Yes, there is always a Captain on board to sail the boat. Bareboat charters are a situation where a captain may be provided by the charterer, or chosen from a list of pre-vetted captains provided.

Your captain will set a course based on your preferences and the conditions of the day to give you the most enjoyable sail. Sometimes the wind and waves will be ideal for cruising up and down the shoreline, and other times straight away from shore. Sometimes your sail will be fast, other times slow. Whatever the conditions of the day, our experienced captains know our sailboats and the behavior of the lake, and will take the course to provide you with the best sail for the present and forecast conditions.

All of our ships have bathrooms (a.k.a. “marine heads”).

Yes, and we suggest the more simple you keep it, the more you will enjoy your sail. Things you can eat with one hand like sandwiches, fruit, bite size things in general, are the easiest to manage on a boat. Please avoid red wine and glass bottles (except for white wine and champagne bottles).

Yes, alcohol in moderation is fine. Please avoid red wine except on our sporting class boats. Please avoid glass bottles (white wine and champagne bottles will be kept down below for you for safety).

Light colored, soft-soled, non-marking shoes like deck shoes or top-siders are best to wear. Gym shoes that do not have dark colors (black, blue, red) in the sole are OK. Please don’t wear shoes such as loafers, which have hard soles and can damage the boats. Most inexpensive flip-flops are not good for boats as the charcoal black soles leave scuffs everywhere, but sandals such as TEVAs are normally perfect. Don’t worry, if you show up with shoes that are not OK, your captain will work something out.

In addition to the map included in your confirmation email, some good suggestions are: simple food and drinks, sun screen, maybe a hat and sunglasses, and possibly some extra clothing (especially on night sails when 75° on shore can feel cool on the lake with the wind). We have all the bottled water, paper plates, forks, knives spoons, cups, napkins, cooler space, drink cozies, tin foil, ice, etc. that you will need.

Please try to AVOID red wines or any other dark staining liquid like grape or cranberry juices, etc. (unless you are on one of our sporting class boats), glass of any kind above deck (except white wine and champagne bottles which we will keep below for you), hard soled, dark soled, or marking shoes (click here for shoe info), metal rivets or buttons on pants (they damage the finish on the boats), and illegal substances.

Though it is uncommon, if there is not much wind, we will motor sail (for example towards Navy Pier for great views of the shoreline). We do not cancel sails for light wind conditions.

We find it uncommon except in people who are prone to motion sickness. If you are worried about it, you may want to take one of the over the counter medications (please read the directions) WELL BEFORE sailing. You must take it well before your sail to be effective. If you are prone to motion or sea sickness, you should probably not book a sail.

Yes, please show up on time unless your captain contacts you asking you to do otherwise. We will use the current and predictive radar, as well as the marine forecast to determine if we will sail. While the weather forecast may say there is a high chance of rain (even on an hourly basis), this is very broad and may not affect the time of your sail or the area where we may sail. So if your sail is at 9am and it stops raining at 9:45am, and looks like it will stay clear, we must consider 9:45am the start of the sail. There is a substantial fee for a sail for which you do not show.

Please arrive on time unless your captain contacts you asking you to do otherwise. We will use the current and predictive radar, as well as the marine forecast to determine if we will sail. If your sail is at 9am and it stops raining at 9:45am, and looks like it will stay clear, we must consider 9:45am the start of the sail. There is a substantial fee for a sail for which you do not show.

We try to make every sail rain free, but sometimes we may catch a shower. Please see our detailed weather policy in the terms.

In some cases sails can be delayed for up to 1 hour at most before departure (which will of course push back the return time by up to 1 hour). Shortened sails are rare, but we will do so for comfort and safety if the situation dictates. Sail fees are prorated for sails which are shortened by your captain. Please see our detailed weather policy in the terms for more specifics.

No, they will not. If you arrive more than 10 minutes prior to your sail and it is raining, we suggest that you wait outside the parking booth without paying the parking fee. This way the captain has a bit more time to contact you in case he is making a sail time decision to delay or cancel your sail.

We will not sail in conditions deemed to be unsafe or unreasonably uncomfortable. Waves are a part of sailing, and sometimes modest waves. Each captain will judge the current conditions as to how the boat will handle in them, and make his decision to whether to sail or not. Sometimes a 4′ wave with an East wind is comfortable, and a 3′ wave with a West wind is not. There are many variables to consider, and our captains are very capable of evaluating the conditions.

