Kid-friendly Activities All Day!

Our cruises are safe and fun for kids of all ages, while at the same time giving you and the family a relaxing break from everyday life! Choose 43' sailboat Therapy or 34' powerboat Irie Vibes. You also have the option of ordering our delectable meals and sleeping aboard overnight. Your Island Chill sales agent will help you choose the perfect accompaniment on your private family cruise getaway.

Charter Inclusive:

♦  Captain & Crew  ♦  Watersports Equipment  ♦  Fuel  ♦  Snacks & Beverages view menu ♦

Special Offer!

Enjoy 10% OFF Full day cruises on any of our boats. Enter CHILL19 at booking.

Sail-A-Brate With Us!


Gourmet Cuisine (Optional)

 Succulent appetizers-Buffet meals

Sunset-Full Moon Cruise

Daily Sunset 5:30-8:30 pm

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Overnight Boat & Breakfast

Great Family Getaway

Our Yachts

Your crewed charter experience begins with your desired yacht. Each offers a safe and exhilarating ride, comfortable spaces with modern features for the best onboard experience.


"Second time with my wife and kids... cruise was exciting, crew super fun... Loved every second!!!" -Simon. Read reviews


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