1. Hoenn Region (Pokemon). There's only one place in the entire realm of fictional worlds that I'd ever really love to go to (besides Equestria), and that would be Hoenn. I've never witnessed a setting before that's so closely bound together by its inhabitants (both humans and Pokemon alike), putting an emphasis on its surroundings and using region's natural resources to great effect. There is a genuine emotional connection between its landmarks and denizens; a kind of great respect you rarely ever find. Entire cities exist in which their foundations happen to be from a portion of a species (Pacifidlog Town is built on top of a whole reef of Corsola), or utilizing the environment around them as permanent settlements (Fortree City exclusively harbours treehouses). Hoenn also harbours some of the cutest (and deadliest) critters in all of Pokemon: Roselia, Kirlia, Torchic, Mudkip, Spheal, Luvdisc, and Clamperl, just to name a few. And it's amusing to know that it teaches us that nature can be beautiful, illustrious, and magnificent (epitomized by Pokemon like Milotic, Gorebyss, and Flygon) but the full power of its otherwise destructive force can strike fear into a lot of folks (exemplified by the likes of Kyogre, Groudon, and Rayquaza). That's the beauty of it all, and it symbolizes what life itself has to offer: a gorgeous figure with rough edges that needs refinement, but as trite as it sounds, it's the flaws that makes it so worth living.
I personally grew up with Ruby/Sapphire/Emerald, and there's not a single game I would trade in my Sapphire version for. It's housed numerous memories -- some glorious moments coupled with very angry ones, but all have been worth it. And for the record, I truly have felt like I was living in Hoenn for the longest time.
2. Foxborough, Massachusetts: I'm a big Patriots fan, and seeing as how I've never been to a live football game in person, it's something I want to get accomplished sometime in my life But eventually, seeing your team win with all those fans around you, knowing that they're cheering for the same thing as you are... it's an incredible feeling, and one I would love to keep soaking in.
3. USS Voyager (Star Trek: Voyager): When I was 10 years old I got into the sci-fi genre, and it's pretty much defined the majority of my character. Being stranded in the Delta Quadrant (that's around 75,000 light years away from Earth) may not be anyone else's idea of a good time but to be a part of Captain Janeway's crew, in a close-knit family like them... it'd be worth it, and even if in some alternate timeline where they didn't get home, I understand the fragility of life and never regret a moment of the experience. And screwing around in the holodeck -- who doesn't love that?