Sailboats have cruised the world’s lakes and oceans for centuries and remain popular among many skilled and dedicated watermen and women. They require a degree of skill and an awareness of the wind and weather while offering a traditional and exhilarating boating experience. Search for new or use... learn more about Sailboats
6,050 New and Used Sailboats
Charleston, SC (United States of America)
45.01 ft.
2011
Used
The VPLP architects, together with Lagoon and the Nautadesign office, succeeded beautifully in developing a new 45 catamaran to replace the famous Lagoon 440. Of course, the irreplaceable qualities of the Lagoon 440 have been retained as a starting point: a steering station on the fly ...
$475,000
Bradenton, Florida (United States of America)
54.99 ft.
1991
Used
She is ready to get in and sail away! This lovely 1991 Tayana 55 Sloop is fully equipped and ready to cruise! NEW BOTTOM PAINT JUNE 2020 Three staterooms (two forward double bunks, aft MASTER stateroom with centerline QUEEN bed), THREE heads with 2 new manual toilets toilets, HUGE gall...
$225,000
Charleston, SC (United States of America)
43.01 ft.
2005
Used
Video Tour
TAO is one of the last Catana 43OC (hull #57) built with the superior options and a high specification featured in this model: carbon mast, Cherry wood and Corian finishes. The 43OC was the evolution of the Catana 431, one of the most successful and popular Catana models. It offers the...
$325,000
Punta Gorda, FL (United States of America)
41.99 ft.
2019
Used
Step aboard the 2019 Lagoon 42 Owner's Version "Dedicated," a meticulously maintained vessel that embodies both luxury and functionality. With a spacious three-cabin, three-head layout, this catamaran is in pristine condition and ready to embark on its next adventure. The Lagoon 42 OV ...
$540,000
Tampa, FL (United States of America)
39.44 ft.
2018
Used
Recent additions/upgrades (All added in December 2024): New 3/8 Anchor Chain - 150' Raymarine Quantum 2 Doppler Raymarine AIS 700 Spectra Cape Horn Extreme 3...
$400,000
Dania Beach, FL (United States of America)
39.99 ft.
2020
Used
2020 ROBERTSON AND CAINE LEOPARD 40 - 3 Cabin - Mai Pen Rai BUILDERS REMARKS: The Leopard 40, a product of South African boat builders Robertson & Caine, featur...
$459,000
Fort Pierce, FL (United States of America)
43.41 ft.
2017
Used
Single owner, 4 cabin Helia 44 available now and priced to sell! Professional photos scheduled for 2/10/2025 Alisei is currently having her bottom painted and hull and topsides waxed in the Safe Harbor yard in Fort Pierce, splashing 2/7/2025 Alisei was professionally operated by the St...
$519,000
Fort Lauderdale, FL (United States of America)
45.01 ft.
2024
New
Only Leopard 45 hybrid to be built! Electric Propulsion System with 2 x 25KW electric motors / 2 x 27KW lithium batteries / 1 range extending 24KW generator / 2KW Fl...
P.O.A.
Beaufort (United States of America)
40.0 ft.
2000
Used
Classic Blue Water Cruiser – Outfitted for transoceanic voyage.. Unruly Julie is ready to set sail on your next great adventure. The current owners have her ou...
$95,000
Rock Hall, Maryland (United States of America)
38.48 ft.
2009
Used
Anastasia Marie is a textbook example of an excellently maintained vessel!!! The Catalina 375 embodies so many wonderful features like separate stall shower, convertible game table in the salon that's perfect for breakfast or cocktail time and center-line queen forward that can be con...
$169,000
Dunedin, Florida (United States of America)
35.99 ft.
2000
Used
36 MkII 4.5' Winged Keel is a dream while cruising, a proven and tested cruiser ! If you are in the market for a cruiser, look no further than this 2000 Catalina 36 MkII, priced right at $66,700 (offers encouraged). This vessel is located in Dunedin, Florida and is in great condition...
$66,700
Placida, Florida (United States of America)
41.99 ft.
1992
Used
1992 DNIEPER 1200!! GALVANIZED STEEL HULL! HYDRAULIC CENTERBOARD! A BEAUTY ON THE WATER! 1992 Dnieper Tropic 1200 This Dnieper is a professionally yard-built Tropic 1200. The hull is flame sprayed galvanized steel. Designed by a mixture of Joubert and Carroff and built by Dinnieper...
$88,900
Ruskin, Florida (United States of America)
37.99 ft.
