Delmarva Charters


Bareboat and Skippered Sailing Charters on the Chesapeake Bay.

Why charter from Delmarva Charters?
    Realize your dream of chartering a sailboat on the Chesapeake Bay.
Delmarva Charters is a charterer of premier sailboats on the Chesapeake Bay and is a part of Captain In You Sailing School, Inc.

We provide both bareboat and captained charters. If you and your crew are already competent to charter a sailboat on your own, you can submit an application form and plan your charter today. You can then arrive the evening prior to your charter start date and stay on board for free. We will go over the yacht equipment and then off you go.

If you feel like you could use a little help making the transition to chartering then we offer sailing instructors which you can hire for a day or more to allow you to make a smooth transition to chartering on your own. We have taught thousands of students to sail and are experts at helping beginning sailors to charter on their own. We also offer sailing classes on every level, including docking, at Delmarva Sailing School, which operates out of the same marina as Delmarva Charters.

We are located at Haven Harbour South in Rock Hall, MD. Haven Harbour South is close to the Chesapeake Bay entrance and offers super clean bathrooms and showers, BBQ grill area, pool, wine and cheese deck, and other amenities.

Rock Hall is the perfect place to start your charter since we are located within one day of many ideal destinations including Annapolis, Galesville, Bodkin Creek, Worton Creek, Fairlee Creek, Baltimore Inner Harbor, and beautiful rivers including the Chester River, Magothy River, West River, Rhode River, South River and others.

Our sailing season starts on April 15 and continues until October 31 every year.

We pride ourselves on presenting our charterers with a clean sailboat in excellent condition. Check out the Our Fleet page and pick out the sailboat of your dreams and begin your sailing adventure today.
Our Fleet
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Delmarva Sailing School
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