1/2 Day, Full Day, Sunset & Overnight Cruises

Kid-friendly Activities All Day!

Our Chesapeake cruises are safe and fun for kids of all ages, while giving you and your loved ones a relaxing break from everyday life! Choose between Therapy 43' sailboat  or Irie Vibes 34' powerboat and enjoy light fare snacks and non-stop entertainment! You also have the option of trying our delectable meals (see our Islan' Grill Kitchen menu)  and sleeping aboard for an Overnight Boat & Breakfast experience. Your Island Chill sales agent will help you choose the perfect accompaniment on your private getaway for you and your party of 5.

Charter Inclusive:

♦  Captain & Crew  ♦  Snacks & Beverages ♦ Paddle boards  ♦  Fuel included

Special Offer!

10% OFF full day cruises on any of our boats. Contact us for details.

Our Yachts

Your crewed family-getaway cruise begins with your desired boat. Each offers a safe and exhilarating ride, comfortable spaces with modern features for the best onboard experience. Click boat below to learn more.


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

Sail-A-Brate With Us!


Islan' Grill Kitchen

 Appetizers-Buffet meals

Sunset Cruise

Daily 5:30-8:30 pm

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Overnight Boat & Breakfast

Family getaway time!


The staff at Island Chill Yacht Charters operate all year round, even when the tourist season for maritime services has ended. In this way, you can keep up to date on our activities. Have any questions? Call us (410) 212 4476 or contact us here. Click on booking link below and allow our crew to take you and your guests on a private Chesapeake Bay cruise to remember!

'To Bring People Together to Create Memories,

 Strengthen Friendships & Family Connections'