Water Activities

Summertime Cruises at Leonardtown Wharf

Summertime classic cruises down Breton Bay to St. Clement's Island, and the scenic waterways of St. Mary's County to enjoy the natural sights and the sunset.

Enjoy a two-hour afternoon or sunset cruise from Leonardtown Wharf with Fish The Bay Charters. Experience Breton Bay, St. Clement's Island, and the scenic waterways of St. Mary's County. These BYOB small group cruises offer guests a chance to relax and unwind on the calm and beautiful waterways of St. Mary's County.

Depart from the Leonardtown Wharf Park and spend 2 hours cruising aboard the Lisa S, a 48-foot vintage Chesapeake Bay charter boat with Captain Phil. Bring your favorite snacks, drinks, and adult beverages aboard, or check out our local suggestions below to grab on your way! Immerse yourself in the beautiful sights and sounds of nature as you cruise to the Potomac River.

Afternoon cruises are on select weekends in August from 3:30 pm to 5:30 pm. Tour Breton Bay and the Potomac River as you spot Maryland wildlife. Grab food and snacks to go from one of our local favorites below for a fun picnic onboard. Guests of all ages will enjoy this late afternoon cruise.

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Sunset cruises are on weekends in August and September, see tickets below for dates and departure times. Take in the beauty of Breton Bay on your way towards the Potomac River. Bring your favorite beverages and share a toast to mother nature and the spectacular sunset! Guests of 12 years old and up will enjoy this evening cruise.

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Pick up local food, beverages, and goodies for your trip from our favorite hometown spots:

  • Order ahead with Botanic Cafe for farm-to-table, made fresh-to-order sandwiches, salads, and sweets. Preorder a special box lunch here for your afternoon cruise, includes a sandwich, chips, fruit cup, and a cookie!
  • Do Dah Deli is a groovy local spot with a creative array of hip sandwich options, fun and funky salads, and "sweet thangs" (their words, not ours!) for you to pick up before your boat ride.
  • Stop by The Good Earth Natural Food Co. for a wide selection of organic and natural snacks and beverages. Local tip...they also have an awesome selection of natural wines, artisan ciders, and gluten-free beers!
  • Port of Leonardtown Winery is offering a special free wine tasting to pick out your favorite wine when you show your cruise ticket confirmation. Wine glasses and snack packs are available for purchase as well.
  • Antoinette's Garden mason jar wine drinks and creative charcuterie boards are a perfect pairing for your sunset cruise.
  • Swing by Social Coffeehouse for a seasonal peach iced tea or cold brew coffee with peach foam to take along with you on the water.
  • Check out Heritage Chocolates for handmade chocolates and confections. Don’t miss their marshmallow s’mores and chocolate-covered bacon! Heritage Chocolates also offers beautiful boxed chocolates to pair with a bottle of wine for your sunset cruise.
  • Summer is not complete without The Salted Scoops farm-to-cone ice cream. They have sweet seasonal flavors like honey lavender and ginger! Grab a flight of ice cream flavors before your afternoon cruise to keep you and the kiddos cool as you cruise the waterways.

Want more fun, on-the-water activities from Fish the Bay Charters and Captain Phil? Find opportunities for charter fishing, watermen heritage tours, and more sunset cruises here.

Not ready for the night to end? Enjoy the nightlife of downtown Leonardtown! Check out all that Leonardtown has to offer this summer here!

Come spend a weekend (or week) in Leonardtown this summer! Stay right in the heart of Downtown Leonardtown at the newly renovated Inn at Leonardtown.