How To Pack For A 2 Week Sailing Trip in the Caribbean? Clothing Check List

How To Pack For A 2 Week Sailing Trip in the Caribbean? Clothing Check List

Martinique to St. Thomas. Four hundred and something nautical miles, 11 islands. 5 Hailing Countries and Cultures. Possible sunshine, thunderstorms, bad seas, above sea level, below sea level. How the HECK do you pack for all of that?! And if you have the photography / film bug -- how do you bring your gear to capture all of these amazing places, people and culture?! Today we're diving into the Clothing element of this equation.

What You Need To Bring Vs. What You THINK You Need To Bring

Whoa, take a breath. What's funny is I planned and photographed what I thought I needed for this trip, and I can say I have MUCH different thoughts after the fact around what I actually used and needed. Let's break it down:

So here was my initial lay out of everything I thought I needed. Red x's are the aftermath realization of what I really didn't need.

So here was my initial lay out of everything I thought I needed. Red x's are the aftermath realization of what I really didn't need.

So we'll start with clothes first:

  1. White tank top: This piece was a STAPLE for looking fresh and chic when traveling through the more high end chic islands like Martinque, Iles des Saintes, and Saba. I paired this with my...

  2. Airy Gaucho Style High Waisted (2 Pairs): I LIVED and sailed in these pants 80% of the time. For real. SO comfy, they breathe super easy, look sexy AF with a bikini top, they cover your low belly so they're perfect for being flattering AND playing Farkle and drinking Rosé all day, uninhibited.

Breezy High Waisted Gauchos with a bikini top. Sexy, covers the low belly, breathable, pairs perfectly with Rosé and hours of Farkle underway.

Breezy High Waisted Gauchos with a bikini top. Sexy, covers the low belly, breathable, pairs perfectly with Rosé and hours of Farkle underway.

What To Pack For A Sailing Trip #3. $10 H&M Tennis Shoes

Okay first things first, I f$%ing hate flip flops. I find I'm constantly flexing to hold flip flops with my toes, I just HATE flip flops. I brought my pair of rainbows and I can say I pretty much NEVER wore them. I loved my cheapy little tennis shoes. They looked chic AF with my gaucho boho pants and my white tank top, they were versible, cleaned up easy, my feet could stay comfortable walking 6 hours on an island or hiking a volcano, and the best part is if something happened to them, it didn't matter- they're cheap tennies. So these guys were lifesavers for me. 

What To Pack For A Sailing Trip #4: One pair of shorts:

Alright, this is actually what I didn't bring ("Oh, it'll be easy - we'll swing into a little boutique and get a keep sake!" was the thinking...) aaaand we spent hours on Martinique trying to find a decent pair (apparently beautiful french women don't have a lot of junk in the trunk like some of us #bigbootyhoes #ownit -- SO -- it's imperative you bring your own pair. I'd suggest linen, airy, breezy, chic.

What To Pack For A Sailing Trip #5. Headbands (2)

This was one of my favorite accessories-- I brought 3 of them, and really only used 1 $10 black and white polka dot adjustable headband with wire to make a bow that keeps it's shape from Walmart... Best purchase ever, and I accumulated another glorious hand dyed ultramarine silk scarf from Maogany in Terre de Haut of Iles des Saintes - such a beautiful, special, FUNCTIONAL keepsake! #sohautrightnow So If you've got long hair, or hair in general actually, sailing is super windy so having something to keep your hair out of your eyes, mouth, nose, existence - is essential. And mega bonus: What a great way to spruce up any look with a sweet headband!

What To Pack For A Sailing Trip #6: Bikinis (3)

And the key here -- get different cuts -- this keeps your tan lines interesting and blended, but also if you do a snorkel sesh on day you can swap them out between drinking-bikinis, sailing bikinis, underwater bikinis... Three was definitely a perfect amount, too.

What To Pack For A Sailing Trip #7: Sports Bra (2)

So I brought one high-intensity sports bra that holds my iPhone in place (Lululemon) if I'm doing jumping or inverted moves, and one lower intensity sports bra that also doubled as a bikini-esque top, which I wore sometimes with my high waisted boho pants while sailing or doing other leisurely-yachting activities (do you like how I just came up with that?)

What To Pack For A Sailing Trip #8: One dress-it-up-or-down dress

Mine was my airy cotton maxi dress. Perfect for our night out at Queens Garden, a nice dinner on the boat, or really any moment you want to be a little cleaner. Bonus Points: Aim for three articles of clothing: Dress, Left shoe, right shoe. You can thank me later.

