Sailing area: Chesapeake bay

Chesapeake bay

Chesapeake Bay lies off the eastern coast of the USA and opens on to the Atlantic Ocean. The arms of the bay are about 300 km long and it is about 50 km wide.
Sailing in Chesapeake Bay
From Annapolis, make your way towards Shady Side, then Chesapeake Beach, Dares Beach, and Calvert Beach-Long Beach, Chesapeake Ranch Estates - Drum Point, Patuxent River, St James, Ophelia, and, finally, Fleeton.
You will enjoy an unforgettable journey as you cross the legendary Chesapeake Bay and you will be able to take advantage of the winds from the Atlantic Ocean to guide your vessel during your cruise. You will find several beautiful mooring spots in Chesapeake bay.

Places to visit in Chesapeake Bay

Annapolis is the capital of Maryland. It is a flourishing town with many water sport activities. Above all, Annapolis is famous for its boat shows: every year, thousands of sailing enthusiasts come together for the United States Sailboat Show and the United States Powerboat Show, during which the best boats are rewarded. With your boat hire, visit Annapolis, a town that also offers many cultural activities. Visit the Colonial Annapolis Historic District which brings together several listed monuments, the town's Capitol, St Anne's Church and magnificent residences, such as the famous Paca House and Brice House. The neighbourhood also comprises two famous establishments, the very beautiful Annapolis naval academy and St John's College.

Shady Side is a relatively calm American town where you can stopover and discover the charms of a quiet small town. With your boat hire, you will be able to enjoy water sports such as water-skiing and wakeboarding.

Stop off at Chesapeake Beach, a town with pretty white sand beaches and limpid waters. You will be able to swim there and enjoy the many water sports. It is also a lively town with its hotels, bars and restaurants. Nearby, you will be tempted by some new experiences, such as flyboarding: fly over Chesapeake bay driven by high-pressure water jets, an experience not to be missed!
At Dares Beach, you will find natural and wild beaches with turquoise waters and white sand beaches. You will be able to swim in this tropical island setting. Enjoy the sun and the ocean and do some scuba diving so as to discover the underwater treasures of Chesapeake Beach.

At Calvert Beach-Long Beach, you will find excellent seafood and fish restaurants. Long romantic walks await you along the bay or along the beach. You will also be able to swim and do some sunbathing on a white sand beach in a relaxing family atmosphere.
At Chesapeake Ranch Estate – Drum Point, a peaceful town awaits you with its magnificent landscapes, exceptional sunsets, charming houses in a lush setting and magnificent white sand beaches. All of the landscapes at Chesapeake Ranch inspire peace and serenity.
Aboard your boat, you will pass Patuxent River, where you will find an airbase belonging to the US Navy. This base was initially designed to accommodate flight instruction and training units. In 1958, the naval base became an airbase designed to house the American marine's flight test units. Therefore, it is a town with a rich history that you will be able to discover in a different manner with your boat hire.

Stop off in St James for a spot of fishing and discover astonishing species of eels and crabs as well as other seafood and big game fish of all types. You will be able to do some canoeing there and you will probably come across dolphins and sharks.
Ophelia is a peaceful town that you will enjoy for its quiet and tranquil atmosphere, its pretty lakeside houses and its stunning beach and deep blue water. It is a town where you can take advantage of the peace and quiet and the sunshine to enjoy delightful walks in the forest or along the coast.
When you reach Fleeton, you will enjoy the sunshine and, above all, the opportunities offered by this windy region for a spot of sailing or even kitesurfing! You will also be able to try your hand at water-skiing and jet skiing, or even take advantage of the beach to swim in a relaxing atmosphere.

In order to ensure you the very best time possible, Coolsailing accompanies you throughout your booking process so as to help you rent the boat of your dreams and build a tailor-made cruise. Do not hesitate to contact us. It will be our pleasure to help you choose the boat of your dreams.

The ports in this sailing area

Annapolis, Baltimore, New york city ...


5-10 knots
15 knots


Jan Feb Mar Apr May Jun
10° 15° 20° 24°
Jul Aug Sep Oct Nov Dec
26° 26° 23° 17° 12°