Photo by Muffy Aldrich
The Modern Guide to The Thing Before Preppy

Monday, January 22, 2018

What should I wear, do, and bring when invited to go sailing or boating?

Photos by Salt Water New England
 What should I wear, bring, and know when invited to go sailing?

Know before:

  • When and where to meet.
  • The name of the boat.
  • Who will bring the food.
  • How many people are with you.  Do not show up with more people than were invited.


No matter the weather predicted, no matter what the weather on land, prepare for:
  • Cold, windy rain and
  • Blazing, hot, bright sun.
Don't wear skirts.  There can be a some climbing up and down levels.

For shoes, look at boat shoes or sneakers.  Shoes with black soles are frowned upon as they can mark the deck.  Don't wear heels or wedges.
"We always ask our guests to bring a second set of shoes for Tigris so that they don't bring any grit aboard from ashore. We keep a basket at the point of entry." (Gavin)

Don't bring messy foods, such as ice cream or chocolate.

Prepare for cold, windy rain...

...and bright sun. 

Always wear shoes.

Wear clothes in which you can climb. Skirts and certain shoes should be avoided.

 "One of the few 'passwords of the day' that I remember from camp in Maine is this: 'Wool keeps you warm when you're wet.'" (John G)
"Try not to bring anything you would be devastated to loose when it falls overboard." (Katy)

Non-marking Soles

Good shoes.  Good ice.


  • Water
  • Ice
  • Sunscreen (One person suggested Badger Sunscreen)
  • Sunglasses
  • Hat for shade
  • Money to offer to pay for gas 
  • Food that is not messy
"If you're bringing snacks on the boat, it can be helpful if they're not super crumby, especially if children are on board. Crumbs and dropped chips, crackers, etc. can make a mess under the boat's decking. Lifts and hoses, etc. aren't always available to make cleanup easier." (Comment)
"What not to bring: beer (or soda) in bottles; a large host/hostess gift, space is at a premium on a boat; anything that can't be placed in a puddle - like a fancy leather bag - your transport to/fro could be leaky; food that needs a lot of prep." (Patsy)
Depending on your schedule, you may easily have some downtime.  This could be unexpected, such as if the wind dies down to nothing, or this could be planned, such as if you are waiting at the windward mark or start for some races. Be ready to pitch in, or even stay out of the way.
"Recommend Bonine over Dramamine as less likely to cause sleepiness for those in need of seasickness meds. Remember to take them before you get on board. Also bare feet are not good on boats with a lot of deck hardware as these trip hazards can cause seriously sore stubbed toes. Deck shoes are best." (Hearthstone Farms
"Whatever your bring, make sure it all fits in a bag or two.  I like bags that can be completely zipped up, and literally tossed from shore to launch or dinghy, launch to boat, or boat to dock." (Comment)

"You might want to get a 'Dummies' book or the like, to learn a few terms and the general etiquette. You'll be given instructions (orders) by the skipper occasionally, and they are to be followed, not discussed or pouted over. I've only sailed a very small amount, as passenger/amateur crew, and unlike a power boat there is a reason for you to be hither, rather than yon, and to pull on that rope-thingey (strangely enough, the line, not the sail, is a 'sheet'). But it's so much more fun to be involved rather than just along."  (NCJack)
Don't wear jewelry with sharp edges or clothes that can snag.

"I'm partial to Badger sunscreens. They only use zinc oxide as their active ingredient. It goes on thick - and white - but it's considered safe and it's effective. I use it every day, sailing or not." (Comment)
 Bring sunscreen and a good hat.

"A hat clip, to keep your hat from going over the side (same for your sunglasses)" (Queequeg)

Wear a PFD
 "....and only Admirals and A**holes stand in the companionway..." (Patsy)
Volunteering to pay for gas is always appreciated.

Be prepared to help...

...or even do nothing at all...

...while waiting for things to happen.
 "If you are a bit queasy, do NOT go below as this will worsen your symptom. Fix eyes on the horizon and stay on deck." (Lane)
 Bags should be able to be completely zipped up and tossed.
 "I tend to wear quick-dry when racing. Love cotton, but is cold and clammy when wet."
"Agree with the one small duffel comments. Not much is so frowned upon as a guest with too much gear. That being said, plan on the temperature on the water being 20 degrees colder than that on land. Plan clothes with that in mind and then add one more fleece on top! ... Also, chances are that your host has foul weather gear you can borrow if need-be. Ask. Do not feel you need to go out and spend hundreds of dollars. I do support the two pairs of shoes option, but the 'street' pair is to stay on the dock or in the dinghy." (Seth)

No Glass

When Leaving:

  • Leave with more trash than you brought aboard.
  • Don't linger at the club or dock after your hosts leave.  

Leave the club or docks with your host or very shortly after.


  1. Following up on the idea that space is at a premium:
    - Do not overpack. Most likely you are spending an afternoon on the water, not a ten-day passage. A day bag of a small soft-sided duffle or backpack is fine.
    - Do not bring a hard-sided cooler -- especially on a sailboat. They do not stow well.
    - Asl the host/owner what you can bring and follow their suggestions. Don't freelance.

    As to where to be on deck on a sailboat -- do not assume that the seemingly empty space in front of the mast is an out-of-the-way zone where you can set up camp. It's not -- things happen up there. Also, don't assume the cabin top is a great place for you to sit -- most likely it's not. Ask where the best place is for you to be.

  2. Great common sense ideas for guests who are lubbers. I see that your trimming the main without gloves, which is another piece of gear that you don’t want to leave the dock without.

  3. Great practical and helpful advice! I certainly learned a lot from this - particularly, if you're a novice, ask questions of those in the know - AND follow orders. I've only been sailing twice (I get seasick) but I love to see photos and hear others' stories.

  4. Excellent post. When we have non-sailing friends onboard, I make a point of sending them very detailed instructions beforehand. The most common error I encounter is someone not bringing a layer that is warm enough once out on the water, so I stress this, and keep a couple of extra jackets onboard. I think people underestimate how chilly it can get once under sail.

  5. Hat clip!!! Never heard of one before this. Should work while riding in a convertible as well. Thanks.

  6. Love this. My advice would be to fellow useless lushes like me: this is not a power boat. You will not sit and luxuriate, you will likely have to do stuff, move around, and employ acrobatic maneuver to avoid spilling your drink. My advice, if you're not the sailing type (it's okay, they will still like you)--you might be better to accept it, maintain your equilibrium, shop around town during the day, and meet everyone at the club afterward! Does it show I've learned this the hard way?!


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