Used Bluewater and Coastal Cruising Sailboats for Sale

$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.

$224,555 - 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.

$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!

$299,000 - Brunswick, GA

Used Swan sailboat that has been kept in freshwater for over 19 years. Sailing the Great Lakes has been her sailor's favorite pastime and this boat is a beauty that has been lovingly cared for.

$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.

$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!

$79,800 - Brunswick, GA

The Hunter Passage 42 has been one of Hunter's best selling yachts. This is a great boat for coastal cruising, sailing to the Bahamas or Caribbean, or living aboard in your favorite marina. If you're looking for an affordable boat option, this is a great value!

$175,000 - 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.

$109,000 - Cape Coral, FL

A used Tayana Vancouver 42' Center Cockpit Cutter Rig that is very well equipped and ready to go the distance!

$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.

$129,900 - 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.

$89,900 - Longboat Key, FL

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

$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.

$94,500 - Punta Gorda, FL

World class bluewater cruiser that has proven her worth in cruising the Caribbean, Liat is a beautiful used 37 foot Tayana sailboat.

$134,900 - 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.

$89,000 - 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.

$46,900 - St. Petersburg, FL

Outstanding example of the very popular and time tested Pearson model used sailboat. "Anne B" offers cruising comfort and safety as a Pearson 365 Cutter Ketch.

$34,900 - Beaufort, SC

Hannah Cole is a beautiful Alberg, a classic sailboat that has been completely updated. This classic cruising sailboat is ready now to take you on a romantic cruise anywhere you choose.

$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.

$74,900 - 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.

$84,900 - 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.

$32,500 - 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.

$69,900 - 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.

$49,900 - 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.

$114,900 - 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.

$76,400 - Dataw Island, SC

The Catalina 320 is a great coastal cruiser or perfect for island hopping. Cahoots is a clean and well maintained small cruising sailboat and is ONE OF THE BEST SAILBOAT BUYS ON THE MARKET!

$49,940 - Anna Maria Island, FL

Great example of the versatile Catalina 30 Mark III. Sea Rose is a nice coastal cruiser, weekender, or racing sailboat. Nicely equipped with marine air, marine refrigeration, autopilot, chart plotter, and electric anchor windlass.