On my 20 in 20 list is a trip to Italy. I’m turning 60 this year and I’ve told my H that 2020 will be the year I finally get this trip. We briefly visited years ago with a Eurail Pass and visited Venice and Florence. I had a flu and never left our pensione in Florence.
Where would your favorite itinerary look like? I don’t have a strong desire to go back to Venice. I like small towns, markets, people watching, nature, water both lakes and ocean. H is not much of a museum goer and not interested in day after day of churches. We don’t want to be moving every day.
We have flexibility but as of now I think we would go late September or early October.
Cinque Terre?
Florence with day trips.
I’ll be watching this thread 
A few months ago I looked at Airbnb listings in Florence (which we visited 1 day during a 2012 cruise) - apartments for 2 couples seemed surprisingly affordable.
If you have not been to Rome, you should.
My daughter has been to Italy every summer for the last 3 years. She spent most of her time in a small town called Latina, 45 mins outside of Rome. She loved every minute of it. She hung out with my Italian friend’s daughter and other Italian teenagers. They go to the beach every day. The town has beautiful churches and caves, water falls (so i was told). I was there a few times for work but didn’t really do the fun stuff in Latina, I only had time for Rome. Latina isn’t a tourist town, it has a few hotels but may not have the touristy accommodations that tourists are used to. But if one is looking for something different, it’s worth it to check it out.
I plan to go back to Italy this summer with my kiddo and stay in Latina for a few days. She plans to stay for a month including a couple of weeks traveling through Europe with her Italian friends.
But imo, if you are in Italy, you may as well see Rome, everything else should be the add-on.
Tuscan and Umbrian countryside, Ligurian coast, lake region north of Milan.
^^ true, somehow I missed the not liking churches and museums part. But keep in mind those places are also very touristy, at least when we were there 5 years ago. I didn’t expect it to be that way compared to Rome but I Had a memory of trying to see something and so crowded we gave up.
My husband is a birthright Italian citizen and so are our three children. We have been to Italy a dozen times and are now planning our trip for the fall of 2020 to searching for a home to purchase.
We have never had a bad trip there are we have stayed in every part, with the exception of the far tip of the ‘boot’ (Calabria) and Sicily. That’s for the next trip.
I am not a huge fan of Venice or Florence as a place for home base. Both are must-see cities, but I prefer to stay in smaller (way less touristy) cities.
Will you rent a car? I find driving in Italy to be very easy once you are out of the walls of a big city. Do NOT plan on keeping a car if you are staying in a medium to large size city. Don’t even think about driving a lot in Rome.
Generally we will rent a villa in the middle of a province we wish to explore and take day trips to the surrounding towns. Most are walled cities with easy parking right outside the wall.
Tuscany is famous for a reason. You will not run out of towns to visit. Florence is the most famous, of course, and is a bustling place but if you’re into art, tough to beat.
If I could have only one more trip to Italy, I would pick a town on the western end of the Chianti region in Tuscany and take day trips from there. I know you said you wanted water, and you could reach Cinque Terre, but that is not an easy place to get to (but worth it). Tuscany’s western border is the Sea, so many resort towns along that route. Lucca, Siena, Montepulciano, Volterra…and many more are all worth visiting throughout Tuscany. The most beautiful drive I have EVER been on (and I have been all over the world for work) is the drive between Siena and Greve-In-Chianti.
If you don’t want to drive, you can rely on trains and buses, but thar will eat a lot of your time. If you don’t want to move around a lot and are more into being around Italians and not tourists, Turin/Milan/Bergamo/Lake Como are doable in a week. They are an hour apart by train.
Many visitors to Italy consider the Sorrento peninsula the best Italy has to offer. Sorrento is a lovely place and the Amalfi Coast is an outrageously beautiful area. Don’t skip the Isle of Capri. That is more of a ‘beach’ type trip, but all of the towns along the Amalfi Coast are worth visiting, and Sorrento is worth a few days alone. We stayed in Positano for five days a couple of years ago and had to be dragged out of there.
Rome will keep you busy for an entire week, and you can take many organized tours from Rome. Not my favorite city, but it is my husband’s. Expensive and busy, but naturally there is much to do.
One consideration is time of year. Northern Italy is cold in the winter. Southern, very hot in the summer.
Be adventurous here and don’t be afraid to pick a spot and explore out from that point. Many Italians speak enough English to help, and pubic transport is excellent. Our most special days have usually involved finding some restaurant in the middle of nowhere where they are not used to tourists and thus made a huge fuss over us. They generally have given us great advice and saw some things no guide book writes about. The Italians are gracious and social and anxious to help.
One last bit of advice…plan ahead if you want to see any famous sights. Don’t show up at the Uffizi or Vatican Museum at 1:00 on a Saturday and expect to get in. For most places you need to buy a reserved ticket weeks in advance.
You can love a trip to Italy and not enter a single church. But it is a bit nuts to skip St. Peter’s in Vatican City.