What To Pack For A Sailing Trip #9: Patagonia Fleece Pull-Over

This one was SO important. You wouldn't think bringing a fleece would make ANY sense to the Caribbean, but your sun kissed skin's going to be more sensitive with that evening temperature, and combine that with SAILING wind, and oh yeah, it's going get chilly. Bring a fleece, it's a life saver. 

What To Pack For A Sailing Trip #10: One Pair Polarized High Quality Sunnies WITH Croakies / Nerdy-Sunglasses-Necklace

THIS is a must, I actually brought 3 pairs of sunnies, 1 of them actually being legit, the other two were mostly for photo ops (Your girl's just being honest!  I'm a photographer and style people for a living... Like these images on the blog? So YEAH, I stage!) - And other than my super epic shots on the fly bridge with my shitty sunnies, I was wearing my Maui Jim's 95% of the time. And you can't skimp on the polarization -- you need that First Class good good because that light reflecting off the waves is no joke, and those proper polarized lenses make a night and day difference.

What To Pack For A Sailing Trip #11: Linen Breathable 3/4 Length Sleeve Blouse (Preferably From Maogany)

So I brought two old crew shirts that are those wicking sun shirts, you know, those ones marketed as "sun shirts" - UV Blocking, long sleeve, blah blah blah, well those MFers don't breathe for $#!t, literally the last thing I want to put on my body when I'm sunburned, slathered in stupid sun screen, and then I'm gonna put on some super lame sun shirt that turns my belly and space between my boobies into a damn green house. No thank you. So instead of these suffocating sun shirts, grab you a chic AF linen or cotton airy breezy longer sleeved blouse. You can hike volcanoes feeling the breeze, protect those sweet shoulders from that Caribbean sun, look cute AF and not a tourist at a Six Flags waterpark. You're welcome.

What To Pack For A Sailing Trip #12: Your Own Mask And Snorkel

Okay so this one may be totally irrelevant for your travels, but after working on boats for almost half a decade I have my snorkel, mask and fins situation pretty dialed in #snorkelsnob -- and knowing we were coming onto a non-charter boat, it was taking a gamble on banking that there'd be snorkel gear on that boat. So I lugged my big obnoxious fins which took up about 25% of my bag, but I tell you what -- we got on that boat, looked everywhere for left over snorkel gear and there was ONE water-leaking mask and ONE pair of terrible blister-causing fins Laura and Danny were having to split during the trip, so even those my mask and fins were a total pain in the ass, I am truly happy I brought them for when I free dove and stumbled across a VERY SPECIAL GROUP OF ANIMALS (I'm not going to give it away, you're just going to have to stay tuned! #spoilalert ), there's no way I would have been able to track with them and been so fluid in my underwater filming without my proper mask and fins.

What To Pack For A Sailing Trip #13: Rainproof Jacket

Better to have it and not need it than need it and not have it.

I brought my lightweight rain jacket just in case we would encounter stormy seas or thunderstorms but lucky for us I didn't have to bust this bad boy out for any foul weather. But I'm still thankful I brought it.

What I DIDN'T Need To Bring:

  1. Yoga Leggings (1)

    So I wasn't sure if this would be necessary and it turns out, they weren't. I ended up doing all my work outs in shorts and a bikini top or sports bra. I wore them sometimes only when I was super cold sailing during a night shift but I could have just doubled up with blankies, too. So for space sake, I say go without.

  2. Stupid Boner-Killing Titty-Sweating UV Blocking Shirts.

    Refer to #11 above.

  3. Three pairs of fancy sunglasses.

    Could have gone without second fancy pair for looks.


Super Easy Packing Guide For Your Caribbean Sailing Trip:

1. White Tank Top

2. Gaucho Style Breezy Boho Pants (2)

3. Cheap Tennis Shoes

4. One Pair of (Non-Denim) Shorts

5. Headbands

6. Bikinis (3)

7. Sports Bras (2)

8. Dress It Up or Down Dress (1)

9. Patagonia Fleece Pull Over

10. High Quality Sunnies (Polarized! Don't Skimp!)

11. 3/4 Length Sleeve Blouse

12. Mask and Snorkel (If Applicable)

13. Rainproof Jacket (Lightweight)

 Have you ever done any sailing trips? What were your life-saving staples for your trip? Add it to the comments below!