Student Cruises


(Boys & Girls: 7 -12 yo / Teens: 13 - 17 yo)

*Sailboat: $85/kid / *Powerboat: $95/kid

Join us for an ‘AYE CAPTAIN!’ 4 hr cruise (Mon-Fri; morning or afternoon) aboard Therapy 43' sailboat or Irie Vibes 34' powerboat. Become a 'captain' for the day, all while having fun on the bay! This program creates the opportunity for 'young sailors' to learn how to raise a sail, steer a boat and navigate on the water. The experience working as a team builds confidence and motivation. Our ‘AYE CAPTAIN!’ program includes a brief lesson on Chesapeake Bay history, the Thomas Point Lighthouse with wildlife views of ospreys, blue herons and (we hope!) bald-eagles.

Activities & Itinerary

Cruises leave the Londontowne Marina and sail the South River. Boats anchor in Harness Creek for snacks and beverages, and depending on age and capability, kids can enjoy swimming, paddle boarding and socializing. We take 6 kids per boat or up to 12 kids for our Sail & Powerboat Adventure! package. Our ‘AYE CAPTAIN!’ program is booked as groups of 6 kids minimum.

We provide fruit, cheese and cracker try, with soft drinks and lemonade. You are welcome to bring your own picnic basket and cooler, or you can also order from our mouth-watering Islan' Grill Kitchen menu.



  • Learn to sail
  • Raise the sails
  • Steering & boat controls
  • Basic navigation
  • Learn brief history of the Chesapeake


  • *10% discount compared to regular cruises
  • Uscg-licensed captain & crew
  • Snacks & beverages
  • Students learn basic sailing & boat terms
  • Thomas Point Lighthouse tour
  • Watersport fun activities
  • Fuel cost (conditions apply)


All kids will be required to wear a Type-II or Type-III lifejacket while on deck and will be tethered by a lifeline to prevent falling overboard. While swimming, all children will be required to wear a Type-II or Type-III life jacket.


Raise the Sails, Steer, Navigate...

Islan' Grill Kitchen 

Order a delicious meal from our menu... 

Sail & Powerboat Adventures

12 Guests, 2 Boats, 3 Locations, 1 Party

Fleet & Reservation...

Choose from  Therapy (43-foot sailboat) or Irie Vibes 34' powerboat and Tallawah 20' bow-rider for your Chesapeake and Annapolis adventure. To see our fleet click here.

Give us a call today (410) 212-4476, or fill out the inquiry form to get started with rates & reservations. For more information, please visit our FAQs.

'To Bring People Together to Create Memories,

 Strengthen Friendships & Family Connections'