Weekly evening cruises aboard Old Point begin Thursday, July 16. (Photo by Sharon Thorpe)

July 9, 2026 | #MyChesapeakeStory

Looking for a new way to spend an evening in St. Michaels? Step aboard one of the Chesapeake Bay Maritime Museum’s historic vessels and discover the beauty of the Miles River from the water.

With our new evening cruises aboard 1909 crab dredger Old Point and 1955 skipjack Rosie Parks, you’re invited to relax and soak in the Chesapeake scenery and maritime history.

Whether you’re visiting for the day or planning a special night out, these individually ticketed, six-passenger cruises offer an experience you won’t find anywhere else. Bring your favorite drinks and snacks and settle in for a Chesapeake evening to remember!

These cruises begin at 5pm, departing from our waterfront. The 90-minute Old Point cruises begin next Thursday, July 16, and continue weekly through Oct. 29, while the two-hour Rosie Parks cruises begin Wednesday, Aug. 12, and continue through Oct. 28.

Buy your tickets now by using the links below or searching our online ticketing portal. CBMM members save 20% on both offerings. Combo tickets are available for a cruise and CBMM general admission.

Cruise the Miles River aboard Old Point

Starting Thursday, July 16, you’re invited to step aboard Old Point, CBMM’s beautifully restored 1909 crab dredger, for a relaxing 90-minute evening cruise on the scenic Miles River. This special experience blends the character of a historic working vessel with the beauty and calm of Maryland’s Eastern Shore.

Complete your Chesapeake evening by pairing your evening cruise with a Thursday Chef’s Table Experience at one of the participating restaurants in St. Michaels. Each week, our local restaurants, wineries, and taverns come together to offer exclusive chef-driven dining experiences, curated pairings, and specials designed to celebrate the flavors of the Eastern Shore.

The cost is $48 per passenger for CBMM members and $60 for non-members.

Our Old Point Miles River Cruises are available on Thursdays from 5-6:30pm. Join us on July 16, July 23, July 30, Aug. 6, Aug. 13, Aug. 20, Aug. 27, Sept. 3, Sept. 10, Sept. 17, Sept. 24, Oct. 1, Oct. 8, Oct. 15, Oct. 22, and Oct. 29.

Weekly evening sails aboard skipjack Rosie Parks begin Wednesday, Aug. 5. (Photo by Sharon Thorpe)

Set sail aboard historic skipjack Rosie Parks

Starting Wednesday, Sept. 2, we’re thrilled to offer two-hour evening sails aboard Rosie Parks, one of the Chesapeake Bay’s last remaining skipjacks. Built in 1955 as a working oyster dredge boat, this vessel offers a rare chance to experience the craftsmanship, character, and history of Maryland’s maritime past.

Cruise past waterfront homes, working shorelines, and marshes along the Miles River that once supported a thriving oyster industry. Along the way, the crew is happy to share how skipjacks like the Rosie Parks harvested Chesapeake oysters and became the nation’s last commercial sailing fleet.

The cost is $64 per passenger for CBMM members and $80 for non-members.

Our Rosie Parks Skipjack Evening Sails are available on Wednesdays from 5-7pm. Join us Sept. 2, Sept. 9, Sept. 16, Sept. 23, Sept. 30, Oct. 7, Oct. 14, Oct. 21, and Oct. 28.