Curating luxury cruises on the Chesapeake Bay
Dana Cubbage Photography
Our Charters
Standard Charters
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9:00am, 2 hours – Up to 6 people (all ages)
$775 includes fresh local pastries, seasonal fruit platter, and cold beverages.
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12:00pm, 2.5 hours – Up to 6 people (all ages)
$925 includes captain, light snacks, and cool refreshments
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2 hours – Up to 6 people (all ages)
Start times vary seasonally, beginning 2 hours prior to sunset
$875 includes charcuterie and a bottle of wine
Special Event Charters
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Join us Tuesday evenings for the Tunesday Floating Concert Series on Back Creek! Listen to live music from local musicians aboard our Hinckley Picnic Boat! 2 hr charter for up to 6 people (all ages) / $875.00 includes charcuterie and a bottle of wine
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Come out with us to watch the Wednesday night sailing regattas! 2 hr private evening charter for up to 6 passengers.
$875 includes charcuterie and a bottle of wine
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We offer transportation for the bride & groom and up to 4 additional guests to local waterfront reception venues. Includes champagne and charcuterie. Please contact us to book.
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Have your photographer capture your special day with the elegance of our Hinckley Picnic Boat and the stunning backdrop of the Chesapeake Bay. Available for the bride & groom and up to 4 additional wedding guests at a time while underway, or for complete wedding parties while dockside. Dockside photo opportunities at local waterfront reception venues are also available.
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Tie the knot in an intimate setting aboard Proud Mary with the stunning backdrop of the Chesapeake Bay. Our captain is a legally certified minister able to officiate weddings and vow renewals. We can accommodate the bride & groom and up to 4 additional guests while underway, or up to 6 additional guests while dockside.
Weddings
Why Choose Us?
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.
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.
“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.
“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.
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 2025 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!