Whether you are a seasoned captain or a confirmed landlubber, the perfect way to explore Annapolis and Anne Arundel County is by water.

Spend a day sailing the Chesapeake Bay, the largest estuary in North America, host a social event on a breathtaking yacht, or kayak the many creeks feeding the Bay.

From performance sailing and boat shows to relaxed sailing charters, there are so many things to do and so much to see!

Charters & Rentals

• Admiral of the Bay, LLC
• American Classic Yachting, LLC
• Annapolis Bay Charters
• Annapolis Sailing Cruises: Schooner Woodwind
• Annapolis Sailing Solutions
• Annapolis Small Boat Rentals, Inc.
• Chesapeake Bay Sport Fishing
• Chesapeake Boating Club at J Port
• Chesapeake Sailing School & Charters
• Harbor Cruises, LTD
• Let's Go Cruising
• Liberte, The Schooner
• Old Bay Charters
• Pintail Yacht Charters & Nautical Destinations
• Pirate Adventures on the Chesapeake
• Sail the Pintita
• Sourth River Boat Rentals
• Springriver Annapolis Canoe and Kayak
• SunTime Rentals, Inc
• Watermark Tours, Charters, Cruises
• West River Cruises

Boating Schools

• Annapolis Sailing School
• Chesapeake Sailing School & Charters
• J World Performance Sailing School
• Kayak Annapolis, LLC
• L.L. Bean Outdoor Discovery School
• South River Boat Rentals
• Womanship, Inc

Marinas

• Annapolis City Marina
• Ferry Point Marina Yacht Yard
• Sarles Boatyard and Marina
• Yacht Basin Company