Cruising the Caribbean Living on a Sailboat – Customs and Immigrations Dos and Don’ts

Below is a nice little article about living on a sailboat and island hopping in the Caribbean. Can’t tell how much I want that to be me in the future. I think I need to add a “Donate” button to this blog to help me on my way. What do you think? Cheers!


We cruised the Caribbean living in a sailboat for 8 years. We did a lot of island hopping in the Windward’s and Leeward’s, from Trinidad and Venezuela in the south to the Virgins in the north.

We were required to check in and out of each island. The rubber stamp business is a big one in the islands.

You should keep all your papers and passports together. When you go in and out of customs 10 to 15 times a season you quickly memorize passport numbers, boat registration numbers, etc.

Here are the dos:

Be polite, in the Caribbean there is a 6 step process before you discuss business 1) you say hello; 2) they say hello 3) you say how are you? ; 4) they respond; 5) you pause; 6) they say how can I help. I do not consider this groveling or being condescending. They are polite; you are visiting, act like a guest.

You fill out the numerous forms, and present your boat registration and passport. They will stamp your passport and inform you how long you can stay. Why is this important to them? They do not want anyone coming and taking a job away from a local. They are especially strict in Trinidad.

Here are the don’ts:

Be anything less than polite. The locals are very slow to anger, but rudeness real or perceived is a great way to test their patience. Island jails, are not the most pleasant places. I do not have first hand info on that situation. You are a guest act like one.

Make any false claim written or oral. Most every island asks if you have firearms aboard. If you do say so, they will take it and keep it at the police station until you leave. If you say you do not and they find out you are lying you will at best be fined at the worse locked up. It is not worth it.

Cruising the Caribbean while living in a sailboat is a lot of fun…do it the right way and remember…you are a guest.

Living on a sailboat Gary Pierce is the webmaster of he retired early at 49, still retired at 64. He has experience in lifestyles that are both fulfilling and frugal. It is 2009 and many are wondering if they can ever retire. Don’t give up until you check out this website. Enjoy.

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By |2016-12-31T11:57:59+00:00December 13th, 2009|Travel Tips|1 Comment

About the Author:

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty.

One Comment

  1. Ric Hilliman December 9, 2010 at 9:10 am

    We have been sailing in the Western Carib for the past 7 years between Mexico and the Bay islands of Honduras.During Huricane season we leave our boat in Guatemala on the Rio Dulce’. It is now time to move on and struggling with the decission of sailing to Panama or heading to the Eastern Carib. Any info you could share with us would be greatly appreciated. Is anchoring off the islands safe and welcomed? etc….
    Kind Regards,
    Ric Hilliman
    S/V Sea Dragon

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