Students Cruises

A fun, edutaining and interactive cruise on Island Chill is perfect for groups of up to 6 students on either Therapy 43' sailboat or Irie Vibes 34' powerboat.

  • Graduation
  • School Leaving
  • Field Trips

All ages are welcomed!  We have different programs set up where the students can:

  • help raise the sails
  • steer the boat
  • learn about the Chesapeake, and
  • understand protocols and terms used by boaters
  • Learn to sail

Enjoy non-stop entertainment on your personalized yacht charter experience. Please try our delectable meals from our catered menu. Your Island Chill sales agent will help you choose the perfect accompaniment for you and your friends.

Charter Inclusive:

♦ Captain & Crew at your service ♦ Watersport Equipment  ♦ Snacks & Beverages view menu


'Took my daughter and her friends for her graduation... BEST TIME EVER!!! ...!' Read reviews

Our Yachts

Your crewed charter experience begins with your desired yacht. Each gives you a safe and exhilarating ride, comfortable spaces, and modern features to give you the best onboard experience. Click charter below and enjoy cruising with us!

Therapy Sail Charter

Relaxin cruiser-Enjoy the helm!

Irie Vibes Power Charter


water tube, waterski, kayak & paddle board rental Chesapeake bay Annapolis MD

Free Watersport Equipment

Paddle boards-Noodles...


Click on booking link below and allow our crew to take you and your guests on a private Chesapeake Bay cruise to remember!