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Semi-Private Sailing Tour on Lake Michigan from Chicago - 2 Hours

Sailing Tours on Lake Michigan

Sailing Tours on Lake Michigan

Enjoy sailing on beautiful Lake Michigan. This semi-private sail is available for groups of 2 to 4 people. You may be sharing a sailboat with 2 to 4 others, but get the same great experience as a Private Sailing Charter, since all cruises are limited to a maximum of 6 guests. Relax on the main deck or help the captain in sailing the vessel.

Your captain will set a course based on the conditions of the day. Sailing along the shoreline towards Navy Pier or sailing straight out away from shore are always crowd pleasers. Relax on the deck and feel the sun and spray on your face. Listen to the wind as you sail along the coast and take in Chicago's breathtaking skyline.

Sails are BYOB, so make sure to bring along your beverage of choice. No matter what you choose to do, you are sure to enjoy this fantastic voyage on a first class sailing vessel!

What to bring

  • Simple food and drinks
  • Sun Screen
  • A hat
  • Sunglasses
  • Possibly extra clothing - The air on the water can potentially dip below 75 degrees.

What to avoid bringing

  • Staining liquids like red wine, grape juice, or cranberry juice
  • Glass is prohibited above decks - the boat has paper plates, forks, knives spoons, cups, napkins, cooler space, drink cozies, tin foil, ice, etc.
  • Improper Footwear - you may be asked to walk barefoot on the decks
  • Metal rivets or buttons on pants - these may damage the boat
  • Illegal substances of any kind will not be tolerated

Frequently Asked Questions

Is there a captain on board?
Yes, there is always a Captain on board to sail the boat.

Where will you be sailing?
Your captain will always try to give you the most enjoyable sail given the conditions of the day. 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, your experienced captain knows the sailboat and the behavior of the lake well, and will take the course that provides the best sail for present and forecast conditions.

Is there a bathroom on board?
Yes. The ship has a bathroom or "Marine Head."

Can you bring food and drinks?
Yes. It is suggested the more simple you keep it, the more you will enjoy your sail - things you can eat with one hand like sandwiches, fruit, and bite-size things in general. These are the easiest to manage on a boat.

Is it OK to bring alcohol?
Yes. Alcohol in moderation is fine. Please avoid red wine - and glass bottles (except for white wine and champagne bottles).

What kind of shoes are best to wear?
Light colored, soft-soled, non-marking shoes like deck shoes or top-siders are best. Gym shoes that do not have dark colors (black, blue, red) in the sole are okay. 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. If you show up with shoes that are not ideal, your captain will work it out.

What about sea-sickness?
If you are worried about becoming sea-sick, you may want to take one of the over the counter medications. 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.

Can we go swimming?
For safety and logistical reasons, swimming is not allowed.

Are children allowed?
Children must be at least 12 years old, accompanied by an adult age 18+.

Can we smoke on board?
There is no smoking allowed on the boat.

Is tipping customary?
Yes, tipping is customary and typically ranges from 10-20% of the cost of the sail (similar to dining out).

48 HOURS MINIMUM ADVANCE BOOKING REQUIRED. This tour does not offer hotel pick-up. Rates are PER COUPLE in US dollars. Price does not include gratuity. Please reserve online or call us toll-free at 888-881-3284.

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