Used Bluewater and Coastal Cruising Sailboats for Sale

$59,500 - St. Petersburg

A used 1976 - Cecil Norris Staysail Ketch with her Ferro-Cement hull provides for a very dry boat. AC, Generator & spacious interior.

$319,000 - Punta Gorda, FL

Gorgeous Gulfstar Motorsailer updated and ready to go. This Gulfstar 54 is spacious and luxurious yet sturdy and dependable for cruising around the world. If you're looking for a blue water sailboat, check her out!

$138,600 - Bradenton, FL

This used 1975 Gulfstar Motorsailor Ketch offers the best of both worlds for the cruising lifestyle. Well equipped with AC, generator, bow thruster, watermaker and more! Great Liveaboard potential.

$199,400 - Amelia Island, FL

Get ready to go cruising in this used Tayana sailboat. She's been well maintained and equipped with electronics and gear to make cruising the world safe and comfortable. Roller furling sails and much more!

$849,000 -

The new Outbound 52 yacht is a true bluewater cruiser with everything you've dreamed of. Whiteaker Yacht Sales is the Southeast dealer for Outbound Yachts and has these sailboats available for order-placement and construction.

$189,000 - St. Petersburg, FL

Used bluewater cruising yacht, this 50 ft Catalina has three staterooms, wing keel, spacious cockpit and more.

$379,000 - Longboat Key, FL

This used Tayana sailboat is a top of the line blue-water cruising yacht. A joy to sail, fast and stable boat.

$39,900 - Beaufort, SC

Beautiful custom Eldridge-McInnis used sailboat that will sweep you back in time. This 1930's boat is in the process of being restored and could be yours to make into a classic cruiser.

$159,900 - Port Charlotte, FL

A used 47' Vagabond Cutter Ketch with AC, generator, watermaker and more! Easily handled by a couple and ready to sail away today!

$128,000 - Isle of Palms, SC

Nicely upgraded and rare to the used market is this beautiful used Irwin Center Cockpit. Perfect for coastal cruising, island hopping in the Caribbean, or as a live aboard boat.

$495,000 -

The new Outbound 46 yacht is an outstanding bluewater cruiser. Whiteaker Yacht Sales is the Southeast dealer for Outbound Yachts and has these sailboats available for order-placement and construction.

$349,000 - NS, Canada

This used Outbound 44' is a solid blue water cruiser, and a "Rare Find" on the used boat market. She is loaded with gear and ready to take you anywhere your heart desires.

$139,900 - Brunswick

A used 1990 Morgan Center Cockpit lovingly maintained, loaded with cruising gear like AC, Generator, NEW U.S roller furling main mast, All NEW Norseman rigging and NEW mainsail, ready to cruise anywhere.

$198,800 - Brunswick, GA

A used 1988 Mason Cutter well maintained with spacious & comfortable cruising layout & loaded with long range cruising gear like AC, generator, nice electronics, Loads of storage space.

$95,000 - Cape Coral

A used Seawolf Ketch loaded with extra cruising equipment and upgrades such as AC, electronics, watermaker, Custom Built deckhouse and more!

$169,000 - Palmetto, FL

This beautiful example of the Jeanneau Deck Salon 42 shoal draft boat is the perfect coastal cruiser or she is ready to take you on extended cruising trips to the Caribbean and beyond.

$149,900 - Panama

Sapphire is a Tayana 42 Center Cockpit sailboat that has been exceptionally well equipped as a cruising sailboat. Start your cruising lifestyle on this beauty in the Caribbean or sail her around the world.

$159,000 - Punta Gorda, FL

One of Catalina's most successful models, the Catalina 42 Mark II is a great coastal cruiser or perfect for island hopping in the Caribbean. She is safe, comfort, and easy to handle.

$142,000 - St. Petersburg, FL

A used 1998 Catalina MKII with the ever popular 2 Stateroom/2 head layout. Raymarine electronics, Wind generator, solar panels are just a few features

$179,500 - St. Mary's, GA

A used 2006 Hunter Deck Salon loaded with cruising gear like 2 Marine AC systems, Fuel polishing system, Upgraded electronics, Northern Lights generator, Bose entertainment system, and so much more...

$79,000 - Palmetto, FL

This is one of the most beautiful Irwin's on the market. This classic beauty is well maintained and is the perfect cruising sailboat prepared now to take you around the world or she would be the perfect live aboard sailboat.

$99,000 - St. Petersburg, FL

Beautiful Classic Sailboat! You will fall in love with the classic lines on this Bayfield Cutter Ketch. But she has more than just good looks. She is a very capable blue water cruising sailboat.

