Advice for Europe in May with 16-month-old

We have always travelled with our kids so no push back from me. They are now 12 and 9 and are great travellers!

I do not have specific recommendations on your destinations but things that have worked for us in the past in general:
1) renting an apartment that already has a crib/play pen so that we did not have to bring one. We still always brought our own sheets/pillow etc Same with a high chair/booster seat for meals if possible
2) If you can afford to, splurge on the extra seat on the flight.. makes a world of difference
3) bring all and any medication that you may use at home. Pharmacies are not open at all hours like they are here and the active ingredients are not always the same in other countries
4) alternate between a child friendly activity and adult friendly activity.. this meant looking for zoos. aquariums, splash pads etc in every city we went too. We also always scoped out cool parks ( we still do this)
5) Take advantage of your early riser to start your day early and get ahead of the crowds and take breaks mid day ( hit sis away apartments are great!)
6) pick family friendly restaurants not the 4 star michelin rated ones but this does not mean going to McDonald's or eating chicken nuggets or hot dogs...
7) above all be flexible.. be open to leaving places when it is time to, skipping some places etc.

have fun!

I think it's just fine to take your son abroad as long as you cover those potential problem areas that would make it a bad trip for his parents. I'm sure you've considered some of those parts.

"From what we have heard, Portugal, Spain, and Italy are the most toddler-friendly places to travel."

To me that sounds like a whole lotta hokum from whatever sources you are using.

It's not the country - it's the specific environment you choose for your child, irrespective of the country. Every country has babies and toddlers, as well as parks, lawns, sand boxes, splash pools, baby supplies, etc. If those are the countries you wish to visit, terrific - go there. Toddler is along for the ride. None of those countries or any other European country is "child-unfriendly" - what will matter is what kinds of places you stay in and how you intend to get from place to place once you are there. I would make a list of the environmental requirements for the child when you are "at home" in Europe and seek out apartments with the best fit.

My guess is that those apartments are unlikely to be located next to a train station... I am a completely devoted train user and won't travel any other way at this point - UNLESS I magically end up with an infant again, in which case I would probably never, ever board a train. I've seen families with kids traveling by train and it looks like a horrible, unwinnable struggle.

Although you "...are looking forward to introducing him to new cultures," I would leave that element completely out of the planning equation. No 16-month-old will be really be absorbing new cultures. What matters to him are his parents' "culture." I would just go to the countries and cultures that are tugging at your sleeves. Gather and develop your own sensibilities about these countries, then when he's a little older, he will have a grip on his home culture, and you can help him learn about some new place that's interesting exciting.

I respectfully disagree that 16 month olds cannot absorb culture.. they can absorb it in the music and language they hear, the food they taste and are exposed to, the things they see etc. I don't think you are giving kids anywhere near enough credit
FWIW, I have been travelling with my kids near and far since they were little. They get on planes like they get in cars, they know how to behave in public and how to converse with people ... you do not get that way, if you do not expose them to things....

I'm so glad to hear from likeminded life-long travelers! My husband and my parents took us everywhere (starting in childhood and continuing) and we feel like it's made travel an important part of our lives because of it.

I should clarify that I mean "toddler-friendly" in that they are ok with a toddler being out and about whenever we are (which is to say when he can handle it and remains comfortable).
We are active and don't mind long walks, prefer cities with a restaurant/cafe nightlife, and have both been to Italy previously (me - two summers abroad, him - a bike trip through Tuscany) and I have been to Barcelona. That said, we know that traveling with a toddler will be a lot different than those trips we took as young adults. We'd love recommendations on cities that might fit the bill for our interests, and particularly whys and advice from parents who have done those cities before (was there a great beach? did your toddler notice the awesome architecture? was your toddler totally wowed by squid ink pasta?)

PP - you are right, a week is probably a long trip for a short stay, I'll see if we can extend it, but because of my husband's work schedule, it will probably not be longer than 10 days.

Of course she doesn't remember it, but we took our daughter to Italy when she was 15 months old and she became fascinated with "statues" and continued to do so back in the States. She also liked "rocks" like the ones she tried to take from the Forum. Be careful around steps-our daughter was about to attempt to walk down the marble steps from the second floor at the friend's house where we stayed in Paris. My in-laws were with us and it took 3 of us to carry her gear-the younger the child, the more stuff you have to take. It was a great day when she was old enough to roll her own little luggage! She does enjoy looking at the photos of herself in Italy at that age.

Hands down, Italy. Get an apartment in a town that appeals to you. I could easily spend a month in Venezia or Firenze (have already lived in Roma for 4 1/2 years). Take walks, day trips by train or bus, and just enjoy being there. You do not have to sight-see in the traditional way to enjoy the culture. And the Italians will love your little boy. Food's good, too.

I advocate taking an agrotourismo. That way, there are animals to see - chickens, ducks, cats. Most 16 MOs like chickens, ducks, cats. We stayed in a ski chalet during June near Altenmarkt S of Salzburg, Austria. My 22 YO daughters like the cats and chickens.

I whole heartedly agree with taking your 16 month old to Europe. My daughter has been traveling to Europe every year since she was 9 months old, she's 6 now, and absolutely loves to travel. She loves to fly, loves seeing new things, loves to explore, loves trying the foods (her favorites - pork knuckle and leberkase) and has always been welcomed by everyone. You've been given a lot of great advice. I will second buying him his own seat, everyone will be more comfortable and be a little more refreshed once you land. You can get a lightweight carseat to use on the plane, use a luggage cart to carry it through the airport or strap it to a rolling carryon. One thing I would suggest you put in your toiletry bag would be a thermometer. My daughter caught her first cold on her very first trip and I didn't have one with me, and really could have used it. I also carried the infant Tylenol/Advil and anything else she might need in that way. If he suffers from ear infections, have him checked 2-3 days before you depart. That way if one is starting you can go ahead and start the meds. It never failed that my daughter developed one just before we left on each trip so I've always had to carry an antibiotic with us, it was almost always one that had to stay cold.
Our daughter has been to Manchester, England, Munich, Berlin, Copenhagen, Malmo, Sweden, Frankfurt, Dresden and a few other smaller towns. We always travel by train, including with an umbrella stroller, always find a zoo, parks, interesting museums, toy stores, etc. We hope to continue this for a long time and are very happy she loves to travel as much as we do. I have plenty of other tips so feel free to ask away.

I'd shorten travel time and zone change as much as possible and head for the island of Madera. TAP has a direct flight from JFK now.

I love Madeira, but to me it's all about walking, and I don't think that's something I'd want to do with such a young child. The island is also very hilly, and it has no sandy beaches.