Let's start with the US:
Hawaii
San Diego
South Dakota
Pacific Coast Hwy
Arizona
I expect to finish these up by the early part of the next decade. South Dakota is the only state that I have visited as a child but not as an adult. The one that I am looking forward to the most is probably the Pacific Coast Hwy because it would involve a lot more than that. I'd fly into LAX then take 395 up to Yosemite NP. I'll pass through Lone Pine and Mammoth Lakes before I hit Yosemite. From there, I'll cut west to Santa Cruz and race a half mary then take the PCH back down to LA, passing through Big Sur and Monterrey. Pretty awesome.
North and Central America:
Newfoundland
Cancun
Cabo San Lucas
Costa Rica
Newfoundland will be tough logistically and will probably require 3 flights but it's necessary for the 10 Canadian provinces goal and it is a beautiful area too. The rest won't be terribly expensive or time consuming. Atlanta has reasonably priced direct flights to both Cancun and Costa Rica, which will both be great winter trips. Cabo will be a bit longer flight but shouldn't break the bank. I plan to stick to the tourist areas and thus will not have to rent a car.
South America
Ecuador
Chile
Argentina
Brazil
Again, the flights here are not too bad and there will be very little jet lag because there will be only a 1-2 hour time zone difference. In Brazil, I'll stick to Rio, which is amazingly beautiful. Chile and Argentina will be done on 1 trip. Fly to Santiago and take a bus over the Andes to Argentina. No rental car for either trip. Ecuador could be a little dicey because attractions are spread out but it would be a nice summer trip. Because of the high elevation, it's 70 degrees year round.
Asia:
Israel
Japan
Hong Kong
Philippines
Here, it will be pricey and very time consuming with considerable jet lag. For Israel, I'd want to go with a Marathon Tours group for Jerusalem. In Japan, Tokyo is a must see but the race is nearly impossible to get into. I may opt for Osaka for the race. Hong Kong and the Philippines could be done on one trip.
Africa:
Cape Town
Durban
Kilimanjaro (Tanzania)
Diani Beach (Kenya)
Accra (Ghana)
Tangiers (Morocco)
Some of my readers may be surprised by a couple of these but I've done my research and all of them could be very enjoyable trips. Morocco would be a 1 day visit across the Strait of Gibraltar from Spain. Algeria really looks like a beautiful country but visa restrictions are tight and attractions are spread out. There is a good race near Kilimanjaro, which would definitely be combined with a trip to the Kenyan beach. There's no surf there but it has the whitest sand and clearest water that I have ever seen on YouTube. As is the case in Durban, you can score a 4 star hotel on the beach for a 2 star price and many hotels offer free airport shuttles as well. Why Ghana? Very nice beaches in a country that is a stable democracy. Many African-Americans trace their ancestry back from there and the slave castles can also be toured. That would be gripping and I do expect to cry. Flights will be costly but I can save on lodging and not having to rent a car.
Europe:
Spain
Austria
Switzerland
Germany
Poland
Scotland
Croatia
Lots to see here. I definitely want to get in touch with my roots in Scotland, Germany and Poland. Croatia looks beautiful as well. Austria and Switzerland as well as Germany and Poland can be done in one trip. Spain is probably the one that I'd most want to see however with its beaches and excellent surf year round. My two race picks are Glasgow and Berlin.
Australia:
Melbourne
Sydney
Gold Coast
Great Ocean Road
This is the toughest logistically and likely the most expensive but man, the scenery is AWESOME!. I'd probably race in Melbourne and drive the Great Ocean Road then fly up to Gold Coast for some surfing on the same trip. Sydney would require a 2nd trip.
Race goals:
I want 2 in each continent in different countries. For example, I'd like to race in both Durban and Cape Town but that's only one African country. That's where Kilimanjaro comes in to play. Since Australia is only one country, I only need to race in 2 different states (Victoria and NSW or Queensland)
As I've said earlier, a country must be peaceful, stable and not terribly oppressive for me to consider a visit. Both Cuba and Iran have some amazing scenery with extremely friendly people but until the current political regimes are toppled, both are no-go zones. South Africa would not be on my list either if apartheid was still in place. I figure that I can afford to take one such trip per year with my current finances. I could be well into my 60s yet still have places that I want to see. Very few people have traveled as much as I have. I've read that the average American visits only 12 states in their lifetime. Get out and be more adventurous!
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