“Take A Trip With Me”
Michael Strotz joined Carefree Boat Club as a member in 2002. After a 5 year membership and boating 250+ times on the Potomac and Chesapeake Bay, Michael became a volunteer at the four club locations: Annapolis, National Harbor, Occoquan and Washington DC.
Michael is a Virginia State Certified Safe Boating Instructor and currently teaches Carefree Boat Club Annapolis’ Safe-Boating Training Class. In that class new members learn about different types of powerboats, boating safety, docking, channel markers, which boat has the right-of-way over another boat in different situations, etc. New members also learn a lot about the Potomac and Chesapeake Bay, the history, where to go, what to do, etc.
There are many interesting places to go on the bay for day and overnight trips. Early settlers on the Chesapeake Bay settled along the rivers so most towns around the bay are located in natural harbors on rivers.
Let me know where you want to go and if it is for a day trip or overnight and I will advise you how to do it. I will help with a float plan if it is an overnight. If you are going for an overnight, you can stay on a 260 Sundancer or you can take a cuddy cabin or deckboat and stay at an inn, B&B or a hotel.
Annapolis Historic Area (Ego Alley)
The historic area of Annapolis are good places to gofor overnight because the historic area offers many shops to browse in, restaurants, bars, ice cream parlors (I know you have a little boy). Even if you have been to Annapolis’ historic area by car, going there by boat and docking in Ego Alley
(the boat lane in the historic area) and overnighting there on the boat is a different experience. The boat gives you a porch on the waterfront to relax and people watch on the waterfront in Annapolis. Going to the historic area of Annapolis takes about an hour as you have to go out in the bay around the lighthouse so as to avoid the shallow. Then proceed up the Severn River to Spa Creek which is the creek where the historic area is located.
St. Michaels on the Miles River
St. Michaels is a 1-3/4 hour cruise from the club on the South River. It is a good place to go for an all-day trip or overnight. St. Michaels has waterfront restaurants, shopping, inns and B&B’s, and the Chesapeake Bay Maritime Museum on the harbor.
The club has a contact, Cathy, who owns Two Swan Inn & Cottages on the waterfront in downtown St. Michaels. Her family owns Higgins Yacht Yard, a small marina next to the inn. She is helpful to us and can often get a boat slip at her brother’s marina even when slips are in high demand in St. Michaels. You can stay on the boat overnight or stay at her inn.
Another trip is to go to Tilghman Island, which is an island connected by a drawbridge to the southern tip of the penninsula where St. Michaels is located. Tilghman Island has a few waterfront restaurants and inns. You can go there just for lunch or do an overnight. If you go for an overnight, take a good book or ipad as there are just a few restaurants on the island. No shopping. It is a 50 minute boat ride from our dock.
Oxford, on the Tred Avon River
Oxford, a very small village (year-round populaton of 650 people) is about 45 minutes east of Tilghman Island. It is described as the most scenic harbor town on the Chesapeake Bay. You can go there for a day trip or overnight. There are 5 B&B’s and inns. Robert Morris Inn seems to be popular.
Cambridge and Hyatt Resort on the Choptank River
Just east of Oxford is the River, which leads to Cambridge. There is a major Hyatt resort hotel there with 3 swimming pools, a beach, lots of children’s activities, restaurants, golf, spas, etc.
Inn at Pirates Cove on the West River
I like the Inn at Pirates Cove, which is a waterfront restaurant on the West River, one river south of the South River. It is a 45 minute boat ride from our club. You can go for Sunday brunch, or lunch, or dinner, or overnight there. The inn has its own dock and is the staging area for the Wednesday night sailboat races on the West River.
There are several dining rooms, a tavern room, outdoor dining on the dock, and a tiki bar courtyard with live music on Wednesdays, Fridays, and Saturdays. The inn has 5 waterfront rooms that are easy to book and only cost about $95/night. There are several other restaurants nearby so if you go to the inn for an overnight you can also try another restaurant as well.
To get there, go out to the bay, head south for two miles, and into the mouth of the West River. Be cautions of shallows and crab pot lines. There is a second river, called the Rhode River, off the northern side of the West River. It is very scenic and calm and a great place to go for waterskiing and tubing. There are no restaurants on the Rhode River, but there are several on the West River.
