Best Places to Sail in Maryland

The Best Places to Sail in Maryland: A Complete Guide to Chesapeake Bay's Premier Sailing Destinations

Maryland's Chesapeake Bay is a sailor's paradise, offering some of the most pristine and diverse sailing waters on the East Coast. Whether you're a seasoned sailor or just beginning your maritime journey, Maryland's waterways provide endless opportunities for adventure, relaxation, and exploration. From the bustling sailing capital of Annapolis to tranquil creek anchorages, discover the best sailing destinations that make Maryland a world-class cruising location.

Why Maryland is a Sailor's Dream

The Chesapeake Bay, the largest estuary in the United States, has established itself as a global sailing destination that showcases natural beauty and rich maritime history. With its rich maritime heritage, picture-postcard towns, and endless coves, creeks, and anchorages, few places on Earth offer sailing as easy and fantastic as the Chesapeake Bay.

The Bay's unique geography provides sailors with protected waters, gentle conditions, and hundreds of navigable tributaries perfect for exploration. Stretching 200 miles from Havre de Grace at the mouth of the Susquehanna River to the Virginia capes, the Chesapeake varies from 3 miles wide in the north to 25 miles wide in the southern reaches.

Annapolis: America's Sailing Capital

The Heart of Maryland Sailing

Annapolis earns its designation as America's sailing capital due to its connection with the United States Naval Academy and its rich marine history, highlighted by the famous Annapolis Boat Show. The city offers everything sailors need, including gear, parts, repairs, advice, and sails, making it a comprehensive maritime hub.

Once the capital of the United States, Annapolis stands as one of the most historic and beautifully preserved waterfront towns on the bay, featuring the gorgeous Maryland Statehouse, the Governor's Mansion, and the classic Naval Academy.

What Makes Annapolis Special

• Year-round sailing events: From Wednesday night races to major regattas, the sailing calendar stays full throughout the season

• World-class marine facilities: Sailors can explore Bacon Sails and Marine Supplies, a second-hand shop that's a must-visit for both bargain sailors and those seeking anything old and obscure

• Spa Creek mooring: On race nights, grabbing a mooring ball in Spa Creek offers an exhilarating experience as races end right in the mooring field

• Walkable historic downtown: Twisting streets lined with maritime houses, restaurants, and shops create an authentic nautical atmosphere

Sailing from Annapolis

The city provides ideal access to both the Severn River and South River, offering protected waters and numerous anchorages. The mooring field in Annapolis harbor operates on a first-come, first-served basis with convenient phone payment, and numerous marinas are available, though advance reservations are recommended.

The Severn River: Annapolis's Backyard

The Severn River offers some of the most sought-after sailing and waterfront living in Maryland. The Severn River serves as a haven for angling enthusiasts and sailing connoisseurs, providing miles of protected waters perfect for day sailing and overnight cruising.

Why Sailors Love the Severn

• Protected waters: Ideal for sailors of all skill levels

• Deep-water access: Accommodates both small sailboats and larger cruising vessels

• Proximity to Annapolis: Easy access to marine services and supplies

• Stunning scenery: Tree-lined shores and beautiful waterfront estates create picturesque sailing conditions

• Private dock communities: Many waterfront properties feature private piers and boat slips

The Severn connects directly to the Chesapeake Bay, making it an excellent launch point for longer cruises to destinations throughout the Bay.

St. Michaels: The Eastern Shore Gem

St. Michaels is a must-visit stop on the Bay, offering a charming colonial seaport town that's become a favorite among sailors and their families. This picturesque Eastern Shore destination combines maritime history with modern amenities.

Attractions and Amenities

The Chesapeake Bay Maritime Museum traces the geological, social, and economic history of the Chesapeake Bay through exhibits featuring sail-, steam-, and diesel-powered craft, with many historic boats on display at the museum's docks. The museum regularly invites guests aboard for short sails on the Miles River, offering unique opportunities to experience historic vessels firsthand.

