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Help Plan My Trip to the Caribbean

June 27, 2016 11:37 am

In a few weeks, I’m heading to the Caribbean. I’ve been to a few islands down there (Bahamas, Curaçao, Grand Cayman) but have never spent an extended amount of time there, so I’m pumped! I’ve always wanted to sail around the region. I’m flying into Puerto Rico on November 2, spending a week there, and then heading to the US Virgin Islands and British Virgin Islands with a friend. After that, I don’t know. My only plan is to head as far south and east as I can get in six weeks. I have no return flight. I’m just going with the flow.

And that’s where you come in.

Since I have no itinerary, I thought you could plan my trip. Let’s turn the tables a bit. If you’ve been in the region, leave a tip in the comments and I’ll follow your suggestion. I’m open to everything else: food, activities, beaches, hikes, restaurants, you name it! I thought it would be interesting to crowdsource my entire six-week trip and do only what everyone suggests. You are the master of my trip.

My only real goal for the trip is to try to see if I can travel the region on a budget. Is it possible? Can it be done easily? How do you do it? The Caribbean is not known for being a budget travel destination, but I’m always out to prove the conventional travel wisdom wrong. As they say, where there is a will, there is a way.

Let’s find that way.

I also need some logistical help:

There’s not a lot of information online about sailing between the islands. I want to avoid flying and take boats as much as possible. If anyone knows how to get between the islands by ferry or through sailing trips, hitching on boats, crewing, or anything else, please let me know. If anyone has traveled through the region this way before, I’d love to hear about your experience and pick your brain for information.

Lastly, if you live in the region, I’d love to meet up, so leave information on how to contact you (if you want to host my friend and me, that would be super, too!).

I’ve been dreaming of a big Caribbean trip for many years. I want to settle into island life and just wing it. Maybe I’ll fall in love with one place and never leave. Maybe I’ll make it to dozens of islands. Maybe I’ll become a boat captain. Who knows!

That endless possibility is one of the reasons why I love travel.

Help Plan My Trip to the Caribbean



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