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Done it a few times. I live in the US and have driven through a large portion of the lower 48 on my own. I've been in LA, NYC, DFW, Miami, Houston, Kansas City, Phoenix and the San Francisco Bay Area along other places. I've also traveled internationally a bit via ship all around the Caribbean where I often have to get around on my own.
I stayed in Montego Bay Jamaica for a little over two weeks at a hostel and walked around town visiting local stores, restaurants, and beaches. At one point I walked a little over 8K to had over to a dive shop and see some of the island.
On April 1st I'm getting on a plane to Cozumel Mexico for a little over three weeks. I'm staying at a hostel while I'm there and will be walking most everywhere while I'm there. The only time I will have a guide is when I'm diving, the rest of the time I will be own my own.
You have an opportunity to get out there and explore the world a little, meet new and potentially interesting people, and have the chance to try something you may have never expected. You can either take the risk or do the things you already have and pay it safe.
BTW learning to dive could provide you with some college credit. https://www.padi.com/college-credit And you would able to say you not only did that but traveled on your own to an island in a foreign country to learn and experience a new culture.