Best 31 things to do in Chesapeake City, MD

Sail toward sunset on a Chesapeake Bay evening cruise

Set sail with Jimmy Buffett hits, scenic canal views, and onboard drink specials

Host your celebration aboard a private party boat with a bar and onboard restroom

Visit four premium estates with a curated palate-flow progression and a gourmet wine-paired lunch

Savor sunset skyline views with music and a full bar on a 90-minute Christina River cruise

See Wilmington from the water on a 1-hour Christina River cruise

Cruise the Christina River with reggae vibes and an onboard bar

Relax on a 90-minute Aloha Hour cruise with music and a cashless onboard bar

Target seasonal sharks and drum on a private inshore charter

Target seasonal species on a bay and ocean charter

Target seasonal species with family and friends

Target sharks with expert guidance on a private charter

Cast for bay species with expert guidance

Fish deeper wrecks for sought-after offshore species

Cast for Flounder, Seabass, and Ribbonfish with an experienced crew

Chase tuna, marlin, mahi mahi, and wahoo in deep water

Fish for tilefish, mahi mahi, and blue lionfish with an experienced crew

See rural South Jersey from an open-air gondola on a narrated train ride

Celebrate aboard a private vintage railcar with pizza, cupcakes, drinks, and themed décor

Ride a heritage train to a working flower farm and create a take-home bouquet

Share charcuterie and bring your own drinks aboard a vintage table car

Continental pastries and scenic rail views from a restored 1930s table car

Host your group on a 2-hour private party boat with a full-service bar

Brunch cruise with classic mimosas and a cashless full bar