on a trip to Italy and found it very nerve-racking in Rome. To me, Rome is a big city. The historical districts of Venice and Florence are more like small towns. I spent most of the time in Rome worried that she would be hit by a car or lost in a sea of people. Florence has limited cars in the center and everyone seems to walk slower. I also found that many, many more people approached us in Rome (street vendors, tour salespeople, etc.) This makes made my daughter nervous.

Posted by
19 posts

Hi Cjean,
Thanks for your ideas. Yes your guess is right! we are leaving in two weeks and haven't booked our accommodations yet. Do you suggest any places to be taken off from the itinerary to cut costs and save travel time?

Posted by
15679 posts

Hi there, Rash -

I am really hoping to get some head start with some good budget
friendly( $80-150/night) reasonable places to stay

First very important question: is this trip THIS year? Like, you are flying out in a little over two weeks with no accommodations booked? If so, you will be traveling during high season to some of the most expensive destinations in Italy and having to finalize arrangements very, very late in the game. People book MONTHS in advance for summer and this is especially true for the Cinque Terre Region. Just a heads up that you likely may need to increase your nightly budget for 4 people this time of year.

Very quickly:
I would eliminate Milan stays on day 1 and 2 and go directly to Venice.

I'd organize the route as Milan>Venice>Rome>Florence>CT/Levanto>Milan or maybe Florence and the CT could be switched.

If you intend to do a lot of day tripping, I'd choose to stay in Florence: your transport options will be best from there.

Definitely add days to Rome: there is a LOT of ground to cover there and it'll be more enjoyable to explore at leisure.

There are attractions in both Rome and Florence you're going to need either prior, timed-entry reservations or organized tours for but some idea of what you want to see in both cities would be helpful.

I'd skip wine tours with the kids but that's just me. Enjoy fruits of the grape with dinner. :O)
(editing to add: I was still typing as some others were posting so some redundancy here)

Posted by
19 posts

Hi virginiaelbon,
Yes that sounds like a good idea with kids. any stay recommendations in Florence?

Posted by
19 posts

Hi kathy,
First very important question: is this trip THIS year?

Yes it is this year and in two weeks we leave!!! My husbands client in in Milan and we initially thought of combining work and pleasure trip. Since the client delayed their conformation we had to delay our booking.. long story short we are going top spend more than what we though!!

I'd organize the route as Milan>Venice>Rome>Florence>CT/Levanto>Milan or maybe Florence and the CT could be switched.
I just checked on a fast train its about 4.5hrs from Venice to Rome. could you pls explain why it makes sense to work your way up ? just curious:)

'maybe Florence and the CT could be switched'
pls suggest the switch which makes sense. I am willing to take off some places from the itinerary need be
Thanks!

Posted by
15679 posts

I'd organize the route as Milan>Venice>Rome>Florence>CT/Levanto>Milan
or maybe Florence and the CT could be switched.... pls explain .

This feels like more of a circular route if having to fly in and out of Malpensa: head directly east, furthest point south, and work your way back up. Besides, Levanto > Venice, as you originally ordered it, would be a 5+ to 6-hour journey. You can cut that down if traveling between Florence and Levanto.

By "maybe Florence and the CT could be switched". I meant the ORDER could be switched: Milan>Venice>Rome>CT>Florence>Milan. I'd do it the other way, though, to take advantage of "fast" trains between Rome and Florence.

Posted by
5955 posts

With just 2 weeks to go I think you’ll be very very lucky if you find accommodations at all in CT

And other locations will be hard to find as well and get ready to double that budget!

Posted by
1224 posts

After a cursory reading of your itinerary, Id say you are staying in too many places for the amount of time, esp. as you mentioned wanting to stay in places for 4 nights and immerse yourself.
Gently, I think you are trying to see too much, in that urgency many first timers have to see as much as they can because who knows if/when they'll be back. You go to Florence but then spend your time traveling elsewhere (Pisa, Tuscany), with one day in Florence. You give yourself 2.5 days in Rome (again, I thought you wanted 4?).
Getting Tuscany from Florence without a car is a time-consuming effort. There is a bus, but it takes about 90 minutes one way. For a day trip with a 6 year old, on the pace you will be keeping, this sounds like a burden rather than relaxing.
Thats my first take. I would narrow your interest. You have 14 full days? What four places do you care most about seeing this time? I went to Italy for 12 days with my three kids. We stayed in 3 places (CT, Florence, and Rome) and my kids enjoyed all of them. We loved Rome, dod not feel overwhelmed (we stayed in the Trastevere neighborhood which was a nice respite out of the main throng of tourists but still within walking distance (my youngest was 9 at the time). Considering the circle you are traveling, I too might drop Rome just because it is the one place outside the circle. We always stay in Airbnb's (family of 5) and find them cheaper and a good way to save because we can cook meals.
Hope that helps some ; /

Posted by
15679 posts

A quick sample itinerary below
You could take a day from Florence, add it to Rome and take an easy day trip from there with the extra time (Ostia Antica?) I'd personally keep Rome as I think it has stuff the kids will find interesting.