$119,900 - Cushing, ME

Custom yacht by Chuck Paine is a sailor's dream come true. World class sailing yacht that truly stands out from the crowd.

$119,000 - Punta Gorda, FL

A used 2002 Beneteau 393, 2 Cabin layout, loaded with upgrades like new color chartplotter, new sails, new opening portlights, 2 CruisAir systems and SO much more..

$79,900 - Longboat Key, FL

Offshore blue water sailing cruising used Vagabond sailboat. "Eagles Wings" is comfortable, heavily built with a moderate draft.

$84,900 - Sarasota, FL

Used 1983 Krogen 38' Cutter with only 3' shoal draft. Spacious & well equipped with AC, Autopilot,GPS and classic lines, ready to sail away today.

$99,350 - Panama City, FL

Used Jeanneau 37 foot sailboat that has room for the entire family. Well equipped and lots of room for storage.

$49,900 - Sarasota

A used & very rare, 1994 Four Winns Express Cruiser. One of only 4 built with diesel engines! Low Hours, professionally maintained with generator, twin AC units, new isenglass and much more.

$129,000 - Brunswick, GA

This Used Prout Snowgoose 37' Sailing Catamaran is a joy to sail and equipped w/ features like Generator, Electric Windlass, Watermaker and much more.

$84,900 - Bradenton, FL

This 2002 Bavaria 36 yacht is a rare find on the used boat market. Gibson Girl has been to the Bahamas and has many outstanding features for cruising.

$134,900 - Tierra Verde

Spirit is a nice example of the classic model - the Sabre 362. From her beautiful flagblue hull to her clean and well maintained teak interior she will inspire you to live the sailing lifestyle.

$89,900 - St. Petersburg, FL

A used TaShing Baba 35 Cutter with exceptional brightwork, AC, generator, GPS, chartplotter, EPIRB ready to go Blue Water sailing NOW!

$137,900 - Placida, FL

Used Pacific Seacraft 34 sailboat, Eileen, is a beautiful cruising boat ready for you to add your belongings and sail away.

$69,000 - Punta Gorda, FL

This used 34 foot Hunter sailboat gives you the best of both worlds; racing and cruising. Several race victories attest to this boat's performance.

$74,900 - Bradenton, FL

This used 34' Catalina MKII is well equipped and ready to sail today.

$44,900 - Bradenton

A used 1987 34' Catalina Sloop, well maintained & equipped with Auto pilot, GPS & wind, depth, speed. Perfect size for family cruising.

$29,900 - Palmetto

A Rare to the market, used 34' O'Day Sloop with shallow 4'3" draft, recent refit with loads of upgrades and ready to sail away today.

$64,900 - Hobe Sound, FL

Used Beneteau 331 sailboat that is fun, fast and affordable! Equipped with mast furling main, autopilot and Profurl Genoa furler and the advantage of a shoal draft.

$104,900 - Dataw Island, SC

One of the last Nonsuch 33's sailboats made, Semper Fi is hull number 66 built by the Hinterhoeller yard in 1993. New cushions, standing and running rigging, low hour Yanmar engine and more.

$44,900 - St. Petersburg

Rare to the market this 33' used CSY sailboat is ready to cruise now. Low engine hours and a completely updated interior at a very low price.

$34,000 - Palmetto, FL

Used classic sailboat with shoal draft and centerboard. Ready for cruising Florida, Keys and the Bahamas. Recently new Yanmar engine with low hours.

$39,900 - Brunswick, GA

A used 1975 - 32' Westsail Cutter in exceptional condition with NEW standing and running rigging and fresh hull, deck & bottom paint. Priced to sell quickly.

$109,900 - Brunswick, GA

Rare to the market, this used PDQ 32LRC Catamaran is truly a Long Range Cruiser; with upgrades like Air Conditioning & a wide open, roomy interior.

$55,000 - St. Petersburg

A used 1978 31' Pacific Seacraft Mariah spacious for her size with a NEW solid teak sole, newer standing & running rigging, beautiful hard dinghy, and lots more..

$24,500 - Palmetto, FL

A used 1986 Catalina 30' coastal cruiser. Well maintained engine, autopilot, LED lights and Newer canvas.

$25,900 - Bradenton, FL

A used 1989 very popular Catalina Tall Rig equipped with autopilot, chartplotter, electric windlass & new dodger & bimini. Affordable and ready to cruise.

$27,500 - Graniteville, SC

A used 1988 Beneteau First 285 equipped with autopilot, newer trailer and everything you need from a weekend pocket cruiser!