Ciao and buona fortuna!
@cypresspat , you lucky, lucky duck! Wow, a house in Italy. I am salivating!
I’m very interested in this thread @mom60 , as we are going in September 2020. H and I went in 2015 and now we are taking our sons. I am just jumping up and down.
I bought the Rick Steves Italy 2020 book yesterday, it’s on sale on his website. I like it because it’s easy to read, like the larger font. Michelin is too small to read for my eyes. I think I might have gotten several from the library to read, but I only purchased RS.
We might only have 8 nights. We will definitely do Rome again, and we skipped Florence last time so it’s a must. We will take a tour out into Tuscany while we are there, visit a vineyard and have lunch.
My younger S, really really wants to see Venice. We will take the train the last day from Florence to Venice and let him experience it before we head home the next day. Fast paced, I know.
But we did that last time and it was fine. Next time it’s just DH and I, I’d love to do the little towns.
We did stay on the Amalfi Coast, Positano, in 2015, and that was spectacular. Lots of vertical climbing, so be prepared for that. I’ve heard Amalfi Town, not near as much. But laying out at the beach and swimming in the sea in Positano is one of those experiences in my life I’ll never forget.
It will be fun to share planning tips going forward with all of you making a trip this year! I’m waiting to hear from S to find out how many days he can take, so I can plan my itinerary. I’ve been searching hotels the last 2 days, I love to plan!
Also, I read that air conditioning is only turned on, by law, from May though September. I didn’t know that. There were reviews for several hotels that were angry and complaining that it was hot in October and November this past year and no air! Very hot in the rooms, no screens on the windows, so mosquitoes could get in. Something to consider if AC is non negotiable like it is for me.
We used to go to Italy few times a year when kids when growing up. We still go every few years. As someone mentioned, we never had a bad trip or bad meal. I am also not a church/museum person and love small towns.
We used to go to a beach town, Viareggio. It is on the west coast of Tuscany, easy drive to many towns, Pisa, Florence, Siena, Lucca.
I would fly into Milan or Rome and either drive or take a train to where you are going to be instead of taking a connecting flight. For some reason they have a lot of weather related issues and flights are often delayed/cancelled. I do agree that driving is very easy in Italy, especially with GPS now.
Starwood has some of the best hotels in Italy. You may be able to use your points to get few nights during an off season. Few years ago I rented a 2 bedroom apartment in Florence via Jetsetter. It had a beautiful balcony over looking Ponte Vecchio.
I was in Italy this October for the first time. We stayed 3 nights in Rome and 3 nights in Florence. We had a car drive us from Rome to Florence stopping in Tuscany at a cheese farm for lunch and in Chianti to visit a winery. It was arranged by a travel agent. We love museums, so the rest of our itinerary wouldn’t suit you, but doing a car between cities (instead of the train) might be a good idea for your trip. BTW - there are a couple of Italy/Rome threads around that are not too old (I know I had one this year and referenced one from the year before).
After all the typical sightseeing in Venice and Florence, the highlight of our trip was a tiny village above Positano called Nocelle. No cars allowed in the village and not many touristy things but it had amazing views and so incredibly relaxing. We hiked part of the Sentiero degli Dei or Path of the Gods. The owner of our rental took us out to her garden to pick fresh vegetables, showed us her father’s olive press and surprised us by teaching us how she cooked pasta. Just remembered that all the guide books tell you to stay in Venice but we couldn’t afford it. We stayed at one of the islands close to there and one of the highlights was watching the local activity-- kids playing soccer on the cobble stone streets, delivery boats bringing food to the restaurants in the morning, etc. We booked all of our train tickets in advance for a very discounted rate.
@conmama. Yes, we do feel lucky. But we will not be purchasing a working vineyard in Tuscany. One can get a nice little 2 bedroom apartment in a mid-sized city for under $100k (less the further south one goes); that’s more our speed. If interested in renovating a property (which is highly regulated in Italy), properties for far less $ are available. In the countryside, there are literally ‘piles of rocks’ for sale for quite a nice price, but you are obligated to restore it using very strict guidelines. That is why Italy is so beautiful wherever you go- they take the aesthetics of the buildings very seriously! The good news is Italy has reasonably priced trades people who take great pride in their work. The bad news restoration takes a couple of years.
So my husband and I will not be lounging on our yacht on the Italian Riviera. We will instead be exploring the outdoor markets probably in Campagna, but not on the swanky Amalfi Coast. On the whole, Italy has a low cost of living, especially the farther south you go. We will maintain a small domicile somewhere in the US and still spend half of the year or so here. Our three kids are psyched about this - they are very busy injecting their requests for location and amenities.
