Nine Packing Tips for a Caribbean Sailing Vacation

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!


By |2016-12-31T11:58:16-04:00October 22nd, 2014|Sailing / Boating, Travel Tips|7 Comments

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.


  1. Angelica @BkChickTravels October 22, 2014 at 10:06 am

    I need to have my bf read this – somehow he thinks he needs 4 pairs of pants at times and 3 pairs of shoes etc.! Such an overpacker, then he wears one pair of shorts.

  2. mm
    RumShopRyan October 22, 2014 at 10:40 am

    I know his pain Angelica! You just think you might go out to a nicer place or something and then then you realize that in the island you can wear super casual clothes and every little ting will be alright!

  3. Ramona October 22, 2014 at 5:25 pm

    We haven’t checked bags in years. We can fit everything that 3 people need for up to 13days so far in 3 carry on bags. We do check non essential food items for the trip, but could do with out them if need be.

    Love traveling without all the EXTRA stuff. We would overpack when we would go on cruises. All the formal wear, it was to much! Island life suits us better. Swim suits, pjs and shirts/t-shirts. Not much more is need besides snorkeling equipment and underwater camera!!

  4. Lisa November 9, 2014 at 9:23 am

    It’s also really helpful when packing to put your clothes into gallon size zip lock bags. You can flatten the air out of them and save space. It also helps to keep things dry as it’s always damp on the boat….and it helps when you stow your clothes away.
    Another good item to,pack is a good fishing type shirt with long sleeves the skin that blocks the sun they are not hot and can really save you.

  5. March 12, 2015 at 6:47 pm

    […] Rum Shop Ryan has his packing list pared down pretty good too for the islands. You can see his list here […]

  6. September 10, 2016 at 7:53 pm

    Nine Packing Tips for a Caribbean Sailing Vacation

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    Nine Packing Tips for a Caribbean Sailing Vacation

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