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Frequently  Asked Questions

How long will it take to learn to sail?

The answer is entirely up to you. The more you sail and study, the faster you learn. As a rule of thumb with all due diligence, you will have basic sailing skills by Skills Training sail number 4-5.


What happens of the weather is bad?

If the captain deems the weather to be dangerous or just plain not conducive for training or fun, she will notify you with at least 3 hours advance notice. The session will be cancelled and your sailing package credit will be available to use for re-booking by the following day.

What if I need to cancel or I do a no-show?

We understand that issues and illnesses come up. It is at the sole discretion of the captain whether your cancellation will result in a refund of your sailing credit. No shows or arriving after we leave the dock are an automatic no refund.


Do I need to bring my own lifejacket?

No. There are lifejackets on board. That said, if you plan to sail often, you’ll want to buy your own vest for best fit and comfort. Plus you’ll be ready to sail on other boats!

Is there parking by B dock in Montrose?

Yes. There is metered parking adjacent to B dock on the West Montrose Harbor Drive. Also, there is a paid parking lot on the left side shortly after you enter the park when coming in on Montrose Avenue and free parking on the Montrose Ave (plan for extra time to walk to B dock).

Warning! During holidays and busy weekends you’ll need to leave plenty of time to find a parking spot and walk to our dock. Occasionally, especially on holidays, the park will get full and the entrance will be closed. If that’s the case you will have to find parking outside the park and walk in. This will definitely take extra time so be sure to plan appropriately because you don’t want to miss the boat!

Is there a bike rack by B dock?

Yes, you can lock your bike up on the rack that is located just outside B dock. Do not bring your bike on to the dock or lock it to the gate area outside the dock. This is prohibited by the harbor authorities.

Can I bring a guest sailing?

Please refer to the guest policy in the Club Guidelines and Policies document you signed when becoming a member. Here’s an excerpt:


  • Sailing Program - No guests are allowed on Skill Training Sails, Pleasure Sails.

  • Social Program - Guests are permitted for Tiki Fun and Special Events. Harbor Clean Up Fun is limited to members only. Occasionally exceptions can be made by contacting Captain Lynda in advance of the event.

  • All Programs - Captain Lynda reserves the right to make exceptions to the guest policy.

Can I book the boat for a private charter?

On occasion all-women or co-ed charters are available. The cost is $150 per hour for up to six people. For availability contact Captain Lynda at 312.766.1886.

What should I wear sailing?

  • 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. On hot days it’s fine to wear to just a swimsuit however during Skills training classes I highly recommend you wear shorts over your bottoms.

  • Bag: We 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 should I bring sailing?


Must Haves:

  • A full water bottle. The best kind are big with a carabiner 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.

  • Note there is no eating or drinking alcohol during Skills Training Sails.


  • Snacks. For pleasure sails bring whatever you want to eat or drink and some ice. There is an ice chest on the boat so no need to bring one of those. For drinks, please bring a sealed top wine/cocktail cup. Drinks spill all the time and you will spend time scrubbing if you spill on Leela’s deck. Note: Red wine is not allowed on the boat, it stains terribly. 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.


  • 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.


Is there an ice chest on board?



What if I get seasick?


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. There are also wristbands for motion sickness that you can purchase at any drug store.


Do not get drunk the night before your sailing adventure. Hang overs increase your change of seasickness 10-fold.


If you are sick but not in physical danger, we will continue to sail because returning to the dock to drop you off takes precious training/fun time away from the other sailors.


Do you provide an ASA or US Sailing certification?

No. Although Captain Lynda is a certified US Sailing Instructor, you will not receive an ASA or US Sailing certification in this program. That said, if you test through to the 1st Mate level of the Club’s sailing program, you will be ready to take and pass an ASA101 or US Sailing Basic Keelboat certification test. In fact, you’ll have WAY more sailing time under your belt than either of those courses provides. Many sailors have told us about taking and passing those courses and still feeling like they don’t know how to sail. This is mostly due to the fact that those courses only give you a few days on the water. With the club, you’ll have a lot more time on the water and likely build far more confidence and skill at the same or less cost!


What if I decide I don’t want to sail and still have sails “in the bank” that I haven’t used?

Membership fees are non-refundable except in cases of a disabling injury or illness. Determination of a refund is at the sole discretion of the club Commodore, Lynda Stephens.


Will we get to do overnight sailing or lake crossings?

Yes. Please see the booking calendar for this year's overnight and long distance sails.


I see it says that only “active” members can participate in the Social Programs. What does that mean?

An active member is one that has paid for membership for the period of time when the social event occurs. To illustrate the point, if you buy a membership for August 1 – August 29 (4 weeks), you are eligible to attend any social events during that time but not eligible to attend events before or after that time.


Is the boat insured for accidents?

Yes. The boat is insured as a club boat with $1,000,000 liability coverage.

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