All inclusive resorts, Groupon deals, and itinerary heavy excursions may be the bane of those that call themselves “true travelers”, but there are many benefits to being “that guy”.
Traveling is exploration. It is exploring a different land, culture, food and life set up. So needless to say, exploration is watered down when you book an all inclusive resort stay in a developing nation, or a two week guided tour through Europe.
You are shuffled through your experience, told what to do where to go and what to eat. It is visual yet somewhat mindless.
However, sometimes that is okay. Traveling is also vacation. A way to get away from the stress of our daily lives, relax and regroup. Thinking is not the main agenda, so why not make your vacation as easy on yourself as possible.
If you go to Europe on a guided tour, you still get to see the sights. You still get to taste the food and talk to the people. It may not be the full immersion but at least you are able to scratch the surface of a culture other than your own.
This initial sightseeing adventure could also act as a lead in to further and deeper travels. You can make your own itinerary of places you would like to come back to. You can befriend locals who can guide you on your next visit. It is about easing yourself in to a different society, gaining knowledge without the stress of say couchsurfing for the first time, alone.
The truth is, if you are going to Jamiaca and staying in a resort, you are staying there for one reason: TO RELAX. You are okay with your Americanized bubble and you paid good money to be left alone. There is nothing wrong with this. We all need it from time to time.
One thing to remember though is that you are still in a developing country. Your usage of resources is affecting the local community, so maybe do a little research on the city (not its tourism) before you leave.
Traveling is a personal experience. How you enjoy it is for you to decide, but as always, intelligence and respect are warranted.