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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
1.5–2 hours
Fitness Level
Casual, suitable for most abilities
Wildlife
History
The Chesapeake Bay has been a vital maritime route for centuries, shaping local culture and economy.
Conservation
The tour operators prioritize eco-friendly practices, including waste reduction and minimal impact on wildlife.
Chesapeake Water Tours - 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.
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.
Arrive Early
Get to the dock at least 30 minutes before departure to secure your spot and settle in.
Dress Comfortably
Wear layered clothing and bring a light jacket for the evening breeze.
Bring Cash or Card
Cash or credit cards are needed for bar purchases onboard.
Bring Your Camera
Capture the stunning sunset and lively performances from the open deck.
Comfortable Shoes
Non-slip shoes make walking on the boat deck safer.
Light Jacket
Evening breezes can be cool, so layer accordingly.
spring;summer;fall
Binoculars
Great for spotting distant boats and wildlife on the water.
Sunscreen
Protect skin from UV rays during daytime cruising.
summer