Experience the Chesapeake Day Sail: Baltimore’s Premier Sailing Adventure
Difficulty
easy
Duration
3–4 hours
Fitness Level
Suitable for most fitness levels; requires moderate mobility for boarding and minor movement on deck.
Overview
Set sail on Baltimore’s Chesapeake Bay with the Chesapeake Day Sail, where history, nature, and urban charm come together for an unforgettable hands-on sailing experience. Discover why this trip stands out as a top outdoor adventure in Maryland’s vibrant harbor city.
Chesapeake Day Sail
Leave behind the city’s bustle and set sail on the Chesapeake
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Adventure Photos
About This Adventure
Escape the city's hustle and embark on a unique sailing adventure on the Chesapeake Bay. Departing from The Inn At Henderson's Wharf, you'll enjoy breathtaking views of Baltimore from the water while learning about safety and the maritime experience. Discover the city like never before, from a sailor's perspective.
Leave behind the city’s bustle and set sail on the Chesapeake
Leave the streets of Baltimore behind as we set sail on the Chesapeake Bay and experience urban life from the water. We'll meet outside of the The Inn At Henderson's Wharf in Fell's Point and quickly hop on the boat. After going over safety basics, we'll sail out of the harbor and explore the city, mariner style.
Adventure Tips
Bring a windbreaker or light jacket
Conditions on the water can be breezy and cooler than on shore, even in summer seasons.
Arrive early for pre-sail orientation
Give yourself time to familiarize with the boat and sailing basics before heading out.
Wear non-slip boat shoes
Footwear with good grip ensures safety on wet deck surfaces.
Use reef-safe sunscreen
Protect your skin without harming the bay’s sensitive marine life.
Local Insights
Wildlife
- Osprey
- Blue crab
History
Fort McHenry near the sailing route is famous for defending Baltimore during the War of 1812 and inspiring the national anthem.
Conservation
The operator supports bay cleanup projects and educates guests on protecting this delicate estuarine environment.
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Frequently Asked Questions
Recommended Gear
Windbreaker or waterproof jacket
Provides warmth and wind protection during cool, breezy spring sails.
spring specific
Hat with chin strap
Keeps sun off your face and secures in variable winds.
summer specific
Layered clothing
Allows for temperature adjustments as the day cools off on the water.
fall specific
Gloves with good grip
Helpful for handling lines in cold weather but not mandatory.
winter specific