Cruising Guide to the Chesapeake

14th May 2019

Chesapeake Bay has the longest coastline of any bay in North America and its 11,600 miles means there’s a lot of sea to cover. Relax and read on as we go through our cruising guide to the Chesapeake, so you can start planning your dream Annapolis yacht charter.

America’s largest estuary, home to many famous writers, sailors and naturalists, has a history that is unquestionably interesting, from its creation via a meteor collision with Earth, through colonial and civil war times and right up to today.

With an average depth of 21ft, some channels are so deep, a submarine can sail through. The width varies from 4 to 30 miles, and over 150 major rivers and streams feed into Chesapeake Bay.

Cruising the Chesapeake should be enjoyed and not rushed, so you can truly appreciate the beauty of this part of the world.

Stop-offs around Chesapeake Bay

If you’re asking yourself, “what is there to do in Chesapeake Bay?”, the answer is you will be spoilt for choice. With so many towns, villages and islands dotted around the bay, there are so many places worth of an itinerary stop off.

1. Rock Hall

Often referred to as the “pearl of the Chesapeake”, this quaint waterfront fishing town is famed for its fresh oysters and crabs. 

If you visit Rock Hall on a weekend, you’ll get to visit the farmer’s market where you can buy fresh produce. If you love the outdoors, you can hike, fish, bike and birdwatch, or just sit and watch the world go by.

2. Baltimore Inner Harbor

There’s no way you can sail the Chesapeake and not pay a visit to Baltimore Inner Harbor. You’ll find plenty of activities going on, whether it’s a spine-tingling evening ghost tour, or a live music performance on the pier.

In fact, Baltimore Inner Harbor is home to many of the city’s most popular attractions, including the National Aquarium, The Maryland Science Center, and the Maritime Museum.

3. Chester River

If you are passing on the Chester River, visit the Eastern Neck National Wildlife Refuge, and be in awe of the magnificent views and wildlife that will surround you.

Enjoy nature walks, try a spot of bird-watching and visit the butterfly garden. Our favorite thing about the refuge has to be the beautiful view of the bay across to Baltimore.

4. Whitehall Bay

A mere three miles away from downtown Annapolis, Whitehall Bay offers a peaceful respite from the bright lights of the big city.

Once you’ve entered the way, pick up the flashing channel marker 320 NW, and find the famous Cantler’s Riverside restaurant. This is an authentic Maryland crab house and Chesapeake tradition.

5. St. Michael’s

One of the most popular yachting centers in the Chesapeake, St. Michael’s is home to the Chesapeake Bay Maritime Museum, which is so large that the entry price includes a two-day pass!

When it comes to dining, you’ll find a wide array of restaurants from gourmet cuisine to pizza.

If you do visit St. Michael’s, be sure to pay a visit to Cannonball House, located on Mulberry Street, which is one of the most historic buildings in the town.

6. Wye Island

Found between the Wye River and Wye East River, this protected island stretches 2,800 acres. It’s committed to preserving wintering waterfowl and native wildlife and there are six miles of trails for you to enjoy. See if you can spot the holly tree that’s nearly 300 years old. 

7. Herrington Harbor

Not one but two marinas can be found in Herring Bay, on Maryland’s western shore. While you’ll need to make a reservation if you visit, it’s certainly worth the stop.

Everything you could want from restaurants, bars and picnic areas, to pools and beaches are located near Herrington Harbor, in addition to several other amenities.

Despite not being far from Baltimore, Annapolis or Washington DC, this harbor offers an exceptionally peaceful and pleasant experience.

8. Oxford

One of Maryland’s oldest towns, this former international shipping center is a charming, tree-lined waterfront village with a vast maritime history.

Having retained its historic charm, if you’re cruising the Chesapeake, you’ll want to stop off in Oxford to experience the laid-back atmosphere and visit the Oxford Museum.

9. St. Leonard’s Creek

Famed as one of the most beautiful areas on the Patuxent River, St. Leonard’s Creek is home to peaceful anchorages that you can easily stop by and pay a visit.

Swing by Perigeaux vineyards and winery, located on a 27-acre farm. Take in the Jefferson Patterson Park and Museum, where you can discover the Indian village, go hiking, have a picnic on the grounds, or even try canoeing and kayaking.

10. Solomons Island

A popular destination for sailors. If you’re vacationing in the Chesapeake, be sure to stop off at Solomons. 

Start off by discovering the Annmarie Garden sculpture park before fossil hunting in Calvert Cliffs.

In the evening, follow the Riverwalk boardwalk to enjoy excellent waterfront views. Here, you can visit some of the town’s several restaurants and shops. No visit is complete without sampling some of the seafood!

Places to eat in Annapolis

Whether you start or end your Chesapeake vacation in Annapolis, there are lots of eateries that serve up delicious food. Here are some places you need to try!

1. Pusser’s Caribbean Grille

Located right in the harbor, Pusser’s is the perfect first stop on our list of places to eat in Annapolis. A famous Caribbean highlight and also on store shelves (yes, they do have their own rum), this Annapolis location is one of only two US outlets. 

