Adventure Brief
Join Sailing Chi for a memorable yacht trip on Lake Tahoe, where you can sail, swim, and enjoy stunning mountain views. Perfect for groups seeking fun and relaxation on the water.
3–4 hours
easy
Family Friendly
No Experience Required
Join Sailing Chi for a memorable yacht trip on Lake Tahoe, where you can sail, swim, and enjoy stunning mountain views. Perfect for groups seeking fun and relaxation on the water.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
3–4 hours
Fitness Level
Suitable for most fitness levels, no prior sailing experience needed
Wildlife
History
Lake Tahoe has been a popular boating destination since the 19th century, with its clear waters and scenic surroundings drawing adventurers and vacationers alike.
Conservation
Sailing trips are eco-friendly, emphasizing minimal environmental impact and promoting responsible water recreation.
On A Boat Sailing
Join Sailing Chi for a memorable yacht trip on Lake Tahoe, where you can sail, swim, and enjoy stunning mountain views. Perfect for groups seeking fun and relaxation on the water.
On A Boat Sailing is a Chicago-based private charter company offering curated sailing and yachting experiences on Lake Michigan.
The company specializes in a range of private cruises including skyline sunset sails, lakefront sightseeing, swim-and-sail playpen outings, wedding and wedding-party charters, engagement and proposal cruises, Navy Pier fireworks cruises, and group yachting aboard larger vessels.
Trips operate aboard a fleet that includes a 37' sailboat, the S/V Dragonfly, and the larger Yacht Guppy for big groups. Each charter includes a USCG-certified captain responsible for navigation, safety briefings, and a professionally managed experience. Add-on services include premium drink packages with pre-ordered wine, champagne, beer, and seltzer, and guests are welcome to bring BYOB snacks and beverages on most cruises.
Bookings are designed for private groups seeking a tailored event on the water, from romantic two-hour engagements to four-hour celebration charters and three-hour fireworks cruises. On A Boat Sailing highlights clear departure logistics from Chicago waterfront locations and offers complimentary light snacks and select beverages on several trips. Safety and comfort are emphasized through certified captains, fully equipped yachts, and adherence to local maritime regulations. The business is positioned for authentic Lake Michigan experiences, delivering skyline views, swimming stops, and customizable itineraries for family gatherings, corporate outings, and special events. On A Boat Sailing provides transparent trip summaries, duration options, and vessel details so prospective guests can choose the best private charter for their occasion. Seasonal options.
Location
Chicago, IL
Departures on Lake Michigan
Boat Types
37' sailboat, S/V Dragonfly, Yacht Guppy
Multiple luxury vessels available
Private Charters
9 trip types
Designed for private groups
Certified Captain
USCG-certified
Safety and professional operation
Select a trip, confirm a USCG-certified captain, and customize drinks and itinerary for an unforgettable Lake Michigan charter.
Bring Sun Protection
Apply waterproof sunscreen and wear hats to stay protected while on the water.
Confirm Group Size
Make sure to book in advance for larger groups to secure your spot on the yacht.
Pack Light and Essentials
Bring swimsuits, personal snacks, and water bottles for a comfortable trip.
Prepare for Lake Conditions
Check weather forecasts before your trip to dress appropriately and stay safe.
Sun Protection
Sunscreen, hats, and sunglasses protect against UV rays during daytime outings.
summer
Swimsuit and Towel
Pack a swimsuit and towel for swimming and relaxing on deck.
summer
Casual Clothing
Bring comfortable clothes suitable for variable weather conditions.
spring,fall,winter
Water Bottle
Stay hydrated with a reusable water bottle during the trip.
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