Chesapeake Bay

Annapolis Sailing Cruises: Schooner Woodwind

Annapolis Sailing Cruises: Schooner Woodwind offers two-hour public sailing experiences aboard classic schooners on the Chesapeake Bay. Visitors help raise sails, steer, and learn about maritime history, wildlife, water quality, and regional heritage through interactive storytelling.

Bay Venture Outfitters, North East, MD

Bay Venture Outfitters in North East, Maryland offers kayak and paddleboard access to the North East River and nearby wetlands. Visitors explore upper Chesapeake Bay tributaries through guided and self-guided tours that emphasize watershed conservation, wildlife observation, and regional history.

Blue Ridge Hills & Hollows

The Blue Ridge Hills & Hollows Bikepacking Route is a 300-mile cycling experience that connects eight memorials honoring displaced Blue Ridge communities. Riders explore scenic mountain roads, rural landscapes, and the headwaters of major Chesapeake Bay tributaries while discovering stories of settlement, conservation, and cultural heritage.

Catamaran Epiphany Sailing Charters

Catamaran Epiphany Sailing Charters offers small group sailing experiences from St. Michaels, Maryland. Guests explore the Miles River and Chesapeake Bay while learning about maritime history, estuarine ecology, wildlife, and the importance of conserving the Bay through personalized interpretation aboard a wind-powered vessel.

Chronic Sailing

Step aboard a sailboat to explore the Chesapeake Bay. Chronic Sailing offers hands-on sailing experiences from Annapolis that showcase scenic coves, lighthouses, and maritime history. Guests can learn sailing skills, paddle quiet waters, and discover the Bay’s natural and cultural treasures from the unique vantage point of the water.

Explore Historic Annapolis on Foot

Explore Annapolis on a self-guided walking tour that highlights centuries of history along the Chesapeake Bay. Visit the Maryland State House, the U.S. Naval Academy’s John Barry Gate, historic churches, homes of free and enslaved African Americans, and the Banneker-Douglass-Tubman Museum. This walk offers a meaningful way to connect with the city’s political, cultural, and maritime heritage.

Historic 1935 Lady Patty Sailing Charter

St. Michaels Sailing Charters offers authentic sailing experiences aboard the Historic 1935 Lady Patty Sailing Charter, a restored 1935 wooden ketch departing from St. Michaels, Maryland. Visitors explore the Miles River and Chesapeake Bay while learning about maritime heritage, local history, wildlife, and the importance of protecting the nation's largest estuary.

James River Batteau Company

Step aboard a hand-built replica of a James River Batteau and explore the history of Virginia’s rivers. Guided cruises include stories of the boatmen who carried goods and culture along the James, complimentary charcuterie and live music, and immerse you in life along the river. This Chesapeake Gateways Network Experience connects past and present through history, storytelling, and time on the water.

Rappahannock Adventures

Rappahannock Adventures offers guided paddling, fishing, birding, hiking, and biking experiences on Virginia's Middle Peninsula. Visitors explore the Rappahannock River and surrounding landscapes while learning about Indigenous history, wildlife, watershed ecology, conservation, and the cultural heritage of the Chesapeake Bay region.

Riverside Adventure Company Outfitter

Riverside Adventure Company in Mount Carmel, Pennsylvania offers paddling and cycling experiences along the Susquehanna River. Visitors explore watershed landscapes, Indigenous heritage, and industrial history while learning about water quality, conservation, and regional outdoor recreation.