Daily sailing cruises out of the Chesapeake Beach Resort

Welcome to Chesapeake Windsail Cruises!


Chesapeake Windsail Cruises is a beautiful way to enjoy all the splendors of the waters of the Chesapeake Bay, the Cliffs of Calvert or the beautiful environment of the region, all during a wonderful 2 ½ hour cruise on the Chesapeake Bay.

Chesapeake Windsail Cruises sails out of the beautiful Chesapeake Beach Resort & Spa located in the bay-side town of Chesapeake Beach, Maryland, where you can dine before or after your cruise at the Rod ‘n’ Reel restaurant.

We hope you enjoy browsing our website and find a lot of useful information for your cruise.


See our offer
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Enjoy A Beautiful Day With Mother Nature

Enjoy A Beautiful Day With Mother Nature

Regularly Scheduled Daily Cruises – (up to 6 persons)

$70 Adults, $65 Seniors and $50 children 12 and under

Private Cruises for 6 persons or less

Private Cruises for 6 persons or less

$450 Private Cruises – (1 – 6 persons)

Themed and Special Cruises

Themed and Special Cruises

$483 Private Cruises – (1 – 6 persons)

Excellent
cruise packages


You are only a few steps away from a wonderful day on the beautiful Chesapeake Bay.
Select your Cruise!

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