Set sail from Chesapeake City for 90-minute themed sails, live-music evenings, seasonal events, and private boat charters on the upper Chesapeake Bay.
Seasonal themed cruises, brunch sails, live-music evenings, family-friendly outings, and private charters departing from Chesapeake City.
boat-charters · Chesapeake City
Celebrate Halloween Chesapeake City-style aboard a 90-minute Boo’ze Cruise featuring sunset views, rum tastings, drink specials, and free entry to the Chesapeake Inn’s costume party. Dress up and join the spirited fun!
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Home port on the C&D Canal
Themed public sails and private charters
Most public cruises run 90 minutes
Bookable for special occasions
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Chesapeake Water Tours - Chesapeake City listing.
Chesapeake Water Tours - Chesapeake City offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Choose a public themed sail or book a private charter from Chesapeake City — easy online booking and secure checkout to lock in departure times.
boat-charters · Chesapeake City
Enjoy a delightful 1½ hour brunch cruise on the upper Chesapeake Bay with tasty breakfast sandwiches and classic mimosas. Set sail from Chesapeake City and take in stunning waterfront views while delighting your palate.
boat-charters · Chesapeake City
Join the 'Don't Worry, Be Happy' Rum & Reggae Sunset Cruise in Chesapeake City for a relaxing evening of reggae rhythms and Caribbean rum tastings over breathtaking Chesapeake Bay views.
boat-charters · Chesapeake City
Set sail on the 90-minute Fall Foliage Cider & Donut Cruise in Chesapeake City to immerse yourself in stunning autumn colors along the C&D Canal while enjoying fresh apple cider donuts and warm cider from Milburn Orchards. Perfect for families and friends seeking a relaxing seasonal adventure.
Unknown · Chesapeake City
Discover the scenic waterways of Chesapeake City, Maryland, on a private sightseeing canal cruise with Chesapeake Water Tours. Enjoy peaceful waters, local wildlife, and fascinating history all in one relaxing trip.
Unknown · Chesapeake City
Set sail on a relaxing Happy Hour Cruise in Chesapeake City, Maryland. Enjoy stunning water views, refreshing drinks, and a peaceful escape along the Chesapeake Bay.
boat-charters · 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.
water-activities · Chesapeake City
Sail into the golden horizon with a 90-minute Sunset Cruise on Chesapeake Bay. Enjoy breathtaking views, a full bar, and an unforgettable evening from Chesapeake City, Maryland.
water-activities · Chesapeake City
Experience a sunset cruise filled with live jazz by Bud Falls on Chesapeake Bay. As the waves gently roll, soak in stunning views and timeless music—an evening not to be missed.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.