For sailors looking to explore the Chesapeake Bay, this suggested 4-day itinerary provided a perfect mix of scenic anchorages and charming small towns. The journey starts and ends at The Sailing Academy’s base at Herrington Harbour North in Tracy’s Landing, Maryland.
Four Day, Three Night Itinerary
Day 1: Herrington Harbour to Harness Creek (18 NM)
Sail Details: Depart Herrington Harbour and head north to Harness Creek on the north side of South River. Watch out for the pound nets (fish trap pilings) between Herring Bay G1 and 83a. They are right it the middle and can be hard to see! This is an easy four hour or less sail. Anchor in Harness Creek just off of Quiet Waters Park.
Where to Anchor: The anchorage off of Quiet Waters Park is protected and picturesque. It is not well marked coming into the creek, so watch the chartplotter and stay in the middle where there is 11’ of water depth.
Activities: The park has a dinghy dock for going ashore, bike rentals, picnic areas, beautiful walking paths and a playground for the kids. There is also a nearby West Marine for any needed boating supplies.
Dining: This is a great spot to eat aboard, but if you don’t mind a bit of a walk (about 20 minutes) follow the main park road to the entrance. Just across the road is Annapolis Smokehouse and Tavern, and Grumps Café, a local favorite.
Day 2: Harness Creek to Downtown Annapolis (11 NM)
Passage Details: Leave the secluded anchorage and head to the “big city” of Annapolis. The shorter sail will allow for plenty of time to explore downtown. Watch out for Horn Point light (Green and white “HP”) just outside of Spa Creek. The downtown mooring balls are just inside of Spa Creek.
Where to Anchor/Dock: Mooring balls are first come first serve, so pick up any available ball, then pay the harbormaster. There is dockage available on the City Docks, but very little privacy from the crowds walking the docks (at all hours of the night). Call the harbormaster for availability and pricing. If you pick up a mooring, you can hail the water taxi on 68 and they will come to your boat and bring you downtown.
Activities: There is a town dinghy dock for those in the anchorage. Stroll the historic streets, enjoy boutique shopping and great restaurants. The Naval Academy offers tours, ask at the main gate.
Dining: Downtown Annapolis has a little bit of everything. Great coffee shops, taverns and upscale restaurants are right near the city dock. A popular local sailor’s hangout is the Boatyard Bar and Grill across the way in Eastport. The water taxi can get you close. Tell them Capt. Jeff sent you.
The best part of cruising by sailboat is that there are no rules, you are the captain, so chart your own course!
Day 3: Downtown Annapolis to Galesville (13 NM)
Pre-Departure: Enjoy a leisurely morning ashore. Make sure to stop in for some great coffee at Bitty and Beau’s Coffee. If you are looking for breakfast, The Iron Rooster and Chick & Ruths are both fantastic.
Passage Details: A late morning or early afternoon departure will still get you to Galesville in plenty of time. Make sure to get pictures as you pass by the famous Thomas Point Lighthouse. Follow the marks into West River carefully and watch out for the edges of the channel. It shoals up to 1’ really quickly on either side. There are some local marks like the yellow PCRC that you want to honor. Leave that one to port going into West River.
Where to Anchor/Dock: The moorings in Galesville are all private, so don’t try to pick one up. There is good holding off of the Yacht Club in South Creek. Anchor in 8’ of water. Pirate’s Cove usually has some slips available. Call Bob the dockmaster as you approach (443) 454-4370. He will not reserve slips ahead of time, but is very helpful once you arrive.
Activities: Galesville is a picturesque town, but very small. There is park near the town dinghy dock. A small store is across the street (closed for renovations last time I was there), and some antique shops.
Dining: Pirates Cove and Stan & Joe’s are both great waterfront restaurants. Both have places to tie up a dinghy and great seafood.
Day 4: Galesville Back to Herrington Harbour North (18 NM)
Sail Details: It is important to honor all the green marks going out of West River, There is a large shoal that extends quite a bit to the east of Curtis Point.
Where to Dock: Stop by C dock for a free holding tank pumpout. This will save on the pump out fee! Then proceed down to The Sailing Academy slips on R dock. Call ahead if you would like someone to meet you.
Activities: Herrington Harbour is a resort marina. If you arrive early in the day, there should be time to enjoy amenities such as the pool, walking paths, work out room, customer lounge and of course the showers! Bike and paddle board rentals are also available.
Dining: Dockside Restaurant is right on site. A short walk away is Wharf 38, a local favorite. Also in the basin is Happy Harbor, and Skipper’s Pier. All have a place to tie up a dinghy, but make sure to ask the staff so that you are not in a private slip.
The best part of cruising by sailboat is that there are no rules, you are the captain, so chart your own course! Stay an extra day in a favorite spot. Change plans entirely and explore somewhere new. Our itineraries are just a framework to help you get started. Plans are meant to be adjusted as you go. So, plan your summertime charter and enjoy some of the best cruising grounds in the US.
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