The One Where We Explored The Chesapeake Bay

If you read my last post (Getting Our Boat Through Canada) or if you’ve been following along on social media- you probably know that we spent quite a bit of time this summer exploring the Chesapeake Bay.

Admittedly, this was Plan B.

When we began moving our boat up the East Coast, we really hoped to spend a lot of the summer in Canada. But obviously that wasn’t possible due to the roadblocks Covid presented (namely the Erie Canal being closed as well as the Canadian border.)

We toyed with the idea of taking our boat towards Maine (not part of the Great Loop.) However, there were also some hurdles there and so many people encouraged us to take our time in the Chesapeake Bay.

After weighing our options, we decided to loosely commit to a month in the Bay. We found a marina in the exact center and used it as a home base. From there we took weekend trips and even drove back to Charlotte for a few days for dentist and orthodontist appointments.

This post on exploring The Bay could easily be 10 seperate posts and maybe one day I’ll break it down more. But for now, I’ll just share the highlights.

Our Chesapeake Bay Highlights Reel

Norfolk, VA

Arriving in Norfolk, VA by boat might be one of the most intimidating experiences of my life. Towering Navy ships line the route into the city. Police boats and coast guard patrol the waterway like ants circling a picnic. If nothing else, we felt super safe!

We stayed at Waterside Marina right in the heart of downtown. Our family had so much fun exploring Norfolk on Lime scooters. And it was very neat to see the highly publicized floating hospital, Comfort, that was sent to NYC Harbor during the initial Covid response.

Lottsburg, VA

Most people would NOT put this place on a highlights reel. However, since this was our home base in the Chesapeake Bay, I had to include it!

It’s hard to find on a map, but this spot is the exact middle of the Bay. It’s also located at the mouth of the Potomac River.

Besides it’s location, the best parts of Lottsburg included a pool, always available courtesy cars, an awesome mexican restaurant, and friends at the marina.

Tangier Island

Known as one of the most remote places in the United States, Tangier Island is an incredibly special place. Unfortunately, it’s quickly disappearing into the Chesapeake Bay. Sadly, many experts believe it will be completely gone within the next 40 years.

It’s only accessible by boat. What it lacks in size, it makes up for in charm! Oh, and it’s also the Blue Crab capital of the world. To say we ate well while we were on Tangier would be an understatement!

Historical Landmarks

One of the coolest parts about exploring the Chesapeake Bay was seeing so many significant historical landmarks.

Major places we visited included Jamestown, Williamsburg, Yorktown, and George Washington’s Birthplace. The kids got to bring a lot of what they’ve learned in American history to life which was really neat for them.

Solomons Island

The more time we spent in the Bay, the more places people told us about that we “couldn’t miss.” Unfortunately, we had to narrow down the list a bit. But Solomons Island made the cut and we’re so glad it did!

This particular island was the exact opposite of Tangier. It’s resort-like, somewhat touristy, and full of great things to see. We had a great time exploring, eating and visiting the Maritime Museum.


We could have easily spent an entire month in Annapolis! It’s one of the best boating cities ever.

It was definitely a highlight of the Chesapeake Bay. We loved being on a mooring ball right in the middle of Annapolis Harbor. You truly can’t get any closer to the action.

We took our dinghy and explored the coastline including a stop at the Naval Academy and to a restaurant. More than anything we enjoyed the other boat traffic and how vibrant the Annapolis waterfront appeared.

Our good friends on Positive Latitude also spent time in Annapolis and wrote a really good perspective on boating there. They also have a crazy police story! Check out their post: The Greatest Boating City.

Harve de Grace

This is the northernmost spot on the Bay. For us, it became an excellent, safe place to ride out a hurricane.

While it may not be the most popular spot on the Bay, we found it to be a great stop full of cute shops, and unique things to see.

Overall our time in the Chesapeake Bay was a lot of fun. At times it felt like we were just waiting on things further north to open up. However, looking back I’m so thankful for our time exploring the area.

As always, thank you for following along on our adventures!

You might also enjoy reading:

The One With Sunsets and Chardonnay

10 Things You Need To See In Washington D.C.

The Freedom Trail With Kids

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  1. Gail Dowis on September 1, 2020 at 2:55 am

    Hi Sarah,
    So interesting that I found your site. Our path is very similar. We were going to go to NY but plan B put us in the Chesapeake. We’ve been to several of the same places. We are currently on Solomons Island a short walk to the Calvert Marine Museum! Headed to Annapolis then on to Baltimore. I look forward to reading more about your excursions. I’ve not updated my blog in awhile due to shabby internet connections. Enjoy your cruising!

    • momwithamap on September 7, 2020 at 9:19 pm

      Hi Gail! Oh, I hope you loved Solomons as much as we did! And Annapolis too. Where will you go after the Chesapeake area? We’re on the Great Loop so we’re continuing through the Great Lakes and will be traveling down the river system this fall. Already looking forward to warmer weather in the Gulf and Bahamas this winter!

  2. Joanne on September 18, 2020 at 8:24 pm

    I am so happy to have this information on your travels. We arrived yesterday at Utsch’s Marina after about 40 hour passage from Block Island Extremely happy here. Everyone is friendly and helpful. Leaving tomorrow for the C&D canal. We have 2 kids in tow also. Thank you!

    • momwithamap on September 21, 2020 at 3:16 pm

      Oh wow, we loved Utsch’s! I agree- everyone was super friendly. I’m sure they loved on your kiddos. How was your Delaware Bay crossing? Where are you planning to stop in the Chesapeake? I’d love to hear more about your adventure!

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