Sunset Sailing on Chesapeake Bay with Classic Sail Charters
Difficulty
easy
Duration
2–3 hours
Fitness Level
Minimal physical fitness required; suitable for all ages and abilities
Overview
Glide through Chesapeake Bay’s tidal rivers on a private yacht with Classic Sail Charters’ Sunset Sail - Licentia. Enjoy wildlife, snacks, and scenic sunsets on this 2.5-hour cruise from Annapolis.
Sunset Sail - Licentia
For up to 6 People | 2.5 Hours
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Adventure Photos
About This Adventure
Experience the breathtaking beauty of the Chesapeake Bay on a private sailing yacht. Glide through its navigable rivers, surrounded by diverse wildlife, for an unforgettable 2.5-hour cruise. Enjoy complimentary beverages and snacks as you create lasting memories with friends or family in this stunning natural setting.
Come sail with us on the Chesapeake Bay!
As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful, fed by countless navigable rivers and home to an abundance of wildlife. Come join us for an unforgettable cruise on one of our world class sailing yachts. We serve clients seeking a unique sailing experience on the Chesapeake Bay.
Rates
- Private Charter (For up to 6 People) - Starting at $595 (2 people/weekday sail)
(25% Deposit due at the time of booking)
Duration
2 hours and 30 minutes
What to Bring
- Sunscreen
- Hats
- Sunglasses
All trips include: beverages, snacks
Adventure Tips
Arrive Early to Settle In
Plan to arrive 15 minutes before departure to get comfortable and receive safety instructions.
Dress in Layers
Evening temperatures on the bay can drop quickly, so bring a light jacket or windbreaker.
Protect Your Skin
Sunscreen and hats are important as the sun reflecting off the water intensifies UV exposure.
Limit Alcohol Intake
Though beverages are provided, keep alcohol consumption moderate for safety on board.
Local Insights
Wildlife
- Osprey
- Blue herons
History
Annapolis has been a central maritime hub since the colonial era, home to the U.S. Naval Academy and traditional Chesapeake sailing culture.
Conservation
Classic Sail Charters supports local efforts to protect the bay’s delicate ecosystems by practicing sustainable boating and educating guests on minimizing environmental impact.
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Adventure Hotspots in Annapolis
Frequently Asked Questions
Recommended Gear
Windbreaker or Light Jacket
Protects against cool breezes during evening sails.
spring specific
Sunscreen
Prevents sunburn from direct and reflected sunlight.
summer specific
Sunglasses
Reduces glare and protects eyes from UV rays on the water.
summer specific
Hat with Brim
Provides added shade and sun protection during the daytime.
spring specific