Enjoy a private, two-hour boat charter on the serene waters of Chesapeake City, Maryland. Customize your trip for daytime fun or a stunning sunset experience on the bay.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for all fitness levels with no strenuous activity required
Wildlife
History
Chesapeake City has a rich maritime heritage that dates back to the 19th century, centered around the Chesapeake & Delaware Canal’s vital waterway.
Conservation
Efforts are ongoing to protect the Chesapeake Bay’s water quality and marine life, including sustainable boating practices promoted by local operators.
Chesapeake Water Tours - Chesapeake City
Enjoy a private, two-hour boat charter on the serene waters of Chesapeake City, Maryland. Customize your trip for daytime fun or a stunning sunset experience on the bay.
Chesapeake Water Tours - Chesapeake City operates passenger cruises on the upper Chesapeake Bay and along the C&D Canal from its home port in Chesapeake City, Maryland. The company offers a variety of public themed sails — Sunset Cruises, Mimosa Brunch Cruises, Rum & Reggae sunset sails, Fall Cider & Donut Cruises, special-event nights like Sinatra at Sunset with live music by Bud Falls, and seasonal events including a Halloween Boo’ze Cruise. Public cruises are typically 90 minutes (some listed as 1½ hours) and feature scenic views of the bay and canal.
In addition to public sails, Chesapeake Water Tours - Chesapeake City offers private boat charters for two-hour celebrations and special occasions, available for daytime or evening sunset departures. Several cruises include onboard amenities and local partnerships: Mimosa Brunch Cruises serve breakfast sandwiches from Cafe on the Bay; Fall Cider & Donut Cruises include complimentary apple cider and donuts from Milburn Orchards; Rum & Reggae and Sinatra events offer rum tastings and a full cash bar on select sails. The Halloween Boo’ze Cruise features end-of-season drink specials, complimentary rum tastings, and free entry to the Chesapeake Inn costume party.
Passengers should book in advance to secure space on themed weekends and private charters. Cruises provide family-friendly options as well as 21+ sailing experiences with full bar service where noted. Chesapeake Water Tours - Chesapeake City presents a focused selection of short-format cruises designed for sightseeing, social events, and private celebrations. Online booking and clear schedules make planning departures simple today.
Location
Chesapeake City, MD
Home port on the C&D Canal
Tours Offered
7 Experiences
Themed public sails and private charters
Typical Duration
90 minutes
Most public cruises run 90 minutes
Private Charters
2-hour Charters
Bookable for special occasions
Choose a public themed sail or book a private charter from Chesapeake City — easy online booking and secure checkout to lock in departure times.
Book Early to Secure Your Spot
Private charters fill quickly, especially for sunset cruises—reserve your preferred time well in advance.
Bring Layers for Evening Cruises
Temperatures can drop quickly after sunset; pack a light jacket or sweater.
Safety Briefing Before Departure
Pay close attention during the captain’s safety instructions to ensure a secure and enjoyable cruise.
Protect Against Sun Exposure
Wear sunscreen, sunglasses, and hats during daytime cruises to guard against UV rays reflecting off the water.
Comfortable layers
Keep warm during chilly mornings or evenings on the water.
fall
Sunscreen
Protect your skin from intense sun exposure during daytime cruises.
summer
Polarized sunglasses
Reduce glare from the water, improving visibility and comfort.
Camera or smartphone
Capture scenic views and memorable moments aboard the boat.