Enjoy your trip! If you are worried about air conditioning (valid concern), check into AirBNBs. Because we are often five people, we do that usually to avoid needing two hotel rooms. The other benefit is you will likely take an overnight flight and usually an AirBNB can be more flexible with check in time if they have notice. in Rome, our favorite area to stay in is Campo Di Fiori. We have an apartment there we always stay in if you wish to PM me for details. The challenge with renting apartments in Rome is actually finding them. Address info is not great in Rome, so important to be clear on location before you arrive there with two kids and suitcases. We have the owners send us a picture of the outside facade of the apartment. Helps finding the darn thing.
Eight days for Rome, Florence and Venice? Flying into Rome and out of Venice? Certainly doable. And the plan is to take a tour of Tuscany out of Florence? Rome is a three hour drive to Florence. If you are at all adventurous, I would rent a car (at Termini in Rome) and drive through the Tuscany countryside to Florence, then get rid of the car there. Once you hit Tuscany, this is a magical drive. Trust me on this one. You can stop at one or two of several towns (September is beginning of harvest - perfect!) and a vineyard on your own time. It will take you all day, but you will see a lot more than on a tour. As a family in the countryside of Tuscany you will be treated like royalty. Would be good to see the people of Italy outside of the big cities. I have many favorite towns in Tuscany which I can recommend for a lunch stop, or a glass of wine, or shopping, or a glass of wine. Did I mention wine? While in Chianti you will drive through some of the world’s most famous vineyards. Seriously…I have been to the Great Wall, Eiffel Tower, Great Barrier Reef, Cliffs of Mohr and outdoor mass at the Vatican served by Pope Francis. Pope Benedict, while leaving the Vatican for his early morning walk in a park he has to be driven to, had the driver stop the car so he could wave to a few of us standing on the sidewalk. Driving though Tuscany beats them all. Honestly I would trade more time in Tuscany countryside than Florence. I know checking in and out is a pain, but staying in a country villa (maybe an Agroturismo?) in the middle of Tuscany, get a fabulous breakfast, feed the chickens and then get back on the road? Ok, I think I’ve made my point!
PS I think RS pretty much nails it with much of Italy. Pay close attention to his advice on logistics of visiting the highlights. Book your tickets for the Ufizzi well in advance, and get the earliest time slot in the morning you can.
And, finally on my unrequested advice, how old are your boys? We have had kids of every age (including toddlers) with us. Sometimes a challenge to keep them content. The coliseum is paradise to a 10 year old, but not a 6 year old! My sons have the oddest ‘favorites’ from their childhood visits to Italy. My youngest most remembers the donkey on the property we stayed at when he was probably 6.
The lake region in the Dolomites is also spectacular, especially if you want to avoid crowds.
My mom is Italian and most of her family is still there. I’ve been all over. Love the smaller towns on the Amalfi coast but we went in March to avoid crowds. (I hate crowds).
Next time we go back, we will stay in Tuscany and do day trips.
Can’t add any more than what’s already been said.
Seconding Cinque Terre. It is one of our favorite spots in Italy. We did an airbnb type lodging right in one of the villages. We were disappointed in Florence, SO touristy and commercial. The museums were beautiful, yes, and we found an amazing deli we ate at 3 times, but throngs of tourist groups and so many “mall” stores. Also, there are no green spaces in the city, at least that we could find.
One of my favorite places is the isle of Capri! Hydrofoil from Sorrento and then a funicular up the hill. Absolutely stunning, pedestrian friendly since there are very few cars allowed, only by residents or taxis. There are boat tours of the grottos, a botanical garden, and a chairlift to the top of the mountain where you can see the water for miles! I think it is the most beautiful place I have ever been!
I would do Rome and Florence plus Tuscany. Cinque Terre is sweet but it’s mostly just pretty views. In Rome and Tuscany you get this sense of living and breathing history on top of the views.
So much great information. I’m going to need to start a notebook with all the suggestions. We are very independent travelers and my H would have no trouble driving and I’m a pretty good navigator.
I’d like to at least book the airfare. I’m thinking into Milan and out of Rome if the airfare is reasonable. If not would I be better off with Rome or Milan? I think those two airports have the most reasonable fares.
I like the idea of getting a place outside of a city and doing day trips. Would we be better off not staying in Florence itself? My H has several friends who are from Italy and another who spends several months a year. We are going to talk with them for suggestions. The one friend said he didn’t love Florence.
Would those of you who can remember, would you share the names of your hotels in Florence? I’ve spent several hours researching already, but I’d like to hear from you.
My plans right now are to fly into Rome (4 nights), fast train to Florence (3 nights), fast train to Venice (1 night), leave from Venice. I always try to get the earliest trains so we are at our destination by noon.
Boys will be 27 and 24 @cypresspat at time of trip.
H and I just spend time in Rome and Tuscany in September for our 30th wedding anniversary.
We stayed at a villa in a small Tuscan village. Amazing experience. We rented through a gal whose family runs a farm near Pienza. She Is mentioned in the Rick Steve’s books which is how we found her. https://www.theisabellaexperience.com/tuscany-luxury-villa/