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Sailing Charters in Annapolis, MD

Certification of COVID-19 vaccination is required. 

Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

Select A Time

2 - 6 People | 3-Hour (AM/PM) - 2.5-Hour (Sunset) Sailing Yacht Cruise | 25% Deposit

Due to COVID-19 and related safety concerns, minimum age: 7 years.

Gratuity not included in pricing

Full Day Sail

7 Hours | 25% Deposit


Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful, fed by countless navigable rivers and home to an abundance of wildlife. Join us for an unforgettable cruise on one of our world-class sailing yachts. We serve clients seeking a unique sailing experience on the Chesapeake Bay.

Overnight Adventure

2 Days | 25% Deposit


Set sail for an overnight adventure on the Chesapeake Bay with your own private charter! This two-day excursion sails along beautiful navigable rivers as you enjoy the surrounding scenery and keep a lookout for our wildlife. Your overnight journey  is aboard one of our world-class sailing yachts where you’ll enjoy an incredible sailing experience.

Chesapeake Bay

Looking for a unique sailing experience on the Chesapeake Bay? Our charters are the perfect way to explore the Bay and its navigable rivers. As the largest estuary in the world, the Chesapeake Bay is a natural beauty filled with an abundance of wildlife. Create your own sailing adventure on the Chesapeake Bay as we work with you to define your perfect excursion and then you may leave the rest to us!

Annapolis, located less than an hour from Washington, D.C., is noted not only as the location of the US Naval Academy but as America’s ‘Sailing Capital.’ It is home to a rich history that includes the oldest working state capitol building in the U.S., noted as the location where General Washington resigned his commission, as well as dozens of first-class bed and breakfasts, hotels, and fantastic restaurants. As a sailing venue, it is second to none.

Annapolis, Maryland

Annapolis Landing Marina

980 Awald Road 
Annapolis, MD 21403


Fajardo, Puerto Rico

Puerto Del Rey Marina