Guided Scenic Trip To Oxford

Departure from South River, Maryland – 10 am
You’ll begin your journey from South River, a beautiful waterway just south of Annapolis. As you head toward the mouth of the river, you’ll see the Thomas Point Shoal Lighthouse, one of the most iconic screw-pile lighthouses in the Chesapeake Bay. This historic lighthouse has guided mariners for over a century and remains a picture-perfect sight against the horizon.

Cruising into the Chesapeake Bay
Once in the Chesapeake Bay, you’ll experience the vast, open waters with gentle waves rolling beneath your vessel. To the west, the shoreline of Maryland’s Western Shore is dotted with small
towns, marinas, and sandy beaches. Keep an eye out for ospreys and bald eagles soaring above, as well as playful dolphins that occasionally surface in the bay.

Passing Kent Island and Tilghman Island
As you make your way east, you’ll pass Kent Island, known for its rich maritime history and seafood restaurants lining the shore. Heading southward, you’ll reach the entrance to the Eastern
Bay, a gateway to the scenic waterways leading to Oxford. Along the way, Tilghman Island appears to the east, a quiet fishing village with a working watermen’s fleet, charming cottages, and beautiful waterfront vistas.

Entering the Tred Avon River to Oxford (Arrival at 12:30pm depart Oxford at 3:30pm)
Upon reaching the mouth of the Tred Avon River, you’ll cruise through calm, winding waters lined with stately waterfront homes and pristine landscapes. Oxford, one of Maryland’s oldest towns, greets you with its historic charm. The Oxford-Bellevue Ferry, the oldest privately- operated ferry in the U.S., shuttles cars and passengers across the river. The town itself boasts colonial-era homes, a picturesque harbor, and The Robert Morris Inn, where guests can enjoy waterfront dining.

Arrive back on the South River at 6pm
Final Thoughts

This scenic boat ride blends history, natural beauty, and charming waterfront towns. Whether you’re seeking a relaxing cruise or an adventure filled with stops in historic ports, this Chesapeake Bay journey delivers an unforgettable experience.

Cancel up to 2 days before the start time.