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    Within 100 Miles Of
    Winthrop Harbor, Illinois

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Cruiser boats for sale in Winthrop Harbor Illinois

There are 52 new and used Cruiser boats for sale in Winthrop Harbor, Illinois. Explore Cruiser brands like Yamaha, Other, Cruisers, Bayliner, Formula, and Saxdor on BoatCrazy. View a wide selection of Cruiser boats from $500 to $497,503.
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  • Cruiser
    Within 100 Miles Of
    Winthrop Harbor, Illinois
52 boats found within 100 miles from Winthrop Harbor, Illinois
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  • 2026 Yamaha AR220

    2026 Yamaha AR220

    $500
    Madison, WI
    • Madison, WI
    • Cruiser
    • 22'
    • 2026 / New
    • $500

    Introducing the 2026 Yamaha AR220, value-packed watersports fun. Offering the perfect blend of value, versatility, and convenience in an affordable 22-foot package. Key Features Pe... View Details

    View 45 Photos and Details Contact Seller
    $500
    VIEW DETAILS
  • 2000 Chaparral SIGNATURE 300

    2000 Chaparral SIGNATURE 300

    $26,900
    Grand Haven, MI
    • Grand Haven, MI
    • Cruiser
    • 30'
    • 2000 / Used
    • $26,900

    Recently buffed and waxed, this freshwater 2000 Chaparral 300 Signature is a well-maintained express cruiser offering an excellent combination of comfort, performance, and value. P... View Details

    View 61 Photos and Details Contact Seller
    $26,900
    VIEW DETAILS
  • 2026 Azimut 48 Verve

    2026 Azimut 48 Verve

    $500
    Grand Haven, MI
    • Grand Haven, MI
    • Cruiser
    • 48'
    • 2026 / New
    • $500

    Free Winterization, Shrink Wrap & Outside Storage Offer Terms: Offer valid with the purchase of an eligible new or pre-owned boat from any participating SkipperBud's location betwe... View Details

    View 3 Photos and Details Contact Seller
    $500
    VIEW DETAILS
  • 2020 Cruisers Yachts 38 GLS

    2020 Cruisers Yachts 38 GLS

    $399,900
    Grand Haven, MI
    • Grand Haven, MI
    • Cruiser
    • 38'
    • 2020 / Used
    • $399,900

    Cruisers Yachts 38 GLS – The Best of Both Worlds Twin MerCruiser 8.2 MAGs | Only 261 Hours | Joystick Piloting Enjoy the perfect combination of day cruising comfort and overnight c... View Details

    View 28 Photos and Details Contact Seller
    $399,900
    VIEW DETAILS
  • 2025 Bayliner D20I

    2025 Bayliner D20I

    $45,356
    Grand Haven, MI
    • Grand Haven, MI
    • Cruiser
    • 20'
    • 2025 / New
    • $45,356

    Act fast on this limited-time offer!Luxury Redefined: 2025 Bayliner D20I Performance Unleashed: Step into the future of boating with the powerful 200 Hp MERCRUISER/MERCURY engine,... View Details

    View 13 Photos and Details Contact Seller
    $45,356
    VIEW DETAILS
  • 2014 Cruisers Yachts 380 EXPRESS

    2014 Cruisers Yachts 380 EXPRESS

    $259,990
    Grand Haven, MI
    • Grand Haven, MI
    • Cruiser
    • 38'
    • 2014 / Used
    • $259,990

    Freshwater-only and single-owner since new, this 2014 380 Express was purchased new from SkipperBud's and has been maintained to an exceptional standard. Powered by twin MerCruiser... View Details

    View 61 Photos and Details Contact Seller
    $259,990
    VIEW DETAILS
  • 2026 Cruisers Yachts 38 VTR EC

    2026 Cruisers Yachts 38 VTR EC

    $497,503
    Grand Haven, MI
    • Grand Haven, MI
    • Cruiser
    • 38'
    • 2026 / New
    • $497,503

