The Chesapeake Bay is a spectacular North American cruising ground that was shaped by a big bang 35 million years ago when a comet or asteroid slammed into what is now the lower tip of the Delmarva Peninsula. That impact left a crater 55 miles wide that became a convenient depression for rivers to flow into as the glaciers of the last Ice Age melted some 10,000 years ago. The Algonquian word Chesepiooc, meaning “at a big river” became the source of the name for the estuary now called the Chesapeake.

The Chesapeake Bay spans more than 64,000 square miles and is home to 150 major rivers and streams. A true boater’s playground, you will find everything you need. From live music and great tiki bars, to cruising with the kiddos, there’s no shortage of fantastic Chesapeake Bay marinas and fun activities here. Below please find a sample itinerary, complete with marina information, deals and discounts.

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  1. - Estimated Mileage: 0

    Harbor East Marina

    View of Marina and Buildings - Harbor East Marina - Baltimore, MD - Chesapeake Bay Marina - Marinalife

    Baltimore, MD



    The best of the Baltimore is located just steps off the docks at Harbor East Marina. Located in the heart of the city, the Harbor East area of Baltimore boasts 12 square blocks of fine dining restaurants, world-class hotels, hip lounges, quaint pubs, and the best of national and local shops. In addition to all that Harbor East has to offer, marina guests can walk to all the major attractions at the Inner Harbor, Fell’s Point and Little Italy including the National Aquarium and the Maryland Science Center. A quick cab ride will take sports fans to Oriole Park at Camden Yards and M&T Bank Stadium. From Harbor East Marina, guests are also just a short walk away from all of the major attractions at the Inner Harbor, Fell’s Point and Little Italy. Nestled in the center of it all, Harbor East is your gateway to discovering the best of Baltimore.

  2. - Estimated Mileage: 22

    Annapolis Yacht Basin

    Annapolis, MD

    410-263-3544 ext 101


    A walking tour of historic Annapolis, which is arrayed like spokes in a wheel from the Maryland State House, will delight architectural aficionados. Examples of Federal, Italianate, Georgian, Queen Anne and Greek Revival styles from the colonial period through the early 1900s abound. Good provisioning near the marina is hard to find. The locals’ favorite, Graul’s Market, with excellent produce, meat and fish is a mile and a half away. However, the marina has rental car and taxi services available to help stock up at Trader Joe’s, Whole Foods and Fresh Market. The Annapolis Yacht Basin has fuel and Annapolis Harbor Boat Yard is a full service maintenance yard that is conveniently located on Spa Creek near the historic district.

  3. - Estimated Mileage: 17

    Haven Harbour Marina

    Rock Hall, MD

    (410) 778-6697


    Rock Hall has everything a boater could wish for from first class service/maintenance facilities, restaurants, a grocery store, and fun events all accessible by bike, on foot, or by the great trolley system that connects all of the marinas. Rock Hall has many antiques and crafts stores including America's Past Antiques, Fishbone's Antiques, Rock Hall Gallery and the Artists of Rock Hall Gallery. You will also find gift stores, jewelry, clothing and accessories including Smilin Jake's Casual Apparel on Main Street. Don't miss Pirates and Wenches weekend aka Fantasy Weekend, which includes a decorated dinghy flotilla and kayak races, Caribbean beach party, treasure hunts, entertainment, contests and games for landlubbers and boaters alike. When looking for a place to grab a bite select from Bay Wolf Restaurant, Harbor Shack with live music on Saturday nights, and Waterman's Crabhouse.

  4. - Estimated Mileage: 25

    St. Michaels Marina, LLC

    St. Michaels Marina - Maryland Marina - Marinalife

    St. Michaels, MD



    For boaters, the focus of this Eastern Shore town is the Chesapeake Bay Maritime Museum with exhibits, restored vessels and hands-on boatbuilding workshops. It is where James Michener did his primary research for his best selling novel, “Chesapeake,” 40 years ago. The picturesque streets of St. Michaels are perfect to stroll along while looking for lunch or dinner. Topping off provisions is easily done within walking distance of the marina at Olivins, a gourmet grocery, or Acme supermarket. Fuel is available at St. Michaels Marina. Higgin’s Yacht Yard is the last full-service boatyard in existence in town.

  5. - Estimated Mileage: 7

    Safe Harbor Oxford

    Safe Harbor Oxford - Safe Harbor Oxford - Oxford, MD - Marinalife

    Oxford, MD



    Oxford’s main attraction is the town itself. It is one of the oldest towns in Maryland, officially founded in 1683. The charming, tree-lined village is a quiet antidote to the hustle and bustle of city life. The Oxford Market, a convenience store, is the only spot in town to buy any essentials for provisioning. If you need fresh fish and seafood, watch for the watermen when they bring their catch in early in the day. The marina is also a full-service boat yard, with gas and diesel available. Hinckley Yacht Services also has a full-service yard in town. Both Brewer and Hinckley provide quality work and craftsmanship.

