Tom and Cheri:
This will be a great trip and it will provide so many variables. On the northern bay, if there is no wind you can anchor off BETTERTON BEACH and enjoy a day on the sand and an overnight off the beach. We had a minivous there one time and it was really fun. See this photo album from 2005
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One of your biggest challenges is running the tides down the Delaware Bay. Usually, you plan it to work out like this: Exit the C&D into the Delaware with one final hour of flood tide, run one hour into this last bit of flood, then you will be running neutral for about an hour, and then the ebb catches you and you ride the ebb for 4-5 hrs and then slack will come and you will end the bottom of the Delaware Bay with about an hr of flood beginning as you reach the ocean. Going north you can actually run a fair tide from Cape May, NJ into the C&D and all the way down the Chesapeake to Tolechester where it will run out. This only works north bound. Southbound it never works this way. We have run the Del Bay 9 times, maybe more, and it usually works out this way. If you are lucky you will have a strong NW wind and you can run a wing on wing or deep port broad reach south.
At the bottom of the bay, by buddy, Carey always anchors up and behind the breakwater walls on the Delaware Side. This could be a good idea for a nice break southbound as you can relax, cook dinner and sleep. Can't really go ashore from there, and the ferry terminal basin is a no anchor zone now so it looks good but no go. I got kicked out of there years ago.
Another great spot to visit in this area is Lewis Delaware. You can enter at Roosevelt Inlet then run south in that canal, which is deep all the way down to Lewis where you can tie up for FREE at the floating city dock. If this is mid week, you should find space, if weekends then you may need to pay for dockage across the way. We like this little town and did this one time also.
As for the lower bay, we have anchored in WILLOUGHBY BAY which is large and easy, but not much ashore. The MDSchool.com uses LITTLE CREEK cause it is close to the ocean. John on LA40 uses Hampton Yacht Club up the Hampton River. We have anchored just inside OLD POINT COMFORT but you do have car noise which can be fun from anchor as you notice the rush hour rat race while you are at anchor. Nice dichotomy.
Going north on the Bay we like so many, have used JACKSON CREEK south of Deltaville, VA which has an interesting entrance where you go to the beach then when you bow sprit is over the sand, turn to port...almost! Great town dock and great anchorage.
We have never run the DelMarVa loop, but we have run the Delaware Bay 9+ times and we have sailed the entire Chesapeake Bay for 20 years. You will have tons to explore and enjoy.
Hayden in Marathon FL