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5,262 Posts
Discussion Starter · #1 ·
We have booked a charter from Bareboat Sailboat Charters on the Maryland Eastern Shore of the Chesapeake Bay
This is our first time in this area.
What would be very lazy, low tension itinerary. I'm thinking two nights anchored or moored and two nights at a dock. Hopefully a $2 a foot not $4 dock.
This is the first time on the water for my wife in 25 years so the watch word is gentle.

5,262 Posts
Discussion Starter · #3 ·
Why do you have to link to Haven Yacht Charters, which gives all their boats and prices?
I have no afiliation with Haven Yacht Charters.
I've been on sailnet for about 3 years now.
I was asked what boat I was chartering.
I'm lazy and figured If I link right to site any other questions about the boat or charter company would be automatically answered.

Is there a reason you ask?

5,262 Posts
Discussion Starter · #4 · (Edited)
The charter company pointed me to this page of destinations.
Anyone have any experience with any of these ports or anchorages.
Quiet, loud, exposed, sheltered, good bottom etc. whatever you would like to share.


Severn River
Annapolis City Marina - Spa Creek
Annapolis Yacht Basin - Spa Creek
Bert Jabin's Yacht Yard - Back Creek
Chesapeake Harbour Marina - Severn, southern mouth
Mears Marina - Back Creek
Port Annapolis Marina - Back Creek
Smith's Marina - Severn, Little Round Bay

Tolchester Marina

Fairlee Creek
Mears Great Oak Marina

Chester River
Castle Harbor Marina
Chestertown Marina
Lankford Bay Marina- Davis Creek off Lankford Creek

Kent Island
Bay Bridge Marina
Mears Point Marina - Kent Narrows

Miles River
St. Michaels Harbour Inn and Marina - St. Michaels
St. Michaels Marina - St. Michaels, formerly Town Dock Higgins Marina - St. Michaels

Tred Avon River
Mears Yacht Haven
Town Creek Marina - Oxford

Tilghman Island
Lowes Wharf
Knapps Narrows Marina
Tilghman-on-Chesapeake Yacht Club and Marina - Choptank

Herring Bay
Breezy Point Marina - Chesapeake Beach
Fishing Creek Landings Marina - Chesapeake Beach
Herrington Harbour North & South
Rod 'n Reel Restaurant/Marina - Chesapeake Beach
Shipwright Harbor Marina

West River
Pirates Cove Marina

Rhode River
Rhode River Marina

South River
South River Marina

Patapsco River
Anchorage Marina
Hammock Island Marina - Bodkin Creek
Harbor View Marina - Baltimore Inner Harbor
Henderson's Wharf Marina
Inner Harbor East Marina - Baltimore Inner Harbor
Pleasure Cove Marina - Bodkin Creek

Middle River
Beacon Light Marina - Seneca Creek
Bowley's Marina - Middle River
Essex Marina and Boat Sales - Hopkins Creek
Porter's Seneca Marina - Seneca Creek
Sunset Harbor Marina - NormanCreek


Ports, Harbors & Anchorages

Ports & Harbors
- For detailed information on Harbors & Anchorages see Guide to Cruising the Chesapeake Bay
- All distances from Rock Hall in Nautical Miles (nm)

Western Shore
Baltimore Inner Harbor (18nm)
Fells Point (18nm)
Canton (18.5nm)
Annapolis (17nm)
Eastport (17.5nm)
Solomons (58nm)

Eastern Shore
Kent Island (10nm)
Saint Michaels (23nm)
Oxford (39nm)
Georgetown (34nm)
Havre de Grace (35nm)
Chestertown (25nm)
Cambridge (48nm)

Western Shore
Potapsco River (15nm)
Bodkin Creek
Rock Creek

Magothy River (12nm)
Dobbin's Island
Sillery Bay
Gray's Creek
Broad Creek

Severn River/Annapolis (15nm)
Spa Creek
Back Creek
Weem's Creek

South River (19nm)
Selby Bay
Harness Creek

Eastern Shore
North of Rock Hall
Still Pond (14nm)
Worton Creek (11nm)
Fairlee (9nm)

Sassafrass River (17nm)
Turner Creek
Skipjack Cove

Chester River (12nm)
Grey's Inn Creek
Corsica River
Langford Creek

South of Kent Island (15nm)
Crab Alley Bay

Wye River (17nm)
Shaw Bay
Drum Point

Miles River (20nm)
Leed's Creek
Long Haul Creek
Tilghman Creek

79 Posts
I chartered from Haven about two years ago. We took out a 44' Hunter that had a bow-thruster (very nice accessory, btw). We went out for three nights but we did St. Michaels the first night (at anchor), Annapolis the second night (in a slip), and Baltimore the third night (also a slip).

