Daily Cruises

Chesapeake Cruises

Half Day / Full Day / Sunset / Overnight B&B

Our daily Chesapeake charter feature a private cruise setting for you and your guests to relax and enjoy. We offer light-fare snacks & beverages, water sport fun activities along with a USCG-licensed captain and crew at your service. Enjoy a morning, afternoon, all day, sunset and overnight getaway on the Bay. Celebrate your Birthdays, Anniversaries and National Holidays aboard! Up to 6 guests per charter; for a party of up to 12 guests, click here.

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

Choose Your Private Cruise: 

Cruise Inclusive: 

  • Captain & crew
  • Snacks & beverages
  • Watersport activities
  • Fuel included (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 bareboat) 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.