Sun,May 26: Malpensa Milan ( 8am) to Venice (3 nights)
Mon,May 27: Venice
Tue, May 28: Venice
Wed, May 29: Train to Rome (4 nights)
Thu, May 30: Rome
Fri, May 31: Rome
Sat, June 1: Rome
Sun, June 2: Train to Florence; this is a Italian Republic Day (5 nights)
Mon, June 3: Florence (national museums closed) take a day trip
Tue, June 4: Florence
Wed,June 5: Florence; take a day trip
Thu, June 6: Florence
Fri, June 7: Train to Levanto/La Spezia/CT (3 nights)
Sat, June 8: CT
Sun June 9: CT
Mon:June 10: Train to Milan; stay near Milano Centrale; dump the bags at a hotel and explore for the day (1 night)
Tue: June 11: Flight from Milan @11.15am

Posted by
2281 posts

hey rash
You understand last minute but with lemons make lemonicello. Check crosspollinate.com, different cities to see what’s available.
Casarabatti.com in Florence
Maybe you can look at lucca apartments.com in if not much in cinque terre. apathtolunch.com for info
cucina-Italian.com has accommodations and cooking class
booking.com. Put in filters on left side and go from there.
It will be busy wherever you go, if plan A doesn’t work plan B.just enjoy, don’t stress, it is what it is. Have a glass of vino, people watch and have fun.
come&seeitaly.com, luccatours.com
You won’t see all you hope, don’t be in a rush, savor what you do get to see. Then plan another trip, you’ll love Italy.
aloha

Posted by
19 posts

Thanks Kathy for a the quick sample. I do like it! My husband has to meet his clients on May 27 and 28th in Milan. After which we are free to travel anywhere. I will tweak up the itinerary a bit and pls tell me if it looks reasonable with kids.

jessica Thank you for the timely advice. Yes My 6 year old can throw a big tired tantrum ...:) I will keep your advice in mind to see three places.

suggested new itinerary: i switched Florence with Rome due to closures in Rome on Republic day. Please tell me what you think
Sun,May 26: Malpensa Milan
Mon,May 27: Milan
Tue, May 28: Venice ( 3 nights)
Wed, May 29: Venice
Thu, May 30: Venice
Fri, May 31: train to Florence ( 5 nights)
Sat, June 1: Florence
Sun, June 2: Florence (this is a Italian Republic Day)
Mon, June 3:Florence take a day trip
Tue, June 4: Florence
Wed,June 5: train to Rome (5 nights)
Thu, June 6: Rome
Fri, June 7: Rome
Sat, June 8: Rome
Sun June 9: Rome
Mon:June 10: Train to Malpensa; ( stay close to airport)
Tue: June 11: Flight from Milan @11.15am

Posted by
19 posts

Hi Princess Pupule,
Thank you so many for so many useful accommodations links.
"Casarabatti.com in Florence": I checked this out. looks really good, looking at the map feels like it located in the heart of florence. Have you stayed here? any thoughts?
Do you have any good suggestions to stay in Venice and Rome?

Posted by
4256 posts

If you go to Rome, I suggest you search for convent accommodations on this Forum. Some of them are more reasonably priced than hotels and are often in locations convenient for sightseeing.

The good thing for you is that many schools don't get out until mid-June, so that may help the crowd situation a little.

If you find accommodations that you like in Florence, you could just stay there and do a day trip by train from Rome. Not the best idea, but it might be easier than finding accommodations in yet another city. Florence is more centrally located, in my opinion.

Posted by
15679 posts

Rash, I'd highly recommend getting onto www.booking.com and searching availability for your dates with 2 adults and 2 children the ages of yours (the site will ask for that info). Italian hotels which will have rooms equipped to sleep 4 are not nearly as common as in the U.S. so that requirement is going to be a time-saving search filter you're going to want to use right off the bat.

