Touring - Crewing on Sailboat for Carribean tour?

In early January-April I'm pedaling off on my second low-budget long-distance tour. My first destination choice is (any combination of) the Carribean Islands via hitchiking on boats, but I can't find any info on people doing this before.

I'd like to work as an inexperienced crew member for my passage, and tour any islands (Cuba, Puerto Rico, Bahamas, etc.) that I can get to.

The obstacles I see are:
*Finding a boat between Charleston, SC and Ft. Lauderdale, FL in January
*Having space on any boat for my loaded Trek 520
*The potential of getting stranded on a small island and not being able to get off.

I do have enough saved up to purchase a 1-way plane ticket if necessary, but would prefer the adventure of the open sea.

Has anyone done this before, or know of someone who has? Any help or resources are much appreciated. Thank you!

A loaded 520? That's going to be a tough sell to most boat-owners, especially if you're an "inexperienced" sailor.

In any case, I would start haunting the sailing and boating forums.

As experienced sailboat ballast I can tell you with absolute certainty that no boat owner in their right mind is going to take an inexperienced landlubber offshore, especially in the winter. Pleasure craft don't have space for bikes anyway.

Learn to sail by pretending to be friends of rich people with boats and maybe then someone will take you offshore. Otherwise just pay to go to the Caribbean on a commercial vessel or take a plane. If you are really desperate you can sign up as low-paid slave on a cruise ship. They'll hire anyone and some of the ships winter in the Caribbean. They'll give you free food and some of the ships will let you take your bike (but you won't have time to ride it because they'll work you 14 hours a day and give you 15 minutes of shore time every two weeks) but you'll be able to see Caribbean islands from the ship.

In early January-April I'm pedaling off on my second low-budget long-distance tour. My first destination choice is (any combination of) the Carribean Islands via hitchiking on boats, but I can't find any info on people doing this before.

I'd like to work as an inexperienced crew member for my passage, and tour any islands (Cuba, Puerto Rico, Bahamas, etc.) that I can get to.

The obstacles I see are:
*Finding a boat between Charleston, SC and Ft. Lauderdale, FL in January
*Having space on any boat for my loaded Trek 520
*The potential of getting stranded on a small island and not being able to get off.

I do have enough saved up to purchase a 1-way plane ticket if necessary, but would prefer the adventure of the open sea.

Has anyone done this before, or know of someone who has? Any help or resources are much appreciated. Thank you!
You might enjoy reading Lynette Chiang's book, The Handsomest Man in Cuba. She hitchhiked on a sailboat with her Bike Friday.

A local guy has ridden his bike down to the SF Bay Area and gotten rides on ships. He is a young, likable, adventurous guy, kind of like Chris McCandless.

If you haven't seen it, the DVD Into the Wild is worth seeing. This guy (Chris McCandless) spent a couple of years hitching and kayaking and traveling around the US and Mexico. The movie is very well done.

There are some tightened restrictions and liability issues on ships these days. I'm not saying it is impossible, but it isn't necessarily a cakewalk either.

If you can bring something attractive to the table -- great culinary skills, or something -- you would probably have a better chance.

Boat and ship environments are not always as pleasant or romantic as they are often portrayed. You might also check out Josie Dew's books, especially Saddled at Sea and The Sun in My Eyes, which involve hitching rides aboard ships with her bike.

In the book Paddle to the Amazon, there is a description of getting a ride aboard a ship from the mouth of the Amazon River north to the U.S. There were some hitches and they had to work, and there were some insurance and red tape issues, but they got the ride, along with their canoe. Some people might help a fellow adventurer out -- there is no guarantee either way.

Kayaks can open up interesting travel opportunities that some people appreciate.

Baja is an island-like destination that some bike tourers like to visit.

I make a living by inspecting boats. I have delivered a number of boats from the river system to the coast of Florida, LA and Texas. You have a tough sell in my opinion. However, boaters are about as weird as cyclists (I am both), so it could happen for you. Not easily, but it could happen.

There was once a day when you could get paid to act as ballast or at least have your expenses covered. Those days are long over. Even a little or no experience might get you on board. Those days are long over.

Last I checked there are some people that actually are getting away with charging their crew for a ride.

It would have to be a rather large boat to carry your bike. It would probably have to be stowed below deck. I know I would not want a bike lashed to the deck of my boat and I am not sure I would want to lash my bike to a deck of a boat on the open ocean. he salt spray and occasional wave would create a lot of problems. Most people with bikes on boats use folding bikes because of the limited space.


Plus as others have said winter in the Caribbean is no place for a land lubber. Ever hear of the Christmas winds? ;)


I did some riding in Tortola. It can be hot, hot hot for bicycle riding. Roads are rough and can be very steep on some islands. And the drivers are just crazy! :) Not to mention goats, sheep, chickens, pigs, cattle all over the roads. :)

I'll chime in with some others; Very likely not gonna happen. Not with a bike. Ocean water and salt will eat your bike alive and in any case, there's really no need for a bike on those islands—they're far too small to tour on. You could walk most any of the Caribbean Islands in less than a day. Where does one stow a bike on a 30-40-50 foot boat? On deck. Not practical. I've seen folding bikes come off of a boat or two and they're pretty much solid rust.

Learn to sail. It's a means and end all unto itself. You won't miss your bike and you'll have adventures aplenty. Sailing is touring.