<<into Brussels the next day where we could get a train (45min) to Antwerp..... $250 per ticket>>

Where on earth did you find that fare? It's under 8€ each way.

Maybe (just maybe). He means the flight from Lisbon to Brussels -- but even that shouldn't cost $250.

Oh, didn't pick up on that, but yes, even that shouldn't cost the equivalent of $250

Toronto to Lisbon to Brussels $250ea using Skiplagged app...... havent purchased anything yet, there are some killer BNB’s in Lisbon, just one nite

Unless they are born there or taken as children, everybody is a first timer to Europe at some point, so don't worry. You have plenty of time to plan.

Do not rush to book flights! Make sure first that your itinerary is what you want! Keep it simple!!

Flights to Europe are long and expensive. IMHO, it makes sense to squeeze out as many days and as much time in Europe as you possibly can, but use it for sight seeing and experiencing, not on planes and in airports! A big mistake first timers make is wasting a lot of time in transport, trying to get a glimpse of many places, while actually seeing too little to remember it. You have already been to Toronto and can go another time. Again, just MO, but I would not complicate the travel and eat up time that you could devote to Europe by going through and stopping in Toronto and again, now considering a whirlwind layover in Lisbon. I am sorry. You have way too little time for that. Your trip will be nothing but a blur! There won't be time to get over jet lag to appreciate seeing anything.

Once your itinerary is firmed, then look for multi-city tickets, into one city and out of another. Get the best flight you can find directly from NYC to Europe. Don't try to string together a bunch of individual flights. Don't fly into a city in which you have no real interest, or RT that will require time and money backtracking. Keep travel simple and straight forward.

So you are not too tired to enjoy it, be in or near Antwerp the day before your concert. You need to be in the city of departure the night before your departure flight. Count on some jet lag, so do not plan intense sight seeing on arrival day.

Depending on how much time you actually have, these (or something very similar) are reasonable options: any could be reversed. Use trains between cities. No waiting in airports.
Into Amsterdam, visit Antwerp and Bruges, out of Brussels
Into Brussels, visit Antwerp and Bruges (or Ghent) out of Paris
Into Paris, visit Bruges and Antwerp, out of Amsterdam or Brussels.
and, similar.

This is not a suggested itinerary, just a way for you to sort days realistically.
Day 1, evening, depart US
Day 2, arrive morning, Amsterdam, get to hotel, walk to get acquainted, perhaps one sight.
Day 3, tour sights in Amsterdam
Day 4, Haarlem or Delft, short ride from Amsterdam
Day 5, travel to Antwerp, check into hotel, sight see in Antwerp
Day 6, sight see and concert
Day 7, train to Bruges
Day 8, train to Brussels for flight home.

Personally, since you have not been to Paris, it would be great if you took the time from Toronto and Lisbon and did into Paris and out of Amsterdam, 3 or 4 nts Paris; 2 or 3 nts Bruges, Antwerp, Ghent area; 2 or 3 nts in Amsterdam.

Yes I agree if not having been to Paris fly there from Lisbon - 4 nights - Antwerp 2 nights Amsterdam 2 nights - book Paris-Antwerp tickets at www.thalys.com.

Agree with sass -if not having been to Paris fly there from Lisbon and say 3 nights - Antwerp - 2 nights - Amsterdam -3 nights. fly home from Amsterdam. Book Paris-Antwerp trains at www.thalys.com.

That 'killer fare deal' via Toronto and Lisbon will end up costing you almost 2 extra days out of your already short 5 to 6.5 days free for the entire trip. It that worth it to you? For me it wouldn't.

And all that would net you is part of one jet lagged day in Lisbon.

Yes janis I agree with - either make it a longer trip or you will have one day in Lisbon jet-lagged and then to Brussels and Antwerp - another whole day in transit. Can't you wiggle a few more days and can't you stay more than 24 hours in Lisbon?

Perhaps you live too far from NYC for it to be a reasonable departure point and perhaps the most important point of my post was lost within my other advice, but it is this.

Fly out of the nearest international airport convenient to your home, straight to one of the interesting cities that is convenient by train to Antwerp. Skip Lisbon, go to Portugal on another trip. Toronto is easy and close to you, visit it again at a different time.

