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Caribbean Travel – How to Sail Around the Caribbean for (Nearly) Free

Caribbean Travel

Caribbean Travel – Sailing in Colombia

If you are traveling around Central America or the northern part of South America, you are going to be seeing a lot the Caribbean Sea. Warm, beautifully blue ocean stretched out for as far as the eye can see… looks pretty inviting doesn’t it? Now if you’re traveling on a backpackers budget, you’re probably thinking that a sailboat ride around the Caribbean is way out of your budget but I have good news – it’s not!

A lot of backpackers to this region of the world actually do end up sailing – from Panama to Colombia or vice versa. Jason has a great resource guide on this trip and some tips on how to find and book a good boat. Unfortunately, the trip is $400+ one-way and only lasts about 3-5 days. This is one of the only ways across the Darien Gap between Panama and Colombia so a lot of people end up forking out the money. I’m going to let you in on a few secrets though that might save you a bit of money and possible help you land a much longer, more exotic trip around the Caribbean.

Caribbean Travel

Caribbean Travel – Sailing on the Coast of Colombia

The first thing to realize is that 99% of the captains approaching you for sailing trips are running “for profit” sailing routes. This is a business and the prices will reflect that. Most of the ships in the Caribbean though are not in the chartering business. Thousands of expats and retirees have made a life out of sailing these waters full time. These are the people most likely to give you a free (or cheap) lift in exchange for some help on the boat or a share of the gas and food.

So, how can you actually get the chance to sail for free around the Caribbean?

Find Your In

Caribbean Travel

Sailboat at the Dock – Photo by Jason Pratt

The difficult, but first crucial step is finding your in, into the sailing community. The sailing community is very tight knit and everyone kind of knows everyone. This is great for any couples hoping to find a free ride for two reasons – 1) It can get a bit old and boring with the same old people so new faces are usually very welcomed. 2) Once you find your in, even if its not a free ride, you will be able to quickly make other connections and find possible rides.

There a are a few ways to get in:

  • Just hang around the docks. Sailors are in general friendly folk and they love to chat about their boats. Don’t jump right in with “Can you give me a lift on your boat?” or you will come off as a bit creepy. Remember, these are their homes. Sometimes the docks will have a bulletin board where people post looking for help. You might start with washing a deck and end up with a ride.
  • Find out if there is a morning radio “show.” In a lot of sailing destinations, the ships get together every morning over their radios to share news, offer services or ask for help, and to update everyone on possible sailing and weather conditions. If you can get someone to let you use their radio, politely introduce yourself and ask if anyone is looking for some extra (unpaid) help on their boat.
  • If all else fails, google “crew wanted” and your starting point. There are multiple forums out there that list jobs (both paid and unpaid) on sailboats around the world. The only problem is that most of these ads are looking for people with sailing experience.

Be Flexible

Caribbean Travel

Caribbean Travel – Cartagena Harbor

Don’t expect to dictate the schedule and sometime you wont even get a say in the destination. Hitchhiking on sailboats is all about going will the flow. Maybe you have your eyes set on going to the Bahamas but suddenly find yourself with a better offer to sail to Aruba. Take what you can get and enjoy the journey. Its also helpful to learn the Caribbean sailing schedules. Many sailors work around the rainy seasons, hurricane season, and high tourist seasons.

Be flexible with finances as well. Some sailboat owners will be willing to take you along for just your help around the boat. Others will ask for you to contribute to gas and food. If anyone asks you to pay $100+ each/per day, they are looking to make a profit off of it… just say no thanks and keep looking.

Mention Your Skills

If you know how to sail, let everyone know! Even if you’ve only been on a sailboat once or twice, mention it. Sailing is not the easiest thing in the world and a lot of times captains (especially those sailing alone) will invite you on board just for the extra help with keeping watch or pulling in the sails.

Never been sailing before? Don’t worry; I’m sure you have some skill worth mentioning. The ones at the top of the list: cooking (you would be shocked by how many sailors can’t cook to save their lives), language skills (Spanish in the Caribbean is always welcomed), mechanic (even if you have never worked on a boat, they will teach you), and any entertainment skills (sailing can be incredible boring when you are out in the middle of the ocean – guitar players seem to be the most popular).

Caribbean Travel

Caribbean Travel – Sailing

Couple Travel Tips

  • Your best bet, when looking for a free ride, is to look for people sailing their sailboats alone. They could probably use the help and are the most likely to have a little extra space.
  • If your traveling as a couple, get use to little or no privacy. That’s part of traveling on a small boat with other people. With that being said, save any arguments until your back on land. You don’t want to be stuck on a sailboat in the middle of the ocean with someone your trying to avoid.
  • And of course, never get on a boat with anyone who you don’t feel comfortable with or how gives you a bad gut feeling. You don’t want to end up in the middle of the ocean and realize your captain is crazy.

This post brought to you by… Tourisme Montreal provides helpful information to people travelling to Montreal.

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