Glide through Chesapeake City's historic canal and waterfront aboard Chesapeake Water Tours' tailored cruises, for moments filled with stunning views, lively music, and local charm.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
1.5–3 hours
Fitness Level
Suitable for all fitness levels; minimal physical exertion required.
Wildlife
History
Chesapeake City grew as a vital canal town serving trade routes between the Chesapeake Bay and Delaware River, still evident in its preserved 19th-century architecture and lock systems.
Conservation
Boat tours emphasize low-impact travel and environmental stewardship to protect the delicate canal ecosystems and surrounding wildlife habitats.
Chesapeake Water Tours - Chesapeake City
Glide through Chesapeake City's historic canal and waterfront aboard Chesapeake Water Tours' tailored cruises, for moments filled with stunning views, lively music, and local charm.
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 for Popular Cruises
Reservations fill quickly, especially for themed and holiday cruises; plan ahead to secure your spot.
Arrive 15 Minutes Early
Give yourself time to board comfortably and settle in before departure on the dock.
Bring a Light Jacket
Even summer evenings can turn cool on the water; layering keeps you comfortable.
Accessibility is a Priority
Contact in advance if you have special needs—staff are accommodating and the boat is designed for easy access.
Light Windbreaker
Protects against breezes and cooler temps on the water, especially at sunset.
summer|fall|spring
Sunglasses
Reduces glare from the water and improves visibility in bright conditions.
summer|spring|fall
Camera or Smartphone
Capture stunning views, sunsets, and wildlife moments during the cruise.
Comfortable Footwear
Non-slip shoes help maintain steady footing on deck and docks.