5 Day trip Northern Chesapeake

Dec 19, 2014
57
Tartan 30 Baltimore
We are celebrating our 30th anniversary over Labor Day Weekend and want to do a cruise from Baltimore to Rock Hall, to St. Michael's (where we got married) to Galesville, to Annapolis and back to Baltimore. Any suggestions, pointers, tips?
We'll probably stay on the hook 3 of the 5 nights and just dingy in to town(s) unless it is as hot as it was 30 years ago when we got married (103 degrees and we had an outdoor reception!!)

Thanks

John & Phyllis
 
Oct 3, 2008
325
Beneteau 393 Chesapeake Bay
Sounds like a great trip. I sail to all those places often. Only thoughts are: 1) have a contingency plan to allow for weather, and 2) it will be crowded. If you don't yet have reservations for slips, do it now. The first three days are 20-24 nm each trip, so allow enough time to get to the destination before too late in the day (check with marina staff re: staff availability).

In Rock Hall, lots of places to get a slip. Personally, I like Haven Harbor and Osprey Point marinas. You can also anchor in Swan Creek (shallow and may be crowded). In St. Michaels, again lots of choices. Higgins is inexpensive but Spartan, and St. Michaels marina is the opposite (nice, but costs more). In Galesville, there is always Pirates Cove (moderate in price and decent enough amenities). And Annapolis? Well, good luck on Labor Day weekend but if you find a place you will enjoy it immensely.

Happy Anniversary!
 
Sep 23, 2009
1,475
O'Day 34-At Last Rock Hall, Md
Love St. Michaels. "Across the street" s the Miles river with calm beautiful anchorages. Last year the water taxi only ran on weekends. Right inside the Miles River entrance is Shaw bay with fantastic sunset and lots of room. I hate the madhouse congestion and lack of wake free zones in Annapolis. Even the areas around bridges are not no wake. Amazing people are not killed every week on the Severn River. Some better alternatives are Magothy River, Whitehall Bay and its creeks, and the West/Rhodes rivers. All have good waterside dinning and lovely anchorages.
Magothy is large enough to spend the day sailing or exploring.
We sail out of Haven Harbour and can recommend it. (yoga classes Sat 9 am that the admiral seldom misses). Also there is plenty of room in swan creek anchorage, mostly 7 feet in the middle third.
We'll keep an eye out for you.
s/v At Last
 
Oct 2, 2008
3,810
Pearson/ 530 Strafford, NH
I think the 30th anniversary is fiberglass, nice that you're on a boat. Toss one back for the rest of us.

All U Get
 
Mar 21, 2004
2,175
Hunter 356 Cobb Island, MD
My point of view $.02, five days is not enough time to accomplish your plan. Schedules will kill you.. Weather, will change and create difficult choices. Plan 8 days and enjoy the ride.....
 
Dec 19, 2014
57
Tartan 30 Baltimore
Thanks for all the input and suggestions. Keep 'Em coming. I only wish we could take 8 days. As long as we get to St. Michaels, we'll be good. Everything else is pretty much "subject to the winds". Thursday from Baltimore to Rock Hall may be a challenge if the winds are on our nose but that makes the trip south to St. Mikes easier.
 
Dec 19, 2014
57
Tartan 30 Baltimore
Well, we made the loop and everything went as planned. A little more motoring/motor sailing than we would have liked but we still got decent winds at least part of every day.
I feel lucky that we had absolutely no issues over the course of the trip. Dodged one thunderstorm by about 3 miles and other than that not a drop of rain.