The Magothy River, just north of Annapolis, is an 8 mile long tidal river. It is a 1-1/4 hour cruise from our club dock on the South River. To get there from our club on the South River, cruise north up the ay, pass under the Bay Bridge, and proceed 4 miles northwest around land to the mouth of the Magothy. A marked channel will guide you through the narrow mouth of the river into the Magothy. Watch out for crab pots on your way in!
The shoreline on the northern side of the mouth of the Magothy resembles a peninsula, but is
Gibson Island, connected at its northern end by a causeway to land along the north shore of the Magothy. A private, gated-community, Gibson Island has 400 $3 – 5 million homes, making it the most expensive community in the country.
Because of its narrow mouth, the Magothy is protected from conditions on the Chesapeake Bay. The water is normally calm which makes for smooth boating. It is a great place to fish, water-ski and tube, and watch sailboats.. The Magothy’s shoreline has numerous inlets and coves to explore. There are two waterfront restaurants (see below).
There is a privately-owned island in the Magothy called Dobbins Island. Boaters gather along the northern side of Dobbins Island and children splash in the shallows and wade ashore. Always approach Dobbins Island from the southeast, never from the southwest where there is a sandbar and the water is deceptively shallow (often 1’ deep). The owner of Dobbins Island has had to fence off some of his shoreline at the ‘mean-low-tide’ line in order to legally preserve his property rights, but at low tide there is a stretch of sandy beach outside his fence where children can play and splash in the shallows without encroaching on his property.
The Point Crabhouse & Grill is a dockside restaurant on Mill Creek, off Dividing Creek, on the south side of the Magothy River four miles upstream (west) from the mouth of the Magothy.
Club members also like Deep Creek Restaurant. It is on Deep Creek, the first cove you encounter on your left (south) after you enter the Magothy River from the bay. Deep Creek Restaurant has a small dock for visitors. It is an indoor restaurant with large windows overlooking the water. In the spring and fall, sit by the hearth.
Rock Hall is on the eastern shore about 30 minutes north of the northern tip of Kent Island. It is home port to a working fleet of oyster and crab boats. Enjoy lunch at any of several waterfront restaurants around the harbor. A club favorite, Waterman’s Crab House restaurant and dock bar,
has slips for visiting boaters. Take the trolley around town to visit shops offering unique gifts and local arts and crafts. Visit the town’s Watermen’s Museum.
Going There – If you are planning an overnight trip, you can stay on the boat on the dock at several of the restaurants in Rock Hall harbor. There are also several marinas in Swan Creek, a scenic inlet just north of the main harbor. We recommend the pretty Osprey Point Inn, Restaurant and Marina, which is at the inner end of Swan Creek. It is just a few blocks from the restaurants in Rock Hall harbor. Another marina in Swan Creek is Rock Hall Landing Marina. You can stay on the boat or get a room in the small motel and it has a pool!
The eastern shore of the Chesapeake Bay is shallow for a half-mile offshore, so stay offshore as you go up the bay towards Rock Hall. Channel markers mark a channel from the bay over sandbars to the town of Rock Hall. Stay in the marked channel as you head into shore. The middle of Rock Hall’s harbor is only 2’ deep, so pay strict attention to the channel markers that guide you across the harbor to the restaurants and marinas. Trim up your prop for shallow depth.
For an all-day or overnight trip, go to Chestertown, about 25 miles up the Chester River at the northern end of Kent Island. the ride up and down the Chester River is beautiful and the water is calm, so doing it as a day trip on a deckboat is enjoyable.
The town was founded in 1706 and is one of a few historic towns in America reknown for its well-
preserved Georgian and Federal architecture. Many grand homes along the river were built by wealthy merchants in the 18th and 19th centuries. Follow quaint red-brick sidewalks along broad shaded streets past specialty shops, art galleries, antique shops, and restaurants. Washington College with many historic buildings is located in Chestertown.
Going There – Cruise north up the bay to the northern end of Kent Island, which is where the mouth of the Chester River flows into the bay. Then cruise an hour up the Chester River to the town. Pay strict attention to channel markers as there are lots of shallow areas, especially wherever the river curves or bends.