For sailors looking to explore the Chesapeake Bay, this suggested 7-day sailing charter 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.
Day 1: Herrington Harbour to Shaw Bay (25 NM)
Sail Details: The sail will take about 5-6 hours depending on wind speed. All wind directions work well except for NE which is rare in the summertime on the Chesapeake. Depart Herrington Harbour and head Across the Chesapeake Bay into Eastern Bay. Turn starboard and head down the Miles River. Watch out for the shoal in the middle of Miles River, to the east R “8”. There is good depth to the north of the shoal, between Orange and White special purpose beacon “Wyr River Day Beacon A” and Green “3” going into the Wye River. Shaw Bay is up the Wye a short distance on the starboard side.
Where to Anchor: The Wye River has several good places to anchor, but the current can be strong. Stay out of the current by anchoring in Shaw Bay. Good depth of 10’- 20’ deep. Holding is good and protection from wind and current is very good. Expect to see bald eagles flying above!
Activities: Explore the Wye River by dingy. There is a nature preserve and place to go ashore by Drum Point. Nice hiking trails, small beach area and picnic tables. Circumnavigation Wye Island is a great adventure by dinghy or kayak. With only 10’ of vertical clearance, the bridge to the north prohibits sailboats from making it all the way around.
Dining: This is a great spot to eat aboard and enjoy a beautiful quiet evening at anchor. There are no easily accessible restaurants from the anchorage. Sit under the stars in the cockpit, it is a great way to start the week.
Day 2: Shaw Bay to St. Michaels (6 NM)
Sail Details: This is a
short sail which allows a leisurely morning and plenty of time to enjoy time ashore once in St. Mickaels. Watch the shoals and honor the marks. The
depth goes from 20’ to 1’ very quickly!
Activities: St. Mickaels is a popular quaint town with plenty to do. Explore the Chesapeake Bay Maritime Museum, stroll the historic streets, and enjoy boutique shopping. There are several great coffee shops, but our captain’s favorite is The Blue Crab.
Overnight Stay: Anchor in St. Michaels Harbor or secure a transient slip at St. Michaels Marina, St. Michaels Town Dock or Higgins Yacht Yard. Make sure to reserve a slip ahead of time, this is a very busy harbor during the season. There is plenty of room at the town dinghy dock for those anchored out.
Dining: Dine at The Crab Claw on the dock for a classic seafood experience, or venture into town for everything from upscale to relaxed café style dining.
Day 3: St. Michaels to Rock Hall (22 NM short route/36 NM long route)
Sail Details: For the short route, head north to Kent Narrows. There are several restaurants that allow boats to dock while dining for lunch in the narrows. Hail the bridge tender for an opening on VHF channel 13. The bridge is on demand. Check the current prior to entering the narrows. It is better to plan to have a favorable current or even slack for going under the bridge. Motor through this area, it is too narrow to sail through. Review the nautical chart, the marks switch sides as you go under the bridge. Northbound is “red right returning” then once through the bridge, the red marks will be on your left.
For a longer day of sailing, head down Eastern Bay, round Bloody Point to enter the Chesapeake Bay. Head up the bay and under the Bay Bridge. Once under the bridge, Rock Hall is to starboard.
Either way, be careful entering Rock Hall Harbor, the marks are a little tricky. If it is the first time to Rock Hall, consider hailing Rock Hall Landing Marina and ask the dockmaster for tips on entering the harbor.
Activities: From the marina, there is a trolley that goes into town. The marina also has bikes for use, a comfortable pool and clean facilities. Several restaurants are within walking distance and there is a grocery store to re-provision the boat. A West Marine store is also accessible. Don’t miss the ice cream shop in town. It has quite a following for good reason.
Overnight Stay: Rock Hall Landing Marina is very clean with friendly staff. There is a place to anchor outside the harbor, but it is very exposed in anything but wind coming from the east.
Dining: There are several good restaurants to choose from, but for great pizza, try “That Place on Main”. For seafood, the Blue Heron Oyster House is popular.
Day 5: St. Rock Hall to Mill Creek (16.5 NM)
Sail Details: Navigate back toward the western shore, Mill Creek is just south of the Chesapeake Bay Bridge on the starboard side. The channel carries good depth going into Mill Creek, but is narrow, follow the marks. Larger vessels may opt to stop in Whitehall Bay.
Activities: This is a very peaceful and scenic anchorage. A great place to paddle board, kayak or jump in for a swim off the stern. The BIG deal is the restaurant (see below).
Overnight Stay: There are several good anchorages in the creek. Pick a spot according to what the wind is doing. For a strong south wind, anchor behind the point after Green 11.
Dining: Cantler’s Riverside is one of the best places to eat crabs on the Chesapeake.
Dinghy over and enjoy their fantastic crabcakes, or local rockfish sandwich. If you have some time, order a dozen or so crabs and start cracking. This is the main reason why people come to Maryland!
Day 6: St. Mill Creek to Downtown Annapolis (5 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. You will find open access
to the Chesapeake Bay along the way. Make it a longer trip by sailing out a way. Coming into Annapolis, 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. Just to the northeast of the mooring field is plenty of space to anchor, but it is exposed to wind from the northeast or east.
Activities: There is a town dinghy dock for those in the anchorage. Or hail the water taxi and tell them what mooring you picked up. They will come right out to you to bring your crew ashore. Stroll the historic streets, enjoy boutique shopping and great restaurants. The Naval Academy offers tours, ask at the main gate. Several local shops on Main Street, make this is a great place to pick up some gifts for those back home.
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.
Day 7: Annapolis back to Herrington Harbour North (20 NM)
Sail Details: After picking up coffee from Rise Up (a favorite Maryland coffee) get an early start. The wind picks up from the southeast in the afternoons, and the trip becomes more uncomfortable later in the day. Get some pictures of the iconic Thomas Point Lighthouse as you head south. Remember to avoid Long Bar coming into Herring Bay. Enter the Bay towards the south, rounding Red “2”.
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. If you do not have your own boat, charter a sailboat from The Sailing Academy. Plan your summertime vacation and enjoy some of the best cruising grounds in the US.