Sailing Cruises in the Bay (April - Oct)

Pricing is per group (booking entire vessel)
Please read 'details' in the checkout page

Sailing Fundamentals

  • 5 hours, 5 guests max
  • $625
  • Vessel: 30ft cruiser Sonora
  • Departs from Shadyside, MD
  • Short pre-studying required
    (material provided)
  • Food and drinks welcome!

  • Learn how to sail! This is a more intensive experience, where students will be learning and applying skills simultaneously. After this class, students will be able to perform all basic sailboat maneuvers, control sail area, and more. Students who have taken this course will be eligible for more advanced classes and invite-only cruises.

    Discovery Sail

  • 4 hours, 5 guests max
  • $549
  • Vessel: 30ft cruiser Sonora
  • Departs from Shadyside, MD
  • Short pre-studying recommended
    (material provided)
  • Food and drinks welcome!


  • Discover why sailing has captivated the hearts of many all over the world. Half sailing class, half pleasure sail. Spend much of the day enjoying being on the water, while learning about how sailing works. Spend time trying your hand at being a crewmember of a sailing boat. Students who have taken this course will be eligible for advanced classes and invite-only cruises.
    Most Popular

    Pleasure Sail

  • 3.5 Hours, 5 guests max
  • $519
  • Vessel: 30ft cruiser Sonora
  • Washroom facility aboard
  • Departs from Shadyside, MD
  • Food and drinks welcome!


  • Being on the water is great, but being in a sailing vessel is amazing. The sail gets hauled up, then gets trimmed. We switch off the engine and the wind fills the sails. The motion of the boat eases, and serenity takes over. Come enjoy a relaxing sail with people you love. Popular option for special occasions!

    Sailing Excursions in the Chesapeake Bay (April - Oct)

    Pricing is per group (booking entire vessel) 30% deposit required
    Please read 'details' in the checkout page

    Destination: St. Michaels MD (2 days)

  • Starts 7:30AM and ends 2-3PM next day
  • Up to 3 guests
  • $1449, 30% deposit required
  • Vessel: 30ft cruiser Sonora
  • Departs from Shadyside, MD
  • Water Taxi included

  • A slice of the true cruising lifestyle, 'living on the hook!' This trip is designed to be inspiring for people interested in becoming true sailing cruisers. It is packed with plenty of sailing, but also with some time at a serene anchorage to enjoy the surroundings at sunset. Includes a short trip on the water taxi to enjoy the quaint town of St. Michaels, including the legendary Maritime Museum.

    Destination: Annapolis, MD (1 day)

  • Starts at 8:00AM and ends at 9:00PM
  • Up to 3 guests
  • $1019, 30% deposit required
  • Vessel: 30ft cruiser Sonora
  • Departs from Shadyside, MD
  • Water Taxi included

  • This lovely daysail takes you to the sailing capital of the world, Annapolis. A bit more of a casual experience than the 2 day cruise, we do a short sail up to Annapolis to enjoy the all the town has to offer. Grab a nice meal at one of the great restaurants in Annapolis, and perhaps check out the museums at the Naval Academy. Enjoy an amazing sail under the sunset on the way home, with the cool evening breeze blowing through your hair.

    Independence Day Weekend Fireworks Cruise

    Pricing is per group (booking entire vessel) 40% deposit required
    Please read 'details' in the checkout page

    2 day Cruise to St. Michaels MD (07/01)

  • Starts 7:30AM and ends 2-3PM next day
  • Up to 3 guests
  • $1499, 40% deposit required
  • Vessel: 30ft cruiser Sonora
  • Departs from Shadyside, MD
  • Water Taxi included

  • All the great things about the St. Michael's excursion cruises, but with July 4th Weekend festivities! This cruise includes the viewing the fireworks from the beautiful anchorage at St. Michaels. We will be surrounded by the vintage boats and the Chesapeake Bay nature. Shoreside activities are included! This will truly be a July 4th weekend to remember.

    Rain date: TBD

    1 day Cruise to Herring Bay Sanctuary (07/02)

  • Starts 11:30AM and ends around midnight
  • Up to 5 guests
  • $1029, 40% deposit required
  • Vessel: 30ft cruiser Sonora
  • Departs from Shadyside, MD

  • This cruise will give you a first-class view of the awesome fireworks at Herring Bay, where we will be anchored close to the fireworks. It has plenty of sailing but also has plenty of relaxing in a festive anchorage next to many other sailors and boaters!

    Rain date: TBD