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Sailing the Southern Chesapeake Bay


Last Updated on September 13, 2023 by Amy

After nearly a year on the hard at Cape Charles, we were ready to get back to the boating life! While we changed our plans many times, we were excited to get out sailing on the Chesapeake Bay and explore all the nooks and crannies we’d been hearing so much about.

When we returned to the boat, we stayed in East Beach, across the bay, for two weeks. During that time, we drove to the boatyard every day, working on projects and overseeing the yard. Also, David flew out for a trip (a week apart!) and my mom flew in for Memorial Day weekend.

All in all, we got to spend a lot of time around Norfolk, which we loved, and then explored up to Deltaville.

This is going to be part one of cruising the Chesapeake. Part two will cover from Baltimore to Solomon’s.

Cape Charles

Cape Charles is an adorable town on the eastern shore of Virginia. We spent a lot of time there while in the yard, but also got the chance to explore the town.

**Note: We do not recommend getting work done in Cape Charles Yacht Center. We were extremely disappointed by the work and would go elsewhere in a heartbeat. However, it is a very cheap place to haul out and store the boat.

Starry Horizons on the hard.
Cape Charles Marina

While we had a car in Cape Charles, we also walked ALOT. The neighborhood is full of coastal beach houses; rentals, most likely. There’s a trail behind the yard that leads to the Cape Charles Natural Area Preserve, where we saw foxes, bull frogs, turtles, and deer and picked black raspberries and mulberries.

A young fox.

Because Cape Charles is a little touristy, there are so many shops and restaurants. The Gull Hammock is a boutique food store and there are two local ice cream shops. Because we had a car for a majority of our stay there, we were able to drive out to the Food Lion and the farmer’s market. The marina does have a courtesy car.

We ate at Hook’s, The Oyster Farm, and, our favorite, Ambrogia. The beachfront is an absolute delight, the warm shallow water being popular with families.

The Cape Charles beach.

A couple downsides of visiting Cape Charles: the anchorage is not protected at all from the bay, so it’s better to grab a slip at the marina. The dock and city water isn’t good quality – our tester said it wasn’t potable! – and there no cell phone service for T-Mobile, so we had no connection from our Google Fi.

But, a positive for us was that there always seemed to be boats that we knew there! In 2020, when we first arrived, we met Chris and Sue from First Forty and Kurt and Janice from Endeavor. Both those boats were back this year too! In addition, our friends and lockdown buddies from Antigua, Peter and Simone on La Boheme, arrived from the Caribbean.

Us with Peter and Simone.

Little Creek

On June 10th, we left from Cape Charles and motored across the bay to Norfolk where we docked at Little Creek Marina for two weeks. The marina was under construction at the time of our visit, and that made the marina stay challenging. The bathrooms were a trailer that didn’t get cleaned enough and our packages were misplaced a lot. That being said, we loved the neighborhood, so maybe I would try Bay Point Marina instead.

We could walk through the (very fancy) neighborhood to the beach, which we did every night. Sunset off the beach was amazing.

Mom and I at East Beach.
Sunset from the Dolphin Run public beach access.
Garden Pergola Park

Saturdays we walked to the East Beach Farmer’s Market for breakfast (OMG the empanadas!). The nearby Cova Brewery hosts food trucks several nights a week. There’s even a boutique imported food and wine shop called Crystal Palate where I bought some fancy snacks and local wines.

David and a hot doughnut.

We were right across from a military base, so we had some big neighbors and even saw some military hovercrafts!

Starry Horizons and a Navy neighbor.
Incoming hovercrafts.


Next we moved to Hampton. We stayed at the Docks @ Downtown Hampton for three nights. The big thing we wanted to do here was visit the Virginia Air & Space Center, which was just a five minute walk from our dock. The museum was AWESOME! They had a lot of high-tech stuff, especially around the Mars rover exhibit, which was really fun.

Starry Horizons docked at Hampton.
The Virginia Air and Space Center.

We also ate out on Queens Way, which was closed off to cars and had been converted into outdoor dining. We picked the restaurant called Venture and had a great meal, including house-made tater tots. And for Sunday breakfast, we popped over to Glazed Doughnuts.

The marina had bikes we could borrow, so on Saturday we biked out to Buckroe Beach (3.5 miles each way) and shopped at the Buckroe Beach Farmer’s Market.

