Curating luxury cruises on the Chesapeake Bay

Dana Cubbage Photography

Hinckley Picnic boat with American flag on water near U.S. Naval Academy in Annapolis, MD

Why Choose Us?

Two crossed triangular flags, one with the American flag pattern and the other labeled 'CCYC' on a pink background.

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. 


Our Charters

Luxury yacht with black hull on water near marina, American flag displayed, bridge and boats in background.

Standard Charters

  • 9:30am, 2 hours – Up to 6 people (all ages)

    $775 includes fresh local pastries & seasonal fruit platter. 

  • 1:30pm, 2.5 hours – Up to 6 people (all ages)

    $975 includes captain, light snacks, and cool refreshments

  • 2 hours – Up to 6 people (all ages)

    Start times vary seasonally, beginning 2 hours prior to sunset

    $875 includes charcuterie and beer & wine of choice

Group of women on a boat with charcuterie and drinks

Special Event Charters

  • Come out with us to watch the Wednesday night sailing regattas! 2 hr private evening charter for up to 6 passengers.

    $875 includes beer & wine of choice and charcuterie.

  • Let Mom relax and enjoy a lovely Mother's Day on the water! 2 hrs, up to 6 people (all ages)

    $975 includes champagne, a bouquet of flowers, and a catered picnic from Main & Market. Morning, afternoon, and evening slots available.

  • Watch the most anticipated event of the season by boat! 4 hour private charter during the Blue Angels shows for up to 6 people (all ages).

    $2,225 includes a catered picnic luncheon from Main & Market.

  • Enjoy quality time on the water with your midshipman and family!

    3 hr private charter for up to 6 people (all ages).

    $1,975 includes a catered lunch picnic from Main & Market.

    Available Monday, Thursday, and Friday-Memorial Day (flexible start times).

  • Dad deserves a carefree day on the water!

    2hrs, up to 6 people (all ages)

    $975 includes a 6-pack of Forward Brewing “Boat Day” beer, a bouquet of flowers, and a catered picnic. Morning, afternoon, and evening slots available.

  • Don your red, white, and blue and celebrate Independence Day on the water! 3 hr private daytime charter for up to 6 people.

    $1,975 includes a catered picnic luncheon from Main & Market.

A couple in formal attire embracing and kissing on a boat with an American flag, set against a sunset over water.

Weddings

  • 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.

  • 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.

  • 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.

Small black cabin cruiser with American flag on water, marina background, bridge visible.
Sunset over water with sailboats on the horizon, reflecting golden light on the surface, and a clear sky with few clouds.
Five women on a boat holding drinks with a scenic ocean background and sailboats in the distance.
American flag on a boat with wake trailing behind, water and shoreline in the background.
A wedding party on a boat called "Lady Mary" with a bride and groom in the foreground, wearing formal attire, surrounded by bridesmaids and groomsmen. An American flag waves at the back.
Sunset view from a boat with American flag, striped seating, calm water, distant boats, and shoreline.
A charcuterie board with assorted cheeses, meats, fruits, and vegetables on a blue and white striped tablecloth. Nearby are plates of crackers, macarons, and appetizer bites, with a bouquet of white flowers in a basket and two bottles in a bucket.
Bride and groom kissing under a starry sky on a dock.
Luxury motorboat named Proud Mary with American flag, docked in a marina.
A table set on a boat with a bouquet of white flowers in a vase, a wicker tray with patterned napkins, a bowl of mixed nuts, a plate of colorful macarons, skewers with tomatoes and mozzarella, and a metal bucket containing bottles of champagne agains
Suspension bridge over a large body of water with cloudy sky
Group of men on a boat, smiling and posing, with one seated and holding drinks.

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!