Advice on chartering on The Chesapeake

[Ranger_12]

I have been sailing Oklahoma lakes for 35 years, currently own a 25ft sloop that I sail 35-40 days a year and am wanting to expand my sailing horizons. I am thinking of chartering a 36 ft sailboat on The Chesapeake near Baltimore for a few days and staying at different marinas each night to experience the local sights. I have ASA 101,103,and 104 ratings.
I was thinking about anchoring out at night but wouldn't experience the local atmosphere and not sure of good anchorages available. My idea is to fly into BWI rent a car and leave it at the charterers marina on the east shore and drop the car off at DCA after spending a day in DC sightseeing.
Is October a good time of year to do this, average temps seem to be 69F day and 52F night. Any advice would be appreciated.
Thanks

[Sparx]

October is prime cruising on the Chesapeake. I will be cruising the Chesapeake the first three weeks of October.

One can spend a lifetime exploring anchorages in the Chesapeake. I suspect your charter is out of Rock Hall, and the charter company can help with anchorage suggestions. From Rock Hall going north consider Wharton Creek and the Sassafrass River. Going south the Chester River is great to explore. Further south St Michaels, Oxford, and Annapolis are all fun to visit.

In general the Eastern Shore tends to be quieter The Western Shore is more developed, with great access to large metro areas and perhaps more waterfront restaraunts.

In October there will be some cool fronts that roll through. Be prepared for some rain and wind.
Reef down when need be and enjoy. Coming from Oklahoma you will find the winds to be pretty tame.

[Ranger_12]

Sparx-- Thanks for the information, that is exactly some of the things I was wanting to know.

[ranger58sb]

Yep, October is usually primo around here. How many days is your charter? Will Rock Hall be your starting destination? Or...?

-Chris

[malbert73]

I love Oct sailing, but for me mid to late Sept is primo as still cool summer weather and not as much chance of the fronts and cold you’ll sometimes see in Oct. of course, sailing to annapolis and anchoring out during sailboat show is a neat spectacle and worth a dinghy ride ashore to check it out

[Suijin]

I would try and get down to St. Michaels and/or Oxford..both very pretty towns and the maritime museum in St. Michaels is worth a visit.

If you want to try the western shore you could make a nice trip around Whitehall Bay/Annapolis/Galesville, all within striking distance of Rockhall. Annapolis has enough to keep you busy for a few days just on its own, but don’t even think of pulling in when the boat shows are going on.

[Ranger_12]

Originally Posted by ranger42c

Yep, October is usually primo around here. How many days is your charter? Will Rock Hall be your starting destination? Or...?

-Chris

I haven't booked it yet but thinking of 4 or 5 days mid week out of Rock Hall. It might be to late to set this up for this fall but I hope not.
Thanks for your reply

[indimini]

Some dates you may want to be mindful of, if you are coming out the first half of October. Baltimore his hosting Fleet week Oct 3-9th. The Annapolis fall sailboat show is Oct 4-8th, and the powerboat show is Oct 11-14th.

If you haven't been to the sailboat show in Annapolis, I highly recommend it but you would need to make plans for where you could anchor/moor/dock as the area around the town gets full quickly.

[ranger58sb]

Originally Posted by Ranger_12

I haven't booked it yet but thinking of 4 or 5 days mid week out of Rock Hall. It might be to late to set this up for this fall but I hope not.
Thanks for your reply

Yep, see those dates for Fleet Week and boat shows.

I suspect 4-5 days is only just about enough time for short visits in Rock Hall, St. Michaels, and Annapolis... assuming sailing time, too.

-Chris

[vlathom]

October can be a little undependable regarding weather, so I wouldn't roam too far from home base if you only have 4 to 5 days. We used to do fall cruises in October a lot, but found ourselves more than once socked-in for a day or two, waiting for the winds to die down.

[rfawcett]

Starting from Rock Hall, you will be able to get used to your boat in protected water if you go south, then up the Chester River to either Queenstown or Cacaway Creek, depending on time. From there back down the Chester and through Kent Narrows into Eastern Bay, exploring either the Wi River or St. Michael’s depending on your preference for civilization. The Maritime Museum in St. Michael’s is worth the stop. Next, I would either Head south naps Narrows and try to get to Oxford, or go back up to Annapolis. The Magothy has some wonderful stops too, if you have time. From there or Annapolis, it’s an easy day sail back to Rock Hall.

[Sirago]

I would charter with Haven Charters, great people and boats. Go around the corner and have crabs at the Watermans then walk into town for ice cream.
You need more time. I double St. Michaels and Easton. Maybe end charter then drive to Annapolis boat show, it is worth seeing.

[Captain Anthony]

Ahoy, I am charting the eastern shore from 8/22 to 8/27 ( next week). I have reviewed the Guide and can endorse all of the places that people have told you about. I have sailed Lake Heffner in OKC when I was in school there. Have you experienced Heffner?

[Ranger_12]

I haven't sailed Lake Hefner but have been there many times, its really a pretty boring lake located in the city. I sail Kaw Lake in northern Oklahoma and it is beautiful the only problem is its only 8 miles from the dam to the first bridge and half the time I cant get under it but we have a few coves we can anchor in and usually very quiet and peaceful.

[Ranger_12]

I would like to thank everyone for the excellent advice. Yes I was planning on the Rock Hall area and the charter group mentioned. Again thanks for all the information.