Mill Creek – Fort Monroe

Okay, we had to cut the power cord at some point, so we dropped the hook at Mill Creek next to Fort Monroe. We stayed at this anchorage for a week. This wide and shallow bay had good holding but did not have good protection. It was a little rolly sometimes. But, we had a public dinghy dock to use in Pheobus, a neighborhood of Hampton that was an absolute delight!

Public dock coordinates: 37.01446481703186, -76.31794951646877

There was a Food Lion in walking distance, and we tried out several of the restaurants, including a hot date night at The Baker’s Wife.

I paddleboarded Mill Creek, we walked around the fort, and made friends with the neighbors. We also watched the Fourth of July fireworks from Mill Creek, and though we could see tons of displays on the horizon, we weren’t front and center for any of them (come on, nothing would beat NYE in Sydney Harbour).

Setting off on a paddle.
Watching the fireworks.

We caught up with some friends and made some new ones too, even having a party on Starry Horizons! Jamie Still, another Helia owner, anchored next door. We met Jim and Linda from Ocean Song, who just brought their boat up to the Chesapeake to transition from charter to private use. Mike and Sharon on Dulce Vita, a Nautitech 46 anchored next door too.

And a big thank you to Kevin and Erin from Water Wings who met up with us several times and even lent us their car.

MobJack Bay – Severn River

Tropical Storm Elsa was coming, and Mill Creek was far too unprotected. We upped anchor and motored to Mobjack Bay and anchored off of Stump Point in the Severn River (this is still in Virginia, not the Severn River near Annapolis). This was a very pretty anchorage where we stayed for four nights.

The winds got up to 40 knots, and we probably should have anchored further into the river, but we held well and didn’t drag.

The next day, one of the neighboring homeowners kayaked over and invited us for dinner. Liping cooked us traditional Chinese food and we enjoyed the excellent company with her family!

Liping and her step-son, Jeremy.
The view of sunset from Liping’s house.
Starry Horizons viewed from Liping’s house.

Mobjack Bay – East River

Our next stop was the East River, where we anchored off Town Point Landing. This anchorage is a tiny, one-boat anchorage, but there’s more room around the corner. We didn’t want to hog the anchorage, so we stayed just two nights.

Starry Horizons at anchor by Put in Creek.

The surrounding area is beautiful, full of pretty homes with docks and lights and Adirondack chairs. David and I paddled around together, enjoying the view.

David paddling.

We took Little Dipper up Put in Creek to the town of Mathews, where there is a Food Lion, General Store, and a local small museum.

On our last day, a neighbor paddle by, just like Liping did, and invited us to use their showers or bikes! It was very kind of them and we were sorry to say that we had to leave instead of stay and make new friends.


Unfortunately one of our boat projects wasn’t going well, and we needed to pull into a dock again to send David up the mast. We made our way up to Deltaville. We wanted to stop at Gwen’s Island for two nights, but the bridge isn’t opening on demand anymore, and the openings are only early morning or late evening, so we had to skip it.

Because we got to Deltaville early, we anchored first on the south side, just off of Deltaville Marina for two nights. The creek is narrow, but there’s enough room for at least half a dozen boats and the holding was good. We had another storm roll through, winds and lashing rain up to 40 knots! Deltaville Marina charges $5 a day for use of the dinghy dock. There is the Deltaville Town Dock around the corner, but it’s a further walk from town than the marina.

The anchorage and Deltaville Marina.

Then we moved around to Regatta Point Yachting Center where we stayed for three nights. This was a beautiful marina with excellent facilities, including bikes and a courtesy car. There are so many boats in Deltaville, it’s no surprise there’s a big West Marine.

While in Deltaville, we briefly caught up with our friend Kate, who we originally met in Guadeloupe and then saw a few times in the South Pacific. Kate and her husband Steve had an Antares 44. We also met our dock neighbors, Colleen and Rich, on a Leopard.

We left Deltaville on July 18th, about five weeks after departing Cape Charles.

Tips for Cruising the Chesapeake

The water is very brown and muddy. If you run your watermaker, you will burn through a filter or two per cycle!

There are jellyfish in the Chesapeake Bay, especially during July and August. We did not swim.

Catamaran slips are pretty much non-existent. When we came to a marina, we always had a T-head dock.

It’s been very still and hot. In fact, somewhere in Mobjack Bay we decided we would be much more comfortable at a marina, so after getting our project done in Deltaville, we hop, skipped, and jumped up to Baltimore where we spent over a month enjoying being plugged in.

We bought the cruising guide Cruising the Chesapeake, and have found it very helpful.

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