Island Chill Brings People Together to Create Unforgettable Memories,

 Strengthen Friendships & Family Connections!

crewed charters Chesapeake bay power boat yacht Annapolis

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Dear Guest, Thank You for cruising with us and taking your time to provide us with your valuable feedback.Whether you live in the Annapolis, D.C., Virginia area, or visitors  from out-of-town, we want you to enjoy an unforgettable Chesapeake cruise experience with endless water activities!

Customers experience is very important to us. Check out what our recent customers say.

"Island Chill was awesome and extremely accommodating! rented the Sailboat and went on the Bay with my hubby and some friends. So much fun! Everything about the sail was amazing & great customer service! Thanks for such a fun day!!!"

"My first time on the Chesapeake and it was endless fun! We even got to sail... Great boat... Awesome experience"

BEST DAY EVER!!! loved waterskiing with my kids, will be doing this again next year!

"Happy spouse! tremendous feeling when I proposed to my fiancé on her birthday on Island Chill.  They really treated us to a great experience and were very accommodating. We can't complain, my fiancé and soon to be wife said 'best time she had in a long time'. Been to Jamaica once for vacation in Montego Bay and this is how I remembered the hospitality.

I have never been on a yacht and Island Chill makes me feel so comfortable. Great relaxing settings for me and the kids. Great hospitality will definitely come again next year!

"Island Chill Yacht Charters is a little mini-vacation cruise right in our own backyard here in Annapolis. Stacii & Sheree, are lovely crew that made it extra special with hospitality!"


Your feedback is highly appreciated and will help us create more lasting smiles and unforgettable memories. For your convenience, we provide you the following three options:

Promotion & Deals for Island Chill Guests!

Special Offer for returning guests, MBX, AACCC, VAAAC members, Military households & Non-profit org.