Best Sailing Destinations Chesapeake Bay

Best Sailing Destinations Chesapeake Bay | Life of Sailing

Last Updated by

Daniel Wade

May 9, 2023

Key Takeaways

  • The best sailing destinations in the Bay will vary based on your desired water activity
  • A sailing trip in the Bay offers scenic views with great food and rich maritime culture
  • Annapolis is the sailing capital of the world and gives Florida a run for its money
  • Choosing the right boat is key to ensuring a safe travel and comfortable experience
  • Summer months might be crowded so be sure to research the best opportunity for you

Arguably one of the best sailing destinations, Chesapeake Bay, boasts beautiful scenery. But what are some of the best Chesapeake Bay sailing destinations?

The best sailing destinations in Chesapeake Bay are Annapolis and St. Michaels along with Norfolk. Other locations worth checking out are Solomons Island and Rock Hall as well as Smith Island. Keep in mind you need to travel the eastern shore of Maryland and Virginia to see all of these locations.

In my experience there is not much that compares to sailing in Chesapeake Bay. Annapolis is America’s sailing capital of the world for a good reason and is a great place to start.


Table of contents

The Top 15 Best Sailing Destinations in Chesapeake Bay

Chesapeake Bay is quite popular for showcasing the natural beauty and a rich marine history. It has turned into a global sailing destination that offers plenty of exciting experiences for sailors of all kinds.

You can explore many top locations for a sailing adventure but it is recommended to start around Annapolis in Maryland since it is dubbed the sailing capital. Annapolis in general features picturesque villages and plenty of water locations to explore. Keep in mind that weather and navigational conditions vary across the bay.


Annapolis in Maryland is the renowned sailing capital for a good reason. It enchants sailors with the United States Naval Academy and has a rich marine history that features the famous Annapolis Boat Show.

Annapolis offers a lot of opportunities for sailors to dock and explore. This Chesapeake Bay harbor town allures with its scenic beauty. Below you can see other key attractions to this area.

  • Abundant amenities to meet your needs
  • Bustling harbor filled with marinas and boatyards
  • Tons of restaurant possibilities

St. Michaels

St. Michaels has turned into a charming location due to its history and abundant sailing community. Be sure to bring a camera along this eastern shore town that showcases a beautiful harbor and Victorian homes. The town also is home to the Chesapeake Bay Maritime Museum where you can dedicate you time to check out the rich history and vibrant culture of the bay and its waterways.


Norfolk is a bustling harbor city on the Chesapeake Bay's southern coast that boasts a rich naval history as the site of the world's largest naval base. Sailors flock to this cultural hub that is renowned for various options below.

  • Museums with rich history
  • Theaters
  • World-class restaurants

Numerous marinas throughout these cruising destinations grant convenient access to sheltered waters. This creates an opportunity for exciting city explorations.

Solomons Island

Solomons Island is another charming and historic town in southern Maryland that sits on the Patuxent River near the Chesapeake Bay. Its protected harbor attracts many sailors and its waterfront park and lighthouse offer scenic beauty.

There are an array of restaurants and shops to check out while staying at one of many marinas. Solomons Island proudly welcomes visitors to explore and unwind.

Rock Hall

Rock Hall can be found on Chesapeake Bay's eastern shore where you will likely see an entire village of people fishing. It is loved by many for its natural elegance and wonderful waters.

Sailors that are drawn to crabbing or fishing experiences will want to stop here. The Chesapeake Bay Environmental Center is another additional location to check out since it offers educational programs to enlighten those about its history.


Deltaville offers fully equipped marinas and comprehensive maritime services that are complemented by a charming center for delightful strolls. Solomons' southbound boats often cross the Potomac River while navigating Virginia's Northern Neck rivers and creeks to reach Reedville or Deltaville in Virginia. Explore the vast waters of Great Wicomico or seek shelter in the protected haven of Mill Creek and capture the essence of the Southern Chesapeake.

Smith Island

Smith Island is a perfect sailing location. Those that are wanting to visit this Chesapeake Bay island must visit by boat since it is the only habitable island in Maryland.

There are three different villages in this location but they each offer clear waters and a calm sailing experience. This island is also famous for its Smith Island Cake.

Wye River

Wye River has a combination of urban and marine areas that allow you to find peaceful surroundings. Wye Island and its 2,800-acre nature preserve are remarkable features that you cannot find anywhere else.

Tuckahoe State Park is one of these beautiful locations that you can check out after sailing. You also have a good chance to see amazing creatures in their natural habitats such as a bald eagle or blue heron. If you have a small enough boat you can explore more areas that are not accessible with larger sailboats.

Tangier Island

Tangier Island is in the Chesapeake Bay's south and is home to serious fishing opportunities. It is also home to the Tangier History Museum that will allow you to check out the island's culture.

There are plenty of boat tours that you could take to experience crabbing or fishing trips if you do not want to on your own boat. The area has secluded waters that make a great escape from reality.


Onancock is another Chesapeake Bay town considered a gem on the Virginia eastern shore. They too have a historic allure and that is coveted by a scenic harbor with a vibrant cultural heritage.

If you are wanting to experience a feeling like home then Onancock is a great opportunity. They have a tight knit community that engages in a lot of fishing and sailing. You can also see a beautiful sunset from many of the docks of your choosing.

Delaware Bay

Delaware City is located at the northern tip of Delaware Bay. This small community can be reached on foot from Delaware City Marina. This used to be a shallow salt marsh but the river becomes more wooded as you go upstream and offers a secure anchoring location with sufficient water depth and swinging space.