1990
Used
Make This Spacious Classic Your Own Reliable Yanmar 4JHBE 44 HP Engine with only 1580 hours Enjoy the reliability and parts availability of the Yanmar reputation. T...
$110,000
New Orleans, Loui... (United States of America)
43.08 ft.
2008
Used
Video Tour
Step aboard a vessel that truly stands apart: the 2008 Island Packet 41 PY Trawler, transformed into a one-of-a-kind motorsailer. Originally designed as a trawler, this rare model has been professionally enhanced with a mast and rigging installed by Mack Sails, adding stability and eff...
$199,000
Stuart, Florida (United States of America)
33.33 ft.
1993
Used
33' Hunter 33.5 1993 with lots of Care and Upgrades Hunter Marine has combined contemporary styling, performance and a very roomy interior for the 33.5, fractional r...
$37,000
Branford, Connect... (United States of America)
27.99 ft.
1991
Used
Brilliant is a classic Morris Linda 28 that has undergone a complete refit in 2022 and 2023.As a practical matter she is as close to new without building her fr...
$129,999
Oriental, North C... (United States of America)
36.32 ft.
1998
Used
COOL CHANGE is a quintessential Catalina 36 MK II with a combination of factory features and owner upgrades. She has lived in the Oriental area for more than 15yrs an...
$69,000
Saint Augustine, FL (United States of America)
44.16 ft.
2023
Used
This is your opportunity to purchase a gorgeous example of the award-winning Balance 442 catamaran! "Kiwa" is fully equipped and ready to go sailing today.She was originally launched in Cape Town, South Africa in 2023 and is hull #8 of this coveted high-performance brand.Kiwa has recen...
$1,380,000
Cape Charles, VA (United States of America)
41.5 ft.
2007
Used
Farrier F-41 2007 Sea Joy is a well-equipped performance cruising catamaran ready to take her new owners to desired destinations in speed and comfort! Sea Joy is cu...
$254,000
Fort Lauderdale, ... (United States of America)
45.73 ft.
2006
Used
Video Tour
A spectacular example of the Island Packet 440, MAWE has had just two owners since new and the yacht has been impeccably maintained over the past 18 years to better-than-new status.The lengthy equipment and upgrade list that follows demonstrates the current owner’s love, knowledg...
$400,000
Sandusky, Ohio (United States of America)
31.99 ft.
1992
Used
1992 Island Packet - 32 Fresh Water - A/C - Only 179 hours With classic good looks, exacting craftsmanship, and reliability and trouble-free service second to none, ...
$69,900
Rock Hall, Maryland (United States of America)
41.5 ft.
1988
Used
This Island Packet has been one of the most popular IP models among cruisers. With her being the first 2 head models and a owners cabin with private head, an abundance of storage and a very comfortable salon. She is as comfortable at anchor as she is underway. Joyful Wings is a one own...
$125,000
Gulfport, Florida (United States of America)
40.91 ft.
2008
Used
With a watertight collision bulkhead forward, water-tight rudder dam, smart charging and fuel management systems, and a convertible cutter rig for handling any sailing conditions, she is well equipped to take care of owners no matter where they may call their cruising grounds. ...
$219,900
Annapolis, Maryland (United States of America)
43.96 ft.
1988
Used
Available now, this classic, beautifully built blue water passagemaker has had many important upgrades over the last few years. More Images and details coming soon!
$165,000
Bainbridge Island... (United States of America)
37.01 ft.
1978
Used
Video Tour
CRUISE THE SOUND OR HIT THE HIGH SEAS IN THIS SOLID BUILT1978 RAFIKI CUTTER!! The classic 1978 Rafiki 37 Cutter Style Sailboat is a true blue-water cruiser designed by renowned yacht designer Stan Huntingford, famous for his elegant canoe stern designs. Pride of ownership is on displ...
$73,400
Pasadena, Florida (United States of America)
33.99 ft.
2001
Used
Specifications ACCOMODATIONS Spacious V-berth forward with lots of storage. The convertible dinette is to port and when fully extended will seat up to eight people. Directly across to starboard is a settee. Aft to port is the spacious galley. Reverse cycle air conditioning keeps ever...
$59,000
Stuart, Florida (United States of America)
38.09 ft.
1982
Used
Kadey Krogen 38 Tandem Centerboard We are pleased to present the well-updated 38 Kadey Krogen. The 38 Kadey Krogen is a centerboard gunkholer. Living and working on ...