The town features beloved restaurants and quaint shops throughout town, providing plenty of options for dining and exploring after a day on the water. The harbor offers excellent protection and a welcoming atmosphere for visiting sailors.

Wye River: Peaceful Perfection

The Wye River ranks as one of the most bucolic and peaceful settings around, offering special magic that eases the urban working grind and helps visitors achieve a Chesapeake Bay frame of mind.

Natural Beauty and Wildlife

This 16-mile-long tributary encircles a 2,800-acre wildlife refuge on Wye Island, located on the northern shore of the Miles River. The area is rife with bald eagles and great blue herons, offering remarkable opportunities to see amazing creatures in their natural habitats.

The Wye River provides easy access to fishing and crabbing destinations, making it a favorite cruising destination for many sailors. Those with smaller boats can explore areas not accessible to larger sailboats, adding to the sense of adventure and discovery.

Rock Hall: The Waterman's Town

Rock Hall sits on Chesapeake Bay's eastern shore, where visitors will likely see an entire village of people fishing. The town is loved for its natural elegance and wonderful waters, attracting sailors drawn to crabbing or fishing experiences.

What Rock Hall Offers

Rock Hall is a fisherman's town where the food is as fresh as the day's catch, with abundant wildlife including bald eagles and hundreds of bird species thanks to the Eastern Neck National Wildlife Refuge. The town provides excellent marina facilities and maintains an authentic working-waterfront character that appeals to sailors seeking a genuine Bay experience.

Solomons Island: Southern Maryland's Treasure

At the confluence of the Bay and the Patuxent River, Solomons Island is a small working fishing town that has quickly become a favorite among sailors due to its abundance of activities.

Activities and Attractions

Solomons Island offers plenty of great restaurants and shops, along with fossil hunting at Calvert Cliffs, the Calvert County Marine Museum, and the Drum Point Screwpile Lighthouse. To make the most of a trip to Solomons, it's recommended to allocate two days, stopping at Herrington Harbor on the way down and St. Michaels on the way back.

The island's protected harbor makes it an ideal staging point for crossing the Potomac River and continuing south to other Chesapeake destinations.

Galesville: West River's Hidden Gem

Galesville is a small town on the western shore of the bay that sits along the West River. Once home to a steamship line connecting Annapolis and Baltimore and many Chesapeake Bay Watermen, it's now a hot spot for pleasure boating and home to the West River Sailing Club and Hartge Yacht Harbor.

This lovely town offers one of the most tranquil and bucolic places in the Bay, with a small community park featuring a boardwalk along Riverside Drive on the West River. The peaceful atmosphere makes Galesville perfect for sailors seeking a quiet overnight anchorage near Annapolis.

Smith Island: Maryland's Only Inhabited Island Accessible Only by Boat

Smith Island is a perfect sailing location, as visitors wanting to reach this Chesapeake Bay island must travel by boat since it's the only habitable island in Maryland accessible solely by water. The island features three different villages, each offering clear waters and a calm sailing experience.

Smith Island is famous for its Smith Island Cake, and the remote location provides a unique glimpse into traditional Bay waterman culture. The journey to Smith Island offers an authentic adventure for sailors seeking to explore Maryland's maritime heritage.

Oxford: Historic Charm on the Tred Avon

Located along the Tred Avon and Choptank Rivers, Oxford is home to the Oxford-Bellevue Ferry, the Tred Avon Yacht Club, and the Oxford Museum. The ferry is believed to be the oldest privately owned ferry, with service dating back to 1836.

The town's access to both the Tred Avon and Choptank Rivers makes it an excellent cruising destination, offering a blend of colonial architecture, waterfront dining, and welcoming marinas.

Baltimore's Inner Harbor: Urban Sailing

Baltimore's Historic Inner Harbor sits at the mouth of the Patapsco River, offering access to numerous marinas that make it a great launch point for day cruising. Sailors can enjoy views of historic Federal Hill and Fort McHenry in the Harbor, and as the Patapsco opens into the bay, additional outdoor destinations like North Point State Park and Fort Smallwood Park become accessible.

