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June 3, 2020

Highlights Of Sailing The Chesapeake Bay

chesapeake bay

Welcome to Chesapeake

The largest estuary in the US, created by a meteor collision, an incredibly rich history and home to some of the world’s most curious characters – welcome to Chesapeake Bay. 

Boasting 11,600 miles of coastline, this is the longest of any bay in North America, which may already give you an inkling as to why it’s such a sailing hotspot. 

chesapeake bay arial

The Bay is fed by over 150 major rivers and streams, and is anywhere from 4 to 30 miles wide. So the first thing you need to know is that Chesapeake is to be slowly savoured, as there’s such a vast wealth of beauty to be explored. 

You’re absolutely spoilt for choice in Chesapeake, with endless islands, villages and towns to add to your itinerary. So here’s our ultimate guide to some of the unmissable places in this incredible corner of Earth. 

st leonards creek

St. Leonard’s Creek

Located on the Patuxent River, this is one of the most beautiful and peaceful spots to anchor up and explore. The Jefferson Patterson Park and Museum will take you on a discovery of an Indian village, with opportunities for hiking, picnics, kayaking and canoeing. Whilst you’re there, stop by the Perigeaux vineyards to sample the local produce. 

oxford maryland


Rich in maritime history, this is one of the oldest towns in Maryland. Oxford offers a relaxed, charming atmosphere and a picturesque waterfront setting. Visit the Oxford Museum to find out more about the international shipping history of the area. 

Rock Hall

The “pearl of the Chesapeake”, so called for its fresh seafood. Swing by the farmers market at the weekend, to pick up local oysters and crabs. Biking, birdwatching, and of course fishing are also perfect activities in this little haven. 

chester river

Chester River

Speaking of birdwatching, if you’re into ‘twitching’, you can’t miss the Eastern Neck National Wildlife Refuge on Chester River. With stunning views across the bay to Baltimore, you’ll find all sorts of interesting birds and butterflies here. 

wye island

Wye Island

This protected island is committed to the preservation of native wildlife and wintering waterfowl. There are six miles of trails across the 2800 acre island. You may even come across the famous 300 year old holly tree.

herrington harbour

Herrington Harbor

On the western shore of Maryland, two marinas await you at Herring Bay. You’ll need to reserve a spot, and it’s well worth it. A wealth of bars, restaurants, beaches and pools are clustered in this harbor, yet it retains a very peaceful vibe. 

chesapeake aqarium

Baltimore Inner Harbor

Some of the city’s best attractions have made their homes in this harbor. The Maryland Science Center and National Aquarium are excellent family activities. Meanwhile you may come across live music on the pier, or perhaps join a spooky ghost tour…

calvert cliffs

Solomons Island

Very popular with sailors, Solomons is definitely worth adding to your Chesapeake itinerary. 

By day, hunt fossils on the Calvert Cliffs and explore the Annmarie Garden sculpture park. By night, the Riverwalk boardwalk will give you stunning views, with many seafood restaurants to choose from.

chesapeake bay maritime museum

St. Michael’s

Home of the Chesapeake Bay Maritime Museum – this is definitely one for the yachting enthusiasts amongst you! With so much history on offer, your entry ticket gives you a two-day pass. 

Don’t miss Cannonball House on Mulberry Street. This is one of the town’s most historic buildings. 

This is a great area for dining out too, with offerings from pizza to gourmet cuisine. 

chesapeake wildlife

Chesapeake Wildlife

The best place to see some of the varied and stunning wildlife in Chesapeake is from your boat. On the water, you’re right in the midst of this thriving, lively ecosystem, surrounded by incredible flora and fauna. 

In summer, the heat and humidity can be high, so we recommend spring and fall for the optimal wildlife-spotting conditions. 

Many species of birds are local to Chesapeake, some of which are migratory. You may see Northern Bobwhite, Laughing Gull and Great Scaup, amongst many others. 

Mammals in the area include bobcats, manatees, deer, foxes and even black bears. 

The waters are rich with Cownose Ray, Striped Bass and Sandbar Shark. And, of course, a whole host of other marine life from crabs to oysters. 

Aside from the wildlife, the vibrant variety of plants and trees in Chesapeake create a stunning backdrop to your vacation. 

A World of Sailing awaits

The incredible variety of Chesapeake is matched only by the amazing variety of sailing options available to you. If you’re a seasoned sailor and are itching to take the helm with a bareboat charter, we’ve got you covered! If kicking back and letting your crew take care of everything is more your bag, just let us know, and we’ll talk you through the many crewed options available. 

Whatever your vision for a Chesapeake charter, contact your consultant today and we’ll be delighted to make your dream a reality.