    Free Winterization, Shrink Wrap & Outside Storage Offer Terms: Offer valid with the purchase of an eligible new or pre-owned boat from any participating SkipperBud's location betwe... View Details

    View 22 Photos and Details Contact Seller
    $497,503
    VIEW DETAILS
  • 2026 Saxdor 400 GTO

    2026 Saxdor 400 GTO

    $500
    Grand Haven, MI
    • Grand Haven, MI
    • Cruiser
    • 40'
    • 2026 / New
    • $500

    Free Winterization, Shrink Wrap & Outside Storage Offer Terms: Offer valid with the purchase of an eligible new or pre-owned boat from any participating SkipperBud's location betwe... View Details

    View 7 Photos and Details Contact Seller
    $500
    VIEW DETAILS
  • 2009 Other Winns 278 VISTA

    2009 Other Winns 278 VISTA

    $44,995
    Grand Haven, MI
    • Grand Haven, MI
    • Cruiser
    • 28'
    • 2009 / Used
    • $44,995

    Clean, well-maintained, and ready to enjoy, "Touching Heaven" is a great opportunity for anyone looking to step into cabin cruising without taking on a large or complicated boat. A... View Details

    View 73 Photos and Details Contact Seller
    $44,995
    VIEW DETAILS
  • 2005 Cruisers 405 Motoryacht

    2005 Cruisers 405 Motoryacht

    $160,000
    Spring Lake, MI

    2005 Cruisers Yachts 405 Motor Yacht  Fresh Water • Low Hours • Major Value Opportunity   Location: Grand Haven, MI  Call or Text: 616-... View Details

    View 32 Photos and Details Contact Seller
    $160,000
    VIEW DETAILS
Showing 43 to 52 of 52 boats found.
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Cruiser Boats on Boatcrazy

Cruisers are versatile powerboats designed for comfort, extended trips, and overnight stays on the water. Offering the perfect blend of performance and livability, cruisers typically feature spacious cabins, galleys, sleeping quarters, and enclosed heads—making them ideal for weekend getaways, coastal cruising, or even liveaboard life.

Available in a range of sizes—from compact express cruisers to luxurious cabin cruisers—these boats often include features like air conditioning, generator power, swim platforms, and entertainment systems. Many models also offer flybridges, hardtops, or sunpads for added versatility and style.

Explore our selection of new and used cruisers from leading brands. Whether you're looking for a family-friendly cruiser or a sleek performance model for harbor-hopping, you'll find a boat that balances comfort and adventure.

Cruiser Boats manufacturers on Boatcrazy

When looking for a comfortable and capable Cruiser boat, consider these top-tier Cruiser Manufacturers

Sea Ray, Regal, Cruisers Yachts, Beneteau, Tiara Yachts, Boston Whaler

Cruiser Boats For Sale by State

Cruiser Boats Frequently Asked Questions

What is a cruiser boat?

A cruiser boat—also referred to as a cabin cruiser—is a powerboat typically between 21 ft and 45 ft in length, equipped with sleeping berths, a galley, and a head—designed for overnight cruising in comfort.

Most cruisers range from 21 to 45 ft, with cabins located in the bow and amenities like berths, galley, enclosed head, and open cockpit or helm area for both comfort and day-use flexibility.

Typical cabin cruisers cruise at around 20–30 knots. Larger models and luxury cruisers can exceed 30 knots, while fuel-efficient models offer long-range capabilities style-wise akin to small yachts.

Cruisers combine indoor-outdoor living with amenities like cabins, galleys, heads, comfortable cockpits, and often flybridge or sun decks—making them ideal for entertaining, weekend cruising, and family overnight outings.

Prices vary widely—from around $100,000 for modest used models up to $700,000 or more for modern, well-equipped cabin cruisers. Luxury or larger models may exceed $1 million.

Cruiser boats are ideal for boating couples, families, or weekenders who want overnight ability, onboard comfort, and multi-day flexibility without the size or expense of a full yacht.