Sit outside on the back dock and enjoy a famous Pain Killer cocktail, a mixture of Pusser’s Rum, cream of coconut, orange juice and pineapple juice. Grab a Maryland Crab Dip appetizer made with crab, peppers, onions and tomatoes in a creamy cheese dip served with a toasted baguette on the side.

2. Dry 85

About a five-minute walk away from Pusser’s is a small bar that will take you back to the prohibition era, speakeasies and bathtub gin. This whiskey bar has over 100 whiskeys to choose from, which can make anyone’s head spin in indecision. 

We suggest grabbing a whiskey flight and an order of fried pickles. Feeling like you could use a full meal to soak up that whiskey flight? Perhaps grab one of Dry 85’s burgers, sandwiches or one of their entrees. You can’t go wrong with an order of their southern shrimp and grits or their bacon-wrapped scallops served in a Crown Royal maple reduction sauce to complement the whiskey flight.

3. Stan & Joe’s Saloon

If the day is coming to a close and you’re looking to just relax with a cheap beverage and some live music, Stan & Joe’s is the perfect bar to end your night. 

Located about another five-minute walk from Dry 85, this bar has the perfect dive bar atmosphere with cheap eats, drinks, an award-winning happy hour and live music. Grab a 16oz Natty Boh, the beer of Maryland, and take it all in. 

Stan & Joe’s has the perfect late-night bar menu that includes shrimp baskets, tacos, wings and even pierogi, served with sour cream and gravy.

4. Iron Rooster

If an all-day breakfast is your thing, then make Iron Rooster top of your list of places to eat in Annapolis during your Chesapeake vacation.

From breakfast nachos to fried chicken, avocado toast to eggs any way you’d like them, you’re sure not to go hungry here.

If you’re lucky, you might even catch one of the charity nights or special events Iron Rooster regularly hosts.

5. The Point Crab House & Grill

Undoubtedly one of the most popular summertime spots, you’ll see long rows of tables filled with people feasting on crabs at The Point Crab House & Grill.

Live musical acts play at the outdoor bar and you’ll also get to enjoy the breathtaking waterfront views.

Chesapeake Bay wildlife

A Chesapeake cruising guide has to include the diverse and dynamic wildlife the area has to offer.

Varied and vivid, the best way to see and engage with the wildlife is on your boat as you sail among the ecosystem and witness a variety of flora and fauna.

Summer brings hot and humid weather, while spring and fall gives you more opportunities to spot the diverse Chesapeake wildlife. 

Discover many varieties of fish, including the Striped Bass, Cownose Ray and Sandbar Shark, in addition to several different crab species and the famous Chesapeake Bay Oyster, which has supported a historical industry all by itself.

The Chesapeake Bay is also home to several species of birds (some migratory) including the Great Scaup, Laughing Gull and Northern Bobwhite. Additionally, the area surrounding the bay supports diverse mammals, such as the black bear, beaver, bobcat, manatee, deer, fox, woodchuck and long-tailed shrew.

Away from the wildlife, the beauty of their habitat can be witnessed too. The varied plants and trees, including the Cardinal Flower, Loblolly Pine and Red Maple, add a vibrancy of color and an outline to Chesapeake Bay and its waters.

Chesapeake Bay wildlife is unquestionably rich with natural beauty that can best be seen up close, and enjoyed by any visitor to the area. However, by experiencing the sights and sounds whilst sailing Chesapeake Bay, you can enjoy being at one with nature and experience all that the bay has to offer.

Chesapeake cruising guide: local tips

We caught up with Erin Houpt, Head of Charter Sales and Brokers for Annapolis Bay Charters, to discover exactly why Chesapeake Bay has built up such a vibrant sailing community with visitors from all over the globe.

“You can anchor while sailing around Annapolis and have the boat open at night while enjoying the friendly nightlife and general cheery atmosphere.

“With Annapolis’ proximity to some of the charming Chesapeake towns, you can access quiet little anchorages off St. Michael’s, Oxford, Herrington Harbor and Solomons Island.

“Over the last 10-15 years, racing events in Annapolis have sky-rocketed. Each year, people participate in local and national regattas, alongside the weekly races held every Wednesday, Thursday and Friday nights between April and August.

“Annapolis also hosts two national boat shows every year, in the spring and fall. The fall sees the largest in-water sailboat show in the US.

“In addition to national sailing events, the Annapolis Yacht Club hosts the NOOD regatta every year, a nine-city sailboat racing circuit, which draws in droves of national tourists and sailing enthusiasts. During the summer season, Annapolis puts on a massive firework show for Independence Day, which sends locals and visitors to their boats for the best view.”

Chesapeake cruising guide with Dream Yacht Charters

Can’t wait to explore the delights of Chesapeake Bay? We don’t blame you! Its vibrant history, mixed with its delicious cuisine and many anchorages make it a great vacation spot.

Whether you’d prefer to opt for a bareboat yacht charter, or skippered charter if you don’t have any sailing experience, you’ll get to enjoy a vacation you won’t forget. If you have any questions, get in touch. Alternatively, for more vacation inspiration, head on over to our blog.