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.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Minimal physical effort required; suitable for most fitness levels.
Wildlife
History
Chesapeake City grew around the C&D Canal and has a rich maritime history tied to trade and transportation on the Chesapeake Bay.
Conservation
Chesapeake Water Tours promotes environmental stewardship by encouraging sustainable tourism practices and minimizing impact on local marine habitats.
Chesapeake Water Tours - 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.
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.
Bring a light jacket
Evenings on the bay can get cool, so layering up ensures comfort as temperatures drop after sunset.
Arrive early
Arriving 15 minutes before departure helps secure the best seating and a smooth boarding experience.
Limit alcohol consumption
Enjoy the rum tastings responsibly to stay safe and fully enjoy the cruise experience.
Check weather conditions
Confirm the weather forecast ahead of time as high winds or storms may cancel the cruise.
Light jacket or sweater
Keeps you warm during cool and windy evenings on the water.
spring
Sunscreen
Protects skin from sun exposure during daytime cruising.
summer
Hat and sunglasses
Provides shade and eye protection against bright sun on the bay.
summer
Camera or smartphone
Capture stunning sunset views and lively moments on the cruise.