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Chicago Sailboat Charters

FAQs

A big boat, sailboat, and yacht sailing into a marina on Lake Michigan in Chicago

Our FAQs cover multiple charter styles and boat types.

Because regulations, capacities, and charter structures vary by vessel, some FAQs apply only to certain boats. These instances are labeled clearly in the question.

Here’s a quick breakdown of our fleet:

  • Sailboats:  These are our 39’ sailboats with very large cockpits, and nice sized foredecks. This type of boat is a classic Chicago experience. This FAQ is specifically for our Sailboats.
  • Yachts (46ft Luxury and 40ft Premium): These are power boats that have very large areas (foredecks) at the front of the boat (bow), and very large areas (cockpits) in the rear (stern) of the boat.
  • BIG BOAT – This is our 36-passenger party boat.

Each FAQ clearly indicates which boat types it applies to.

Getting Started and Booking

Please go to our Availability page or call us at 773-236-7245.

You can check available dates/times online or call us. Please call if you need to cancel or change your reservation (or if you are considering it). Please note that if you are rescheduling or cancelling a charter, change fees will apply as specified within the terms (6-pack terms, bareboat terms, BIG BOAT terms). Higher fees apply for specials events dates. The further in advance you make a change or cancellation, the lower any applicable fee will be.

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

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

Pricing and Payments

Sailboats and Yachts: We take a deposit of $100 when you make a reservation and charge the same credit card the remaining balance 14 days prior to the charter.

Big Boat: We take a deposit of 15% when you make a reservation and charge the same credit card the remaining balance 60 days prior to the charter.

Chater Types and USCG Rules

A 6-pack charter is when the charter company offers you a charter for 6 people or fewer and you make the entire arrangement with the charter company. The charter company arranges for and pays the captain in this case. Gratuity is still given directly to the captain.  

  • When you have more than 6 people in your group (except on BIG BOAT), US Coast Guard regulations dictate that this MUST be a Bareboat charter. You can have up to 12 people in your group on a bareboat on one of our sailboats.
  • A licensed captain will be hired by and paid for by the charterer (the person renting the boat). The pricing we provide includes both the cost of the boat rental and the cost that you will pay to the captain.

We will provide a list of pre-vetted captains for you as your charter date approaches. We are not allowed to line up the captain for you (USCG regs), and captain fees must be made directly to the captain and cannot be made through us.

Captain and Crew

Yes, all charters include a licensed captain on board. BIG BOAT charters also include an additional crew member.

You will receive a text providing the captain’s cell number for the day about 60-90 minutes before your charter. Prior to that, please contact the office with all questions. If you have a bareboat charter, you have already had contact with your captain, but a text will be sent to you the same as all other types of charters.

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

BIG BOAT: BIG BOAT charters have a standard gratuity included in all pricing. Should you feel that your captain and crew did a fantastic job, feel free to show them your appreciation with any extra gratuity that you wish.

Location, Parking & Meet-Up

Please meet at the spot indicated on the map included in your confirmation email.

There will be a map and directions in your confirmation email. Do NOT simply put our name into a search engine or map app, as we have three locations.

Please use the directions included in your confirmation for parking.

Please use the directions included in your confirmation for ride drops.

Please arrive at the meeting point at least 15 minutes before your charter time. Your captain will meet you there a couple minutes prior to your charter. 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 charter early. You can also enjoy a walk along the beautiful shoreline if you are early.

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 will 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 charter, 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 cocktail. There are no discounts or refunds for charters shortened due to late arrivals.

Weather & Lake Conditions

Sailboats: A small craft advisory is very general and can be very misleading. For example, a fresh West wind can cause large waves 3 miles off-shore, but almost no waves in the first couple miles – and you will typically be within a mile from shore or less. Advisories are typically only updated every 6 hours, and some advisories are issued with conditions that are favorable for sailing. There are also a few 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 some of the best of the season, and we sail for hours before the weather service realizes that they should cancel the advisory.

Yacht and BIG BOAT: A small craft advisory is very general and can be very misleading. For example, a fresh West wind can cause large waves 3 miles off-shore, but almost no waves in the first couple miles – and you will typically be within a mile from shore or less. Advisories are typically only updated every 6 hours, and some advisories are issued with conditions that are favorable for sailing. There are also a few 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 some of the best of the season, and we sail for hours before the weather service realizes that they should cancel the advisory.

Sailboats and Yachts:  We try to make every reasonable effort to charter rain free, but sometimes we may catch some rain and do go out in scattered showers. We cannot cancel charters for scattered showers. Please see our detailed weather policy in the terms (6-pack terms, bareboat terms).

