Bahamas

While not always the most authentic experience for Americans, traveling to the Bahamas can be a great experience. I have not had the pleasure of experiencing the true towns and locals of the Bahamas (I went there on a cruise) but they are beautiful nonetheless. As a popular destination for American travelers, the Bahamas has many activities for you to do. Enjoying some Caribbean drinks by the pool or beach is a relaxing way to spend you trip. One of the best experiences to have in the Bahamas is exploring the wildlife. The scuba diving and snorkeling here is some of the best in the world. You can find creatures such as whale sharks, manta rays, dolphins, sea urchins, and so many more. With crystal clear water it'd be a shame not to go explore while you're there. 

One thing that the Bahamas does have is multiple ways to get there. While many island nations require flights (sometimes multiple on regional planes), the Bahamas has dozens of ports that bring in ships and most notably cruises. Cruise ships can be a good way to see multiple destinations and is a great option for older travelers looking to relax. Just be sure to treat the locals with respect, they don't work for the cruise ship.

Image by Fernando Jorge
Image by Jakob Owens
Image by Rinald Rolle
Image by Alix Greenman