  6. - Estimated Mileage: 30

    Safe Harbor Zahniser’s

    Safe Harbor Zahniser's Marina - Safe Harbor Zahniser's - Solomons Island, Maryland - Marinalife

    Solomons, MD



    Located at the mouth of the Patuxent River, Solomons Island was famous for its wooden sloops, schooners and bugeyes, built for the island’s fishing fleet. Today, visitors come to see the Calvert Marine Museum and the restored Drum Point screw pile lighthouse exhibit. Zahniser’s Yachting Center is an institution on the Chesapeake for boat owners. Not only do they have a full-service boat yard and marina, they also boast a swimming pool with a bar and grill for transient boaters. The pool is a fine summer’s treat after a day on the water. For additional provisioning, Zahniser’s provides a car with a driver to the nearest grocery store. Gas and diesel can be taken on at nearby Solomons Yachting Center or Spring Love Marina.

  7. - Estimated Mileage: 43

    Parks Marina

    Tangier, VA



    Tangier Island is the home of working watermen who get up well before dawn to get their boats ready for crabbing and oystering. The island is most well known for its soft shell crab, for which it claims to be the world capital. With a total population of about 700, most who live there can trace their ancestry back to a handful of families. The small settlement is unique to the Chesapeake and wandering its lanes is the ideal way to pass the time after lunch or dinner at one of the two local restaurants. And, of course, order soft shell crab and crab cakes. Parks Marina is just across the harbor channel from the many crabbing shacks built on stilts along the shore. The marina is owned and operated by 85-year-old Milton Parks, and is a simple affair with fixed docks, pilings and a faded signboard. Milton gladly offers advice on how to dock in the strong current and, once your boat is tied up, he will spin many a story of the island’s inhabitants and history. Daley & Sons is the only grocery store on the island. There are no repair or fueling services for recreational boaters on Tangier Island, but in a pinch a waterman may be able to provide some assistance.

  8. - Estimated Mileage: 26

    The Tides Marina

    Irvington, VA



    While at the marina, it is well worth taking advantage of all Tides Inn has to offer. The resort was developed from a waterfront farm 70 years ago, and today its outstanding amenities make it a premier resort. Play a round of golf on the Golden Eagle Golf Course or try classic treatments at a Chesapeake Bay inspired spa. Just a 10-minute walk from the marina is the Steamboat Era Museum, paying homage to the steamboats that connected the waterfront communities on the bay from 1813 until 1937. The best option for provisioning is the Tri-Star Supermarket located about 5 miles from the marina. And both diesel and gasoline are available at the marina’s fuel dock. Rappahannock Yachts is a family-owned full-service boatyard on Carters Creek, close to the marina.

  9. - Estimated Mileage: 10


    This beautiful, rural peninsula hosts 24 marinas and 10 boatyards. Its location makes it a popular home port as well as a convenient cruising destination. If you need anything for your boat, you can find it here: service, provisions, marine supplies, all served up with welcoming smiles. Deltaville residents take pride in their community and love to share a lifestyle of fishing tournaments, sailing races, local festivals and firehouse dinners. Local restaurants include The Table at Wilton, Cafe by the Bay, Cocomo's, Merrior, Taylors Restaurant and more. There are consignment and antique shops to browse on a lazy day in port and if you are in the mood for some touring, head for Deltaville Maritime Museum in Holly Point Nature Park. The museum chronicles the history of Chesapeake Bay watermen and its 36 acre park features outdoor sculpture gardens and a venue for waterfront plays and concerts. If you have time, see the tip end of Deltaville, called Stingray Point. Local lore says Captain John Smith was stung by a stingray here and was given the antidote for the bite by local Native Americans.

  10. - Estimated Mileage: 26

    Cape Charles Yacht Center

    Cape Charles Yacht Center - Virginia Marina - Marinalife

    Cape Charles, VA



    Some cruisers who have visited this revived, historic railroad town on Virginia’s Eastern Shore say it’s one of the Mid-Atlantic’s best-kept secrets. Life is easy in this inviting bayside town, with bikes and golf carts sufficing for transportation and menus heavy with local seafood. With most of its structures built between 1885 and 1920, Cape Charles has one of the largest concentrations of restored late-Victorian and turn-of-the-century buildings on the East Coast. Many of these beautiful structures are now transformed into bed and breakfasts, galleries and specialty boutiques. The Gull Hammock Gourmet Market and Drizzles are two high-quality groceries for additional provisioning. They are adjacent to the historic district and conveniently located on your way back from the beach to your boat. At Cape Charles Yacht Center, yachts have full access to nearby Bay Creek Resort, featuring a Beach Club pool as well as two signature golf courses designed by Jack Nicklaus and Arnold Palmer.