Packing for our sailing trip in the British Virgin Islands turned out to be a cinch. Honestly, I found, once we got back, that I had done a bit of over-packing and probably added a few unnecessary pounds to my luggage. Speaking of luggage, space was tight in our 36-foot catamaran cabin, so it would have been nice to have a flexible duffel bag. Kristi and I both brought your standard roller carry-on and they fit just fine in the cabin and bathroom closets, but anything bigger would have been trouble.  Just remember, when going to the islands: simpler is definitely better.

OK, down to brass tacks  Apart from a pair of clothes for traveling (reused on the way back of course), here are my suggestions for a trip to the BVIs:


An admirable goal would be to kiss shoes goodbye for the duration of the trip, however, we did find it useful to have some foot protection in specific applications.

Flip Flops: At $5.95, H&M’s basic flip flops did the trick for me for most days.  Whether you’re walking around a wooden dock or through hot beach sand, the flip flop reigned supreme as easy footwear to slip on and off or simply toss in the back of the dinghy.

Light Trail Shoes: Last year I ran the Tough Mudder, and made the investment in a pair of New Balance Minimus trail shoes.  They were perfect for that race, and they turned out to be perfect for climbing on rocks and reefs as we navigated the not-so-sandy shores of some of the more remote places in the British Virgin Islands.

Boat Shoes: One Word: Sperrys.  What boat would be complete without boat shoes?  OK, so to be completely honest, I didn’t end up needing my trusty Sperrys while on the trip – but they would likely be the perfect go-to option if you wanted one pair of shoes for the entire trip, airport to boat to beach.  Long live ascot, cardigans, and single malt beverages on the rocks.  Want to look like a yacht regular?  Then you want these on your trip.


The appropriate number of shorts was a tricky thing to plan for this excursion.  The critical question was (and always is): will I be in my swimsuit most days or will I be in and out of dry clothes?  Easy answer: the swimsuit will likely reign supreme.  I wore shorts about three times over the course of the entire trip.  Island culture dictates that comfort always trumps complication and the temptation to be in the water is constantly upon you (snorkeling, swimming, diving, snorkeling, and…um…snorkeling).  The only time you may want to sport some shorts is to go ashore for provisions or for a restaurant-y meal (or if you’re tired of walking around the boat in a wet swimsuit).  I packed 3 pairs and wore only one of the three.


As mentioned, I wore a swimsuit for about 95% of my waking hours while sailing the BVIs.  I packed three and basically rotated through them all week.  It worked like charm.  I picked up two of my suits from H&M and one from J Crew.  H&M has some dope styles this season and the 6” line from J Crew also fits like a glove…er, nicely cut swimsuit.


Shirts are nearly an accessory when you’re sailing the BVIs.  Again, you’ll want them for a provision run or a nicer island meal, but by and large – it’s just easier to go without them for most of the trip – though if you do, be conscious of your sunscreen application schedule.

Tank tops are a perfect option for the tropical weather, but v-necks are also a good move.  There are times where a crew neck t-shirt or polo shirt might work, but while we were there it was in the mid-high 80’s and I couldn’t bear the thought.  Easier and lighter is better for sure.


I wouldn’t recommend bringing socks for anything other than your travel days, once we got down there, the socks came off and it felt great. I’ve since decided to wear socks as little as possible.


You know the drill.  Choose wisely what will go under those bathing suits, gentlemen.  Confessional: I started wearing H&M boxer briefs years ago and never looked back.  They are perfect for any style of pants, shorts, or swimsuits.  Confessional completed.  Personal information shared.


OK, so there are a few things to consider here that will help to make your trip much more enjoyable.  I spent a bit of time thinking through this one because I really wanted to pack light but decided that there were a few essentials that would make my time on the yacht an absolute breeze (pun very intended).

Obviously, I would highly recommend a solid pair of sunglasses.  I typically sport Wayfarers, however, I decided that it wasn’t worth the risk of losing them over the boat’s port or starboard sides.  I picked up some $14 wayfarer knock-offs at Urban Outfitters and was quite happy with the selection.  If they had gone overboard, it wouldn’t have damaged my wallet or soul.

A good hat will go a long way to ensure that you’re not squinting for 8 hours a day or that your face doesn’t see an unbearable amount of sunshine.  If you can’t borrow a fedora from Jason Mraz, feel free to pick one up at any of the million shops that currently offer them.  I chose a less conspicuous cap of the baseball variety.  I wore it quite a bit.  Not sure about you, but I am part-Irish, and that means I have to care about getting too much sun.  Sure, I can tan, but I am a complete master at getting sun burnt–which leads me to my next point…

I rocked SPF 50 the entire week until the last day.  Don’t underestimate the need for sunblock and keep track of your application.  I had a fantastic week on the sea and part of the reason was that I was not nursing sunburn while still under the sun’s great and powerful might.  For five days, the four of us brought about 5 bottles of sunscreen (including Aveeno’s fantastic variety made especially for faces).  We polished off about half of the bottles – no joke.  We are all from the Northeast and we require it, so I leave you to your best judgment on this one.

The ship came equipped with flashlights, however, I brought my own halogen lamp – which turned out to be a really nice accessory. Whether you’re searching for items in your bag at night, spotting the giant and beautiful tarpon beneath the boat, or shining a light ahead while motoring ashore in you dinghy – a good flashlight is a good thing to have around.

If you have a good camera, you may want to bring it.  We left ours at home, and I regretted it.  I was afraid the salt air might do a number on the lens, however, as long as we wouldn’t leave it out in the elements, I believe it would have been fine.  The views are amazing and iPhones and Andriods don’t quite capture it the way that a nice DSLR could.

I forbid you to bring your laptop, but there is WiFi on the boat, and having our smartphones did enable us to share our pictures and memories in real time with our friends – which made the experience that much better because, in a way, we were experiencing it with our community back home.

Got it?  Here’s the final list for a perfect 5-day trip:

  • Flipflops
  • Trail shoes
  • Boat shoes
  • 1 (or 2) pairs of shorts
  • 3 pairs of swimsuits
  • 3 tank tops
  • 3 v-neck or crew neck t-shirts
  • 5 pairs of boxer briefs
  • Sunglasses
  • Hat
  • Sunscreen
  • Flashlight
  • Camera
  • Smartphone