I Go North!
Chaguaramas, Trinidad and Tobago

After contemplating the myriad exciting paths before me, I've decided to join the crew of the Odessa and sail north into the heart of the Caribbean.

I was really torn between heading south with Stephan or north into the island chain with Bill (and Andy). Ultimately, some of the deciding factors for me revolved around the uncertainty of my sea legs (I would have been hooking out into the middle of the ocean with Stephan for three weeks without seeing land); the feeling that I burned past this region of the world (completely skipping over a dozen countries and territories); the opportunity to travel relatively cheaply in one of the most expensive parts of the world; as well as many of the social aspects of meeting new people and exploring the yachtie subculture.

Given the right port/marina/harbor, It's actually really pretty easy to get on one of these boats (even with zero saltwater experience). Look for the big boats (15–20 meters), and put on a smile. It's almost like picking up someone in a bar… You chat for a bit, size each other up, and before you know it you're offered a place to sleep!

The Odessa

The Odessa is a 20 meter (65 foot) MacGregor 65 sailboat, captained by William (Bill) Penistan. The racing boat is long and narrow, which is definitely reflected on the inside of the boat (for example, there isn't a shower). Andy has a couple of photos of the vessel up on his site.

We're pushing hard to try and get the Odessa in the water. Bill and Jakob have been dry-docked for a month now, and there's still a whole mess of repair work to be done. Andy and I have stepped into project management mode, putting up a list of priority action items that need to be accomplished before we can get back into the water.

There seems to be an overwhelming desire for captains to work on their boats—there's always something important to fix. With so many opportunities to sail north, Andy and I don't have any intention on waiting around for month to get into the water, so we're trying to get everyone's passport stamped for a Monday departure (just to ensure we get of out Tobago).

I believe it's Bill's intention to hit every island he can on the way up to the British Virgin Islands, over a three month span of time. Afterward, he'll be sailing the boat up north to the New York area.

I'm not sure how long I'll be on the Odessa, but it looks like crewing on these boats is a great way to move between islands and continents on the cheap! This is going to be interesting.

Explore photos from Trinidad and Tobago

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