The distances were good except the trip back from Baltimore the last day... that took a lot longer than I expected and we almost missed our return deadline, which wouldn't have been a problem except the fuel dock closed so we probably would have incurred an additional charge.

Overall, I liked the trip. I don't know if you're familiar with the Bay but I would probably avoid Baltimore in the future. I had been there before but a couple of people I was with hadn't so we decided to make it a stop. The Inner Harbor is nice, but the trip up the Pataspsco River is far from scenic.

If you're doing four nights, you might be able to hit Fairly Creek, which is a good anchorage although it does tend to get crowded on Saturday nights. Also, Swan Creek, which is right by Haven, is a very nice anchorage. You may want to do St. Michaels, Annaopolis, Swan Creek and then Fairly Creek. Let me know how you make out.

- Kevin

Somewhat Senior Member
619 Posts
Annapolis is a favorite destination of mine, love to catch a mooring ball at just $25 per night, dinghy to shore or catch the water taxi. Reservations not accepted so don't arrive late on a Friday "in-season" and think there will be a vacant mooring, they fill quickly. Mid-week or early on Friday and you'll be okay.

While the Patapsco isn't a scenic river there is plenty to see, large merchant vessels (there's plenty of room, just stay out of the channel), the Francis Scott Key Bridge where there is a Star Spangled bouy marking the spot Francis Scott Key penned the Star Spangled Banner. Further up the river you'll actually pass Fort McHenry and ultimately into Baltimore's Inner Harbor. You'll want to stay at a marina.

Try anchoring in the Magothy River south of Baltimore for a "quiet get-away." As mentioned Swan Creek is right at Haven Habor and is a favorite for some. Take a trip up the Chester River (Eastern Shore) and there's plenty to explore including several creeks providing great anchorages.

St Michaels would be a good trip too and is approx 22 NM south of Rock Hall.

There's plenty to choose from so decide what you really want to experience and go for it. Let me know via PM if I may provide additional info.


2,248 Posts
when i chartered with them we anchored out the last nite behind dobbins island in the magothy river. very nice quiet place to anchor (my wife loved it) and an easy sail back across the bay to return the boat on time

Somewhat Senior Member
619 Posts
Behind Dobbins Is is a great place to anchor. I've continued around the hook of land east of Dobbins into Eagle Harbor which offers good shelter and a beautiful horse farm at waters edge.

59 Posts
Just curious, what boat are chartering?
I love St. Michaels and usually visit two or three time in a season. I can't justify the cost of a transient slip when I go there so we alway plan to have dinner at the Crab Claw. The food is good and they have several guest slips - no charge. If I'm there late and the crowd is thinning I'll ask the dock master (I think he's also the bus boy) if I can spend the night. A nice tip might help get the answer you're looking for. If it's not late, I'll motor over to the Wye river and and spend the night on the hook. I highly recommend making the Wye River one of your destinations.

1,086 Posts
My suggestion with your preference of two nights anchoring and one night docking:

Night #1: Anchor: Shaw Bay or Wye River (via Kent Narrows)

to Eastern Bay, around Bloody Point, North to...

Night #2: Marina Annapolis--Port Annapolis Marina--Price is less than $3/foot for transients, has a pool, Water Taxi into Annapolis;

North to.....

Night #3:Anchor either behind Dobbins Island OR

Northeast to Corsica River (via Chester River)

then South back to Rock Hall.


5,262 Posts
Discussion Starter · #11 ·
Wow, Thanks for all the great tips.
I'm supposed to get the Lippincott.
It's old and small but I wanted something I could handle by myself if necessary. My wife has has recent knee surgery so while she can walk OK now, I don't want to put her in a situation where she has to do more than she is comfortable with.
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