Summer is the perfect time to explore all that the Chesapeake Bay has to offer, and in one weekend trip you can hit several unique destinations. We set out from Baltimore and head east across the bay toward Kent County, Maryland, stopping first in Fairlee Creek, a lovely anchorage spot that's a favorite of many Eastern Shore boaters. The marina in Fairlee is an excellent place for a family getaway, with many kid-focused features, plus beach parties and live entertainment on the weekends for adults. From Fairlee Creek, it's a scenic cruise to historic Georgetown, where the marinas have terrific amenities, including restaurants that are destinations in their own right.
After cruising to Fairlee Creek, dock at Mears Great Oak Landing, recently voted Best of the Bay by Chesapeake Bay Magazine readers. The 350-slip, full-service facility has top-notch amenities, including a fuel dock, WiFi, and a well-stocked ship's store, and it provides loads of recreational opportunities. Kids will love the basketball, tennis, and volleyball courts, not to mention the swimming pool, bouncy castle, waterslides, and weekend movie nights. There's also a private, sandy 180-foot-long beach along the creek.For grown ups, there's a hot tub overlooking the bay, as well as the popular Jellyfish Joel's Tiki Bar. The casual, tropical-themed watering hole hosts live bands on the weekends (R&B, classic rock, reggae), and during the summer there's a Hawaiian-style luau party every Friday night. Don't miss trying one of the bar's infamous frozen drinks: the Painkiller, the Rum Runner, and the Pain n'de Ass.
From Fairlee Creek, cruise along the Sassafras River to Georgetown. The Sassafras is one of the true treasures of the Chesapeake region, and is considered by many to be one of the prettiest rivers in the upper bay. At the end of the eight-mile-long river there are several marina options or a peaceful anchorage. The 300-slip, family-owned Georgetown Yacht Basin offers a variety of complementary services, including a water taxi, the Two Toots, that will shuttle guests anywhere in the area. There are also kayaks, paddleboats, and bicycles for visiting boaters to use. The quaint town of Galena is an easy pedal away and has boutiques, curiosity shops, and cafes. There are several restaurants within a short walk of the marina, and many are pet friendly and offer outdoor dining. The owners of the Georgetown Yacht Basin also own the Kitty Knight Inn & Restaurant, which sits on a hill overlooking the marina. The property is named for local patriot and hero Kitty Knight, who persuaded the invading British not to destroy part of the town during the War of 1812, and who was rumored to have been one of George Washington's dance partners. The restaurant is open daily and offers both casual and fine dining, as well as drinks on the outdoor deck, which has stunning bay views. Don't be surprised if you spot an osprey or eagle soaring through the sky.
The full-service Sassafras Harbor Marina has 200 slips and can accommodate boats to 120 ft. Relax by the pool or stroll along the beautifully landscaped boardwalk. There are horseshoe pits, pool tables, and ping-pong tables when you're ready to take a break from simply enjoying the scenery, plus a fun on-site gift shop. Harbor Café, located on the marina grounds, is laid back and inviting, with dishes such as crab chowder, oyster stew, flatbread pizzas, and house-made cannolis. Order a box of the ricotta-cream-filled treats to go, and continue to savor the weekend's adventures even after you've returned to your home port.
If you have access to a car and are interested in doing a little more exploring, the burg of Chestertown is an easy drive from both Fairlee Creek and Georgetown, and well worth a visit. The historic town dates back to 1668 and sits along the beautiful Chester River. It is home to many boutiques and antiques shops; Washington College, founded in 1782 and one of the country's leading liberal arts institutions; and the Imperial Hotel, with its excellent restaurant. (208 High Street, 410-778-5000). Walk the streets and admire the many Colonial-era homes, some of which were built in the 17th century. It's also possible to visit Chestertown by boat -- the Chestertown Marina offers dockage for boats up to 100 feet.