Caribbean Program Island Hopping

Island Hopping in the Caribbean

Obtaining Crew for Coastal Cruising in the Caribbean

(or anywhere else)

Delivery vs. Cruising

Cruising around the Caribbean is substantially different from helping someone on a long passage. We meet boat owners, often short-handed who need help moving their yacht top or down the island chain. They would sail solo rather than inexperienced people they do not know. OPO has hundreds of Members who pay a small fee to be on our list to learn about boat owners and delivery skippers who need crew. The busy season is the spring and fall with the change of season with boats heading north or south to get out of the hurricane belt. During the winter sailing season we still have OPO Members who have time and want sail in the Caribbean.

What's Cruising All About?

The difference between helping on along non-stop delivery and joining for a week or longer cruising in the Caribbean is huge. In this situation it is totally reasonable for the owner of a boat to ask crew to help with expenses and chip in for provision, yes, fuel, perhaps, mooring and dockage fees, maybe. There is a benefit to all crew to be on a secure mooring or dockside since you do not have to worry about dragging or organizing dinghy rides to and from the boat.

Need Crew?

Need help writing up a crew request? I will work with you to decide what you think is fair. Anyone wishing to charge too much is a charter boat and we do not want any part of helping people wanting to fill their cruising kitty. Our Members join OPO to sail for free helping other people move their boats and a mutiny would occur if I started posting crew opportunities that cost money. But it is totally fine with our OPO policy to have our crew join a boat for a cruise and chip in for reasonable expenses.

Working with OPO is Easy

If you are looking for crew to join you for a Caribbean cruise it is very easy. All we need to know are a few details about you and your boat. Thinks what you would want to know if you were going to take time off and buy a place ticket to join a boat and a skipper you do not know. You would want to know a little about their sailing history, how long you have owned the boat and what shape she is in. Who else might be aboard, if you have a pet and what is the drinking or smoking policy. In addition crew would need to know exactly where and when you would like them to join you and for how long and where to depart from.

The Process

Once I have that information from you, I issue an email to our OPO Members who then respond to you with a sailing resume (see samples of recent postings here). You will not see any name or contact information listed. This is not where your posting will sit waiting for people to find it. The message board is to show non-Members the type and frequency of our opportunities.

We stress quality over quantity. The crew posting gets sent just once and does not sit on a message board getting old with you receiving emails  weeks afterwards. Everyone reads their email each day so you will hear within 24 to 48 hours of any interest and you will hear from crew right away or not at all if it does not sound like a good opportunity. If things go well, we can send out another crew request for you as your itinerary and plans change with time as you plan your next adventure. Crew you like will become friends and you will build up a new list of crew and friends to contact in the future to see if they can join you again before you ask me to send out another crew request for new crew. In time you will build up a new list of crew and will not need us anymore.

Need Help?

If you wish for us to send out a crew request for you, simply email me at or complete our crew request form. I may have to ask you a few more questions to get an effective posting and make sure it is a good opportunity our Members. I do try and pre-qualify opportunities in an effort to help our Member avoid make a mistake by joining a skipper who may not be nice to crew or may have an unsafe boat. We do realize this is a two way situation sort of like hitch hiking in the good old days where a driver has to think twice about picking up a hitchhiker, but the hitchhiker also worries about who is stopping to pick him up.