Look for our upcoming events: July 4th Fireworks, Island Chill Party Cruise (large groups) - See all upcoming events.

Bareboat Charters

Be your own captain, sailing on the Chesapeake Bay on either powerboat, sailboat or bow-rider.

Crewed Charters

Experince the spirit of the Islands with our USCG licensed Captain & Cruise Director for your comfort, safety & entertainment!

Cruise Packages

Celebrate birthdays, anniversaries, family outings, corporate events, sight-seeing & watersports; music videos.

Our Boats

Irie Vibes

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

sailboat Chesapeake bay Annapolis md rental south river boat


46' Center-Cockpit Sailboat - Rates as low as $125/h


20' Wellcraft Bow-Rider - Rates as low as $120/h

Who we are

We cater to guests seeking unique, mini-vacational cruise adventures. We offer comfortable performance yachts with the flair of a tropical island to ensure that your private charter is truly memorable.

All Inclusive Mini Vacation Cruises:

  • Special Occasions: Birthdays, Anniversary, Bachelorette...
  • Visit lighthouses & the Chesapeake Bay Bridge (see destinations)
  • Lightfare food on deck
  • Anchor, swim & BBQ (grill provided)
  • Fishing
  • Fuel
  • Kayaking, Water Skiing & Paddle Boarding
  • Water-front Restaurants
  • Corporate outings
  • Team building

"Happy spouse! tremendous feeling when I proposed to my fiancé on her birthday on Island Chill. she said 'best money spent' lol.  Island Chill was very accommodating to us. Been to Jamaica once and this is exactly how I remembered it, very chill crew!

"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, your lovely cruise director makes it extra special with hospitality!"

Client satisfaction

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

See Island Chill in Action




Guests Last Year


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Guests per Trip

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