Then narrow down by review scores, price, distance from center etc. Star ratings only reflect the amount of amenities a property has so have no bearing on their overall quality. A clean, comfortable 2 or 3-star without a lot of extras can beat a dirty 4-star with noise issues. You can search for apartments on that site too: see the filter choices on the left side of the page (I linked Florence but you can change locations):

https://www.booking.com/searchresults.en-gb.html?city=-117543

Oh, and your itinerary looks fine. :O)

Posted by
2281 posts

hi rash
Didn’t use but I saved it as a place for us friends. Used cross-pollinate and liked them, they are also associated with the beehive.com
As kathy has said booking.com with filters will help you. an apartment is better for your family, then renting 2 rooms. this late you’ll be lucky to find family/quad room. all people need to be listed. look at map where especially Venice. It’s walking over steps bridges carrying your bags. We found a place near train station, canareggio area and how tired and cranky kids and parents can get. europeforvisitors.com lots of info.
in Rome we liked Piazza Navona, trestavere, Monti. Everyone has all kinda opinions, likes, dislikes. Get your places booked soon then you can ask questions, these posters are great to help you not stress and enjoy Italy, you’ll love it and have fun. Have a glass of wine, people watch, relax and don’t be in a rush, savor what there is to offer
Aloha

Posted by
839 posts

Rash: Our experience with Booking is to try to stay at places rated higher than 8.5, but their ratings are skewed in values based on location (a great location outweighs lots of the other variables they list in their ratings criteria).

Booking.com does list 200+ hotels in Florence for your dates (June 1-5, 2019) but you best get on it quickly there. A car rental in Florence may be useful (pick it up and return it at the airport so you don't have to drive in town) to visit wineries and other towns with kids (Siena, Montepulciano, etc.). Just google "Wineries, Tuscany, or "Winery Tours, Tuscany" and you will get an idea of what is available. Also mapsgoogle.it will give you the local place names spelled properly for making bookings/train reservations, as will the RS guidebook.

https://www.trenitalia.com/en.html is very useful for getting travel times and fares down if you have not already done so.

We loved staying in Levanto rather than the CT. Booking.com lists 69 properties right now for your dates. Nothing is very far away there, but hiking/biking paths can be blocked after winter rains so ask around.

Similarly we stay in Padua rather than Venice - it is an easy commute in and out and is a much more laid back base (cheaper too). You miss the evening activities but it is a cool university-centered town with the Scovegni Chapel that has some of Giotto's finest frescos. http://www.cappelladegliscrovegni.it/index.php/en/

Have fun and bring tablets preloaded with kid friendly music and videos to calm the boring bits for them.

Posted by
19 posts

Thank you NickB for calming my nerves a little! I really appreciate your suggestions and your message instantly gave me hope:)
Thank you princess and kathy. Ive been Booking.com , Expedia and seems like we might luck out.. but I still have hours of research trying to find a good one.
NickB: i did think about Padua after reading RS Italy. 2019. I wanted to stay in Venice to experience the night life. how convenient was it commuting in and out of Venice? by boat or train?
we are staying 3 nights. technically we have 2 full days. what will make sense .. stay in Padua in the quiet pr in Venice?

Posted by
15679 posts

I wanted to stay in Venice to experience the night life. how
convenient was it commuting in and out of Venice? by boat or train?

Night life? With a 6 year-old? I might be confused but figure a child that young won't be up very late? LOL, maybe your little one is a night owl, eh?

You don't want to be "commuting in and out" of the historic island of Venice if Venice is what you want to explore, especially if you do want to experience some of its after-dark ambiance. Those golden hours after the hordes of day-trippers arrive and after they leave are some of the best times to be there!

Posted by
15679 posts

A car rental in Florence may be useful (pick it up and return it at
the airport so you don't have to drive in town)

Just putting an exclamation point on this previous mention. A car can be useful for exploring countryside outside of the city but best not to have to deal with one IN the city. There are many restricted areas you cannot drive the thing, and parking can be an expensive pain. There are Tuscan small towns you'll be required to park outside of to sightsee as well. If you want one for countryside/smaller town exploration, rent/return one for the day as suggested.

Posted by
19 posts

Hey folks,
Good news!! I am able to find good apartments for $140/night in cross-pollinate. very good website// Thank you all!
NEED ADVICE: fLORENCE : 4 NIGHTS. WE PLAN TO DO DAY TRIPS TO PISA , LUCCA AND TUSCANY. I am getting these apartments in the heart of Florence near the city center. I know it will be super convenient to go around Florence. but also a lit noisy. overall does it make sense to stay in the center near trains station for day trips also?

Posted by
15679 posts

NEED ADVICE: fLORENCE : 4 NIGHTS. WE PLAN TO DO DAY TRIPS TO PISA ,
LUCCA AND TUSCANY.

