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Deciding what islands to explore during your sailing vacation is the hard part. Melody Delgado at has plenty of suggestions to help you decide on the perfect vacation. Once your sail charter is booked, the next decision is what to take with you. Nothing can be easier than packing for a sailing vacation in the Caribbean.

Unfortunately, most first time sailing vacationers pack too much! With plenty of sun and sea, life on the Islands is very casual, and you really need very little. The following nine tips should help avoid over packing and ensure you have a great sailing vacation.

The first thing to keep in mind is that storage space on a sailing vessel is usually limited and not conducive to hard-sided suitcases.

Thus, strong duffel bags work best because they can be folded up when not in use. In addition, their size limits what you can bring. Most importantly, a duffel bag fits in the overhead bin of an airplane.

Too often, I have seen family and friends check luggage for an island sailing adventure only to have it not arrive. Islanders are laid back. As one friendly airline agent on Beef Island, BVI replied to my sister’s inquiry about her lost luggage, “If it’s not here, Mon, it’s somewhere else.” That somewhere else happened to be a round trip flight from Puerto Rico to Martinique and back before finally ending up back at her home in Wisconsin three weeks later. Thus, the first tip is to use a duffel bag and carry it on the plane! This avoids the stress of dealing with lost luggage.

To read the rest of the packing tips click here – Nine Packing Tips for a Caribbean Sailing Vacation.

What I’m Packing

I’m notorious for over packing, but I’m getting better. Here’s a list of what I’m packing for next week’s sailing trip through the BVI.

  • 3 pairs of boardshorts
  • Camera gear
  • 5 tank-tops
  • 2 pairs of shorts
  • 1 pair of flip flops
  • 1 pair of Keen hiking shoes
  • 4 hats – Mount Gay, No Shoes Radio, Castaway, saggy sun hat. (excessive I know, but they make for good photos too!)
  • 4 t-shirts
  • 1 button down casual shirt
  • Underwear

This will all fit in one duffle bag, one waterproof backpack…done and done.

Am I forgetting anything, probably.

Have to save some room for extra shirts and hats purchased on island for the return trip!


P.S. – Leaving soon? These recommended links below will help you save money and book your trip:

We use all the companies listed here or on the resource page. By booking through these links, the small commission we earn helps us bring you more Caribbean content so that you can save money and have a better island vacation. Crystal and I greatly appreciate any support!

About the Author: RumShopRyan

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. To learn more, visit our About Us Page.