The western end of Cape May Canal marks the start of the harbor approach from Delaware Bay.

This expansive and exposed body of water stretches in a Southeast to Northwest direction. Before crossing Delaware Bay it is crucial to carefully check the weather forecast and can be an exhilarating journey under favorable conditions but caution is necessary in this particular area.

Kent Island

Kent Island is located in the heart of the Bay and shows off tons of rich marine history. It is surrounded by sheltered waters and it draws in sailors from all over the world.

You can find the Chesapeake Bay Bridge on this island which is a remarkable feat of architecture that connects the Bay's eastern and western shores. The harbor is a great place to hang out and to enjoy some of the best views for a perfect sunset.


Galesville is a delightful bay town on the west bank that once served as a steamship line hub connecting Annapolis and Baltimore. It was also home to numerous Chesapeake Bay watermen.

You will now see that the area is a sought-after destination for leisure boating with the West River Sailing Club and Hartge Yacht Harbor. This small peninsula offers a charming community park that features a 14-mile boardwalk along Riverside Drive and shows off scenic views of the West River.


Reedville is a charming fishing village at Chesapeake Bay's northern tip. It has a rich maritime history and thriving fishing industry to compliment the serene haven which lures sailing enthusiasts to its pristine waters.

When you explore the scenic harbor you can also check out these options below.

  • Local boutiques
  • Famous eateries
  • Captivating heritage of the Chesapeake Bay's fishing traditions


The Patapsco River flows into Baltimore's Historic Inner Harbor and is an ideal starting point for sailing with numerous marinas. Explore the Harbor to admire landmarks like Federal Hill and Fort McHenry.

As the Patapsco opens up into the bay you can discover outdoor attractions such as North Point State Park and Fort Smallwood Park. Baltimore is a must-visit city for sailors that offers Henderson's Wharf Marina in Fells Point for a convenient anchorage near top pubs or taverns and music venues. There are abundant sailing and racing activities along with other limitless opportunities that might leave you feeling that you have only scratched the surface.

Key Benefits and Drawbacks of Sailing in Chesapeake Bay

Sailing in the Chesapeake Bay’s beautiful waters is a sight you have to see. The experience is definitely worth the trouble but some sailors could argue there are some drawbacks. Below are some of the common pros and cons to consider before sailing in the Bay.


  • There are plenty of sailing locations to help you find a perfect experience. Each spot has its own appeal catered to sailing, fishing, or food.
  • The Bay is famously known for its cuisine. You cannot miss out on the crab cakes and oysters but there are other options too if you do not like fresh seafood.
  • There are plenty of secluded waters to explore. This offers sailors the perfect sailing environment no matter where they plan to go.
  • You will find many marine historic sites and landmarks. This is a perfect opportunity for history buffs to brush up.
  • You will be able to see various forms of wildlife like dolphins and bald eagles.


  • There are a handful of expensive overnight dockage fees at certain Bay marinas that increase the cost of sailing in the area compared to other destinations.
  • The Bay's sailing experience is impacted by environmental challenges like pollution and overfishing. This raises concerns about its quality but actions are being taken to currently help clean up the environment.
  • Navigating certain areas of the Bay can be challenging. The summer typically has an increase of recreational boats and often creates crowded waters.
  • The Bay endures demanding weather with strong winds and rough waters at certain times of the year. This is especially difficult in the winter months.
  • Certain sailing spots within the Bay may offer limited access to essential amenities like grocery stores or repair facilities. You should also check in advance to be close to medical services in the event of any issues.

Ideal Boat Types to Sail in the Chesapeake Bay

Choosing the right boat is important for a safe and enjoyable sailing experience in Chesapeake Bay. Your ideal boat type will correlate on your needs and desires as well as the sailing conditions.

It is best if you conduct proper research based on your needs and the boat type you may already have. If you happen to be in the area you could also chat with local sailors to get their opinion.

Chesapeake Bay typically has these popular boat types:

  • Daysailers are a perfect boating option designed for casual sailing. Those that are new to sailing generally gravitate to this boat type.
  • Cruisers are an appealing sailboat type that offers a comfortable ride and speed. They also offer both relaxation and excitement. These are larger than daysailers but still easy to handle.
  • Catamarans: This multihull boat provides stability and speed while also remaining comfortable. This allows for swift travel and tons of room on the boat for large groups.
  • Center Console Boats are versatile options for anyone that wants to go fishing and cruising. They are usually small enough to go exploring Chesapeake Bay's inlets and coves. They also provide excellent visibility and handling no matter your experience level.

Why You Should Sail in the Chesapeake Bay

Choosing to sail in the Bay could lead to an unforgettable opportunity. There is more than a day’s worth of things to do in any location that you choose.

Appealing Scenery

There are not too many locations that you can sail to that have a balance between urban or city life and sailing. You will be able to see a lot more than people that do not have boats and the tours can only provide so much.

Calm Environment

Chesapeake Bay offers calm waters most of the time but checking the weather conditions is always best before making the trip. It does not matter if you are a first time boat owner or experienced sailor the weather will impact your performance. Thankfully the Bay has dependable weather.

Exciting Opportunities

Whether it is your first time sailing or you are visiting again the Bay offers endless opportunities. These could be fishing or crabbing and maybe even a new restaurant to try out. All of the locations have different historical aspects as well.

Best Memories

In combination of taking the opportunity to explore you will be making some of the best sailing memories. There is a reason why Annapolis is the center for sailing and the Bay is a perfect representation that offers the perfect package.

Best Sailing Destinations Chesapeake Bay
Daniel Wade

Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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