Mexico is OK as long as you stick to the tourist areas. It isn’t a place to rent a car and drive around and look at things.
I can see the appeal of this for you. Being stuck and here’s your way for a change of scenery. Are there things you want to do in Canada? If that was part of the trip then that would be fun. I don’t have a dog but I can see what that is a big consideration. I would also want a back up plan if for some reason I got stuck, this would be my biggest worry.
London – Cancun — Orlando – London appears to be a thing and is much cheaper than the Toronto option.
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I’m not sure you would have to stay in Canada for the 14 days. Entry requirements have shifted for international travel depending upon vaccine status as negative testing prior to arrival here. Air Canada and WestJet are resuming direct flights to UK to broader CDN cities - Toronto, Montreal and Ottawa and Halifax. Halifax is not an extremely long flight and your exchange to Cdn dollars would make it a less expensive pit stop.
If you could shorten the 14 day requirement prior to WDW, I would say it is worth it for your mental health. It’s been a long go since March 2020.
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A resort in Cancun is it’s own bubble. You go from the airport to the resort and back, no need for any hassle. Also, Mexico’s tourism infrastructure is amazing. And everyone you would meet speaks English.
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This is from Cozumel, September 21st 2018 (one of my favorite vacation days ever). Note the weather. The water is also warm.
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Some additional notes about the rules.
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Can I fly direct from the UK to the US? No. Duh. That’s the whole point of this. But — and this is important — I can’t fly to the US from anywhere if I’ve been in the UK within the last 14 days. That’s why I have to stay in Canada for 14 days. (This, by the way, is fricken ridiculous and unjustifiable and why I hate you people.)
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Can I fly from the UK to Canada (via France)? Yes, and — in the COVID scheme of things — relatively unencumbered. But I would have to stay in Canada for 14 days because of the US rules.
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Can I fly from Canada to the US? Yes, relatively easily.
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Can I fly from the US to the UK? Yes, relatively easily.
What about the Mexico option?
- Can I fly from the UK to Mexico (via France)? Yes. But this introduces a new complication. I cannot then fly back to the UK from the US unless I stay in the US for (at least) ten days. Otherwise I have to quarantine in the UK at a government hotel at enormous expense and horror. This may be the dealbreaker for Mexico.
I’m more interested in going to Canada than I am Mexico. It’s on the UK’s “green list”, everyone speaks English, Toronto is a city with stuff to do. Mexico is on the UK’s “red list”, I’m really not into hot, beach holidays.
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It sounds to me like you really want to do this, which is all that matters. If you can figure out what to do with Calvin while you’re gone, I say go for it.
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Sarah says she can look after Calvin. I’m getting really serious about this now. I’ve found an ideal hotel in Toronto. And I’ve found a very nice flight price for the transatlantic sectors.
I hope people will get on board with this and offer their support and help. I may start a new thread (lol).
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I say go for it! Yes, WDW is different (isn’t everywhere different now?) but I don’t think that’s a reason not to go. After living in a pandemic for now 18 months, I am all about seizing the day. Find what brings you joy and go for it!
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Oh my good lord! No hesitation. YES, you should do it!! It will be amazing!
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If you think the joy WDW would bring you would outweigh your guilt for leaving Calvin then do it. I was honestly completely shocked you were so quickly over the cruise and ready to go home. After finally having a long and proper holiday I figured you would want to extend it as long as possible. This is 3 times that long so I’m surprised you are even considering it.
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I think it was probably because it wasn’t WDW, so it was never the vacation he wanted. Had he been in WDW, he would not have been in a hurry to get home. Is that accurate @sanstitre_has_left_the_building?
Matt, this plan sounds completely doable as long as you have Calvin taken care of. If I didn’t have a family here, plus a dog, and a job I have to be in person for, I would totally work remotely while vacationing for weeks at a time. I say do it! Toronto is a wonderful city, I hope to get back there eventually. Go and have a great time, and then an even better time in WDW. Maybe it will finally scratch that itch that no other vacation will scratch.
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Do it!
Niagara Falls is only 1.5 hours away from Toronto with lots of things to see and do.
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I’m selfish and want him in Orlando on my birthday. I bribed him with loads of epic things. 
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Totally get it. I think he should just move to the US personally. Calvin can come too and we’ll all have a party.
Btw are you the sparkly shoes Julia I went on a fireworks cruise with?
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I am!
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I finally put it together 
. Now I’m sat here wondering how many others of you I may have met lol
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