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Old 07-21-2019, 01:40 AM   #1
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Best time for extended cruising around the Chesapeake

Some time in 2020, we hope to have 12-16 weeks to spend on and around the Chesapeake. Apart from the on-water experiences, seems like there are great landside trips and sights as well.

If your timing was un-constrained, what is the optimal window you would shoot for having regard to weather conditions? Note though....we don't do really cold weather!
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Old 07-21-2019, 04:36 AM   #2
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I live on the Chesapeake, and I think it's too cold for boating from mid-November to sometime in late March to early April. There's also a point when it gets too hot and humid. Most people avoid going outside in August. July is especially hot this year, but it's typically pleasant. You can start in the spring and reliably have 3-4 months of comfortable cruising, or start in the fall for 2 to 3 months, depending on your definition of comfortable. There will be plenty to do and see during either of those periods. The Chesapeake is large enough that spring comes earlier at the south end and summer fades sooner at the top. If you have the luxury, you can plan your trip to increase your time in the comfort zone.

Best of luck, and have a great time!
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Old 07-21-2019, 05:23 AM   #3
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I would agree that July and August are often too hot. Starting in late April and ending in early July would be my recommendation. While September into November can be some of the best months to cruise the Bay, the increased winds of fall, the later half of hurricane season, and the possible early arrival of cold weather make fall more risky for a smooth extended cruising period.

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Old 07-21-2019, 05:53 AM   #4
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For any 14-16 week period you are goung to be cold or hot sometime in the Chesapeke. I remember cold, wet and windy weeks in early May, but also cold, wet and windy weeks in November. Forget July-August as others have said.


So, pick your poison- spring or fall.



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Old 07-21-2019, 06:33 AM   #5
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I did several 3 week cruising vacations there in July and enjoyed the weather.
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Old 07-21-2019, 08:13 AM   #6
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Some time in 2020, we hope to have 12-16 weeks to spend on and around the Chesapeake. Apart from the on-water experiences, seems like there are great landside trips and sights as well.

If your timing was un-constrained, what is the optimal window you would shoot for having regard to weather conditions? Note though....we don't do really cold weather!
16 weeks: either mid-March through mid-July, or August through November.

Either way, July and August are usually the hottest months. It's been in the mid-90s F this whole last week and through today at least, heat index in the 100s.

What are your intended start/stop points?

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Old 07-21-2019, 06:17 PM   #7
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[QUOTE=ranger42c;What are your intended start/stop points?

-Chris[/QUOTE]

It is a chicken vs egg problem. If we went with the Spring window, we'd start in the south and work north and vice-versa if we took the mid-August to end-October window.

