How to Pack for a Sailing Adventure


My husband, Drew, and I have the extreme privilege of leading marriage retreats aboard a 54 foot catamaran in the Caribbean for a week. One of the questions I’m often asked is, “How should I pack for such an adventure?” I figured I’d put all the answers here in an easy accessible location.

sailing couple

First, you must know that sailing feels a lot like glamping, aka glamorous-camping.  The clothing attire reflects that. Cute and comfortable is my go-to. Cute, because sailing feels like an activity for cute attire.  Comfortable, because you’re floating on a moving object in the ocean.

A bathing suit will be your uniform for the week. We spend plenty of time in the water and enjoying the sun  We ask that a tankini or one piece style bathing suits be worn. They lend themselves best to getting in and out of the dinghy {small transporting boat} and moving aboard close quarters on the boat. PACK 2-3  {I pack 4}

Bathing Suit Cover Ups aren’t necessary, but nice to have when you’ve had enough sun or are transitioning from sea to land. {One is plenty, I usually pack 2}

We are known to hike while on land.  Be sure to include a comfortable pair of sneakers  or Tevas/Chacos, whatever you prefer.

5 short sleeve  t-shirts will be plenty for the week.  I also include 2 long sleeve “water shirts” that dry quickly when I’ve had enough sun, but I don’t want to be hot.

4-5 pair of shorts get me through the week. I usually pack light weight, cotton, elastic waist, running-type shorts.  Remember comfort is the name of the game. I could easily get away with 3 pair since I’m really in my suit most often and shorts may be taken off, but the t-shirt stays on.

how to dress dress

2 cotton a-line dresses are what I pack for the 2 evenings we  head off the boat for dinner. I always wear a pair of biking shorts underneath my dress.  Let me tell you about the one time I forgot and, as I attempted to climb aboard the dinghy, the wind caught my dress and gave the whole crew quite the view!

When it comes to shoes, less is more.  I include a pair of flip flops, something that’s easy to get in and out of without using hands to assist.  Shoes aren’t typically worn on the boat. It helps to keep the boat clean and allows you to walk more easily while underway. I also include a water shoe of sorts for times when my feet will get wet but I need my shoes to stay on. Finally I pack a pair of sneakers.

One pair of pajamas, if you need them at all.  It is a marriage retreat, after all, and you have your own private state room and bathroom.

Just in case there is a cool evening, I wear a pair of leggings with a layering piece on top through the airport  The coat I wear is a lightweight rain coat, so I have it in case of rain o note boat. The raincoat is not necessary AT ALL.  I just really like mine, it a sailing brand and I feel cool when I wear it. Did I just admit that?

When it comes to toiletries and make-up, I also pack light!  There will be days it feels silly to have make-up on, it will only be coming off as soon as you get in the water.  Just pack your essentials. Of course, deodorant, shampoo and conditioner should come along, all the things to keep you fresh while sharing close quarters.


A few things I find helpful in the “toiletry” department you may not naturally think of: baby wipes, Poo-pourri, band-aids, SUNSCREEN, I can’t emphasis that one enough.

A hat ,headband {band style} and sunglasses help to shade from the elements. However, keep in mind on a moving boat things fly off easily. Plan accordingly with hat style. And glasses cords.

I bundle all those items into a soft sided carry on size piece of luggage.  There is very limited storage on the boat. Having a suitcase that is able to  collapse or be made smaller is best.

sail backpack
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