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Prior to our heading south, everyone was dying to know what we were going to do about hurricanes. Our answer was simple… we just won’t be going “that far south” until the end of hurricane season. And we haven’t! So why is it that we need to be concerned about Earl causing problems here in the Chesapeake? We kept up our end of the bargain, didn’t we?

Like just about everything else sailing and cruising related, dealing with storms like this is way new for us. Fortunately we have at least half a dozen people looking out for our best interests. We have received numerous emails and phone calls from people, both in this area and abroad, offering us places to stay and intel on where to go and what to do.

Curious to see what a “hurricane hole” looks like (a place where one could safely weather a storm), we followed the Sassafras River almost to its end where Skipper Bob recommends anchoring in what he refers to as a hurricane hole. Well, we’re here now and I’m not entirely sure what would make this place so special. Perhaps our blog readers who are more educated on this subject could tell us what would make a secure and safe hiding place?

I guess it was a bit premature to be singing the following song, eh?


  1. sail far from land, heavy wind will not brake your boat (with out sails up of course) there will I put my money, maybe crazy!? god luck any way you choose!

  2. Hurricane holes are deep, narrow coves or inlets that are surrounded by sturdy trees or bluffs which block the wind. Trees provide a tie-off for anchor lines, if needed. The bottom should be good anchoring/holding, with no rocks in case all the water is blown out of the cove and your boat grounds.

    Luckily, the Chesapeake offers you lots of options! I can think of 3-4 spots on the Magothy alone.

  3. I’m a cruiser in the making, so I won’t give my unexperienced opinions about hurricane holes…I am curious how crowded places like that get at the first hint of a storm coming up the coast. There are lots of people heading south and lots that read skipper bob. Are you surrounded by other boats looking for the same limited safe spot?

    • Good question! I don’t know. We were the only boat anchored there last night (although there were a few on moorings that are likely always there) but it’s still early I guess.

    • Jeff, it is always a scramble here on the bay during a hurricane, especially this time of year when there are extra boats passing through on their way south. Many haul out and strip the boats bare, however there are not nearly enough facilities for that. We never have, choosing instead to ride it out in the water, usually well tied in a slip. Even more difficult to find facilities to handle cats with their wide beams. The good news, as Mary says, there are many many crooks and crannies to hole up in and hunker down. Most bottoms are “sticky” mud (don’t ask, p.u.) and holding is quite good. Many of the creeks and rivers have high, treed banks with winding channels that cut down on the straight fetch which help reduce the wind and wave action. The main concern here is the storm surge, which tends to be dictated by the path the storm takes. Most piers, docks and walls in the area are built with our average 2.5′ tide swing in mind, not 10-15′ storm surge, so tying up properly requires studying the habits of spiders and a good understanding of scope. And you always have to watch out for the other guy(s).

  4. Here’s hoping that “Earl” isn’t too much of a thorn in your side. Glad to hear there’s so many offers of help out there. By the way, cute video!

  5. At first glance, I actually the rainbow reference was for the colorful legend of storm categories on the forecast chart.

    My memories of our times on the Chesapeake include:
    It was hot
    The crabs know how to swim there
    Rays flapping by in the water
    So many jellyfish that swimming wasn’t possible without one of those “floating pools”
    It was hot
    Crab pots everywhere
    Beautiful sunrises
    It was hot
    They do not include:

  6. I’m wondering the same thing as Jeff. Sandy Hook may not have trees, but at least it’s all sandy bottom, and I’m anchored in pretty shallow water. Also with winds coming out of the North East, as predicted, I should be pretty well protected. There is another spot, down river, with more protection, shallower water, and plenty of trees to tie to, but it’s a not a big area, and I’m afraid if it really gets bad, it will get crowded there.

  7. This topic is worthy of at least a chapter if not a book. Basically, in the Chesapeake area, you try to match your options to the projected path and characteristics of the storm. Some fare well on land, some not so much. The storm surge can be greater on the western shore or the eastern shore depending on the storm path in relation to boat location. The projected path will also dictate whether a N/S or E/W oriented tributary would provide the better protection. High shoreside banks and lots of swing room with less company also is helpful. Local available service for support is also helpful. A place to hole up on shore with the ability to check on the boat and possibly make mooring adjustments is good. Bottom holding quality makes a huge difference. Nothing can be done about imbedded tornados. Lot’s of friends to help (each other). And on and on. And let’s not forget luck. (good thing you didn’t scripmp on the champagne at the christening!) It can be a case by case basis.