A small craft advisory can be very misleading as far as sailing is concerned. Advisories are typically only updated every 6 hours, and some advisories are issued with conditions that are favorable for sailing. There are several times each year that there is no advisory, yet the sailing is terrible and we cancel sails. There are many more when an advisory is issued, the sailing is fantastic, and we sail for hours before the weather service realizes that they should cancel the advisory.

One perfect example was Saturday 8/20/2011, the first day of the Chicago Air Show. The morning was awful, the air show was put on hold, and the weather services all said that there would be continued strong storms throughout the entire day ending around 8pm. At 1pm the rain stopped, the skies cleared, the radar cleared, and the show started. By 3pm we had blue sky and some of the best sailing we had seen all year (the small craft advisory was never removed). This is why we use current conditions and Doppler radar, coupled with marine and local forecasts, instead of obscure non-specific small craft advisories.

Please wait until the night before to book, and make sure you are 100% happy with the forecast. There may not be availability, and it may not be possible to get a captain with such short notice, but that is the only way to be sure that the forecast meets your criteria.

You can check available dates/times online or call us. Please call if you are need to cancel or change your reservation (or if you are considering it). Please note that if you are rescheduling a reserved sail that is less than 30 days in advance, change fees will apply based on the type of boat (Power Boats, Big Boat, Sailboats). Cancellations are subject to the same fees, as well as a fee for cancellations made more than 10 days in advance. Higher fees apply for specials events dates. The further in advance you make a change or cancellation, the lower any applicable fee will be.

Reservation changes made less than 30 full days in advance are subject to change fees. Cancellations are subject to the same fees, as well as a fee for cancellations made more than 30 days in advance. Higher fees apply for specials events dates.

We would really like for you to bring the map that came with the email so that you do not end up in the wrong end of the harbor (which may lead to delayed departure and a shorter sail).

You will receive a text (or phone call if no response is received to our text) providing the captain’s cell number about 30-60 minutes before your sail. Prior to that, please contact the office with all questions. The reason the captain’s number is not provided prior to an hour in advance of your sail is that there is a possibility that crew assignments will change.

Please arrive at the meeting point at least 10 minutes before your sail time. Your captain will meet you there about 5-10 minutes before your sail. If you can, we strongly suggest arriving earlier in case you hit any delays along the way. If you arrive early, please let your captain know you are there, and if possible you can begin your sail early. You can also enjoy a walk along the beautiful shoreline if you are early.

Please click here for a map and directions. There will also be a map and direction in your confirmation email. We are in the NORTH end of Belmont Harbor and sails meet near the picnic table outside the “H” dock gate.

Use the map linked above, and park in the paid parking or the tennis court parking, but you MUST NOT use Belmont Avenue as that is the wrong end of the harbor.

You can be dropped off right at the meeting point indicated on the map.

Please meet at the spot labelled “Meeting Point” on the map included in your confirmation email. We meet in the NORTH end of Belmont Harbor near the picnic table outside the “H” dock gate.

Please contact your captain if you think you are going to be late. Of course your captain will wait for you if you are late, but he may still have to return to the dock at the scheduled time. To completely avoid this issue, we suggest that you plan to arrive well in advance of your sail, and plan for traffic delays and time to park. Even if you are there 45 minutes early you can enjoy a walk along the shoreline, or along the harbor wall. Please be warned that drinking alcohol on park district property is illegal, so you will want to wait until you board to enjoy a cold one. There are no discounts or refunds for sails shortened due to late arrivals.

Unfortunately since we will have already reserved a crew and your boat for you, we will still have to charge you the full cost of your sail if you are not able to make it for whatever reason. If you give us some advance notice, lesser change fees than the no show 100% charge will apply.

During daylight hours, as long as the conditions are determined to be safe by your captain, you can go swimming. Please let your captain know in advance that you wish to go swimming so he can plan for it.

Of course. We do like to talk to you about the ages and the number of children so both you and we know what to expect. We also need to make sure that there is a reasonable number of adults for the number of children on board.

There is no smoking on any of our boats.

Yes, tipping is customary and typically ranges from 15-20% of the retail cost of the sail (similar to dining out).