Fall Cruises

Chill Into Fall

Set sail for an exciting and scenic fall cruise, September 11th to October 31st, bring your cameras! Sail along the tree-lined tributaries of the South River and Chesapeake. Whether sail or powerboat, enjoy gorgeous views as the leaves change color and bask in the last warmth of our Indian Summers. Boats take up to 6 guests per charter; for a party of up to 12, click here.

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

Cruise Inclusive: 

  • Crew
  • Snacks & beverages
  • Fuel cost (conditions apply)
  • Non-stop Entertainment
  • Alcohol & cameras allowed!

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

Powerboat Fall Cruise

 Sailboat Fall Cruise

Islan' Grill Kitchen 

Try a delicious meal from our menu 

Our Fleet...

Choose from  Therapy (43-foot sailboat) or Irie Vibes (34-foot powerboat) and Tallawah (20-foot bow-rider) for your Chesapeake and Annapolis family 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.


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