  8. Big spiderweb of lines, lots of trees to tie to, BIIIIGGGG, ENORMOUS anchors, NO COMPANY. Stay safe, all three of you!

  9. We’re actually still in cape May, waiting until Thursday, when we expect a nice wind boost. Whether this is a wise call….

  10. I’ve been following your blog for a while now and glad to see you are in my neck of the woods. I just bought a boat up in Rhode Island and took 2 weeks to bring it home to the Chesapeake, so I did much of the route you are doing now. If you need a place to hole up and get a hot shower and you are headed up the Potomac River, I am based out of Colonial Beach, VA, 35 miles upriver from the Chesapeake. Shoot me an email and I will be happy to give you a ride for whatever supplies you need if I am in town or let you use my spare bedroom if you need to get off the boat. The Bay is a great place to explore…enjoy it!

    • Hi Brett

      We’ll definitely be in your area. We’ll be sure to give you a shout when we have a better idea on the timeline for that part of our trip.

      Thanks so much for the comment and the offer!


  11. Peter is headed to Matthews Point(coast of NC) in the morning (Wednesday) to anchor our boat in a hurricane hole. Our marina has us evacuate once a storm is predicted with winds higher than tropical force winds. We are lucky there are 3 fairly large holes since the marina has around 100 plus boats. This will be our first time anchoring out. We’ll let you know how well s/v Isabella survives.

    You guys stay safe. Your following is getting bigger and everyone is cheering you on!

  12. Mike,

    I hope you have found a spot that is somewhat shallow (read 15 ft or less) with a sandy bottom for good holding, put out every anchor you have onboard with a scope of 7 to 10 times the water depth. I also hope that the spot you pick is protected by tall trees, cliffs, buildings, anything that can break the wind. Also I hope you are far enough up river to minimize the effects of a storm surge. Make sure you have stripped the boat completely….roller furler down and stowed, mainsail stowed below, consider removing the boom and lashing it down on deck, remove the bimini, remove any antennas you can, make it a BARE BOAT if you can! If you can run lines to trees or bulkheads so the boat is in the middle of a spider web of lines and the boat being the spider that is close to an ideal situation. Also remove your dinghy and then last but not least comes the hardest part….you and your wife must leave the boat and go to a safe place ashore. If the hurricane force winds reach your boat, there is nothing you can do during the sotrm and aboard the boat to save it, but you would be placing your lives at risk.

    Hopefully you will only see some serious rain and a little wind, but you never know, I’ve been through a number of hurricanes on the Chesepeak, at Barneget, on Cape Cod, and more than I want to remember here in florida….stay safe…I will keep you both in my prayers!


    • Thanks so much Jim for the well wishes and the good info. We are here in the Magothy river now with our friend Kirk. I think his large Lagoon should act as a nice breakwall for us.:)

  13. Hopefully Earl loses all his steam before getting close to you and your preparations can be just a great learning opportunity.

  14. Oh wow! We have no relevant experience to offer but lots of empathy at having to cope with a hurricane your first season out. Lots and lots of luck and we’ll be thinking of you!

  15. I hope you weather Earl well. I am sure you will be reducing windage above decks like removing sails, barbecue, dodger etc. We look forward to your first post after Earl has past. Halifax is preparing for the worst by the way with perhaps a direct landfall and with warm water predicted to add to the storm’s strength.

  16. We have been reading your blog daily and find it fascinarting as we too are newbie sailors. When we took our boat to the Sea of Cortez we were quite concerned with Pacific hurricanes. We read an article in Blue Water Sailing Sept 2005 that described a cruising couple that rode out hurricane Marty in Mexico in a hurricane hole. It was a good reference article. We will keep reading your blog.
    Good luck.

  17. the new star of The Carribean Got Talent!!

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