Sailing in the Caribbean: A Packing List.

Last year I spent 10 days in the British Virgin Islands on a chartered sailboat (you can read about that wonderful adventure here).  I’d been to the Caribbean before, and I’d been coastal sailing before, but never simultaneously.  I filled my suitcase with all the wrong things and ended up wearing the same clothes for nearly all of the 10 days – which, to be fair, isn’t really a problem, or even out of the ordinary for a sailing trip.  “Read More” to see my  list of the things I couldn’t live without, wished I had packed, and wished I’d left at home….

Couldn’t have lived without:

  • Sun block – you bring too much with you.  It’s expensive to buy once you’re there and you’ll be applying it several times a day, no matter how god your base tan is.  For my face I love Clarins, I put the cheap stuff on the rest of my body.  Go higher SPF that you think you’ll need!
  • Polarized Sunglasses – By far the best purchase I made in preparation for this trip.  Not only do they protect your eyes from the glaring sun as it reflects off the water ALL AROUND YOU, but the blues and greens lok so much more spectacular through polarized lenses.  And often you can cut through the glare and get a better view below the surface into the clear waters of the Caribbean sea.  I love, love, love these by Peppers.  They are inexpensive and extremely sturdy.  The lenses were great.  Per dollar, these are the best sunglasses I’ve ever bought.  Better than my Persols (also polarized but 10x the cost) and the lenses were far superior to any of my designer sunglasses (ie. Fendi, Gucci).  A little pricier but also a great value are Ray Bans.  I adore these folding Wayfarers!
  • Cotton/Linen Long Sleeve Button Downs – I lived in these.  They are cool and breezy, but they protect you from the sun when you’ve had enough.  They dry relatively quickly, they are comfortable, and sexy warn over a bikini.
  • Swim Suits – The other thing I lived in (during the day), my bikinis.  I brought 2 for 10 days, but wish I’d had three.  Vitamin A makes some really attractive ones, and well made too.  You can always go cheap with Old Navy. Nice price point, and decent quality.  Believe me, I’ve put them through the test!
  • Light Weight, Casual, Little Black Dress – Maybe it’s just me, but I think every woman’s packing list should include 1 little black dress no matter the destination.  I brought 2, could have managed with one.  This one from American Apparel is my go to.  It’s sexy, but oh so simple, needs no special care when washing, and manages to stay relatively wrinkle free when packed away.  I really think it looks good on every body shape and size.  If you prefer something a bit more modest, this is my other recommendation.  Loose fitting is always nice after a day of painkillers and lobster…
  • Khaki Shorts – When I did need shorts – for hiking, motorbiking, or that one time I had to ferry back to St Thomas to visit a medical clinic (long story), these were exactly what I wanted to put over my sun burned legs.  My favorites were made by J. Crew literally 17 years ago.  I don’t wear shorts much, so I’ve managed to get many many years of wear out of these.  These are the ones I will purchase when mine finally wear out.
  • Flip Flops – Probably the only shoes you will need.  I finally splurged and bought a pair of Havianas after wearing nothing but flip flops for 8 months.  I have no regrets!  I was also pleased with my Gap flip flops (r.i.p.).  They were cute and very hearty.


Wish I had packed:

  • Sarong – I learned to love these in SE Asia.  They serve a a nice cover-up, a beach towel, shawl, scarf, and probably a million other useful things.  I’m not sure how I live without them for so long.  They are cheap, although I’m sure Prada makes a lovely one, and fold up into a tiny square in your suitcase.  If I were going to be stranded on a deserted tropical island and could only have one item of clothing this would be it.  You can buy them in just about any tropical location, but if you want to arrived prepared I suggest this one, it has a nice clip which is handy.
  • Dry Bag – Thankfully one of my friend’s was had the forethought to bring one.  It was oh so handy when we anchored or moored off shore and swam in to enjoy the beach and/or beach bars.  They range in size, design, and price but I will purchase this one for my next sailing trip, simply for it’s great color options!
  • Argon Oil – For your sun dried hair, skin, and lips.  this is nature’s leave-in conditioner and deep moisturizer.  I use this one at home.  It’s a little tiny bottle of magic.

For more of my favorites, click here!

What I wish I’d left at home:

  • Anything Denim – I live in jeans at home, even in the summer, but these never left my suitcase.
  • Sweaters – i was sure I’d get chilly at night, but even on the coolest nights I never needed anything more that my button downs (see above).
  • Leggings – Another staple at home, but if you are sure you will need long pants go with something super lightweight and loose, like these.
  • Hard Soled Shoes – Can’t wear them on the boat, and won’t want to wear them on land.  Can probably get away with nothing more than a good pair of flip flops.  I even wore them on our hikes.
  • Hair Styling Tools – My hair was a lost cause, but more importantly I didn’t spend anytime thinking or caring about how it looked.  My hair was crazy out of control, and I loved it.

    Sailing Rout
    Sailing Route



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