April is the shoulder season. Joker's Wild, for weather conditions. Daylight Savings starts in a few weeks, well before your trip. You'll have later evenings with 13 hours of daylight.

I think you're looking at 48 miles from Annapolis to Cambridge. Assuming an average of 5 kts, that's 9.6 hours.

If you catch a northerly that is fast but not too blustery, you could conceivably make it there in one shot. If you have to slog into a southerly or you set off in a light northerly, you might have to settle for stopping at Dun Cove and finish the final bit the next day. Another way to do it, might be to sail 10 miles from Annapolis to the West River, anchor for the day and take the bigger bite of the trip the next day, and sail from the West River down to Cambridge.

In general, the most accessible "bail out" stops are:

West River
Herrington Harbor
Dun Cove

 

Ditto on the weather. I would plan on a two day sail, both coming and going. In my experience, the wind will be coming from wherever you're trying to get.

Shoals extend well below Tilghman Island, so cutting through Knapps Narrows is a time saver. I wouldn't do it with more than 6' draft. KN is also about the half way point. A slip can be had there and restaurants are walkable.

Oxford, up the Tred Avon River is also a good ditch point. You can anchor and there are also free slips for overnighters at Capsize (the restaurant) and no, you don't have to eat there!

This is a great trip - take your time and have fun with it.

 

Annapolis to Cambridge would be a decently long day on my Catalina 36. I think I second the idea to consider breaking the trip up, while holding open the option of going the full distance if the stars align properly.

I would lean toward some destination on the Eastern shore over stopping at West River or Herring Bay.

If you have a shallow draft the suggestion of stopping at the Narrows isn't a bad one. I personally avoid KN, even drawing only 4' and change. I've touched bottom going through more than once paying strict attention to stay in the channel. The stress just isn't worth it for me but I don't have as far to go as you do in this case.

If I had to break it up, I'd likely opt for Oxford after rounding Black Walnut point. Be sure to look at your chart so you don't go out of your way rounding Black Walnut.

 

Knapps Narrows is shallow coming in from the bay. Tow Boat US hangs out there and has plenty of business. I would only use it at high tide.
It's about 38 nautical miles going around Tilghman Island.(the long way) You cut off 7 or 8 miles of that using Knapps Narrows. The prevailing winds will be from the NW. I go from Cambridge to St Michaels in a day fairly easily with good wind. If you have 12+ knot favorable wind it won't be a problem. Don't miss Oxford on the Tred Avon River.

 

If the weather is noserly the smartest thing to do is to go somewhere else. The Wye River and St. Michels is nice.

If you are just a little short on time, I agree that Oxford is a keen choice, well worth a trip in its own right.

Knapps Narrows keeps changing, but this by fall, any draft over about 4.5 feet was getting tricky at low tide.

Having gone around the Delmarva numerous times in smaller boats, the important thing is to get out of bed early and leave when the sky first starts to glow. Combined with twilight, that adds another hour. Barring bad weather, you'll have time to spare.

The town bulkhead probably makes more sense than anchoring in Cambridge, but you should take extra fenders and a fender board. The bulkhead is concrete. Stringing fenders vertically is a good way of dealing with the tide, since single fenders can hang-up. There is also the town marina, but I like the bulkhead better.

Circumnavigating the Delmarva--A Guide for the Shoal Draft Sailor
https://www.amazon.com/dp/B0149SB2CI

Sail Delmarva: The Bookstore

 

We sail from Annapolis . We visit the Choptank quite a bit when the wind is favorable on a weekend trip.

From the Tolly Pt Green marker through the Knapp’s Narrows to the Choptank Red 12 is 21.3 nm , straight line
From the Tolly Pt Green marker around Black Walnut Point to the Choptank Red 12 is 22.9 nm straight line i

There is very little difference. There a many many shifted shoal areas on the way in to the K apps Narrows, a bridge which must open. We draw 5 and bumped here a few times. That was 4 years ago so I no longer go this way

Dunn Cove, Oxford on the Tred Avon , La Trappe Creek good stopping points as is San Domingo Creek the back door to St Micheals.

We’ve stayed at both theconcrete free wall and city marina in Cambridge. You risk the fish factory smell on the wall if the wind is blowing your way, it’s pretty pungent. The Marina is near some ok restaurants.

 

I also sail out of Annapolis, although I sail out of Whitehall Bay just north of the Severn. The Choptank isn't a bad sail for a fast boat. Personally I find that sailing, or motoring the last leg between the mouth of the Tred Avon all the way up the Choptank to Cambridge is a pain in the butt. There are much nicer places than Cambridge on the Choptank and the last leg from the Tred Avon is a typically a long slow slog, or more often, motor.

As others have said, Cambridge is a very long day's sail. Usually a large part of the trip is a beat, although I have made the whole trip without tacking or jibing on a day with strong northwest winds.

On a slow, 30 footer, this can easily be a 14-18 hour trip.

As others have said, it probably would make sense to make a short 14 mile hop to the Rhode River the evening before, and then jump off from there. The Rhode River is easy to enter and does not add all that much to the overall length of the trip.

Knapps Narrows is a mixed blessing. On a fast boat, by the time that you drop sails, motor carefully up the channel, wait for the bridge, and raise sails on the other side, Knapp's Narrows doesn't save much, if any time. But if you draw 4 feet or less, and hit Knapp's Narrows near high tide, and you don't have a fast boat, then Knapp's Narrows can save maybe an hour.

The trip home is typically slower than the trip down since in our prevailing winds, it can be a dead run almost all of the way.

Personally, I am not a big fan of Dunns Cove as a bail out. It only makes sense if you are going through Knapps Narrows. I more typically go into either Edge Creek or Leadingham Cove off of Broad Creek, which are less of a detour than Dunns and really nice places to anchor for the night.

If you are shallow, you can always duck into Trappe Creek as well.

I have anchored in the River at Cambridge but that is a really bumpy anchorage. When I have been in a marina I have tied up at the Yacht Maintenance Company which is the first working boatyard that you pass on the east side of the channel into Town Creek. There isn't much in the way of facilities, but it was quiet and cheap and an easy walk to town. If you make arrangements in advance you can also stay at the Municipal Yacht basin. The municipal yacht basis used to be more expensive but they have very nice facilities.

Jeff

 

Learn to sail with the weather. If on your departure date it's blowing from the south then have a plan B to sail to a northerly destination. If you get lucky and there is a good breeze from the north you could make it all the way to Cambridge under sail. Time your arrival at the entrance to the Choptank so that you are not making an entry during an ebb tide, it can get very interesting if you do.
BTW in addition to the anchorages mentioned above, I have anchored in Lecompte Bay just a few miles before Cambridge. It's a good bailout spot if you are getting overrun by darkness. Easy entry and exit and best of all it's a sandy bottom so your ground tackle comes up clean the next morning.

 

There are so many other nice places in that direction, make it part of a 2-3 night trip. Much better.

 

With the bay, you just never know what to expect.
2 years ago, we went to Solomons for the weekend, from VA. About a 35-40 mile run. We had to motor up the bay as we had a 20 knot wind on our nose the whole way up. 2 days later, coming home, we had to motor again as we had a 15 knot wind on our nose the whole way back.
So why didn't we tack up and back...we didn't want to make a 6 hour run into 9-10 hours or more.

When we bought our boat, we made a 100 mile run in one day. A very long day, but we did it. Left 6 am and pulled into our home marina at 7:30 that evening