To give a bit more context: we're experienced Australians planning to buy a boat (or find a long-term charter/lease deal with a private owner) in the US and keep it there for 2-3 years. We want to do the Loop, Bahamas and the Down East Loop in 3-4 month sessions, returning home to attend to family matters (and avoid the Winters!) in between. The Chesapeake of course is one area where we'd like to spend time. We expect to find the boat we want in Florida or around the Chesapeake region itself (the 12-16 week cruising window excludes time spent sorting the boat).
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Old 07-22-2019, 06:22 AM   #8
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The Fall for me. But Spring isn't bad either. As everyone mentioned, July and August are just brutal.
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Old 07-22-2019, 08:20 AM   #9
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The Fall for me. But Spring isn't bad either. As everyone mentioned, July and August are just brutal.
What is it about the Fall that makes you prefer it as a cruising window ?
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Old 07-22-2019, 09:14 AM   #10
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Having lived on the Southern Bay my whole life (Va Beach) I would pick September and October. They are by far the most pleasant months. You do run the risk of having to hole up for a hurricane warning but I'm not sure that is much worse than holing up for Nor'easters in the spring. The spring also has an abundance of North wind until late spring. North winds can make the bay a mess. Personally (and I say this with caution) I think 12-16 weeks is too long to spend on the Chesapeake. In 16 weeks you could run from the Keys to Baltimore at a leisurely pace and have amazing experiences. But that is just one man's opinion.
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Old 07-22-2019, 02:12 PM   #11
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Personally (and I say this with caution) I think 12-16 weeks is too long to spend on the Chesapeake.
That may be because you live there. When we spent 3 boating vacations there, we thought we could easily spend an entire boating season there. (Maybe 2 seasons).
There are plenty of areas to explore.
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Old 07-22-2019, 06:45 PM   #12
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I boat lower Chesapeake, and great spring and fall weather cruising, even all the way to beginning of November. But I like it cool. Summers cab be brutally hot, lots of 90's and high humidity. It honestly is hotter than Miami.
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Old 07-22-2019, 09:09 PM   #13
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What is it about the Fall that makes you prefer it as a cruising window ?
Humidity has dropped and nights are cool for comfortable sleeping without having to run air conditioning. This is especially beneficial for anchoring out which the Chesapeake has plenty of well protected and beautiful anchorages. There are fewer bugs in the cooler weather and more likely to have a breeze to keep the few stragglers away. The winds are definitely higher which is really beneficial for sailing but if you have somewhere to go, as long as you leave early the bay is usually calm in the morning. In some of the smaller harbors, the shops and museums aren't open late in the season but the larger harbors have services year round. You are definitely more likely to have a few days where the bay is too bumpy to enjoy comfortably but as long as you aren't on a tight schedule, waiting a day or too will yield a smooth ride. If you like to swim in the bay, the water usually comfortable Midway through October. I grew up on the bay, swimming and water skiing. I still get in it but stay away from treatment plants after large rains.

The spring can be nice too but is more likely to be too windy for comfortable transit. The wind off of the cold water can be less pleasant than the fall but it is still better than sweating to death.

I do most of my boating in the summer due to my kids being in school but I am quick to take a slip with pool access or run the generator on the hook to sleep in comfort.
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Old 07-22-2019, 09:49 PM   #14
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I boat lower Chesapeake, and great spring and fall weather cruising, even all the way to beginning of November. But I like it cool. Summers cab be brutally hot, lots of 90's and high humidity. It honestly is hotter than Miami.
I've boated in that area into Dec. Boating until Thanksgiving is usually no problem and there'll be a lot less traffic and crowds. Some marinas roll up the sidewalks in Oct. so you need to check with whatever marinas you plan to use.

Some of the "summer" towns will be pretty quiet after Oct.
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Old 07-22-2019, 11:40 PM   #15
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What is it about the Fall that makes you prefer it as a cruising window ?
Kiddies go back to school
No jet skies jumping your wake.
Actually get seats in restaurants without 45 min wait
Fewer bowriders passing on both sides in narrow channels
Don't need to reserve a slip or mooring by noon
No mosquitos
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Old 07-23-2019, 12:05 AM   #16
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Kiddies go back to school
No jet skies jumping your wake.
Actually get seats in restaurants without 45 min wait
Fewer bowriders passing on both sides in narrow channels
Don't need to reserve a slip or mooring by noon
No mosquitos
Or black flies.
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Old 07-23-2019, 06:12 AM   #17
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What is it about the Fall that makes you prefer it as a cruising window ?

For all the reasons others have already mentioned before I got back to this thread.
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Old 07-23-2019, 12:12 PM   #18
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For all the reasons others have already mentioned before I got back to this thread.
Wow fantastic feedback for a non-local...thank you all very much for taking the time to comment. I'm persuaded by the arguments in favour of a late Fall schedule.....which will mean we put the boat away for winter at the end of our cruise, which is convenient. I'll bounce back to you folks with a draft passage plan as our dates firm up.
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Old 07-23-2019, 12:26 PM   #19
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12-16 weeks is a long time. You don't need to constrain the trip the Chesapeake region. You could venture north to New England during the really hot months, or south during the cooler months.

"we don't do really cold weather!"

This is relative. Ask someone in New England and someone in Florida and you'll get two very different opinions about what "cold" is.
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Old 07-23-2019, 12:28 PM   #20
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At 16-17 C

A Floridian is putting a jacket on.

A New Englander is taking a jacket off.
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