Rash, Florence is the capital of Tuscany so if you're basing there, you're already IN Tuscany. :O)

Central Florence is reasonably compact so you don't have to stay within mere steps of S.M. Novella for catching the trains from that station. The addresses of accommodations you are considering will help us review locations.

One caution? You have not yet made mention of the sorts of things you are interested in seeing during your time Italy? Florence is FULL of Italian Renaissance treasures and history so I wouldn't short the city itself for too many day trips. With 4 nights/3.5 days, I would spend 2.5 days of it in town unless you're not much interested in what it has to offer.

Posted by
19 posts

Hey folks,
I have made few more changes to the itinerary after reading the whole chapter on Rome in RS Italy guidebook. With our kids (6 and 12) being young, we thought it would be best to focus on places and activities which they can relate to:) No Rome this trip.
Milan: 3 nights
Venice: 4 nights
Florence: 4 nights
CT:5 nights?
want to visit Lake Orta and Lake maggiore from CT if possbile
Any suggestions on this itinerary,, Need suggestions on
1. place which is familly friendly with fun activities
2. which other places can be added to taken out
thanks!

Posted by
15679 posts

...want to visit Lake Orta and Lake maggiore from CT if possbile

Yikes! Both are MUCH too far away for day trips from the CT. It's at abt. 3 hours from Levanto just to Milan and those lakes are some distance further north of there. If you want to do the lakes, then stay at or much nearer them.

I have made few more changes to the itinerary after reading the whole
chapter on Rome in RS Italy guidebook. With our kids (6 and 12) being
young, we thought it would be best to focus on places and activities
which they can relate to:) No Rome this trip.

I'm a bit curious what would be more relate-able to them in Milan versus Rome? And can you help us with what sorts of family-friendly fun you're looking for?

Posted by
19 posts

BethFL,
'How about one of the lakes-Lake Como or Maggiore instead of CT?"
I have heard very good recommendations to Lake Garda. Take a booked tour is better vs taking a train and exploring the place and stay overnight and then head to Venice.

Posted by
19 posts

Kathy,
The reason we dropped Rome is due to its rich historical heritage. To enjoy all the tourist spots my kids are not mature enough to appreciate and enjoy Rome yet! probably in two years.

Posted by
2281 posts

hey rash
read about your new changes about traveling. i'll add my 3 cents for other things that may interest you and kid friendly.
cutting down a day from milan and florence, 2 days from CT, adding those days (4) to lucca.
stay within the walls, apartmentslucca.com or booking.com for an apartment. (casa paolino, the antique walls, residenza degli artisti. are places to stay)
rent bikes for the family to ride around inside or outside walls, plazas (piazzas) to walk, have pizza and wine, people watch and kids can play. hopefully not as crowded and busy as CT. take a morning train to pisa to see tower (book ahead of time if anyone climbing to top opapisa.it (read words of advice on climbing tower), take the train to viareggio beach for afternoon swimming, walk along the promenade with shops, cafes and restaurants. read up on beach area, some private you can rent umbrella and chairs or public beach also. look up the town of collodi, home to pinocchio and theme park, carousel, carnival rides and puppet making/shows. across the park is garzoni gardens and butterfly park.
in venice, take a boat ride to the lido. at the end of santa maria elisabetta avenue is a public beach for all to swim and enjoy. maybe pack a picnic lunch, drinks, snacks or have lunch at a cafe. make sure they bring the swim suits maybe a towel, eat gelato and pizza at as many shops to see which is their favorite in all the cities you visit. we stop by delis/bakery for snacks in room and let the kids taste there. ride a gondola on the back canals where ii's less crowded (75E for ride, not per person), a walk to rialto market to see all the seafood, every shape, size and color they can oooh and ahhh at. europeforvisitors.com great website for info
withlocals.com has kid friendly things to do. lots of walking, travel as fast as you can with the kids, stop along the way to rest, sit, stairs, steps and bridges will make them tired. you know your kids. maybe a pizza or gelato making class, ask host/hostess where you're staying or tourism kiosk in city center to see whats going on. rome2rio.com is map and trains/times to get to places. maybe a festival is happening while you are there, fun to go to.
hope this helps you out on some things and places to check out. don't want them burnt out on museums, churches, art (attention spans are short) and get them "grumpy". enjoy your vacation and planning. soon your vacation will start and no stressing. do come back and let us know good bad and ugly
aloha

Posted by
19 posts

Thank you so much Princess Pupule!!!!!!:) I love all your suggestions. will definitely use all the advice you have given me. just reading your reply I feel a little relaxed :)
Will definitely give you a full trip report.