• Boats
  • Cruiser
    Within 100 Miles Of
    Pewaukee, Wisconsin

Filter Boats By

Filters

from

Boat Type / Category

Cruiser boats for sale in Pewaukee Wisconsin

There are 40 new and used Cruiser boats for sale in Pewaukee, Wisconsin. Explore Cruiser brands like Yamaha, Other, Cruisers, Crownline, Saxdor, and Beneteau on BoatCrazy. View a wide selection of Cruiser boats from $500 to $389,995.
  • Back
  • Boats
  • Cruiser
    Within 100 Miles Of
    Pewaukee, Wisconsin
40 boats found within 100 miles from Pewaukee, Wisconsin
Back
Filter
  • 2008 Cruisers Yachts 390 SPORTS COUPE

    2008 Cruisers Yachts 390 SPORTS COUPE

    $189,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 40'
    • 2008 / Used
    • $189,900

    The Cruisers 390 Sports Coupe is a luxury-class express with more going for her than styling alone. One of the first builders of the era to combine a modern hardtop styling with an... View Details

    View 63 Photos and Details Contact Seller
    $189,900
    VIEW DETAILS
  • 2027 Other Ray SLX 280

    2027 Other Ray SLX 280

    $500
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 28'
    • 2027 / New
    • $500

    Step up to confidence, comfort, and power with the 2027 Sea Ray SLX 280 (Stock #223209). Outfitted with a 430hp Mercury engine and luxury features throughout, this versatile 28-foo... View Details

    View 31 Photos and Details Contact Seller
    $500
    VIEW DETAILS
  • 2005 Regal COMMODORE 4260

    2005 Regal COMMODORE 4260

    $199,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 45'
    • 2005 / Used
    • $199,900

    Check out this Regal 4260 Commodore listing from SkipperBud's! Highlighting one of Regal's finest layouts, this cruiser features rebuilt Yanmar engines with under 250 hours since r... View Details

    View 46 Photos and Details Contact Seller
    $199,900
    VIEW DETAILS
  • 2003 Other Ray 50 SUNDANCER

    2003 Other Ray 50 SUNDANCER

    $324,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 50'
    • 2003 / Used
    • $324,900

    Performance & Power Unleash exhilarating power with twin CUMMINS QSM-11 engines, delivering a striking total of 616 horsepower. This vessel is designed for adventure, ensuring a th... View Details

    View 38 Photos and Details Contact Seller
    $324,900
    VIEW DETAILS
  • 2026 Other Ray SDX 250

    2026 Other Ray SDX 250

    $500
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 25'
    • 2026 / New
    • $500

    Elegant design. Superior performance. The 2026 Sea Ray SDX is engineered to offer exceptional capability for full days spend on the water. This adaptable sterndrive model features... View Details

    View 24 Photos and Details Contact Seller
    $500
    VIEW DETAILS
  • 2026 Other Ray Sundancer 320 Outboard

    2026 Other Ray Sundancer 320 Outboard

    $500
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 32'
    • 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 42 Photos and Details Contact Seller
    $500
    VIEW DETAILS
  • 2021 Crownline 264 CR

    2021 Crownline 264 CR

    $88,500
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 26'
    • 2021 / Used
    • $88,500

    FRESHLY DETAILED, BUFFED & WAXED! Turn heads next season with this beautiful 2021 Crownline 264 CR — a perfect combination of luxury, performance, and comfort. With only 150 hours,... View Details

    View 25 Photos and Details Contact Seller
    $88,500
    VIEW DETAILS
  • 2026 Saxdor 320 GTC

    2026 Saxdor 320 GTC

    $500
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 32'
    • 2026 / New
    • $500

    Act fast on this limited-time offer!2026 Saxdor 320 GTC (Stock #210937) delivers European flair and innovative functionality in a versatile cabin cruiser. Designed for adventure an... View Details

    View 41 Photos and Details Contact Seller
    $500
    VIEW DETAILS
  • 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
  • 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
  • 1998 Cruisers Yachts 3870 ESPIRIT

    1998 Cruisers Yachts 3870 ESPIRIT

    $59,900
    Madison, WI
    • Madison, WI
    • Cruiser
    • 41'
    • 1998 / Used
    • $59,900

