Sailboats For Sale in Maryland

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1984 Passport 40 in Tracys Lndg, MD

149,900.00 USD

Sailboats For Sale in Maryland by owner | 1984 Passport 40

 

Used Sailboat for sale by owner
Location: Tracys Lndg, MD
Remarks: Manitou has been well maintained by her previous and current owners. A recent survey values Manitou at the top end of P 40s at $154,000. Some of the most recent updates include:... (read more)

Sailboats For Sale in Maryland by owner | 2003 Island Packet 485

 

Used Sailboat for sale by owner
Location: Rock Hall, MD
Remarks: Island Packet 485 Priva Sea V is a beautiful vessel resonating with the renowned qualities and features of Island Packet's flagship along with the conscious care and improvements ... (read more)

Sailboats For Sale in Maryland by owner | 1999 Amel Super Maramu 2000

 

Used Sailboat for sale by owner
Location: Easton, MD
Remarks: Immaculately maintained Amel Super Maramu 2000 ocean cruiser ready to sail anywhere. Lots of upgrades including enclosed cockpit enclosure, solar array on a davit rigged tower, pvc... (read more)

Sailboats For Sale in Maryland by owner | 1978 Westsail 42

 

Used Sailboat for sale
Location: Middle River, Maryland
Remarks: Stock #417211 Reason for selling is Not Using it. . ANY and ALL offers will be put in front of our seller! Submit your offer today! Nice Westsail Cruiser! These boats have sail... (read more)

Sailboats For Sale in Maryland by owner | 1988 Pearson Pearson 33-2

 

Used Sailboat for sale by owner
Location: Cambridge Marina
Remarks: Watercolor 2 is the Wing keel version with a continuous reefing system with all halyards led aft, this means you can reef the mainsail without leaving the cockpit. Features an encl... (read more)

Sailboats For Sale in Maryland by owner | 1970 CAL 39'

 

Used Sailboat for sale
Location: Baltimore, Maryland
Remarks: Stock #247131 Video of this vessel available at www [dot] popsells [dot] com/view/247131 Reason for selling is owner is out of state so not much use . ANY and ALL offers will b... (read more)

Sailboats For Sale in Maryland by owner | 1988 Performance Cruising 3000 Gemini

 

Used Sailboat for sale
Location: Severn, Maryland
Remarks: Stock #460811 This Performance Cruising has recently been added to market (Aug 1st). Submit your offer today! The performance of the Gemini is unmatched in the coastal and offsho... (read more)

Sailboats For Sale in Maryland by owner | 1985 Sabre Mark 1

 

Used Sailboat for sale
Location: Baltimore, Maryland
Remarks: Stock #301168 Reason for selling is Not Using . ANY and ALL offers will be put in front of our seller! Submit your offer today! Excellent Cruiser. Many updated features. Ready ... (read more)

Sailboats For Sale in Maryland by owner | 1981 Tartan T33

 

Used Sailboat for sale
Location: Saint Leonard, Maryland
Remarks: Stock #428252 Reason for selling is Not enough time to use . ANY and ALL offers will be put in front of our seller! Submit your offer today! Beautiful, Well Equipped, Very Nice... (read more)

Sailboats For Sale in Maryland by owner | 1981 32 foot Pearson Sloop

 

Used Sailboat for sale by owner
Location: Lynch, MD
Remarks: Great Boat, just getting too old for it.27

Sailboats For Sale in Maryland by owner | 1983 Hunter 34

 

Used Sailboat for sale
Location: Deale, Maryland
Remarks: Stock #432668 ANY and ALL offers will be put in front of our seller! Submit your offer today! 1983 HUNTER 34 CRUISER READY TO SAIL AWAY! You have been asking for this 1983 Hunte... (read more)

Sailboats For Sale in Maryland by owner | 1985 Ericson Yachts 32

 

Used Sailboat for sale
Location: Cobb Island, Maryland
Remarks: Stock #323583 Reason for selling is No longer using . ANY and ALL offers will be put in front of our seller! Submit your offer today! Classic sailing yacht! Updated electronics... (read more)

Sailboats For Sale in Maryland by owner | 2002 MacGregor 26X

 

