Schooner Woodwind Sailing Cruises

Set sail on an unforgettable Chesapeake Bay adventure aboard the Schooner Woodwind, where kids can experience authentic sailing while learning about marine life and maritime history. These interactive cruises let children help hoist the sails, steer the boat under crew supervision, and spot dolphins playing in the bay's waters, making it an educational adventure that feels like pure fun.

• ✓Hands-on sailing experience where kids can help raise sails and steer the boat
• ✓Dolphin and marine wildlife spotting on Chesapeake Bay
• ✓Educational commentary about sailing, local history, and bay ecology
• ✓Stunning views of the Annapolis Harbor and Naval Academy
• ✓Opportunity to explore a historic 74-foot wooden schooner

1. 1.Book the morning cruise when winds are typically calmer and kids are fresh,afternoon sails can be breezier and more energetic
2. 2.Arrive 20 minutes early to secure parking at nearby garages and allow time to explore the historic Annapolis waterfront before boarding
3. 3.Bring layers even on warm days,it's always cooler and windier on the water than on land
4. 4.Ask the crew if your kids can help with sailing tasks; the staff loves engaging young sailors and teaching them the ropes (literally!)
5. 5.Pack motion sickness medication if your child is prone to it, though the schooner's gentle ride is easier on stomachs than powerboats

Late spring through early fall (May-September) offers the warmest weather and best sailing conditions. Weekday cruises tend to be less crowded than weekends, and morning departures provide calmer waters and better wildlife viewing opportunities when marine life is most active.

Office hours are Monday-Friday 8 AM-4 PM for bookings and inquiries (closed weekends). Cruise times vary seasonally, so check their schedule online. Parking is available at nearby public garages within a short walk. Limited snacks and beverages are available onboard, but you're welcome to bring your own.

Cruises operate primarily from April through October, with peak season in summer months. Limited or no sailings during winter. Special sunset cruises and themed sails are offered during peak season. Always check availability as sailing schedules depend on weather conditions.

Walk to Chick & Ruth's Delly (iconic Annapolis spot with huge kids' menu and famous milkshakes) or Davis' Pub (casual waterfront dining with burgers, crab cakes, and a relaxed atmosphere perfect for hungry sailors after their voyage).