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Sailing in Lisle


Tall Ship Red Witch: Sail Aboard Tall Wooden Ship Red Witch in Chicago (Up to 52% Off)

Sail Aboard Tall Wooden Ship Red Witch in Chicago (Up to 52% Off)

Tall Ship Red Witch

Burnham Harbor - J Dock

Passengers relax on Chicago’s only wooden tall ship while viewing the skyline or fireworks; Readers’ Choice award winner

$60 $29

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SeaBreeze Charter: Two-Hour Private BYOB Sailing Charter for Up to Six People at SeaBreeze Charter (50% Off). Two Options.

Two-Hour Private BYOB Sailing Charter for Up to Six People at SeaBreeze Charter (50% Off). Two Options.

SeaBreeze Charter

Central Chicago

American Sailing Association–certified captain entertains passengers during two-hour charters

$400 $200

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Offshore Adventures Chicago: Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 70% Off)

Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 70% Off)

Offshore Adventures Chicago

The Loop

Daytime or sunset Lake Michigan cruises delight with views of the Chicago skyline; passengers can bring their own drinks and playlists

$220 $69

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The Salty Dog Sailing Co.: 2.5-Hour Private BYOB Cruise on a Sailboat for Up to Six People from The Salty Dog Sailing Co. (Up to 49% Off)

2.5-Hour Private BYOB Cruise on a Sailboat for Up to Six People from The Salty Dog Sailing Co. (Up to 49% Off)

The Salty Dog Sailing Co.

Burnham Harbor

At Burnham Harbor, board a 34-foot yacht for a nautical adventure on Lake Michigan complete with BYO food and drinks and skyline views

$490 $249

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3rd Coast Cruising: One or Two Three-Hour Introductory Sailing or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)

One or Two Three-Hour Introductory Sailing or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)

3rd Coast Cruising

DuSable Harbor

US Coast Guard–certified captains and certified instructors welcome sailors aboard 30-foot or larger boat

$300 $99

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Chicago Sailboat Charters: Luxury First-Class Sailing for Two or Six from Chicago Sailboat Charters (Up to 50% Off)

Luxury First-Class Sailing for Two or Six from Chicago Sailboat Charters (Up to 50% Off)

Chicago Sailboat Charters

Chicago

Captains ferry groups of up to six onto Lake Michigan for relaxing excursions and stunning views

$199 $99

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Select Local Merchants

  • Fox Valley Marine
    Take a nautical adventure around Naperville when you rent a vessel from Fox Valley Marine. Looking for a bite to eat? This center also has an awesome restaurant. Families will feel right at home at this center with its kid-friendly atmosphere. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    9740 Illinois 59
    Naperville, IL US
  • Bass Pro Shops
    There's no better place than Bass Pro Shops in Bolingbrook to find all of the latest and greatest sporting goods on the market. At Bass Pro Shops, you can find easy in-and-out parking for you to take advantage of during your shopping spree. Bass Pro Shops makes bikers feel at ease with the multiple storage racks outside. Don't show up to your first practice unprepared stop by Bass Pro Shops in Bolingbrook and find all of the gear you need to start your new sport.
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    709 N Janes Ave
    Bolingbrook, IL US
  • Marine Navigation
    If it's the boater's life for you, you'll want to check out the incredible seaworthy vessels for rent at Marine Navigation in La Grange. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    613 S La Grange Rd
    La Grange, IL US
  • Denna Lawn and Marine
    Get your sea legs ready! Denna Lawn and Marine in Bensenville provides quality vessels so you can have a boating experience that is both relaxing and fun. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    560 N York Rd
    Bensenville, IL US
  • Skyline Sailing School
    Jessica Ferris can trace her interest in sailing back to her childhood in Chicago and northern Michigan, where she plied Lake Michigan's waters with her family. As she grew up, she expanded her boating territory to the Gulf of Mexico, the Caribbean, and the Atlantic and Pacific Oceans. As an adult, she brought her talents home to Chicago as an ASA-certified keelboat captain and the founder of Skyline Sailing School. Here, she passes on her seafaring knowledge in classroom courses that teach sailing principles such as basic terminology, rules of open-water travel, points of sail, knot tying, and choosing the right shoulder parrot. She also engages students with hands-on open-water classes aboard 26-foot keelboats, which begin with an exploration of basic sailing skills and progress to lessons in more advanced maneuvers.
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    116 Matthias Court
    North Aurora, IL US
  • Geneva Kayak Center
    The die-hard paddlers of Geneva Kayak Center stay on the move throughout the year—both in their watercraft and across the globe. From May to September, they are headquartered in and around Chicago, where they teach kayaking during courses, workshops, and quick orientations, and dole out kayaks, canoes, and tubes for those who want to explore the Fox River's whitewater on their own. When cold breezes start to blow through the Windy City, they head to Saint Marys, Georgia, to lead kayak camps and sea adventures on the Cumberland Island National Seashore. They also lead curated adventures off the costs of Alaska and Maine and in Wisconsin's idyllic Door County, where kayakers might spot deer grazing on grass or nibbling on cheese curds.
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    34 North Bennett Street
    Geneva, IL US

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