The prompt for day two of Bloganuary is “What is a road trip you would love to take?”

If money was no obstacle and time was on my side, my road trip would be an exploration of the Caribbean by way of a sea vessel preferably a yacht , but I am sure if bridges connected every Caribbean island, I would opt for that road trip as well.

As a person who grew up on an island that is 174 km2 (67 sq miles), I do not find road trips pleasing. While scenic routes are welcomed, sitting in a car for hours isn’t my style, but the reality is I often have to do it. Don’t get me wrong, I love the open road and specifically love it when I accidentally find breathtaking landscape and whimsical backdrops on my way to my mundane existence.

I believe there are many hidden gems in this part of the world that we seldom spoke about or know unless you are from the Caribbean, work on a vessel, or are privileged enough to experience some lesser-known locations.

My yacht road trip would start in Florida. Then, I would sail into the Gulf of Mexico and head towards the Caribbean Sea, touching all the islands within this area. On this road trip, special attention will be lavished upon smaller islands that are less popular. Islands such as Bonaire, Isla La Orchilla, Tortuga, Mustique, Nevis, Saba, Bequia, and many other small countries. It would be a wonderful experience to blog about the food, culture, people, things to do, and all my sailing experiences in the Caribbean Sea. I would spend at least 3 to 5 days on each island, and I have determined this would be a 2-year trip. While I know this  is over the top for a road trip, it just feels like living the life of a modern-day Robinson Crusoe is much better than sitting in an office from monday to friday.

After my Caribbean adventure, the other road trips I would love to take would be to drive from California to Alaska or from California to Argentina. California to Alaska would be the easiest of these three road trip ideas, followed closely by the Caribbean exploration. An interesting fact about a road trip to Argentina from California would be that currently, the length of that trip would be about 9 or 15 months. So technically, it would be the same amount of time as visiting most of the smaller Caribbean islands.

For those who consider my sailing trip as a worthy endeavor, but don’t want to downgrade their lifestyle, perhaps a world cruise would be more your style. Before I end this, I wanted to say that traveling the Caribbean is possible if you plan and save for it. Occasionally when my mind started wandering, I would google up information about this trip, and one place where I find the best insight is on Yachting World’s website. One of my favorite informative pieces is “Caribbean sailing: Top tips from two years of exploring this cruising paradise.”

So, does anyone out there think this dream is unobtainable, or do you think I can make this road trip a possibility?