Used Sailboat for sale by owner
Location: Annapolis
Remarks: Engine • 50HP EFI Mercury Big Foot with oversized shaft and propeller (manufactured by Yamaha) • New water pump • New fuel hose and primer bulb • Steering system clean... (read more)

Sailboats For Sale in Maryland by owner | 1989 Hunter 30

 

Used Sailboat for sale
Location: North East, Maryland
Remarks: Stock #285844 Reason for selling is No time to use. . ANY and ALL offers will be put in front of our seller! Submit your offer today! Beautiful classic Sloop Ready for a sailor... (read more)

Sailboats For Sale in Maryland by owner | 1981 Pearson 28

 

Used Sailboat for sale by owner
Location: Georgetown, MD
Remarks: A really nice racer/cruiser that I really enjoyed refitting and sailing. This Pearson 28 handles very well in light to moderate winds. I have maintenace records of the last 10 year... (read more)

The Truth About Boating in Maryland: What Tourist Guides Won’t Tell You - Article Summary

Our article on boating in Maryland by Captain Bill Rountree offers a detailed guide and can be found at the link below. Boating in Maryland offers scenic views and exciting destinations like the Chesapeake Bay, Deep Creek Lake, and Baltimore’s Inner Harbor. However, the reality is far more complex than tourist brochures suggest. Boaters face strict regulations, unpredictable weather, and a local boating culture shaped by unspoken rules. Understanding both the law and local customs is key to having a safe and enjoyable experience on Maryland’s waters.

To legally operate a vessel in Maryland, anyone born after July 1, 1972, must carry a Certificate of Boating Safety Education. While some visitors are exempt (such as out-of-state boaters staying under 60 days), fines for noncompliance can reach $500. Boating under the influence is treated as seriously as drunk driving, with penalties including jail time and steep fines. Beginning in 2025, Maryland will link boating DUIs with driving records, raising the stakes even higher.

Tourist hotspots like Baltimore’s Inner Harbor, Assateague Island, Solomons Island, and Gunpowder Falls each present unique challenges. The Inner Harbor is beautiful but congested, especially during summer and events like Harbor Fest. Assateague has hidden sandbars and strict wildlife regulations. Solomons Island suffers from limited dock space and narrow channels. Gunpowder Falls may seem peaceful, but it’s under-patrolled and has hazardous underwater debris. Local knowledge and preparation are essential at all these locations.

Beyond official rules, unspoken cultural expectations shape the boating experience. Local boaters often expect visitors to yield, even when navigation rules suggest otherwise. Fishing zones are another flashpoint. Longtime anglers have unofficial claims to spots—especially near the Chesapeake Bay Bridge and Point Lookout—and new boaters should ask before anchoring nearby. Seasonal events such as the Eastport Yacht Club Lights Parade or Tilghman Island Workboat Races can also disrupt access and create temporary no-entry zones that surprise unaware visitors.

Maryland enforces safety equipment requirements strictly. Every vessel must have enough Coast Guard-approved life jackets, and kids under 13 must wear them while underway. Fines also apply for missing fire extinguishers, flares, and sound-producing devices. Registration and titling can be confusing as well, especially since Maryland requires both for many vessels, even if they are U.S. Coast Guard documented.

Experienced Maryland boaters recommend avoiding crowded summer weekends. Spring and fall offer better conditions and fewer crowds, while early weekdays are ideal for peaceful boating. Afternoon thunderstorms are common in summer, and boaters must plan around sudden weather changes. Apps like Navionics, C-MAP, KnowWake, and Maryland’s DNR app are invaluable tools for navigation and safety.

Ultimately, the key to successful boating in Maryland lies in preparation and respect—for both the rules and the local culture. A friendly wave, yielding to locals, and avoiding conflict at popular fishing spots can go a long way. Maryland’s waterways are rich with beauty and adventure, but only for those who are informed and considerate. With the right mindset and knowledge, visitors can enjoy unforgettable boating experiences far beyond what any tourist guide promises.

Click here to read our entire article - The Truth About Boating in Maryland: What Tourist Guides Won’t Tell You