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What to   Wear and  Bring 

What To Wear
  • Clothing: Always check the day’s weather forecast for downtown Chicago area. We do sail in the cold and the light rain. Layers are best as the temps tend to shift while we are on the water. At a minimum you’ll want to bring a light windbreaker.

  • Bag: I suggest using a small to medium size soft-sided duffle or backpack type bag. Waterproof or water resistant is always a good idea.

  • Sun Protection: Bring a hat, sunglasses and sunscreen (no spray sunscreen it makes for slippery decks).
    Note: Hats and glasses come off and get lost at sea if they are not tethered to you. So look online and you will find hat tethers that have a clip on each end. One clips to the hat, the other to your shirt. Sunglass tethers (Croakies) are in every drug store. You slip your glasses in to each end and they stay on even if you bend over to look at the water!

  • Cell Phone Protection: You are welcome to bring your phone but they don’t float and decks can get wet so I suggest getting a holder that floats and protects from water or keep them in your bag below for safekeeping.

  • Footwear: Do wear shoes or sandals that have light or white colored soles and excellent gripping power. If you choose sandals, make sure your toes / the front of the sandal is enclosed. This prevents toe injuries when walking on deck. Do not wear flip flops or heels.

  • Swimsuit: On really hot days during Pleasure Sails we may want to stop for a quick swim, pack a suit and a towel and join the swimming fun in the beautiful blue water (usually late June – early September).

  • Gloves: Some ladies like to wear sailing gloves when they steer the boat or pull the lines. It definitely protects from blisters and helps strengthen your grip. I always wear gloves, I just feel stronger with them on. For Skills Training, I’d say they are a must. For pleasure sails, it’s definitely optional. You can find them online and I recommend the ones that are “three-quarter fingers”. This means most of your fingers are covered but fingertips are open.

What To Bring

Must Haves:

  • A full water bottle. The best kind are big with a carribeaner so you can hang it on the lifeline near you. This stops it from flying around in the cockpit where peeps can trip on it.

  • Seasickness remedy(s). If you think you might feel queasy, take Dramamine a half hour BEFORE you get on the boat. Bring ginger chews (Trader Joes) too. Ginger is great for settling tummies.

  • For Wine and Cheese sails please bring a sealed top wine cup. Drinks spill all the time and you will spend scrubbing time should red wine get on Leela’s deck.


  • Snacks. For Pleasure Sails snacking is welcome anytime. It’s nice to bring some to share, but not required. Please don’t bring messy items so we can keep Leela tidy. Chips, veggies and dip. Cut fruit and sandwiches work great. For Skills Training, hand snacks only and only when you are not in the working rotation. Think nuts, dried fruits, power bars.

  • Music. Feel free to bring music on your phone or ipad. We have a Bluetooth speaker onboard. Please be mindful that others enjoy your music selection. We also have a great sailing playlist too.

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