    Step aboard the 1998 Cruisers Yachts 3870 Esprit — a timeless express cruiser that blends classic styling, spacious comfort, and proven performance. Designed for both entertaining... View Details

    View 38 Photos and Details Contact Seller
    $59,900
    VIEW DETAILS
  • 2020 Beneteau ANTARES 27

    2020 Beneteau ANTARES 27

    $189,995
    Madison, WI
    • Madison, WI
    • Cruiser
    • 27'
    • 2020 / Used
    • $189,995

    This is an express cruiser design. With twin Mercury 200 V6 outboards, it delivers impressive performance, a reassuring and comfortable ride, and a level of versatility that will e... View Details

    View 28 Photos and Details Contact Seller
    $189,995
    VIEW DETAILS
  • Price Drop 2024 Crownline 260 XSS

    2024 Crownline 260 XSS

    $123,900
    Oshkosh, WI
    • Oshkosh, WI
    • Cruiser
    • 0'
    • 2024 / Used
    • $123,900

    Like brand new condition. This Crownline 2024 XSS comes to us as a trade in with only 21.5 engine hours. Comes equipped with a fold down arch, well equipped head, and a Mercury 350... View Details

    View 22 Photos and Details Contact Seller
    $123,900
    VIEW DETAILS
  • 2006 Monterey 282 Cruiser

    2006 Monterey 282 Cruiser

    $54,995
    Oshkosh, WI
    • Oshkosh, WI
    • Cruiser
    • 0'
    • 2006 / Used
    • $54,995

    A true weekend cruiser with overnight accommodations, a full galley and plenty of cockpit space for entertaining on the water.Highlights: Twin MerCruiser 4.3L Sterndrives 440 HP T... View Details

    View 31 Photos and Details Contact Seller
    $54,995
    VIEW DETAILS
  • 2007 Chaparral 290 Signature

    2007 Chaparral 290 Signature

    $47,995
    Oshkosh, WI
    • Oshkosh, WI
    • Cruiser
    • 0'
    • 2007 / Used
    • $47,995

    A spacious express cruiser set up for weekends aboard, with comfortable overnight accommodations and thoughtful upgrades throughout.Highlights: 440 HP Upgraded Isotherm Cockpit Re... View Details

    View 40 Photos and Details Contact Seller
    $47,995
    VIEW DETAILS
  • 2006 Rinker 360 Fiesta Vee

    2006 Rinker 360 Fiesta Vee

    $79,995
    Oshkosh, WI
    • Oshkosh, WI
    • Cruiser
    • 0'
    • 2006 / Used
    • $79,995

    Big-Block Power, Spacious Overnight Accommodations & a Cockpit Built for Entertaining This 2006 Rinker 360 Fiesta Vee is a substantial express cruiser that offers the space and ame... View Details

    View 40 Photos and Details Contact Seller
    $79,995
    VIEW DETAILS
  • 1998 Cruisers 2870 Rogue

    1998 Cruisers 2870 Rogue

    $39,995
    Oshkosh, WI
    • Oshkosh, WI
    • Cruiser
    • 0'
    • 1998 / Used
    • $39,995

    Documented repower featured by Boating Magazine! Extensively updated express cruiser with major mechanical improvements and refreshed onboard comforts. Highlights: Twin MerCruiser... View Details

    View 40 Photos and Details Contact Seller
    $39,995
    VIEW DETAILS
  • 2024 Trophy T25 EXPLORER OB

    2024 Trophy T25 EXPLORER OB

    $139,995
    Oshkosh, WI
    • Oshkosh, WI
    • Cruiser
    • 25'
    • 2024 / New
    • $139,995

    2024 Trophy T25 EXPLORER OB Discover the thrill of adventure with the stunning 2024 Trophy T25 EXPLORER OB, now available at SkipperBud's Oshkosh in Oshkosh, WI. This luxurious ves... View Details

    View 16 Photos and Details Contact Seller
    $139,995
    VIEW DETAILS
  • 2026 Other Ray SLX 280 Outboard

    2026 Other Ray SLX 280 Outboard

    $500
    Oshkosh, WI
    • Oshkosh, WI
    • Cruiser
    • 28'
    • 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 101 Photos and Details Contact Seller
    $500
    VIEW DETAILS
Showing 22 to 40 of 40 boats found.
Prev Next

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.