I've been almost everywhere within America itself... so I'll go ahead and list 5 cities that I actually haven't been to, and then the 5 that I most want/need to plan a trip back to, so that I can actually comment as if I've "been there" (either too long, or never actually explored the city).
Never Been:
1. Duluth (I get the feeling I'd like the North Shore in general, really)
2. Utqiagvik (was today years old when I found out name had been changed from Barrow in 2016. Also, want to watch a HS game on the blue turf on the Arctic Ocean. Probably one of the most unique settings in all of sports IMO.)
https://www.google.com/maps/place/Ba...4d-156.6630337)
3. Pensacola (Most urbane/historic place I've never been in FL. Want to do a driving trip up the Emerald Coast)
4. Lawrence (I have no recollection of stopping here ever. Also, I've only seen the airport in KC. Would want to do a trip when it's and hit the Naismith Center for a game, along with College Basketball Experience in KC)
5. Ithaca (This just strikes me as a really neat and beautiful college town... and I've never actually been even though I grew up like 4ish hours from it. Would love to do a fall weekend in this vicinity, perhaps combined with some time back home in Cleveland along with maybe a couple days in Toronto.)
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Been, but need to get back to:
1. New York City (Obviously. And, I feel like I've never actually fully experienced this. I would like at least 3 full days of wandering around here and 1 additional day in the Hudson Valley.)
2. Cincinnati (I lived in Ohio for 18 years. Yet, I can only remember 3 days in my life I've spent in Cincy. One in Great American Ballpark, one in the former Cinergy Field, and one time viewing the city from above in Devou Park in 2015, most recently. Would like very much to at least perhaps spent a full day exploring here with an overnight when passing through between Florida and Cleveland.)
3. Los Angeles (Including this one and NY, I almost feel basic doing so, but again, I want to have a full LA experience. I've spent time in various parts of this area, but would probably want to spent at least one full day exploring Downtown, one day exploring Koreatown/MacArthur Park, and one hybrid day (perhaps a trip out to Pasadena, to feel complete).
4. Miami (this one seems odd to include. But, while I was just there in June, I feel like I want to form more of a relationship with this "Alpha Global City" that's in my backyard basically. My goal is to eventually have some form of business or otherwise relationship with the city and have making a 3.5 hr. drive here be something I get to do at least 4-5 times a year, if not more, given that I don't know when I'll be able to move, and this can at least do a decent job of giving me a more urban/global city fix)
5. Vancouver (Even though this isn't an American city per se, I feel like it fits here. My last visit here wasn't that long ago... but I loved it. I'd like to rent an AirBNB for a week here during, well anytime really, and I feel like this is one of those places where I could visit almost without an agenda and just sort of enjoy it's pleasantness.)
10 Elsewhere in North America:
1. Dawson City, YT: A classic, rugged, authentic place, where I would like to take in the town vibe, and perhaps also visit in winter if possible to take in the Aurora and cross that off the list.
2. St. John's, NL: This looks like an absolutely beautiful city, a place that would be considered one of the most gorgeous towns in Scotland or on the Ring of Kerry, except that it's on our side of the pond. I bet it's so removed too that it just has a really, REALLY cool vibe. Check this photo:
https://www.google.com/search?q=st.+...NHwwjZgA6v93DM Similar to Vancouver.. a place I could be perfectly happy just having a week with no agenda and taking life there as it comes.
3. Guanajuato: This place looks absolutely gorgeous, perhaps moreso than any city in North America, and perhaps as photogenic almost as any place in the world. Again, I could be content just eating, and being here. The fact that it isn't that big isn't really relevant to me:
https://www.google.com/search?q=guan...Q5WiH6Pl_Bq_dM
4. Havana: This is really high on my list as city tourism goes. Just 300 miles from me, too. This is a place that I think would just be really compelling to visit, mainly just for a weekend is fine, but would like to do so in the next couple years if at all possible.
5. Merida: Similarly high to Havana-not the easiest to get to.. but a beautiful looking town, relatively safe and calm, and surrounded by a plurality of the most impressive Mayan sites. A global hub for archaeology. I may fly to Cancun and spend a night in the main tourist area there to add a beach element into the visit even though that wouldn't be primary goal.
6. Santo Domingo: I've heard mixed reviews about this one. On one hand, it's perhaps the "Capital of the Caribbean" from a world city standpoint at this time. OTOH, I've heard mixed reviews about aesthetics, walkability outside core, and it's appeal for visitors. That said, I would like to complete the trifecta of SJ/SD/HAV and hit the Caribbean Big 3, so I could see doing a few days in DR, or perhaps even stopping over on a cruise ship.
7. Puebla: I debated putting Panama City or Guadalajara here instead, but decided in favor of putting this one here because of how much I fell in love Mexico City perhaps as much as any urban destination on the planet, and the proximity Puebla has to this, and ecotourism opportunities (mountains). It also just generally looks like a cool city, and you get a two for one on the visit with Cholula, too.
8. Port-Au-Prince: This one is perhaps a controversial site. I mean it from the fact that visiting and observing the urban landscape, but also the desperate circumstances here is something to be aware of as a citizen of this continent-but perhaps also to help with. It looks like a visually captivating place, that's for sure:
https://www.google.com/search?q=port...bsgqIZ830RQLyM
9. Granada, Nicaragua:
https://www.google.com/maps/place/Gr...!4d-85.9560005
This place looks magnificent both as a city center with old world charm, and also as an ecotourism destination, with it being set right on the largest lake in Central America (3000 sqmi) and less than 25 km removed from the still active Masaya Volcano. Also, knocks off Nicaragua, one of the remaining countries I haven't been to in Central America, and is only a few hours removed from the Costa Rican rainforest which I could combine a visit to almost by driving.
10. St. George's, Bermuda: Does this count as North America? Regardless, I would like to visit.
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