The Inner Harbor combines city amenities with sailing access, making it ideal for sailors who want to experience Maryland's urban waterfront culture.

Planning Your Maryland Sailing Adventure

Best Sailing Season

The peak boating season runs from mid-May to mid-October, give or take a couple of weeks on each end. Spring and fall offer pleasant temperatures and fewer crowds, while summer provides warm weather perfect for swimming and water activities.

Charter and Sailing Tour Options

Multiple charter companies offer various options, from half-day and full-day charters where you pick your own destination and activities, to weekend and multi-day cruises for live-aboard sailing experiences to explore multiple ports. Sunset cruises provide a special way to soak up the serenity of the Bay.

What Makes Chesapeake Bay Sailing Special

There are few places in the world where boaters have all the resources at their fingertips to learn every aspect of powerboating and sailing, from boat rental clubs to diesel mechanics, electricians, riggers, and seamanship schools. The Bay is teeming with nautical experience, making it one of the easiest places to learn the ropes of boating.

The picturesque bay is shallow but soft and forgiving, with numerous anchorages that are protected, peaceful, and usually have good anchor hold. This combination of excellent facilities, protected waters, and welcoming communities creates an unmatched sailing environment.

Waterfront Living and Sailing in Maryland

For those who dream of combining their love of sailing with waterfront property ownership, Maryland offers exceptional opportunities. The Severn River, in particular, provides stunning waterfront estates with private docks and direct access to some of the Bay's best sailing waters.

Living on Maryland's waterfront means waking up to water views, stepping aboard your boat from your private dock, and experiencing the sailing lifestyle every day. Communities along the Severn River and throughout Anne Arundel County offer the perfect blend of maritime heritage, natural beauty, and convenient access to both sailing and modern amenities.

Start Your Maryland Sailing Adventure

Whether you're planning a weekend getaway, an extended cruising vacation, or searching for your dream waterfront property, Maryland's sailing destinations offer something for everyone. From the vibrant sailing culture of Annapolis to the peaceful anchorages of the Wye River, each destination provides its own unique character and charm.

The Chesapeake Bay's protected waters, rich maritime history, and welcoming communities make Maryland one of the premier sailing destinations in the United States. With proper planning and a spirit of adventure, you'll discover why generations of sailors have fallen in love with Maryland's waterways.

Ready to explore Maryland's waterfront properties and sailing lifestyle? Contact The Waterfront Group to discover exceptional homes along the Severn River and throughout the Chesapeake Bay region. Our expertise in waterfront real estate can help you find the perfect property to match your sailing dreams.

Sources

1. Sail Magazine. "The Chesapeake Bay's Great Cruising Destinations." June 2016. https://sailmagazine.com/cruising/chesapeake-bays-great-cruising-destinations/

2. Visit Maryland. "Chesapeake Bay Sailing Tours." https://www.visitmaryland.org/chesapeake-bay-sailing-tours

3. Red Beard Sailing. "Cruising the Chesapeake Bay by Boat: 13 Best Destinations." https://redbeardsailing.com/blogs/red-beard-report/top-13-chesapeake-bay-cruising-destinations

4. Life of Sailing. "Best Sailing Destinations Chesapeake Bay." December 2024. https://www.lifeofsailing.com/post/best-destinations-chesapeake-bay

5. Waypoints Yacht Charters. "Top 10 Cruising Destinations on the Chesapeake Bay." June 2021. https://waypoints.com/top-10-cruising-destinations-chesapeake-bay/

6. Better Sailing. "Best Sailing Destinations in Chesapeake Bay." November 2021. https://bettersailing.com/best-sailing-destinations-in-chesapeake-bay/

7. Waterway Guide. "Chesapeake Bay Loop: South to North & Back." https://www.waterwayguide.com/knowledge-center/news-post/11921/chesapeake-bay-loop-south-to-north-back

8. Chesapeake Bay Magazine. "Best of the Bay Boating." December 2022. https://www.chesapeakebaymagazine.com/best-of-the-bay-boating/