Our Boats

34ft powerboat rental Chesapeake bay Annapolis, MD charters captain birthday, anniversary, bachelorette, family, business, music videos, photoshoots, boat, yacht rentals near the south river and Baltimore, Washington, Philadelphia

Irie Vibes

34' Formula Cruiser Motor Yacht - Rates from $150/h

sailboat Chesapeake bay Annapolis md rental south river boat


43' Center-Cockpit Sailboat - Rates starting at $125/h


20' Wellcraft Bow-Rider - Rates as low as $125/h


Crewed Charters

Allow our crew to take you on a tour of the Chesapeake Bay and its tributaries. With the spirit & welcoming hospitality of the Islands.

Cruise Packages

Celebrating birthdays, anniversaries or just a special night,  make your day extra special on your own private yacht & a crew at your service.  

Bareboat Rentals

Be your own captain, sailing on the Chesapeake. Go where you want, do what you want, explore, snap moments.


Upcoming events: July 4th Fireworks,  Happy hour party

About Us

Island Chill Yacht Charters hosts private Crewed or Bareboat, Sail & Powerboat on the Chesapeake Bay. We cater to guests seeking a unique, All inclusive mini-vacational cruise adventures. We offer comfortable performance yachts with the flair of a tropical island to ensure that your charter is truly memorable.

All Inclusive Mini-vacation Cruise:

Client satisfaction

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

"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.

"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!!!"

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!"

See Island Chill in Action




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