$84,900
Westbrook, Connec... (United States of America)
31.99 ft.
1975
Used
Alice's has 10 brass opening ports and a forward hatch for superior ventilation while on anchor or at the dock.Two deck prisms are mounted in the main cab...
$39,999
* Price displayed is based on today's currency conversion rate of the listed sales price.
Sailboats have cruised the world’s lakes and oceans for centuries and remain popular among many skilled and dedicated watermen and women. They require a degree of skill and an awareness of the wind and weather while offering a traditional and exhilarating boating experience. Search for new or used sailboats for sale in your area in all sizes and prices to begin your journey.
A sailboat is classified as any boat that harnesses the power of the wind for propulsion. In real terms, this covers a huge variety of vessels, from small sailing dinghies to daysailers, single-masted boats, twin-masted boats, racing sailboats, and sailing superyachts. Depending on the size of the sailboat, it might have cabins, a galley, one or more heads, or more simply a small covered space for storage.
Sailboats were traditionally constructed of wood, and it is still possible to find brands producing classic wooden hulls. However, these days most sailboats are made from materials such as fiberglass, aluminum, and even carbon fiber.
When it comes to sails, rigging configurations are widely varying and are used to further classify sailboats into their relevant categories. Likewise, the keel of a sailboat can vary, from a full keel to a fin keel, or catamarans which have twin hulls with or without significant keels or daggerboards.
Sloops make up the largest segment of sailboats and are characterized by a single mast rig that commonly has a triangular mainsail and a headsail. They are popular with beginners who find their rig simple to handle, but also with sailing pros who enjoy their ease of maneuverability. They are also frequently seen as racing boats thanks to their speed and good windward performance. They can be of any length from an 8-foot pram to a 258-foot superyacht and are often versatile with regards to their layout and ability to cruise in many conditions.
Although similar in appearance to the sloop, a cutter has markedly different rigging with two headsails (a headsail and a staysail). This allows for good control and stability, especially in adverse weather, although it makes it a little more complicated to sail. Cutters also commonly have a spar extending from the bow known as a bowsprit.
Large schooners have been around for centuries and are characterized by their multiple masts. They were originally designed for fishing or offshore voyages and able to handle even the roughest of sea conditions but often require more crewmembers to handle the complex rigging.
These two-masted sailboats are similar in their appearance as they have a mainmast in front that is taller than the mizzenmast behind it. The difference lies in the positioning of the mizzen—behind the rudder post on the yawl and forward of it on the ketch. In general they are not as fast upwind as a sloop sailboat, but because of their shorter masts and smaller sails they often better suited to handling rough sea conditions. They can vary in size and often make good long-range sailboats.
The smallest sailboats are dinghies and daysailers, which are ideal for beginners or fun days out on protected waters. They are easily trailerable and simple to rig and handle. Dinghies are 8 to 18 feet in overall length, while daysailers can be small or quite a bit larger, accommodating more passengers. Both have a single mast, although the rigging can vary widely.
The motorsailer uses a combination of wind power and engine power. While these are less common than sailboats and motorboats thanks to their higher price, they can offer the best of both worlds with the space and ability to power against the wind like a motor boat and the wind power of a sailboat that can increase its range and even invite its sailors to turn off the engine when conditions are right. They are popular for long-range cruising and long-term living.
Catamarans are double-hulled vessels with a shallower draft than monohull sailboats. Small catamarans are fun and fast, sailing right off the beach. Larger catamarans provide much more deck and interior space thanks to their wide beam, and larger models have cabins in both hulls with a spacious living area above the waterline. They don’t heel or tip the way monohulls do and are typically more stable except in extreme windy or wavy conditions
Listing the best sailboats brands is no easy feat as there are hundreds of excellent builders to choose from. There are brands currently producing new sailboats as well as those many that are no longer in operation but whose boats are available on the used market.
Some of the top brands of sailboats include long-time builders such as Catalina, Jeanneau, Tartan, Beneteau, and Hallberg-Rassy, the latter who are known for their blue water yachts.
Other brands worth mentioning are Hobie and their ultra-popular dinghy catamarans, Lagoon Catamarans, Hinckley Yachts, and Dufour to name just a few.
Sailboats give sailors the quintessential boating experience. They offer the chance to learn new skills together as a family, whether it’s on a small dinghy-sized sailboat for beginners, or a larger yacht that you might one day sail you around the world. Sailboats can be purchased for very different price points and styles to suit all skill levels.