Sailing Adventures with Schooner Woodwind in Annapolis
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; moderate mobility recommended for moving safely on deck.
Overview
Experience Annapolis’s Chesapeake Bay aboard Schooner Woodwind, a classic schooner offering private sailing cruises with expert crew and stunning views of historic lighthouses and serene waters.
Adventure Tips
Arrive Early for Boarding
Arriving 15 minutes before your scheduled sail ensures a smooth check-in and allows you to get settled on board.
Dress in Layers
Even on warm days, it can get breezy on the water. Bring layers to stay comfortable throughout your sail.
Wear Non-Slip Shoes
The deck can be slippery, so shoes with good grip help keep you safe while moving around the boat.
Bring a Camera or Binoculars
Capture views of the lighthouse, sailboats, and wildlife, or bring binoculars for birdwatching along the shores.
Local Insights
Wildlife
- Osprey
- Great Blue Heron
History
Thomas Point Shoal Lighthouse, featured on the sailing route, is one of the last surviving Chesapeake Bay screwpile lighthouses, built in the late 19th century.
Conservation
Schooner Woodwind actively promotes eco-friendly sailing practices to minimize impact on the bay's delicate ecosystem, including no-waste policies and awareness education.
Frequently Asked Questions
Recommended Gear
Windbreaker or Light Jacket
Protects against wind chill and sudden weather changes while on the water.
spring|summer|fall|winter specific
Sunscreen
Essential for protecting skin during long exposure to sun and reflective water surfaces.
spring|summer|fall specific
Comfortable Non-Slip Shoes
Provides steady footing on the wet and sometimes slippery boat deck.
Hat and Sunglasses
Helps shield eyes and face from glare and enhances day-long comfort.
spring|summer|fall specific