Curating luxury cruises on the Chesapeake Bay

Dana Cubbage Photography

Hinckley Picnic boat with American flag in the Annapolis Harbor with the U.S. Naval Academy in the background.

Why Choose Us?

Two crossed burgees, one with the American flag pattern and the other with our signature 'CCYC' logo. Logo by @amandacbee.

Classic Luxury Yachting 

If you are seeking an exclusive and comfortable yachting experience on the Chesapeake Bay, look no further than Chesapeake Classic Yacht Charters! 

Our pristinely maintained Hinckley Picnic Boat offers modern comfort, classic style, and luxurious amenities for your pleasure.

Curated Cruises

Whether you’re celebrating a special event or just looking to enjoy a relaxing day on the water, we can customize your cruise to offer you the perfect experience.

Annapolis: The Sailing Capital of the World

As the Sailing Capital of the World and the Crown Jewel of the Chesapeake Bay, Annapolis is the place to be! 

Discover the rich maritime history of our town and the treasures of the Chesapeake Bay by boat. 


A couple taking engagement photos at sunset aboard Chesapeake Classic Yacht Charters' Hinckley Picnic Boat. Stephanie Wyvill Photography
Two women enjoying a glass of wine in Chesapeake Classic Yacht Charters' custom outdoor Yeti drinkware with the iconic Thomas Point Shoal Lighthouse and the Chesapeake Bay in the background. lyzapyvovarova photography / The Lucky Knot
A wedding party wearing formal attire on a Hinckley Picnic Boat called "Proud Mary". Chesapeake Classic Yacht Charters offers wedding transports and wedding photography. Photo courtesy of Dana Cubbage Photography.
Group of five women enjoying a luxury private sunset charter in Annapolis, MD with Chesapeake Classic Yacht Charters.
Our Hickley Picnic Boat's American Flag with the Annapolis Harbor in the background. Photo courtesy of lyzapyvovarova photography / The Lucky Knot
Stephanie Wyvill Photography
A couple enjoying a luxury private daytime charter in Annapolis, MD with Chesapeake Classic Yacht Charters. Photo courtesy of lyzapyvovarova photography / The Lucky Knot
Luxury Hinckley Picnic Boat named Proud Mary with American flag cruising in the Annapolis Harbor. Photo by Martha Janney.
A group of six people enjoying a luxury private daytime charter with Chesapeake Classic Yacht Charters in Annapolis, MD to celebrate their wedding anniversary.
Five women enjoying a scenic luxury private sunset charter in with Chesapeake Classic Yacht Charters in Annapolis, MD.
Chesapeake Classic Yacht Charters' signature Navy Blue Yeti drinkware with our custom CCYC Burgee logo and chilled Fiji bottled waters in a nautical tray aboard our Hinckley Picnic Boat. Photo courtesy of lyzapyvovarova photography
View from a private luxury sunset charter with Chesapeake Classic Yacht Charters on the Chesapeake Bay in Annapolis, MD.
View of the Chesapeake Bay Bridges from aboard our Hinckley Picnic Boat during a luxury private charter with Chesapeake Classic Yacht Charters.
A couple celebrating their 40th birthdays with a private daytime charter with Chesapeake Classic Yacht Charters.
Group of people enjoying a private sunset charter with Chesapeake Classic Yacht Charters, with the sun setting over the Chesapeake Bay and an American flag.
Elegant display of some of our luxury charter offerings, including chilled Veuve Cliquot champagne, assorted macarons from Sweet Hearts Patisserie, fresh cut flowers, and assorted appetizers from our local caterer.
Photo of Chesapeake Classic Yacht Charters' Hinckley Picnic Book with its classic wooden trim cruising on the Chesapeake Bay. Photo by lyzapyvovarova photography
A couple celebrating their engagement aboard our Hinckley Picnic Boat during a private luxury sunset charter with Chesapeake Classic Yacht Charters. The sunset, American Flag, and Chesapeake Bay are in the background. Photo courtesy of Stephanie Wyv
A group of men enjoying our Wednesday Night Sailing Race private charter aboard our Hinckley Picnic Boat in Annapolis, MD. Our Wednesday evening charters in the spring and summer set out to watch the Annapolis Yacht Club weekly sailing regattas on t
A couple celebrating their engagement on the bow of our Hinckley Picnic Boat during a private luxury sunset charter with Chesapeake Classic Yacht Charters with the sunset and Chesapeake Bay are in the background. Photo courtesy of Stephanie Wyvill Ph
A family enjoying a luxury sunset charter aboard a Hinckley Picnic Boat with Chesapeake Classic Yacht Charters in Annapolis, MD
Our signature charcuterie board from our local award-winning vendor Artisan Charcuterie Co.
Wedding under a starry sky on a dock with Chesapeake Classic Yacht Charters' Hinckley Picnic Boat in the background.
Family enjoying a luxury sunset charter aboard a Hinckley Picnic Boat with Chesapeake Classic Yacht Charters in Annapolis, MD

What our Customers Have to Say

“This is the best looking boat in Annapolis, and every time I've had the pleasure of being on board Proud Mary it's been an exceptional experience. Kaitlin and Donald are the perfect hosts!”

Paige S.

Five women sitting on a boat at sunset with an American flag, water and a bridge in the background.

“We 3 California couples celebrated our common 60th wedding anniversaries in Annapolis. The highlight was a magnificent Chesapeake Bay tour on Proud Mary, a gorgeous and immaculately-maintained classic picnic boat.  She was skippered expertly by her genial owner, Captain Donald Patterson, who happily shared his extensive knowledge of the Bay.”

Tim N.

Group of six older adults on a boat, holding drinks, with a shoreline of houses and trees in the background.

“I have enjoyed cruises through Chesapeake Classic Yacht Charters 3 times and every time has been exceptional!
The boat itself is stunning! Plenty of space to move about and enjoy the sights but also spacious and comfortable.
Donald was a great captain, maintaining a comfortable speed and keeping our cruise smooth and enjoyable. Kaitlin handled every detail and made our experience one we will never forget!
You will not regret chartering Proud Mary, we cannot wait to book another cruise again soon!”

Mal H.

Five women standing on a boat at sunset, holding drinks, with a body of water and sailboats in the background.

Contact Us

When you want to spend the day on the water, sit back, relax, and cruise the Chesapeake Bay in style aboard our 36 ft luxury Hinckley Picnic Boat! Your trip will include a captain, fuel, light snacks, and cool refreshments. 

We are currently accepting bookings for the 2026 season (April 15-December 15) in Annapolis, MD.

Please fill out your information and we will be in touch soon. We can’t wait to hear from you!