Big Boat: Charters will go out in the rain (feel free to take cover in the large covered area if you choose), but not persistent electrical storms. We will not begin a charter during an electrical storm, or if we believe that such approaching conditions will be unavoidable during a charter by altering course or returning to harbor. Please see our detailed weather policy in the terms.

Sailing: 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 perform in them and make his decision whether to sail or not. Sometimes a 4′ wave with a wind from the East is comfortable, and a 3′ wave with a West wind is not. There are many variables to consider, and the captains are very capable of evaluating the conditions.

Yachts and Big Boat: Waves do not typically affect BIG BOAT or Yacht charters since we are harbored at Navy Pier Marina which is behind the offshore break wall. Waves are broken on the wall before they get to the charter area.

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.

Please wait until the day before to book, and make sure you are 100% happy with the forecast. Even then, the forecast may be wrong, and you may not get the conditions you are seeking. 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 confident that the forecast meets your criteria.

No, parking is not refundable. If you arrive a long time prior to your charter and it is raining, we suggest that you stay in your car and wait to pay the parking fee. This way the captain has a bit more time to contact you in case he is making a charter time decision to delay or cancel your charter.

Yes, please show up on time unless your captain contacts you to do otherwise. We will use the current and predictive radar, as well as the marine forecast to determine if we will go out. 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 charter or the area where we may travel. So if your charter 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 charter. There are no refunds for a charter for which you do not show.

In some instances, charters may be delayed for up to 1 hour at most before departure. Shortened charters are not common, but we will do so for comfort and safety if the situation dictates. Charter fees are prorated for trips which are shortened by your captain. Please see our detailed weather policy in the terms (6-pack terms, Bareboat terms, Big Boat terms) for more specifics.

What to Wear & Bring

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 (even when it is 75° on shore, it can feel cool on the lake with a breeze). We bottled water, paper plates, forks, knives spoons, cups, napkins, cooler space, tin foil, ice, etc. that you will need.

Please AVOID red wines or any other dark staining liquid like grape or cranberry juices, etc., glass of any kind above deck (except white wine and champagne bottles which we will keep below for you), hard sole, dark sole, or marking shoes, metal rivets or buttons on the backside of pants (they damage the finish on the boats), and illegal substances

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 best. High heels are not allowed. Please don’t wear shoes such as loafers, which have hard soles, which are slippery on boats. Sandals such as TEVAs are normally perfect. Don’t worry, if you show up with shoes that are not OK, your captain will work it out with you.

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 suitable for you (please read the directions and speak to your doctor) WELL BEFORE boarding. You must take it well before your charter to be effective. If you are prone to motion or sea sickness, you might find it best to avoid boats in general.

Food & Drinks

Yes, and we suggest the more simple you keep it, the more you will enjoy your charter. Things you can eat with one hand like sandwiches, fruit, bite-size things, 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. Please avoid glass bottles. White wine and champagne bottles are kept down below for you for safety

We can guide you to several caterers on Navy Pier that are conveniently located for your charter with us on BIG BOAT. We do not have any business arrangements with those vendors and are not responsible for their service or provisions in any way, we are only making the introduction.

Yes, we have optional beverage packages on BIG BOAT cruises, but you are free to BYO if you prefer.

Onboard Amenities & Rules

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

No, not under any circumstances.

There is no smoking on any of our boats. Ash generating smoking and use of cannabis products is not allowed. E-cig/vaping is allowed in areas designated by your captain at appropriate times.

Destinations & Activities

During daylight hours, if 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. If there are any children, one person over 18 will have to be in the water with each person under 18. A minimum charter duration of 3 hours or more is typically needed for sailboat trips if you wish to get in the water as it takes a bit of time to get to and back from the protected area for anchoring.

Sailboats: Additionally, a minimum charter duration of 3 hours or more is typically needed for sailboat trips if you wish to get in the water as it takes a bit of time to get to and back from the protected area for anchoring.

Sailboats:  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 away from shore. Sometimes your sail will be fast, other times slow. Whatever the conditions of the day, the 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.

Yachts and Big Boat:  Your captain will set a course based on your preferences and the conditions of the day to give you the most enjoyable cruise. Shoreline cruises and anchoring in South Monroe or The Playpen are popular choices.

Guests and Group Policies

Maximum capacity depends on boat type:

  • 12 people on Sailboats
  • 13 people on Yachts
  • 36 people on the BIG BOAT.

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 and have the correct size and number of child life jackets on board. We also need to make sure that there is a reasonable number of adults for the number of children on board. This will depend on the number and age of the children, and the type of charter.

Sorry, no animals are allowed.