Chesapeake Bay Charter & Rental Destinations Half, Full or Multiple Day Boat Charters / Rentals


Time spent PREPLANNING your itinerary is the key to a truly enjoyable cruising adventure. Decide if you want to spend the evenings at anchor or at a marina transient slip; and whether you want to sleep on board or on shore.

You will need to reserve a slip and/or room nights in advance as the availability for these may determine your final itinerary. The advantages of spending the night at a marina are that most have restroom and hot shower facilities (the boats do not have hot water) and restaurants and sightseeing attractions either on premises or within walking distance. The advantages of anchoring in a creek or quiet cove are that you might find it more private and cozy and there is no additional expense for slips or rooms. At some destinations, you may be able to find an anchorage area that is serviced by water taxis that will take you into town or to a restaurant.

Listed below is a sampling of the marina, hotel, restaurant, and visitor information for some of the popular destinations. We highly recommend that you order the Guide to Cruise the Chesapeake to aid in your preplanning and as a reference during your trip.

Click here to order:

Also in planning your trip, keep in mind that the boats are truly “bare” boat rentals. Think of your trip as camping on a boat. If you plan on sleeping on board, you will need to bring sleeping bags or sheets, blankets and pillows. You will also need to bring towels and bath soap. We provide toilet paper. The galley is not equipped so bring whatever you will need for cooking such as pots and pans and utensils. The boats have a cook top but no oven or microwave (there is only 12 volt electricity). We do provide a grill with fuel for outdoor cooking but you need to bring grilling utensils. We recommend that you bring paper plates and plastic flatware. The galley has a small ice box that will hold several bags of ice. If you wish to pick up some of your supplies just before you arrive, just south of the Rt.2/South River Bridge there is a CVS on the left that sells ice and little further on the right there is a Giant grocery store. Although the boats have all the necessary safety equipment including a VFH radio, we recommend that you bring a cell phone. There is cell reception out on the Bay. Pack your clothing and supplies in containers that can be folded or collapsed and easily stowed as there is no storage area on a boat for suitcases

Destination Contact Information

South River
Mike’s Crab House 410-956-2784

West River
Pirates Cove & Big Mary’s Dockside Bar & Grill 410-867-2300
Topside Inn 410-867-1321

Annapolis Harbor
City Dock slips and moorings: 410-263-7973; VHF channel 09 or 17
Water taxi: Contact taxi driver on VHF Ch 68 or Phone (410) 263-0033
Carroll’s Creek Café 410-263-8102

Baltimore Inner Harbor
Public Docking: 410-396-3174
Baltimore Marine Center: 410-675-8888

Waterman’s Crabhouse & Marina 410-639-2261
Rockhall Landing Marina 410-639-2224
Sailing Emporium 410-778-1342

Chestertown Marina 410-778-3616
Great Oaks Marina 410-778-5007
Old Wharf Inn 410-778-3566

Magothy River
Deep Creek Restaurant & Marina 410-757-4045

Whitehall Bay
Cantler’s Riverside Inn 410-757-1467

Kent Island West Side Bay Bridge Marina 410-643-3162
Kent Island Depot 410-604-3000

Kent Island & Eastern Bay

Kent Narrows South of Bridge:
Angler’s Restaurant & Marina 410-827-6717
Fisherman’s Crab Deck 410-827-6666

Kent Narrows North of Bridge:
Harris Crab House 410-827-8807
Hemingway’s Restaurant (Kent Island at east end of bridge) 410-643-2722
The Jetty at Kent Narrows 410-827-4959

Herring Bay
Herrington Harbor South Marina 410-741-5100
Skipper’s Pier 410-867-7110

Eastern Bay / Kent Narrows
Mears Point Marina 410-827-8888
Angler’s Restaurant & Marina 410-827-6717
Harris Crab House 410-827-9500
Hemingway’s Restaurant 410-643-27228
The Jetty 410-827-4959

Miles River / St Michaels
St Michaels Harbor Inn and Marina 410-745-9001
St Michaels Marina 410-757-2400
Harbor Shuttle 410-942-2198
Crab Claw 410-745-2900
Town Dock Restaurant 410-745-5577
St. Michaels Crab & Steak House 410-745-3737

Knapps Narrows / Tilghman Island
Knapps Narrows Marina & Inn 410-886-2720
The Bridge Restaurant 410-886-2330
Tilghman Island Inn 410-886-2141
Tred Avon River / Oxford / Easton or
Mears Yacht Haven 410-266-5450
Easton Point Marina 410-822-1201
Latitude 38 Restaurant 410-226-5303
Pier Street Marina & Restaurant 410-226-5171
Robert Morris Inn 410-226-5111
Schooners Landing Restaurant & Marina 410-226-0160

Choptank River / Cambridge
Cambridge Municipal Yacht Basin 410-228-4031
Hyatt Regency Chesapeake Bay Resort 866-378-7077
Harrison’s Chesapeake House Restaurant & Marina 410-886-2121
Portside Seafood Restaurant 410-228-9007
Suicide Bridge Restaurant & dockage 410-943-4689

North Beach, Chesapeake Beach
Rod’N Reel Restaurant 410-257-2735/ Marina 800-233-2080
Patuxent River (Solomons Island)
Zahniser’s Yachting Center 410-326-2166
Comfort Inn Beacon Marina 301-326-6303
The Captain’s Table Restaurant & dockage 410-326-2772
Lighthouse Inn 410-326-2444
Vera’s White Sands Restaurant & Marina 410-586-1888 (Lusby, MD on St Leonard Creek)



Call 1-410-956-9729 or contact us and a member of our team will respond promptly.