Specialty Cruises

Chesapeake Cruises 7 Days A Week  

Specially Designed  For You!

Our specialty cruises make any day unforgettable during the Chesapeake's sailing season from the April spring to October's fall. Up to 6 guests per charter, for a party of up to 12 guests, click here.

While cruising or at our secluded anchorages, enjoy a delicious meal ordered from our Islan' Grill Kitchen menu.

Choose Your Specialty Cruise: 

Cruise Inclusive: 

  • Captain & crew
  • Snacks & beverages
  • Watersport activities
  • Fuel cost (conditions apply)
  • Non-stop entertainment
  • Alcohol allowed!

While you may bring your own picnic basket, you can also order from our mouth-watering Islan' Grill Kitchen menu

Our Fleet...

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

Call us (410) 212-4476, or fill out an inquiry form to get started with booking and reservations.