Itinerary for European Trip, Multi-Country?

If you haven't already, you'll probably want to carefully consider the realistic travel times involved in this itinerary. Total travel time will include not only actual travel time but also the time required to get to the train station, getting from the station to your destination lodging, waiting for trains, time in the hotel it takes to pack and unpack before you hit the street, and similar thing.
And after you have developed realistic estimates of total travel time, consider how much time you'll actually have at your destinations to do and see what you're going there to do and see.

Thank you for your reply. I have absolutely considered that, having done a few of these "sampler" type of tours before in Australia and the surrounding areas, as well as into and out of Italy and its surrounded countries. I've been considering axing Milan from the whole thing since I've done a lot of Italy lately...but I so love Italy.

Many travelers feel Milan is not as must-see as Florence, Rome, Venice, etc.

Good to know. If I did axe it, I would probably add more time to Spain and/or Portugal.

Nazare is nothing but an overrated beach resort, therefore it’s not the place to visit in February, when it certainly won’t be beach weather. Spend this day in Evora or have a day trip to Cascais or Sintra.

The Sierra Nevada could be quite snowy at that time of year. Madrid will be cold too.

Feb 10 - Arrive in Madrid

Feb 11 - Madrid

Feb 12 – Madrid

Feb 13 – Travel to Amsterdam (Stay in the town of Haarlem upon arrival - 30 min from Amsterdam and 17 min from Schiphol airport).

Feb 14 – Amsterdam

Feb 15 - Amsterdam

Feb 16 - Amsterdam

Feb 17 - Milan (Travel to Milan)

Feb 18 - Milan

Feb 19 - Milan

Feb 20 - Travel to Lisbon

Feb 21 - Lisbon

Feb 22 - Lisbon (Day trip to Cascais or Sintra)

Feb 23 - Lisbon

Feb 24 - Travel to Granada

Feb 25 - Granada

Feb 26 - Granada (Day trip to Córdoba or Málaga)

Feb 27 – Travel to Madrid

Feb 28 – Fly back to NYC

You scored super low flights to/from Madrid, but to cover so many other destinations quickly, are you planning on using cheap, budget airlines, like Vueling or easyJet?

18 days minus 2 air travel day plus other travel days to other countries, I am fearful, for you, that it may turn out to be a bit much.

I would focus on Spain and Portugal. Transportation will more likely include air. Suggest Madrid (maybe side trips to Toledo or Zaragoza), Granada, Seville and Cordoba if you have not been. The Sierra Nevada may require winter gear. I wonder where the high surf is in February? We did a two week trip from Madrid with a car and our bikes to the Pico's and the NW coast for two weeks. It was early May and wet suit surfers were the only ones in the water. The scenery was beautiful.

We spent over two weeks in Portugal with 4 nights in Lisbon, 2 nights in Sintra, 2 nights Tomar, 2 nights farm stay outside Evora, 2 nights Seville, ES (missed this on 3 other trips to Spain), 3 nights southern Portugal beach (Begur) and 2 nights Faro. A bit more than two weeks and I would like to return to Portugal.

Most of these destinations will be more practical to connect by flight than by train; see www.skyscanner.com. The one daily train between Madrid and Lisbon is an overnight train.

I would not travel that distance to visit Milan, although I would for Venice or another place with a good Carnival/Carnevale celebration.

• http://www.carnevale.venezia.it/en/

• https://www.storicocarnevaleivrea.it/?lang=en

• https://travelinspires.org/spain-top-carnivals/

Thank you for all of you who fear for my tight timeframes. I am used to this kind of travel, and prefer it when I am solo. I have the means to return to all of these places, and want a sample of many so that I can properly plan my duo or trio trips later on. That said, I am considering taking Italy out of the picture altogether (I was there twice in 2019) and focusing on Spain and Portugal, with a side trip to Amsterdam (I have friends there) -- and all country switches are by flight.

It looks like one of you thinks I shouldn't do the Sierra Nevada and opt for other places instead? I'll look into those. I liked the idea of the personal 4WD hire... but if it's snowy and not a good time for that?

My next travel will be Summer 2020.

For me, Milan is a big city with not enough sights to make it worthwhile to go out of one's way to be there. If you haven't been to Andalucia, I encourage you to add Sevilla/Cordoba to your itinerary. There are flights from Lisbon to Sevilla, and then train to Cordoba/Granada/Madrid. That would also give you the option (if you don't mind spending a lot on a train ticket) to stay in Granada for a day trip to Sierra Nevada - depending on current weather conditions - or spend the time in another Spanish town. Although Malaga and Antequera are possible day trips from Granada if the Sierra Nevada trip isn't possible.

Many travelers feel Milan is not as must-see as Florence, Rome,
Venice, etc.

Exactly. It puzzles my why people don't see Turin instead, which is by far the more interesting city in this region.

From my origin in the US, Milan and Rome are typically the cheapest Italian cities to fly into. I imagine the same is true from many other origins. And there's The Last Supper, which it seems many people want to see. Also the Duomo, which is very impressive and takes a nice picture.

Turin will be on my itinerary the next time I hit northern Italy, but I haven't researched its sights and cannot tell you one single specific sight there I especially want to see. I'm not religious, so the Shroud holds no interest for me; I don't even know whether it's on display in Turin these days. Most tourists don't go to a major city just because it has a nice historic district; they want to see big-name sights.

Well, Turin was the seat of the House of Savoy, and a major European capital for 300 years.
Just a few random impressions:
Royal Armoury (one of Europes finest)
Random square in the centre
Inside Palazzo Madama
View from Monte Cappuccini
National Car Museum
Inside the Royal Palace
Stupingi (inside)

Staying around Andalucia sounds great, actually. I DO hope to venture to Amsterdam for a bit, as I have friends to see there, but let me crunch the numbers.

My primary reasons for travel are 1) Food 2) Natural wonders 3) Architecture 4) Art. Framing all of that is of course culture, people, cities, and such things.

This is all fantastic feedback. Thank you.

" My primary reasons for travel are 1) Food 2) Natural wonders 3) Architecture 4) Art. Framing all of that is of course culture, people, cities, and such things."

Since you mentioned these are your reasons to travel then these 3 countries should fit the bill.

Madrid and Andalusia - Architecture, Food, Natural Wonders

Portugal - Natural Wonders, Food

Amsterdam - Art, Architecture

Two and a half weeks and you plan to visit Spain, Portugal, Netherlands and Italy.

Scratch two countries and enjoy your time without having to travel during your vacation time.

Last time I visited Portugal, I spent over two weeks and except for day trips to Salamanca and Santiago de Compostela in Spain, all was in Portugal.

I suggest eliminating Italy and/or Netherlands on this trip.

As stated above, I am used to this kind of travel on my solo "sampler outings" so the multi-country itinerary doesn't phase me. That said, I will most likely excise Milan from the plan and focus solely on Madrid/Andalusia and Amsterdam (as I said, it's part of the trip: I'm visiting a friend) -- with potential to Portugal for a bit if it feels right.

Thanks for the feedback!