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Cruising the Southern Chesapeake Bay to the Dismal Swamp

Cruising the Southern Chesapeake Bay to the Dismal Swamp

Outward’s 2021 Cruise

Liz and Al Sutherland


Cruising the southern Chesapeake Bay is one of our favorite cruises. There are endless ‘gunkholes’ one can visit for a couple of days, or as we prefer a week or more.

This June we plan to cruise south to the Dismal Swamp and back – anticipating the trip to take about three weeks. Why the Dismal Swamp as a destination? Well……

  • Five years ago we sailed Outward (our 38 foot Sabre) south through the ICW (InterCoastal Waterway) to the Florida Keys, staying in Marathon through the end of March. We fell in love with the Dismal Swamp and the Pasquotank River.

  • Three years ago (October 2018) we attempted our currently planned trip only to encounter one boat problem that led to another; Zahnisers Marina thought they fixed the problems, so we headed out again. No luck – serious ‘banging’ from the engine forced us to find refuge in the Little Choptank where we called Boat US for a tow back to Galesville. Turns out the AquaDrive failed and had to be replaced.

  • Two years ago (August 2019) we had a new AquaDrive and everything was in great working order. We were ready to head south again. Four days after we left Galesville, we arrived at Cape Charles and had a wonderful dinner. The next morning, we woke to predictions of Hurricane Dorian coming up the Chesapeake Bay. We talked about trying to continue south, but at the rate Dorian was moving we would be taking a big chance. So – we headed back home. Unfortunately, at one of the anchorages, Liz missed a step going into the galley which resulted in a broken fibula requiring surgery and a plate.

  • Last year (2020) we all know was Covid time – no sailing until the end of season!

  • This June 2021 – third time should be a charm!! We are both in good shape, boat is working as it should and we are ready to go! We are attempting a June trip in hopes of not encountering bad weather.

When we cruise, we enjoy anchoring out as much as we can. However, there are a number of stops we enjoy staying at a marima – along with an opportunity to re-provision and fill up with fuel, pump out and replenish the water tanks. The challenging part of planning this trip is always provisioning. When we did the ICW trip, we found a number of very helpful books and articles written by sailors/boaters providing great tips!


Provisioning when you have a small refrigeration ‘box’ and tiny freezer is a challenge but doable. I have found that using plastic bins with lids is a great way to store fresh produce, deli food, cheeses and some fruit. We enjoy lots of fresh produce and found that buying Romaine lettuce and spinach lasts for quite a while; tomatoes we get somewhat green and a couple that are ripe. Cabbage doesn’t need refrigeration and can be used for many things; carrots and celery do well. Fruits can be a little challenging, but we find that apples, oranges, kiwi, blueberries, peaches and grapes do well -- strawberries always get me into trouble. Dairy products can be challenging, but for long trips we have on hand evaporated milk and boxed milk that doesn’t need refrigeration until opened. Eggs that have never been refrigerated or washed can be kept at room temperature for a couple of weeks; and yogurt can be used in place of sour cream. We also prefer seafood and chicken – salmon and tuna purchased in frozen individual servings are great – as are bags of shrimp. For chicken, we freeze thighs and breasts in ‘seal-a-bag’ so they are compressed and fit well in the little freezer. The trick with the freezer is to leave just a little bit of room for ice so we can enjoy our evening cocktail!


Lesson learned from the ICW is to not pack much bread – it does get moldy after a week as do bagels. However, soft tortillas are great and can be used for sandwiches and dinners! English muffins do ok. Canned beans, tuna, chicken are great to have on hand along with pasta and quinoa.

Cookies, chocolate and snack crackers (the ones with either peanut butter or cheese) are a MUST when cruising. Often you are unable to put together something for lunch and these tidbits get you through!


Probably the most important thing to keep in mind is that you have no control over weather and other ‘surprises’ that always seem to happen on a boat. Learning from friends that travelled the ICW before us, they emphasized this along with the importance of each night planning your trip the next day – but with a second ‘possible’ destination. We were faithful doing this, wrote down everything regarding mileage equal to hours/fuel (we normally like a leisure cruise of +/- 40 nautical miles a day – about 7 hours/day at 6 knots) and try to plan to be at anchor or marina between 3 and 5 p.m. We prefer to get up early and arrive early!

Our 2021 cruise will include the following:

  • Galesville to Solomons; anchoring in Mill Creek

  • Solomons to Mill Creek south of Reedville, at anchor

  • Mill Creek to Gwynn Island (friends that have a home on the river with a pier for us!

  • Gwynn Island to East River in Mobjack Bay (anchored in sight of the Tide Mill at John Lennon’s plantation.)

  • Mobjack Bay across the Bay to Cape Charles; at the marina for fuel, water and pump out

  • Cape Charles to Portsmouth (Tidewater Marina). Remain here for a day, reprovision, if necessary, etc. Found a great Tapas restaurant “STILL” that we will look for again.

  • Portsmouth to Dismal Swamp and tie up at the Welcome Center; normally a number of boats that tie up together – great way to meet new folks!

  • Dismal Swamp to Goat Island

  • Goat Island and start heading back north – either back to Portsmouth or to the Dismal Welcome Center again.

  • Portsmouth to Cape Charles; at marina (this has become one of our newer favorite stops)

  • Cape Charles to Onancok, at anchor (if time permits, dinghy into town and be spoiled with a visit to a great bakery)

  • Onancock to Crisfield (can fuel if needed)

  • Crisfield to Solomons – Zahnisers Marina

  • Solomons to home.


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