Our Charters

When you want to spend the day on the water, relax and cruise the Chesapeake Bay in style aboard our captained 36 ft luxury Hinckley Picnic Boat!  Request a specific itinerary or destination or let your experienced captain handle the itinerary for you!  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.

Five women posing together on a boat under a bridge, with a river and American flag in the background, a bucket with a champagne bottle and colorful macarons on the table in the foreground.
Group of women in colorful dresses and sunglasses sitting on a boat, with a waving American flag, water wake, and sunset in the 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

Picnic table with a charcuterie board featuring watermelon slices, cheeses, berries, and crackers, red and white striped straws in cups, cookies with sprinkles, sushi, and a bouquet with American flags, all on a striped cloth.

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 kissing on a boat with an American flag, against a sunset backdrop.

Wedding Charters

  • 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. (Photographer not included).

  • 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.

Contact Us

Celebrating a special event? Have questions or custom requests? Fill out your information and we will be in touch shortly!