Check out these maps and the info below to get more insight into our Youtube videos of our 3 and a half months cruising the Chesapeake Bay. It was our first time going into the area by boat, it was hurricane season, and we didn’t really know what to expect. We were there from July 1st to just past the middle of October.
Well, after most of our cruising being in Florida, specifically the Keys and the west coast, some Bahamas, and then the ICW, I can tell you that I never knew just how limited my anchoring choices per area had been! Countless are the beautiful protected anchorages and connected cruising grounds that abound in the rivers, bays, and tributaries branching off in all directions from the Bay. I’m talking thousands upon thousands. You could spend most of forever trying to visit all the cool little towns. And, need some open water sailing? The actual Chesapeake Bay is huge with all the sailing you could want. All that being said (or typed)….here we go:
After exiting the ICW at Norfolk and entering the Chesapeake, we quickly learned that “cruising the Chesapeake” meant going up the rivers that branch off the Bay. Of course, you use the main Bay to get from one river to the next, but the anchorages and the towns are mostly up one river or another. In the lower western portion of the Chesapeake, Mobjack Bay, Gwynns Island, and the Rappahannock River were our first tastes of this.
Another theme of Chesapeake cruising had to do with the time of year we were there. It was July, and it was stinking hot! If it looks like we are sweating in the videos, it’s because we are….profusely. Luckily, we were surrounded by water, and I got in it regularly.
Highlights were the strip of beach on Gwynns Island and the anchorage at Irvington. This video spans about our first 10 days of the Chesapeake Bay:
The next river we cruised was the giant Potomac River. The mouth of the river is so wide (11 miles or so), you can’t see the other side. It narrows gradually as you go up toward Washington DC, but for much of the river it is still 5 or so miles across. Another striking feature was the tall bluffs of the banks of the river. Both sides seemed to be over 50 feet tall most of the way up the river (Lindy said 100 was me exaggerating). It was beautiful.
A lot of cruisers we talked to choose not to go up the Potomac. It’s 90 miles to DC (that’s a long way on a sailboat), there is a current that can slow you down if not timed well, and bad weather can make this large body of water very uncomfortable. We decided to just go for it because…..what else are we gonna do? It ended up being one of the neatest experiences. Plus, Lindy’s brother lives in DC, and we were pumped to see him.
Approaching DC aboard Holiday was surreal. We stayed there on a mooring with a view of the Washington Monument for about 4 days.
Highlights were getting shot at in the live firing range, beautiful sunsets, obviously…DC, and Smith Creek at the end which was one of my favorite anchorages of the Chesapeake Bay. This video spans about our second 10 days in the Chesapeake Bay:
After a stopover in awesome Solomons Island, we made our way to Lake Ogleton in Annapolis. We had also entered a time where we were getting sailing wind a little more often. The first 3 weeks in the Chesapeake had been mostly still (and did I mention HOT?!)
Lake Ogleton isn’t really a lake at all, but a protected cove off the Bay. Lake Ogleton is also where great friends of ours live. The kind of friends that let you stay on their dock for however long you need to work on your boat and hide from hurricanes. Oh yeah, and also stay inside when it gets too hot. Oh yeah, and use their cars to run errands whenever you need. Words can’t express the gratitude we have to Jesse, Alison, Daniel, and Samantha. Not to mention, we had an absolute blast hanging out the whole time!
We spent most of the next 2 and a half months in Lake Ogleton. We also mixed in weekend trips to the Annapolis mooring field, a cruise to the Eastern Shore (more on that in a sec), as well as some land trips to see family. When we weren’t on these trips, we were working on Holiday at the dock. The boat work is not covered in these videos and will wait for another post. The importance of the boat work to this post is that it went on for longer and became more involved than we had anticipated. We had thoughts of going further north during the hurricane season, like to New York or further north into New England. But Annapolis ended up being the furthest north we visited. This was fine by us because we absolutely loved the area!
From Lake Ogleton, we took a week long cruise to the Eastern Shore with our friends Daniel and Samantha and their kids. They aboard their sailboat Temptation and us on Holiday. The cool thing about the trip was each night we would raft the boats together at anchor. It was awesome!
Oh yeah, and the Eastern Shore is awesome too. This rural, quaint, agricultural area full of parks and forests was like the western side we had been cruising: one river after the other with endless anchorages and beautiful little towns. The only difference was that it was even more remote and more sparsely populated.
Highlights were some great sailing, Oxford, St Michaels, and the Wye River……basically the whole thing! This video spans 4 or so days between Solomons Island and our arrival to Lake Ogleton, then skips about 2 weeks where we were working on Holiday, before finishing with our week long cruise of the Eastern Shore.
After our cruise of the Eastern Shore, it was the end of August. The rest of hurricane season (the next month and a half), Holiday was either at the dock in Lake Ogleton (with us working on her) or hanging out in downtown Annapolis. We had some great times and loved the area.
We had a scare with hurricane Florence projected to come our way, but she ended up turning further south. All in all, it was a great place to hide from hurricanes.
The weather did turn cold quickly though. Literally it was hot as can be in mid October, then the remnants of hurricane Michael came through, followed a day later by freezing temps (well freezing for this Florida boy).
A couple of days after that, on October 17th, the wind was blowing the right direction, and we pulled out of Lake Ogleton bundled in all our cold weather clothes for an overnight sail to Norfolk. 29 hours later, our three and a half months in the Chesapeake Bay came to an end as we dropped the anchor at Hospital Point and got ready for our trip south in the ICW.
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