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Used Daysailer in Florida, USA

  • Trusted Seller
    2023 Hallberg-Rassy d1-30

    2023 Hallberg-Rassy d1-30

    • Manufacturer: Hallberg Rassy
    • Hours: 216 h
    • Fuel type: diesel

    Hallberg-Rassy 340, the latest stunning 34-footer from Rassy, is more spacious, faster, and more comfortable than ever before. Exceptionally well-built from 2023 and in like-new condition. The current owner order...

    East Coast of the United States, USA
  • Trusted Seller
    1978 Herreshoff Meadowlark 37

    1978 Herreshoff Meadowlark 37

    • Manufacturer: Herreshoff
    • Lifting capacity: 4 kg
    • Fuel type: diesel

    L. Francis Herreshoff Design! Shoal draft with Lee Boards Recent Sails! Yanmar 24 HP! Stock #445947 Reason for selling is "Moved out of area". ANY and ALL offers will be put in front of our seller! Submit your ...

    $25,000 USD

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    Est. $471/mo

    Bradenton, FL
  • Trusted Seller
    2021 Flying Scot 19

    2021 Flying Scot 19

    • Manufacturer: Flying Scot
    • Fuel type: electric

    Well maintained 2021 Flying Scot 19 sailboat! Ready to hit the water! Stock #459151 Reason for selling is "Not Using enough". ANY and ALL offers will be put in front of our seller! Submit your offer today! 202...

    $23,000 USD

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    Est. $433/mo

    Sarasota, FL
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    2025 2025 J BOATS J/9 HULL #52

    • Manufacturer: Hull

    Gt: 0 | Crusing/max speed: / | Engines: Yanmar 2YM15 15hp 0hrs | Builder: J BOATS | Flag: United States | Length: 28' (8.53m) | Beam: 2.56M | Draft: 1.49M | Hull: Fiberglass

    Bal Harbour, FL
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    2001 2001 TOFINOU 7M

      A very nice example of this wonderful daysailer. We delivered this boat to the owner when new and it has been well cared for all these years. Delivered from the Thousand Islands area of upper state NY, she has ex...

      $35,000 USD

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      Est. $659/mo

      Bal Harbour, FL
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      2009 MAHALIA

        Friendship 40, Hull No. 18 Absolute unrivaled quality is synonymous with the Friendship Yacht Company. Incorporating many elements from his large custom yachts, designer Ted Fontaine has created the FRIENDSHIP 40...

        $735,000 USD
        Bal Harbour, FL
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        2015 FILLY

          FILLY is a pristine W-22 daysailer that perfectly blends classic design with exceptional sailing performance. Crafted by Artisan Boatworks in Rockport, Maine, and designed by Joel and Steve White, she features a ...

          $49,500 USD

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          Est. $932/mo

          Bal Harbour, FL
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          2023 DAY DREAM

            Ocean Voyager 64 Offer a memorable experience with a 2023 Ocean Voyager 64 catamaran, a vessel with a maximum capacity of 92 passengers. Its shape, with a width of 10 meters, makes it even more stable than other ...

            $1,736,987 USD
            Bal Harbour, FL
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            2024 WELCOME

              "As new" Dutch masterpiece with stunning lines and outstanding sailing performance.

              $505,000 USD
              Bal Harbour, FL
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              2026 2025 EAGLE 44

              • Manufacturer: Eagle

              Leveraging on the successes booked and experience gained with the Eagle 36, Leonardo Yachts decided to take day sailing to the next level. The Eagle 44 is designed by Gerard Dykstra & Partners where the designers...

              Bal Harbour, FL
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              2007 ANTILLANO

                Upgrades and features: New Volvo Penta D1 30hp installed in 2016 Bow Thruster Garmin model 3210 GPS map Raymarine ST6002 autopilot Raymarine model ST60 Plus speed wind and speed, depth Cockpit shower with hot and...

                $295,000 USD

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                Est. $5,552/mo

                Bal Harbour, FL
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                2024 WISP

                  Fresh off the drawing board of the renowned Stephens Waring Yacht Design in 2024, WISP is a fresh take on a gentleman’s/woman’s day sailer .

                  $1,100,000 USD
                  Bal Harbour, FL
                • 2025 Maxus EVO 24 |

                  2025 Maxus EVO 24 | 24ft

                  • Manufacturer: Saic
                  • Lifting capacity: 10 kg

                  Discover the Maxus EVO 24: The Perfect Compact Cruiser Looking for a sailboat that offers the perfect blend of performance, versatility, and comfort, all in a compact package? Meet the Maxus EVO 24, a game-change...

                  $111,496 USD

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                  Est. $2,098/mo

                  Miami, FL
                • 2025 Maxus 35 | 35ft

                  2025 Maxus 35 | 35ft

                  • Manufacturer: Saic

                  Introducing the Maxus 35: Your Perfect Companion for Sailing Adventures Looking for a versatile, performance-driven sailboat that combines comfort, elegance, and ease of handling? The Maxus 35 is your answer. Des...

                  $220,000 USD

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                  Est. $4,140/mo

                  Miami, FL

                Overview

                Daysailers are small, nimble sailboats built for short outings, day trips, and casual coastal sailing. Usually 14–26 feet long, they focus on easy handling, simple rigs, and quick launch rather than extensive overnight comforts. With cockpit-centered layouts and modest storage or tiny cabins, daysailers suit single-handed sailors, small crews, club racing, or relaxed sails near shore.

                FAQ

                What should I check before buying a used daysailer?

                Inspect the hull for cracks or blisters, check keel and rudder condition, examine deck for soft spots (delamination), review standing and running rigging, assess sails for UV or tear damage, test any engine/outboard, and verify trailer condition if included. A pre-purchase survey is recommended.

                How can I ship or transport a daysailer safely?

                Smaller daysailers can be trailered; measure beam, weight and mast length for legal permits. For larger moves use a marine transport company with proper cradles and lifting gear. Secure rigging, remove loose gear and protect the cockpit and sails during transit.

                What routine maintenance does a daysailer need?

                Regularly rinse and dry the boat, inspect and lubricate blocks and winches, check rigging tension and fittings, clean and repair sails, and keep the hull antifouled if kept in saltwater. Replace worn lines and inspect the hull annually.

                Do I need to winterize a daysailer?

                Yes—haul out if possible, drain and flush the bilge and engine cooling system, remove and store sails and electronics, ventilate any enclosed spaces, and use shrinkwrap or indoor storage to protect from weather and UV.

                Are surveys, registration, and insurance necessary?

                A pre-purchase survey helps identify hidden issues. Registration requirements vary by region—check local authorities. Insurance is recommended for damage, liability, and transport coverage.