Plan your Trip to Europe to use all possible time seeing the treasures of towns and villages in that area and in a departure city that is also easy by train. Canada and the US is so different, It is impossible to make clear how much there is to do and see in a small area of Europe. Once you are there, it will be obvious.

janisj makes an excellent point about how much time is lost and more money spent trying to take advantage of a "killer" deal. It is easy for travelers to get caught up in that. People fly into a place in which they have no interest, then spend time and money getting to their place of interest. They use points to secure a hotel in some remote place, then half their time going back and forth trying to see things of interest. Don’t fall into that trap.

Wow, more to this than meets the eye. KISS is the acronym of the day, i get it !
Thank you guys/ladies, thats why im here, all good advice.

I concur with all of the above. I see absolutely no point at all in including a minimal, jetlagged glimpse of Portugal on this trip. You have a very, very short trip to Europe in store for you. Don't waste any of it being places you don't have time to appreciate and that will cost you time and headaches from which to move to other places.

As others have suggested, fly direct from NYC to either Amsterdam, Brussel or Paris. That way you have only the trans-atlantic flight, and everyting else you do by train. Avoid one-night stays; you spend too much time checking in - checking out - packing to enjoy anything.
Sassafrass' itinerary is a good one.

I read all ur posts, here is a revamp.....

tues 7pm fly out of YYZ(toronto)
wedn noon arrive Brussels(BRU)
wedn train to Antwerp, arrive 3pm-ish
check into BNB try to stay awake and get to bed early
thurs morning 3hr Antwerp bike tour morning, concert that nite.
fri morning train to Bruges stay til sunday morning
sunday morning train 3hr to Amsterdam
stay in Amsterdam til wednesday
wednesday fly out home, we may stay overnite in Toronto and drive home thursday morning...

just a rough draft :0)

Antwerp is pretty small, you can walk most of it in 3 hours. Cycling is not that easy in Antwerp, with the trams and cars and narrow cobblestone streets. I would just walk it.
Are you going to stay in an Airbnb? I wouldn't do that for just 2 nights; hotel is much easier.

Although I stayed there a week once, biking, going to the beach, etc., Bruges needs only a day. See if you can work in Ghent on the way to Bruges or walk in Bruges on Friday and go to Ghent On Saturday as an easy day trip.

From Amsterdam, do visit at least one of the smaller towns like Haarlem or Delft. You could even stay in Haarlem and see Amsterdam as a day trip. Although peak tulip time is earlier, that whole area will be gorgeous in May. OTOH, just the major museums in Amsterdam could take one whole day, if they are of interest.

You will arrive home on Thursday. Is there any way you can extend your time in
Europe another day or two and arrive home on Sat?

All in all looks very nice!

I’ve been using skiplagged app to search out ticket prices, i started my search on saturday and had a fairly low rat of $365 per ticket for YYZ to BRU May 21 2019, as the time progressed to wednesday its up about $100 each per ticket. Will this be a permanent increase in price, or will it follow a trend and go back down to $365 next sunday ???
this is new to me, as is planning a trip like this for the first time, i guess the web would concider me a Noob :0)
WTS, should i concider Promo codes if i can find them, any advice would help TY

Honestly nobody really knows how the trend is. Seems it always goes up, but with ups and downs. May 2019 is still pretty far away.
My exp recently was when I booked my tickets to Mexico (I think) tickets from AF from CDG were ok on monday, expensive on wed but Lufth from Frankfurt were ok, by the time I checked the trains to take the flight to FKT, the price was down in CDG with AF and I bought them.
Same happened lately - I wanted to go to Sri Lanka, price went up then down, then I took tickets to Rangoon...

Bottom line : don't wait too much, check and when the price seems acceptable buy. Don't wait for the fabulous deal.
Or bite the bullet a little bit later before they become real expensive.

Flight Tickets:

How do i get the best pricing ? The best i can do so fare is about $800 to europe and $800 back home. If you think this is about right let me know. Each has one layover about 1.5hrs. Total flight time 12ish hours.

do you use the apps to search then purchase direct from the airline ? Are
flight points the only was to get discounts ? Where are promo codes obtained ?

so glad i have 8 months, theres alot to learn :0)

YYZ to BRU and AMS to YYZ