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Starboard Sailing of the Chesapeake LLC logo

Starboard Sailing of the Chesapeake LLC

21220, USA

About

Starboard Sailing is located just north of Baltimore on the Middle River, offering a peaceful and protected setting ideal for both beginners and experienced sailors. The school's fleet consists of cruising sailboats similar to those used worldwide, featuring large, stable cockpits and comfortable cabins. Fully equipped with wheel steering, inboard diesel engines, and electronics, these boats are well maintained to ensure a safe and enjoyable sailing experience. The calm waters of Middle River provide a perfect environment for learning, while just a short sail away lies the Chesapeake Bay for practicing more advanced skills.

Courses (3)

ASA Certified

Basic Keelboat Sailing

101All Levels
3 days1-2 per berth

Contact for pricing

Bareboat Cruising

104All Levels
3 days1-2 per berth

Contact for pricing

Coastal Cruising

103All Levels
3 days1-2 per berth

Contact for pricing

Location

Starboard Sailing of the Chesapeake LLC, 3501 Red Rose Farm Road, Middle River, Maryland, 21220, USA

The Area

Nestled along the Middle River just north of Baltimore, our location offers a calm and protected environment ideal for learning to sail. The area provides easy access to the Chesapeake Bay, allowing students to gradually expand their skills from the sheltered waters of Middle River to the open bay. Our facilities feature docks and amenities designed to support a comfortable and efficient learning experience, ensuring that students can focus on developing their sailing confidence and techniques in a relaxed setting.

Getting There

From Baltimore/Washington International Thurgood Marshall Airport (BWI), the most convenient way to reach Starboard Sailing is by car or ride-hailing service. The drive typically takes about 25 to 30 minutes, depending on traffic. Once you arrive, take I-695 North toward Towson, then merge onto MD-702 North (Middle River Road). Follow Middle River Road east for several miles until you reach Red Rose Farm Road; the school is located at 3501 Red Rose Farm Road. If you prefer, you can also rent a car at the airport and drive directly to the school, enjoying the scenic route along the Chesapeake Bay area. Public transportation options are limited for this route, so a taxi, ride-share, or rental car is recommended for the most convenient and efficient journey.

Best Time to Go

The best time to sail in the Middle River area is from late spring through early fall, typically from late May to early October, when the weather is warm and the winds are steady. Summer weekends are especially popular, offering ideal conditions for both beginners and experienced sailors to enjoy the Chesapeake Bay.

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Frequently Asked Questions

Starboard Sailing of the Chesapeake LLC offers the following courses: Basic Keelboat Sailing, Bareboat Cruising, Coastal Cruising. Please review the listings above for details and pricing.

The primary training location is in 21220, USA. You can view the exact meeting point and map in the location section on this page.

Yes, Starboard Sailing of the Chesapeake LLC is an internationally recognized ASA school offering official certifications.

You can contact Starboard Sailing of the Chesapeake LLC directly using the contact buttons (email, phone, or WhatsApp) provided on this page to check availability and book your spot.

See something wrong or have a question? Message us at hello@sailingtree.com

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