Where to go when.

You're likely already aware that March would still be pretty cool in Korea. Probably only a little warmer than Toronto. If you do your trip in April, you might luck out with the sakura (cherry blossom) festivals in Japan.

I have no experience in Asia and limited shoulder-season experience in Europe. Without digging into weather statistics (timeanddate.com for actual, day-by-date stats), I don't know whether April-June would be much warmer than September to mid-November. And I think the precipitation pattern varies, some areas being drier in the spring though others are drier in the fall. What is definite is that the days will be longer during the first time period. But a lot of folks don't care about that at all. Thinking about what the countryside will look like, I'd stick with Trip One and Trip Three as they are, because I can imagine a lot of brown in southern Italy and Spain at the end of the summer.

If you don't already realize this, it will become clear as you dig into your guidebooks: 2-1/2 months is actually very, very little time for Portugal, Spain, southern France and Italy-including-Sicily. I assume you'll be traveling slowly and savoring places to avoid crashing and burning. Sicily alone needs more than 2 weeks (3 weeks if you want to include the Greek sites, possibly more if you also want to go to the Aeolian Islands).

Edited to add: You're clearly a strategic thinker. I would take it farther and give absolutely top priority to the areas you know you don't want to visit on future summer trips. That's most of the places included in Trip One, but not all of them. The stretch of northern Spain from Galicia to the Pyrenees is fine in the summer (though if you get very far from the coast you lose its moderating effect). I think the same is true of northern Portugal but am not sure. The French Pyrenees seemed like they would be OK in summer. The French Basque Country seemed cooler (and wetter) than the Mediterranean Coast, but I haven't researched its weather stats for mid-summer. Places at altitude in the Italian Dolomites are great summer destinations.

I have happily rolled the dice and visited Normandy (also Brittany) and the UK in the summer. I had a couple of heat-wave days in Brittany this year, but otherwise I was comfortable enough. I wouldn't "waste" this rare opportunity to travel April-June by spending spring in the UK or that part of France. I'd redistribute the problem areas of Spain, Portugal, southern France and Italy across both trips. Germany is highly variable. You can suffer through sunless days or it can be very hot, at least as far north as Berlin.

It is good to see someone that want to take in history, culture and art, not going to the beach in Europe, which you can do at home in North America.

We have visited China and Japan. Did China in September and Japan in October. Those months worked very well for us. Do not go to China, Korea or Japan in the Summer months.

Southern Europe and the Med area is also hot in the Summer, but nice from September to October. It can still be a bit hot in early October in Southern Italy and Greece. Not sure about November, you will likely run into chilly weather.

April for Northern Europe (England, France and Germany) is still on the chilly side, but by May it would be fine.
We did a great self drive car in S. Wales and England for four months (in October) and it was nice until the last week when we had rain.
We recently did Portugal in May and it was great.

Not sure why you didn't mention China, it is amazing, but your need to take a tour if you go there. The sights are special, the Great Wall, Forbidden City, Terra-Cotta Warriors, Yang-zee Valley, Shanghai and more. Only issue there is the pollution is terrible.
Japan is special, especially Kyoto. We did Japan on our own, but booked tours through Viator, then took a cruise that ended in Hong Kong.
Why did you leave out South America?
Here are my detailed reviews of trips that may work for you.

Japan and a little bit of China
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=518503&et_cid=2531924&et_rid=17221689&et_referrer=Boards

 
Singapore to Dubai
 
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=501167
 
South America
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=248878
 
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=94024
Black Sea and E. Med
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=228545
British Isles
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=221137
Transatlantic
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=221136
Australia
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=216863
W. Med  NCL Epic
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=103808
AMA Rhone River
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=103733
Southern Caribbean
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=99934
Spain, Canary Islands and Morocco
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=80907
E. Med and Adriatic, NCL Gem
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=70129
Russia, Kiev and Baltics
http://boards.cruisecritic.com/showthread.php?t=1478384
China
http://boards.cruisecritic.com/showthread.php?t=1718320
 
 
North Sea/Atl and Transatlantic
 
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=264272
 
 Portugal, the Douro River and a bit of Spain
http://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=535267

28 days in Britain and Celebrity Eclipse home
https://www.cruisecritic.com/memberreviews/memberreview.cfm?EntryID=599139

Hi,

If it's voting for which trip to take, I would vote for trips #2 and #3. I travel solo mainly but for #2 would opt out for a tour, likewise going to China.

For #3 I go solo, prefer going in the summer, ie, from mid-May to late Sept., using public transport, no rental cars, no lounging on beaches and am planning such an extended trip earmarked for 100 days max in 2020 with England and the Schengen zone as the itinerary

Focusing on certain parts of France and the breadth of Germany from the Rhine to the Oder can be easily done as long as you aware on the imposed Schengen time constraints.

Given that you live in Toronto, you can fly to Europe more easily (faster, cheaper) than the Far East. It's not unreasonable to consider future trips of 1.5-2 weeks over school breaks and the UK can be okay in summer (though who really knows, the way weather patterns are changing). Add to that, winter is a great time to be in Southeast Asia. Why not consider an extended Asian trip. Vietnam and Thailand are amazing places to visit, full of color, culture, scenic beauty, nature and history, they are easy to visit solo (I've done it more than once), and they are also cheaper than Europe. January/February is the best time of year for Thailand and southern Vietnam. Get to northern Vietnam in March on the way to Korea and Japan, neither of which I've been to.

Thank you for the responses.

I have already been to Thailand, Vietnam, Laos and Cambodia. While it would make sense distance and location wise. China is not calling me. I have thought about it a few times but it is not drawing me.

I am thinking of taking Southern France out of the first trip and flying from Barcelona to Milian. I can add this to another trip. I was thinking of Lyon and Arles so they are very doable with a trip that includes Paris.

I am thinking of South America for Jan/Feb but have to think about cost. I will be spending a great deal of money (to me) on this trip and as always plan to travel in the future.

I have been to Europe the past few summers and hope to continue to be able to do so.

Japan, Spain and Italy are the places that I am basing my trips on. They are were my travel bug is focused on for the moment..
I am willing to move others around save till another trip to hit these at the best time.

Wendy

Regarding your proposed trip to Japan and Korea: as was previously mentioned the Cherry Blossom festival in Tokyo is worth seeing, so scheduling your visit for early April would be a good choice. Both Japan and Korea are quite pretty in Springtime ... and although it can be somewhat rainy that time of year, the rain usually comes in the form of passing showers with plenty of sunshine to follow.
Personally, we always preferred to visit in the Autumn, ie in October when the changing colors of the trees made for some spectacular scenes, especially in around the city of Kyoto - one of the prettiest places in the country. We usually experienced Indian Summer weather that time of year too - making it very pleasant to be out and about.
Getting between Tokyo and Seoul is both easy and cheap if you take advantage of budget flights connecting the Tokyo city airport (Haneda) and the one in Seoul (Gimpo) rather than using the larger international airports at Narita and Incheon. Suggest booking your trip as an open jaw, flying into Narita and home from Incheon, to save a day by not having to backtrack for your return flight to Toronto.
Also, you really needn't spring for an all inclusive tour of either country. Both have modern and efficient train systems that are easily navigated by English speakers, and once established in Tokyo or Seoul there are plenty of day trip and multi-day tour providers that'll take you where you want to go at reasonable prices.